The holidays are upon us and there’s so much happening in Annapolis this season!
I did hours of research (so you don’t have to!) organizing ALL the holiday fun in ONE PLACE! I will be updating the list as events continue to pop up so check back!
*Please note – While I make every effort to crosscheck links and event details, I encourage you to do the same before making final plans. If details are missing or incorrect, please let us know so that I can correct them. Thanks for your help!
This list is generously sponsored by Erica Baker, an Associate Broker at TTR Sotheby’s International Realty. Erica is a trusted real estate advisor and lifelong Maryland resident, boasting over eight years of dedicated client service. Her unwavering commitment to exceeding expectations is evident in her ability to align clients’ goals with property buying and selling strategies. With prior experience in home remodeling, she brings invaluable insight to each home evaluation, enabling her to serve clients effectively. Erica Baker’s passion lies in transforming the spaces that encapsulate your life, ensuring a truly inspirational environment. If you’re interested in selling or buying a home, contact Erica Baker!
Thanksgiving to New Years Day
First 2 Hours FREE at Downtown Metered Spaces: Parking at downtown metered spaces (individual meters and kiosks) will be free for the first two hours. You can also get the first hour FREE at Hillman Garage!
To get the two hours free, use the code ParkDTA on ParkMobile.
November 17th | 7-8pm
The first 500 families to arrive will receive our 1st Annual Annapolis Town Center Ornament to take home! Join us for a DJ, games, fireworks, Vintage Views Mobile Bar. Santa arrives to help light the tree around 7:45 pm. Tickets are free and required for headcount purposes.
November 18th | 5-8pm | Davidsonville location
Immerse yourself in the breathtaking sight of over 250,000 lights illuminating the enchanting properties of Homestead Gardens. Get ready to witness the magic as you step into a winter wonderland at our Davidsonville, MD location. Experience a dazzling Grand Illumination event like no other, where every corner is adorned with twinkling lights, creating a whimsical atmosphere.
November 26th | 4-7pm
The annual Christmas Tree lighting ceremony will include carolers, music, hot cocoa, and crafts for the kids, plus candy canes and general merriment! This event is free and open to the public. Join Santa, Mrs. Claus, and Elfie as they arrive to light the Christmas Tree.
December 1st | 5-6:30pm
We are so excited to hold our Annual Open House and Tree Lighting at the Chamber! Fun for the entire family to enjoy singing, dancing, music, cookies and warm cider, and more!! Elves provided by the Toast of Severna Park Toastmasters Club. Enjoy performances, music and more! Get your family pictures taken with Santa AND the Grinch. Free and fun!
BOAT TOURS + BOAT LIGHT PARADES
November 25th | 5-9pm
The annual boat parade starts in Nabbs Creek, near the Broken Oar Bar & Grill, goes up and down Stoney Creek, and ends on Rock Creek at PYY Marine.
December 9th | 6-8pm
It’s a beloved Annapolis tradition! Every year on the second Saturday in December, magic happens on the water of the Annapolis Harbor—boats suddenly appear out of the cold winter night illuminated with thousands of colored lights and crewed by jolly revelers!
December 10th | 6pm
Part of the Solomons Christmas Walk festivities, the lights parade begins at dusk is expected to arrive at the Riverwalk around 7:15 p.m. Coordinated by Solomons Island Yacht Club, Southern Maryland Sailing Association, Patuxent River Sail and Power Squadron, Solomons Yachting Center and Sail Solomons, this parade caps off a day of Christmas Walk events including a new vendor village in 2023.
CHRISTMAS TREE FARMS & SHOPS
Fresh Fraser fir trees, greenery and more! More information to come via Instagram.
November 24th | 9am – December
Friendship Trees is a cut your own Christmas tree farm featuring Fir, Pine, and Spruce Christmas trees. Don’t want to cut your own? We have beautiful Fraser Firs from North Carolina. Be sure to visit our Christmas Shop for a wide variety of holiday items. We are a member of the Maryland Christmas Tree Association. Be sure to follow us on Facebook
Offering the freshest varieties of fir Christmas Trees & Greenery in a fun, family friendly setting. More information coming via their Facebook page!
Explore the winter wonderland with 23 themed trees, immerse yourself in delightful events, purchase your Christmas tree and check out the train displays!
November 24th | 8:30-4:30pm until they’re sold out!
Cash and Local checks only, no cards. Snack shack with hot chocolate, hot spiced cider, sodas, hot dogs and chips on-site.
More information to come on their Facebook page. They also sell handcrafted wreaths, garland and decor. Enjoy coffee, apple cider or hot chocolate plus snacks to purchase.
December 7th | 5pm
Join us as we light the first candle on the Menorah in celebration of the Hanukkah season on December 7 at 5pm! Located across from J. Alexander’s Restaurant.
This lighting of the world’s largest menorah is viewed by tens of millions across the nation and around the world via news broadcasts and other media, many of them hundreds of miles from any Jewish community, which makes it very difficult for them to otherwise celebrate and enjoy Chanukah properly. Prominent guests including the President, Vice President, members of the Cabinet, Congress and the diplomatic corps, as well as numerous senior Administration officials and international dignitaries and celebrities, have all attended and participated in annual lighting ceremonies of the National Menorah since it was first lit in 1979.
December 10th | 5:30pm
Join us for a spin at the annual Menorah Car Parade here in Annapolis. An experience you won’t want to miss! The parade will be leaving Safeway (2635 Housley Road, Annapolis, MD, 21401) on Sunday, December 10th at 5:30pm so please be there at 5:00pm if you are planning on joining the parade. Parade Destination – City Dock – Annapolis, MD at approximately 5:45pm where we will kindle a giant menorah and celebrate the festival of lights. (Each car Menorah will be attached to the car with four strong magnets covered with a soft magnet cover to prevent scrapes.)
HOLIDAY SHOPPING EVENTS
Super excited to have this gorgeous space through the holidays. Stop by to say hello and come check it out. We have gifts (this includes gifts for yourself), houseplants, pet products including dog food, festive photo ops & the friendliest staff.
November 17th | 10am-8pm
We are excited to bring back our PINK FRIDAY EVENT! One huge FUN FILLED day to #shopsmallfirst Our mission – support your favorite small businesses! Before black Friday, before the big guys…this is community over competition at its finest! Be sure to make your lists and check them twice because we will be celebrating ALL DAY LONG in Severna Park and Annapolis with drinks, discounts and retail therapy!
November 17th-December 22nd
Come celebrate ALL things LOCAL by shopping SMALL & HERE. this holiday season! Lots of days to make a difference + keep your dollars in our community! We promise you this is the best one yet with the most unique and beautifully made items for you to choose from! xo, El & Crew + over 80 LOCAL makers
November 24th | 11am-5pm
November 25th | 10am-9pm
Shop over 90 retail stores and 80 restaurants in the downtown Annapolis Maryland area and you will find unique gifts that are not available elsewhere. Plus it’s fun to shop in this historic setting that is getting all decked out for the holidays. When you shop locally your friends will appreciate the time you took to find something unique and special. Gift cards are also a fun gift to your favorite downtown Annapolis restaurant, shop, inn, sailing cruise, performing arts venue, or other downtown experience. Plus the holiday decorations will have started going up in downtown Annapolis which makes the area feel magical as you stroll the many shopping streets downtown including Church Circle, Compromise Street, Dock Street, Main Street, Market Space, Maryland Ave, State Circle, Randal Street, and West Street. Free Parking all day at the Calvert Street Parking Garage at 19 St Johns Street and $6 all-day parking at Whitmore Parking Garage at 25 Clay Street.
November 30th & December 7th | 5-7pm
Join us for two special Thursday evening shopping events. Bring your Holiday list and check it twice for all of those who were naughty or nice. Make it a girl’s night out! Enjoy lite bites and bubbly with friends while supporting small local businesses.
The Shop Small Holiday Crawl is a social initiative to encourage our local community to shop small and local this holiday season! These participating open-air markets local to the Annapolis area: Wildberry’s Vintage Christmas Market (Two dates: 12/2 2pm-6pm and 12/9 2pm-6pm (rain dates Sundays, same time)), Heroes Holiday Market (Running December 3rd: 8am-11am), Midnight Madness: Downtown Annapolis (Three dates: 12/7 4pm-midnight, 12/14 4pm-midnight and 12/21 until 11pm), and HERE. A Pop-Up Shop (Open daily 10am-6pm, Midnight Madness photo check-in point on December 7th, 14th and 21st). Attend any or all of the open air markets listed above, and snap a pic, a selfie, or a photo of your haul and post it publicly to your Instagram feed with the tag #ShopSmallHolidayCrawl2023. Each public post will enter your account into a drawing to win one of 12 Shop Small Holiday Crawl Tote Bags designed by Jami Creates and printed by Blk Ankr Originals. Totes are also for sale and can be purchased online! All proceeds from sales of the totes will go toward the brand new Wildberry Small Business Fund! The Wildberry Small Business Fund is a new initiative by Wildberry to help local small and micro businesses who may be struggling to stay afloat with funding to attend the 2024 Wildberry Field Market season. Future opportunities will include micro grants and funding opportunities to help small and micro businesses attend other local open air markets.
December 1st | 4-8pm | 928 Hilltop Road, Arnold
Join Jen Denney in supporting local small businesses this gifting season: I am hosting the 2nd annual pop-up gift show at my home. Come have a SIP, get to SEE friends or meet new people, and SHOP to support small business owners in our community. We have some amazing local vendors bringing all sorts of great gifts for everyone on your shopping list: artisan charcuterie boards, custom tree skirts, one-of-a-kind stained glass, decorated Chesapeake Bay oyster shells, permanent jewelry (on-site and gift cards), trendy clutches and bags, curated gift packages, unique stocking stuffers, tasty sweet treats, handpainted ornaments, personalized wall art, sporty home team jewelry, and home organization packages to give you back time and peace of mind.
December 1st | 6-9pm
Kick off the holiday season with a stroll down Maryland Avenue and State Circle! Our shops will be decked out in twinkling lights and our windows filled with festive displays. Stop by for refreshments, to visit with friends, and to shop local!
December 2nd & 9th | 2-6pm
The Vintage Christmas Market is BACK for the FOURTH season, and better than ever! Wildberry Market Stand, Wildberry Farm to Table Food Trailer (with a NEW winter menu!!), over 60 small businesses each date, FREE holiday balloons from Clementine the Clown, a beer garden by @crookedcrabbeer , Santa, and so much more! Mark those calendars for 12/2 + 12/9 2pm-6pm (rain dates 12/3 + 12/10, same time). We can’t wait to see you up on the farm!
December 3rd | 8-11am
Mark your calendars! We’ve scheduled our 4th Annual Heroes Holiday Market for December 3rd from 8-11am! Tons of your favorite vendors! @cane_collective and @graywolfspirits specialty cocktails! Breakfast sammies! Photo ops with Santa and his crew. AND our infamous raffle to benefit @The Blue Ribbon project! See you there!
December 3rd | 11am-4pm
This family-friendly celebration of all things cocoa. 2023 marks the 9th year of the event, and some new activities are coming your way! Special Santa arrival at noon, along with music, children’s activities, a mobile escape room from Mission Escape, and, of course, delightful chocolate creations! One of the highlights of the Annapolis Chocolate Binge Festival is the Gingerbread Decorating Contest; see what fantastic creations area bakers dream up this year, and vote for your favorite at the Visitors Center.
December 7th, 8th, 9th & 10th
December 7th, 4 -10 PM. Friday and Saturday hours: 11 AM – 9 PM. Sunday hours: 11 Am – 5 PM
A fun new Holiday Market filled with great gifts handcrafted by artisans. The perfect place to stroll, shop, and be entertained. The market is located along the city dock waterfront area of historic Annapolis, Maryland. Admission is free so bring the whole family. While you are here enjoy taking a ride on the Jolly Express Cruise and enjoy a meal overlooking the festival area at Latitude 38. After you shop here, take a stroll downtown and enjoy all the great shopping from 90 stores. Plan your holiday parties by making reservations at one of 80 downtown restaurants. Special evenings include Thursday evening when all of downtown Annapolis enjoys the Midnight Madness shopping night and Saturday evening during the Eastport Yacht Club Light Parade. Visit the website for parking and lodging tips. Sponsored by the Downtown Annapolis Partnership. Tour buses are welcome. Vendor space available.
December 7th, 14th & 21st | 4pm-MIDNIGHT
The downtown Annapolis area, including West Street, Maryland Ave, Main Street, and the City Dock area will be filled with traditional holiday decorations including beautiful storefront windows, garland, wreaths, holiday lights, a snowflake alley, light canopies, a large Christmas tree, and a menorah. This will create a fun, safe, outdoor environment for late-night shopping and dinner with your family. On-street entertainment will be throughout downtown Annapolis. For the first Midnight Madness (Dec 7) you can also enjoy the opening night of Annapolis Holiday Market on City Dock from 4pm to 10pm. You will also find many of the shops open late until 9pm on other evenings in December, especially Friday and Saturday evenings. Free parking is at the Calvert Street Parking Garage (19 St Johns Street) from 6 pm to 6 am, and $2 parking from 4pm to 6am is available at the Whitmore Parking Garage (25 Clay Street). The free circulator bus will pick you up and drop you off at the Park Place and Knighton parking garages. On-street metered spaces on commercial streets are free for short-term parking.
December 8th | 6:30-9pm
Join us for a night full of delicious handheld food, wine, vendors, raffles, and live music. Our school’s gym will be transformed to an exclusive holiday market including 30+ local vendors, gift wrapping table, school merchandise, and more!
December 9th | 2-6pm
The holidays are right around the corner! Let’s come together for the Holiday Jazz Fest and $20 Craft Bizarre. This is an excellent event for families – particularly children who can go Climbing with Santa. We’ll also have a hot chocolate bar and live jazz music to accompany the festivities. Are you a crafter? We’d love to have you at our $20 Below Bizarre. Artisans and craft enthusiasts wanted! For vendor space, RSVP to [email protected]. We look forward to seeing everyone!
December 10th | 4-7pm | Downtown Severna Park
Join us Sunday, Dec. 10th from 4-7pm for our Annual Holiday Shop & Stroll in Downtown Severna Park! We have SO MANY amazing vendors coming this year, Live Music, and Coffee, of course! Partnering up with Danielle at @blendedessentials again this year in Olde Severna Park at SP Center, and we can’t wait to see you all there!
December 13th | 5-9pm
We can’t wait for Nordstrom Pop-up – Holiday Shopping! Light Fare and Beverages!! It’s happening Wednesday December 13!
December 13th | 6-9pm | Davidsonville & Severna Park locations
Indulge your senses as you sip and sample a selection of fine wines and craft beers carefully curated for this occasion. Our knowledgeable sommeliers will be on hand to guide you through the tasting notes and flavor profiles, ensuring a delightful experience for your taste buds. As you make your way through our beautifully adorned showroom, you’ll also have the opportunity to shop for thoughtful gifts that will bring joy to your loved ones this holiday season. From charming home decor pieces to unique stocking stuffers, we have something for everyone on your list. But this special evening isn’t just for the ladies – it’s open to gentlemen as well! We believe that holiday cheer should be shared by all, so bring your friends and loved ones along for an enchanting evening of shopping, sipping, and mingling. In the spirit of giving, we’re proud to announce that for every $5 beer and wine purchase, a portion will be donated to designated non-profit organizations. By attending this event, you’ll not only have a memorable time but also contribute to making a positive difference in our community.
December 17th | 9am-2pm
Join us for some holiday shopping with our local vendors, enjoy our amazing beverages from The Coffee Trailer, and support the Providence Center with a hot bowl of soup! ‘TIS THE SEASON!
SANTA RUNS & PARADES
December 2nd | 8am
Join the DeCesaris/Prout Cancer Foundation in Annapolis, Maryland on Saturday, December 2 for the 12th Annual Jingle Bell 5K Run/1M Walk. The perfect way to start your holiday off and running! This annual fundraiser is designed to raise awareness for lung and ovarian cancers. The Jingle Bell Run/Walk is geared towards the general public as an incentive to participate in a healthy lifestyle while offering an opportunity to educate everyone about early detection of lung and ovarian cancers. In addition, the event is also designed to raise much needed funds to support various educational research programs and patient services.
December 9th | 10am-3pm
Join us for a magical visit with Santa on the Trail! Make this season bright with your donation of non-perishable food items to the Anne Arundel County Food Bank, which can help spread love and warmth to those in need this holiday season. Together we can make this festive season even brighter for everyone.
December 9th | 12:30-6:30pm
Wear Santa costumes, Ugly Christmas Sweaters, Elf attire, holiday onesie or whatever puts you in the holiday mood! Bring a toy or donation if you are able to support local families in need this holiday season! Sign-up link will be provided shortly. What you get: Free Santa hat with ticket purchase! Wristband for entry and drink/food specials! Bar visits along downtown Annapolis. Bring in the holidays with the most festive and jolly bar crawl in Annapolis! 50/50 raffle with proceeds going to toy purchases for local families in need during the holidays! Participating Bars (Subject to Change): Dock Street Bar & Grill, Stan and Joes, Acme and more to be announced! Please thank our sponsors in Chesapeake Beverage/White Claw and Smoke Lab Vodka! See you all there!
December 10th | 3pm
The Annapolis Santa Run is a all volunteer event that is sponsored by Annapolis Firefighters Local 1926. Each year on the second Sunday in December Santa and his elves set out in search of new toys for needy children in Annapolis and Anne Arundel county. With the help of the community, local businesses, Annapolis Fire Department, Annapolis Police Department, Anne Arundel county Sheriffs Office, and many volunteers we have been able to brighten Christmas morning for almost 5000 children over the past ten years.
December 10th | 6-7pm
It’s that time of year again!!! Time for Santa to arrive on the Fire Engine and collect toys from us for our neighbors in need. EVFC is hosting the final stop for Santa during the Annapolis Santa Run. Please join us for some merriment while we wait for Santa to arrive on the fire engine. We will have hot cocoa, cookies and music. Please bring an unwrapped present for children 0-18.
ALL ARE WELCOME!
December 16th | 11am-3pm
Annapolis’ most unique holiday tradition continues! Drop off your donations then join us for Christmas carols, photos, the RUN then an after party with the Timmie Metz Band featuring Tambo!
December 16th | 7:30am
Join us on Dec 16th for the Naptown Half Marathon & 10K/5K in Historic Annapolis, MD‼️
December 26th | 1-4pm
Join us for food trucks, vendors, games, activities and more for adults and children! The event will run from 1-4 p.m. Be sure to get there early to have lunch with the Budweiser Clydesdales from 1-3 p.m.!
December 27th | 10am-4pm
Join us for food trucks, vendors, games, activities and more for adults and children! Gameday kicks off at 10 a.m. ET with the Military Bowl Official Tailgate showcasing military displays, games and music, with food and beverage available for purchase. At the same time, the Military Bowl Parade steps off at City Dock and concludes at the stadium, featuring the world-famous Budweiser Clydesdales, Medal of Honor Recipients, pageant winners and a variety of youth, community and military-themed groups.
CHRISTMAS LIGHTS AND TOURS
Off Main Street in downtown Annapolis across from Chick n Ruth’s Delly.
November 18th-December 30th
A unique and magical holiday experience of over 1 million twinkling lights spread across 18-acres of winter wonderland where it is guaranteed to “snow” every night! The largest and most spectacular light show in the Washington DC, Virginia and Baltimore areas, Winter City Lights is one of the most technologically advanced Christmas light experiences in the Country. Complete with 33 bonfires, Winter City Lights includes an enchanted 1.5-mile long trail of Christmas lights and displays through the woods, a 52-foot tall programmable Christmas lights tree with light shows, a 200-foot diameter canopy of Christmas lights, an 8-lane Snow Tubing Ride, tasty concessions, s’mores, hot chocolate, funnel cakes, fried Oreos, BBQ sandwiches, fresh hot pizza, amazing soft pretzels, adult drinks, light up toys & more.
November 19th-January 1, 2024
The SPCA of Anne Arundel County is de-LIGHT-ed to be returning to Sandy Point State Park for their 29th annual Lights on the Bay holiday light show! Come enjoy the magic of the holiday season while driving through two miles of 70 dazzling animated and stationary displays illuminating the roadway along the shore of the Chesapeake. Lights on the Bay is open to the public beginning Sunday, November 19th, 2023, and will share its cheer through Monday, January 1st, 2024. The light show will be open Monday through Thursday from 6-10 pm and Friday through Sunday from 5-10 pm. Want to hear something even more exciting? Lights on the Bay is even open on holidays! This year, add Lights on the Bay to your list of delightful holiday traditions. We hope to see you there!
SPECIAL DISCOUNT NIGHTS + SECRET SAYINGS TO EARN $5 OFF YOUR ADMISSION
- 11/25: Wadsworth Financial Consulting Night. Save $5 when you say “I am enjoying a smooth sailing retirement” at the gate.
- 11/30: Graul’s Market Night. Save $5 when you present a Graul’s receipt at the gate.
- 12/1: Annapolis Subaru Night. Save $5 when you bring a donation for the shelter at the gate.
- 12/2: Liquified Agency Night, save $5 admission when you make a donation to the SPCA of Anne Arundel County.
- 12/9: Spoiled Rotten Dogs Night. Save $5 when you say “my dog is spoiled rotten” at the gate.
- 12/16: BrightKey Night. Save $5 when you mention BrightKey at the gate.
November 24th-December 30th
Take a self guided walk to the North Pole! The North Pole Fairy will send you on your way through the garden lights, artic animals and other lighted scenes of Christmas to Santa’s Cabin! New scenes added every year. Santa is here in his Garden Cabin! Tickets are available online or at the entry.
November 24th & dates throughout December
Celebrate the season with a holiday tour of the William Paca House! Bring family and friends to enjoy the elegant decorations, learn about 18th century Maryland holiday traditions, and stories of Christmases past. This guided, one-hour candlelit tour highlights how the Paca household prepared for their holiday guests. The historic home is ready to greet you with music, garlands, a sweet treat, and a take-home recipe!
November 24th-January 1 | 5-9:30pm
We can’t wait for the Winter Festival of Lights! The dazzling lights are back this year to help spread some holiday cheer. Our official opening day is Friday, November 24 at 5 pm. We’ll see you and your family there!
November 24th-December 31st
Annapolis’ favorite holiday activity makes its return for the 2023 holiday season. Miss Anne will be adorned with reindeer spirit for an intimate 45-minute “sleigh ride” including hot cocoa, holiday music, and good cheer. Captain Santa is at the helm during this festive evening cruise on Spa Creek. Blankets will be available to stay warm and cozy. This is the perfect opportunity to start a family holiday tradition. In the spirit of the season, a portion of proceeds will be donated to Historic Annapolis.
November 24th-December 30th
Welcome the holidays with an evening walking tour of Annapolis. Your period-attired guide will lead you by lantern as you stroll around Maryland’s state capital, trimmed in greenery. Hear holiday traditions of times past as you walk by colonial mansions, Victorian homes, and quaint shops. Bring home the holiday cheer with a goody bag of treats including George Washington’s famed eggnog recipe!
1707 Urby Drive | Crofton
December 6th | 6-8:30pm and December 10th | 11am-1:30pm
‘Tis the season! Get in the holiday spirit with this festive new experience. Begin your adventure with a gourmet meal in a beautifully decorated room at the historic Maryland Inn. The three-course, prix-fixe menu will feature specially chosen seasonal selections, along with fresh artisanal breads, and non-alcoholic beverages. Alcoholic beverages will be available for purchase from the bar. During your dessert course, you will be greeted by a period-attired guide who will begin to introduce you to a variety of holiday traditions through the ages. Ending inside with a celebratory toast of eggnog or spiced cider, you will continue your journey with a 60-minute guided walk around Church Circle, the Maryland State House, and nearby vicinity, to hear more about how the holidays were celebrated through the ages, as well as the beginnings of many of the modern-day customs we partake in today. Bring home the holiday cheer with a goody bag of treats including George Washington’s famed eggnog recipe! Check out the delicious menu.
December 9th | 5-8pm
Join Watermark and Ken’s Creative Kitchen aboard Raven for an intimate holiday dinner. Enjoy live jazz and holiday classics by Fred Hughes and dinner on the enclosed main deck. Then, venture to the open-air top deck to take in the scenery and see the Eastport Yacht Club’s Lights Parade. Included in the ticket are an open beer and wine bar, butler-served hors d’oeuvres, as well as dinner and dessert service at a private table. Seating is limited, and reservations are for tables of two, four, or six; Larger parties may select multiple tables; Please specify if you will be joining another party and your entrée selections in the reservation notes. Check out the delicious menu.
December 14th | 6-8pm
Indulge in delicious food and drinks as we cruise and carol our way through the festivities. Hospitality includes holiday snacks, hot coco, and optional shots of peppermint schnapps. Song sheets will be provided. 21+. The cruise will be departing from the AMM Docks at 723 Second Street Annapolis.
BREAKFAST WITH SANTA
November 19th | 9:30am-11:30am
Join us for a jolly morning at Maggiano’s Little Italy on Annapolis Mall Road, Annapolis, MD, USA. Santa Claus is coming to town, and he’s stopping by to enjoy a delicious breakfast with all the good boys and girls. This event is the perfect opportunity to share your Christmas wishes and snap a memorable photo with Santa. So, mark your calendars for Sunday, November 19th, and get ready for a merry morning filled with festive fun! Breakfast buffet includes: Assorted Muffins & Pastries, Fresh Fruit, Fran’s Potatoes with Roasted Peppers & Onions, Crème Brûlée French Toast, Scrambled Eggs, Bacon, Hot Chocolate, Coffee, Tea, and Juices. $40 per Child/Parent Pair. $20 additional adult. $16 additional child 2-12.
December 3rd | 10am-1pm
Join Tuscan Prime for Brunch December 3 from 10am – 1pm. Reservation count MUST include all children and all guests dining at the table, including highchairs and booster seats. Additional seats/space may not be available for additional individuals to join your table. Please contact the restaurant to confirm. Tickets are required. Food and Beverages sold separately.
December 3rd, 10th & 17th | 10:30am-2:30pm
Join us for breakfast with Santa! We will have a kid’s Christmas craft station, an incredible breakfast buffet, visit with Santa and professional family portraits available featuring a backdrop by Woven Dreams by Emily. Adults $39 and Kids 12 & under $19.
POP UP BARS + ADULT ONLY FUN
November 17th-December 23rd
Join us at the Holly Jolly Hideaway, in festive attire, ever so desired. Bring along a guest, to join the quest, to spread cheer to all the rest. Twenty-one and over, stop on over. Clink your drinks, fun is a must, wanderlust you can trust. Hint: You won’t find this on the map, wander North of Santa’s Cottage, you’ll be there in a snap! No tickets required! Check out the different weekly themes!
Holiday Carol-Oke nights | 7-9pm
- November 19th and 26th and December 3rd, 10th, 17th and 23rd
December 5th | 6-10pm
In honor of our 1 year anniversary and the passing of the 21st Amendment that repealed prohibition we’re throwing a party! Come dressed in Roaring Twenties / Flapper styles. Free Hors D’Oeuvres. $8 Each Cocktails.
December 6th | 6pm
Celebrate the season with your co-workers and friends at the Chamber’s Miracle on Bestgate Holiday Party! Join us for an evening of Jingling and Mingling at the Atreeum at Soaring Timbers. We have several options for you to attend the Holiday Party including discounted party packs so you can bring the whole crew!! We’ll have a fantastic silent auction along with our wreath auction. You will enjoy delicious food, drinks, networking, a great mix of holiday music, snapping pics in the Annapolis Town Center Photo Booth with the big guy from the North Pole and more!
December 8th | 6-9pm
All are welcome to join in this evening of celebration, camaraderie and local seafood. This is the 9th consecutive year that I have hosted this event and it is bound to be the best yet – we will have a fully stocked raw bar, grilled oysters, apps/samples of local fish, kegs of beer, a rum bar and more! Tickets are $25 and 100% of the proceeds go directly to the maritime museum in support of their education programs. Get your tickets before they sell out!
December 12th | 6:30pm | Parley Room Annapolis
Bring the positive vibes to the Capital SUP Holiday party and celebrate the winter season with us! This is a private event – ticket includes your invitation inside, one complimentary cocktail, hors d’oeuvres, and music. Tickets – $60. Join us at Parley Room Annapolis at the Capital Hotel for a private holiday party – Tuesday, December 12th at 6:30pm. There will be an assortment of hors d’oeuvres such as crab cakes, oysters, steak toasts, burger sliders, charcuterie, dips, dessert, and much more. Your ticket will include one complimentary drink and the bar will be open to purchase additional beverages. Each guest will leave with a small gift as a thank you for spending your holiday season with us! This is a ticketed event and Parley Room will be closed to the public for the evening. We hope to see you there!
HOLIDAY STORYTIMES , COOKING CLASSES & CRAFTS
November 18th | 3-4:30pm
Enjoy making Crafts with Mrs. Claus at the Holly Jolly Hideaway! Your child will decorate their own holiday frame complete with a 4” x 6” professional photo with Mrs. Claus! Kids will also bring home some reindeer food to scatter on your lawn Christmas Eve! Vintage Views Mobile Bar will be on site for snacks and beverages, at a separate cost. One Ticket includes: 4” x 6” print of your child with Mrs. Claus, Frame Set, and Reindeer Food Bag. Register your child only. Adults do not need tickets. If you have more than one child attending please register each child separately. Space is limited. Suggested ages 3 – 10. Up to a maximum of (2) adults may attend with their child. Adults are required to stay with their child. No outside food or beverages allowed.
November 20th & December 5th | 10am & 3pm
Join us for a delightful Kids Craft Workshop: Pinecone Ornaments! Experience a festive atmosphere filled with holiday cheer and creativity. We have limited spots available, so be sure to reserve yours soon. The $5 registration fee covers all materials for this fun and creative activity, including pine cones, googly eyes, ribbon, paint, felt, pom poms, and more! Let your little ones unleash their imagination as they create cute owls, adorable reindeer, and beautiful trees. Our dedicated craft tables await, providing plenty of space for crafting and exploration. While the kids enjoy their crafting adventure, parents can relax and indulge in a cup of hot chocolate or coffee, served by our friendly staff. Don’t miss out on this memorable experience for the whole family!
November 25th | 12-1:30pm and 2:30-4pm
Paint your own Buoy in the Holly Jolly Hideaway – surrounded by the holliest, jolliest Christmas decor! Creatively demonstrate what keeps you ‘afloat’ this holiday season or paint and gift to one of your loved ones. Vintage Views Mobile Bar will be on site for snacks and beverages, at a separate cost. One Ticket includes: One Person Admission, 1 buoy, paints and brushes. This craft is open to all ages. One ticket per participant. Space is limited. Up to a maximum of (2) adults may attend with their child if adults are not participating. Adults are required to stay with their child. No outside food or beverages allowed. No outside food or beverages allowed.
November 29th & December 3rd | 2-3pm
Join us for the story of the Nutcracker and a preview of the ballet by The Chesapeake Ballet Company.
December 2nd & December 16th | 3-4:30pm
Get into the holiday spirit, create beautiful gingerbread houses, and make cherished memories with loved ones. Whether you’re a sprinkle pro or a first-time decorator, this event is perfect for all ages and skill levels. Vintage Views Mobile Bar will be on site for snacks and beverages, at a separate cost. One Ticket includes: (1) Gingerbread House and Supplies. This craft is open to all ages. One ticket per participant. Space is limited. Up to a maximum of (2) adults may attend with their child if adults are not participating. Adults are required to stay with their child. No outside food or beverages allowed.
December 6th & 7th | 9:30am & 3:30pm
It is sure to be a magical time! Christmas themed sensory play and crafts for kids 18 months – 6 years old. We will have a least 2 sensory play stations and 2 crafts as well as a Christmas playdough table and other fun activities. $23 for your first child, $13 for each additional participating child. Purchase additional child’s spot by buying the add on.
December 6th | 6:30pm
Meet us at the Westfield Christmas Tree Farm near CPK for a magical pajama storytime! Bring your slippers and your stuffies for songs, stories and some fun.
December 7th-December 16th
Join us for a delightful event where Mrs. Claus, with her warm and comforting voice, reads from our enchanting collection of books ranging from modern tales to beloved classics. Additionally, Mrs. Claus will personally assist children in crafting heartfelt letters filled with their wishes and dreams, addressed to the one and only Santa Claus himself. Don’t miss this wonderful opportunity to create lasting memories and embrace the joyous spirit of the holiday season!
December 9th | 1:30-3pm
Mrs. Claus will host a book club read along followed by conversation for ‘How The Grinch Stole Christmas’ and ‘I Got the Christmas Spirit.’ Each child will receive a cookie to decorate from a local bakeshop. Vintage Views Mobile Bar will be on site for snacks and beverages, at a separate cost. One Ticket includes: 1 Child Admission and 1 Cookie. Register your child only. Adults do not need tickets. If you have more than one child attending please register each child separately. Space is limited. Suggested ages 3 – 10. Up to a maximum of (2) adults may attend with their child. Adults are required to stay with their child. No outside food or beverages allowed.
December 10th | 1-2:30pm and 4-5:30pm
How did the Grinch lose Christmas?! Find out as the Grinch visits the Westfield Annapolis Mall to read this NEW sequel to the Dr. Seuss classic. Join us for storytime at 1 pm followed by a photo opportunity with the Grinch. Please bring your own camera or phone to take the photo. Book Tickets: All families attending the event must purchase a book ticket. You will receive one copy of the new book HOW THE GRINCH LOST CHRISTMAS! PLUS, admission to the storytime for one child and parent(s). Additional Kid Ticket: For families with more than one child: please purchase one book ticket and then add additional kid tickets to your cart for your other kiddos. Your family will then receive ONE (1) copy of the book AND each child will have a ticket to the storytime and be accounted for in the photo line. (This is important as we must have time for everyone with a ticket to meet THE GRINCH. The event is limited to ticketed kiddos only). Proceeds from the event tickets will go towards the Discoveries Community Pantry.
December 14th | 11am
Join us at the Train Garden at Marley Station Mall (upstairs by Macy’s) for a train themed storytime!
December 14th | 6:30-8pm
Grab a spot and join us for a Christmas Ornament Paint & Play. In addition to playtime, kiddos can choose a Christmas ornament to paint. These pottery pieces make perfect holiday gifts for those hard to shop for loved ones! Ornaments will be fired and ready for pick up within 1 week of the event. $25 per child
December 23rd | 9am-1pm
Ho Ho Ho! ‘Tis the season for a Story Time & Sing Along with Santa! Join us for cookies, crafts & selfies with Santa in Mrs. Claus’ Kitchen and glitter tattoos.
Dates throughout December
Join us at Taste Buds Kitchen to make Gingerbread making, Reindeer donuts, Holiday cookies, Milkshakes for Santa, Penguin cupcakes, New Year’s Cupcakes and so much more!
SHOWS, CONCERTS & BALLETS
November 24th-December 10th
Prepare to be amazed and witness shocking performances and death-defying stunts from @doportugalcircusofficial for an unforgettable show for all ages to enjoy! 🎪 The one hour and 45 minute family friendly show features talented artists from around the world including motorcyclists in the globe of death, aerialists, jugglers, clowns, dancers, acrobats, flying trapeze, magic and so much more! For over 25 years, Do Portugal Circus has performed across the globe as a traditional family-run circus. The all human cast (no animals!) will have you gasping in awe as they take you on a journey of laughter and pure amazement.
Children’s Theatre of Annapolis | December 2nd | 2-5pm
Showcasing performances from past and present CTA talent, fun holiday snacks and games, along with a visit from Santa and his bag of gifts, this promises to be a wonderful and joyous holiday celebration!
Lone Oak Farm Brewing Company | December 2nd | 4-8pm
We’ll be serving craft beer, seltzer and delicious BBQ served by Lone Oak Farm Brewery. We’ll have a host of festive activities including live music, crafts & facepainting for kids, and Santa! Your ticket includes unlimited food & drinks, and kids are free! Lone Oak Farm Brewery is located in a bucolic setting in the heart of Montgomery County, Maryland. The event will be held in the Branch Pavilion overlooking the farm. The pavilion is covered and outdoors but will be heated. Dress festive but warm!
December 2nd | William Paca House & Garden
You are cordially invited to celebrate a colonial holiday with Historic Annapolis! Bring the entire family to welcome yuletide at the William Paca House and Hogshead. It’s the year 1773, and you’ll experience the holiday traditions, music, and stories of Christmas past. Spend a fun afternoon with us at this joyous celebration! Your Colonial Yuletide admission includes both sites, and you may begin your experience at either location.
December 8th | 8pm
One night only! It’s the most wonderful time of the year – especially for this community favorite and family tradition! Many Annapolitans kick off the season with this concert, which features a sleigh full of holiday cheer provided by the Annapolis Chorale, Chamber Orchestra, and Artistic Director J. Ernest Green, along with special musical guests like audience favorite Mark Berman at the piano!
December 9th | 3pm
Do you play tuba, euphonium or baritone horn? Come join us and perform sounds of the holiday season! All ages and ability levels are welcome.
Children’s Theatre of Annapolis | December 9-11 and 15-17
December 12th | 7pm
The Annapolis Blend Chorus presents a Holiday Concert for adults, teens and children.
SANTA PHOTOS + EVENTS
NOW- December 24th
Get a FREE 4×6 photo with Santa plus, receive a FREE shareable video!! Advance reservations are required in all locations and can go quickly. Reserving is easy and free.
November 18th-December 23rd
Experience the magic and capture the spirit of the holiday season with a visit to Santa’s Cottage where you will meet Santa himself and take home a photo for the whole family to treasure. Reservations encouraged. Walk-ins accepted.
November 14th | 11am-7pm
Capture the comfort and joy of the holidays by wearing your coziest pajamas for Santa photos! PJ Photo Day is available on Tuesday November 14th. We are proud to be partnering with St. Jude Children’s Hospital.
Baby’s 1st Santa Photos at Westfield Annapolis Mall
November 15th | 11am-7pm
Capture the joy and wonder of your baby’s first Christmas with enchanting Santa photos.
November 16th | 11am-7pm
You’re invited to dress in your ugliest holiday sweater or other festive attire to capture a memorable photo with Santa!
November 25th-December 17th | Davidsonville + Severna Park locations
Get into the holiday spirit and celebrate the season of joy and wonder with Photos with Santa at Homestead Gardens. Bring your family and friends to share in this delightful opportunity to create lasting memories with the one and only Santa Claus himself. Capture the magic as you gather around, wearing your favorite festive outfits, and create cherished moments that will warm your hearts for years to come. Don’t miss out on this enchanting experience that will fill your holiday season with happiness and joy!
December 8th | 5:30-8:30pm
Get ready to usher in the holiday cheer because Santa is coming to town! Capture the festive spirit with a picture with Santa himself, and to double the fun, we have a special holiday guest lined up just for you! Let the harmonious voices of our local choir fill your hearts with joy, while you indulge in our divine Hot Cocoa Bar kindly donated by The Big Bean. For all you cocktail lovers out there, Moveable Mixtures drink truck will be there to add a bit of sparkle to your evening. Unleash your creativity with our Arts & Crafts section or get your groove on with Dance Star Elite! Shop small and support local at our Holiday Marketplace with over 20 local vendors. In the spirit of giving, we are hosting a toy drive for children at Luminis Health Anne Arundel Medical Center’s Geaton and JoAnn DeCesaris Family Foundation Pediatric Emergency Department and Inpatient Unit. Please bring a toy and spread some holiday cheer. Check out the toy drive details and wish list! Let’s make this festive season a memorable one!
November 10th-December 24th
Discover a world of twinkling lights, festive decor, and the warmest of welcomes from Santa’s Elves and Santa Claus himself. Children and adults alike will be transported to a realm of magic, where cherished memories are made and holiday dreams come true. We have kids activities while you wait, and even more that we just can’t give away until you see for yourself. Don’t forget to experience our custom photo opportunities for the whole family to enjoy. We have kids activities while you wait, and even more that we just can’t give away until you.
December 2nd | 1-3pm
December 3rd | 9-10:30am
Celebrate the magic of Christmas in an inclusive, sensory-friendly environment with Santa photo experiences curated for those with autism and their families. We are proud to have partnered with Autism Speaks to present this opportunity to the community!
December 8th | 11am-4pm
Sensory Santa is for families with children who have special needs and have difficulty handling the hustle and bustle, noise, lights, and crowds in typical Santa settings. With Sensory Santa your child will enjoy a sensory-friendly environment for a more successful visit with Santa! This opportunity is COMPLIMENTARY, however donations are greatly appreciated and will be sent to Gold In Fight (GIF) in an effort to raise funds for local families who have children suffering from childhood cancer. Children who experience any sensory sensitivity, siblings and caregivers are welcome, too! RSVP HERE!
December 9th | 9am-4pm
Grab a spot and join us at Play Street Museum Severna Park on Saturday December 9th for a Sweet Time with Santa! Bring your camera and get ready to take lots of pictures! Enjoy crafts, playtime and a visit with Santa! Each child receives a special gift, milk, and cookies from Santa at the end of the event.
$40 per child – maximum of 2 adults per family please!
December 9th | 11am-3pm
Find the spirit and magic of the holidays!! What better way to put a smile on everyone’s face? Cookies, Bonfires, Hot Coffee, Hot Chocolate, Baby Goats, Rescue Farm Animals, Fun Outdoors, Holiday Photo Ops and it is all FRE! Join Us December 9th 11am-3pm. Stop by anytime! We want to give back to our community for helping us grow this past year. If you can donate to the farm, great…if you can’t, please still come and enjoy! We know how expensive the holidays can be for all of the events we plan for our families. Mark your calendars and see you soon!! Questions/Rsvp’s – Email [email protected]
November 17th & 18th | 5-9pm
For two nights only, animal lovers are invited to bring their pet and walk through the light show on foot. All pets are required to be on leashes for this event. Proceeds benefit the SPCA of Anne Arundel County.
November 20th, 27th, December 4th and 11th | 4pm-7pm
We know family members come in all shapes and sizes, and sometimes have fur and four legs! That’s why we’ve partnered up with The Humane Society of the US to host Pet Photo evenings. Guests are invited to bring their leashed, well-behaved four-legged members of the family to one of three special Pet Photo evenings to capture that perfect holiday memory with Santa.
December 1st | 4-7pm | Davidsonville + Severna Park locations
Join us at Santa Paws 2023, a joyous celebration where your furry friends can bring along their beloved humans to Homestead Gardens! Capture the perfect holiday memory with a heartwarming picture with Santa amidst a magical backdrop of twinkling lights and festive cheer. You’ll be responsible for snapping the photo, immortalizing the special moment forever. We are proud to announce that Santa Paws 2023 is co-sponsored by the esteemed VCA South Arundel Veterinary Hospital.
Experience the magic and capture the spirit of the holiday season with a visit to Santa’s Cottage WITH YOUR PUP where you will meet Santa himself and take home a photo for the whole family to treasure. Reservations encouraged. Walk-ins accepted.
Opening day November 17th
The Quiet Waters Park Ice Rink is located in front of the Visitor Center and offers a pleasant and safe environment to enjoy ice skating outdoors. We have skates, helmets, and we sharpen skates on-site. Come out for fun with family and friends. Check their Facebook page for daily updates.
Check out the BRAND NEW CapitalSUP CapCafe powered by the Big Bean Coffee House at Quiet Waters Park Ice Rink for hot cocoa, coffee, tea, pastries, merch and more! Friday – 4:00pm-9:00pm and Saturday + Sunday – 9:00am-9:00pm.
November-end of February
Hopefully this will open this year! Stay tuned via their Facebook page for updates!
* No Ice Skating at Annapolis Town Center this year but STAY TUNED for something super fun in the Spring!
HOLIDAY TRAIN DISPLAYS
The villages grow larger every year as new pieces are added so it’s fun to come back to see what’s different! This is the perfect place to take your train obsessed kids. The area is huge with plenty of areas to stand and sit on the benches while your kids explore the village details and watch the trains go by. The train display is FREE to see and open during store hours. Go shopping in the amazing kids area, pick out new ornaments and look at the 23 stunning trees, each with a unique theme.
The Severna Park train is currently still under construction but should be open soon! Check back for details!
Marley Station Mall | November 18th – January 7th
Choo Choo!! All aboard the Marley Station Train Garden. Mark your calendars to stop by to see what’s new at the Train Garden this year. Days and hours may vary. We hope to see you there!! The Train Garden supported by Emmanuel Lutheran Church. On the upper level near Macy’s. Net proceeds will be donated to the Emmanuel Lutheran Church Food Pantry and Emergency Fund.
NOON YEARS & NEW YEARS EVE EVENTS
December 30th | 11:30am-12:30pm
Help us bring in the New Year 2024 with crafts and music! A countdown and celebration will occur right before noon with dancing following.
Join us for a very special New Year’s Eve tasting menu by Chef @matthewtlego. We’re offering two limited seatings at 6pm and 8pm, with three courses celebrating the best of our local purveyors. Add our wine pairing for an extra treat, and expect some surprises!
The City of Annapolis will put on a fireworks display on December 31, 2023, at Susan Campbell Park. This family-friendly event has been drawing tourists to the shores of Annapolis for years! The spectacle of the fireworks from the shores or on one of the many charter boats in the county makes for a festive and exciting way to ring in the new year!
December 31st | 8pm-midnight
Celebrate New Year’s Eve on the rooftop at our exclusive gold party! Our culinary team has put together an unforgettable standing buffet and menu of passed hors d’oeuvres featuring some of Choptank’s most popular signature dishes. The menu will also feature an impressive raw bar and carving station! Cocktails: Our OPEN BAR will feature signature cocktails, liquor, beer and wine. You will also be able to start a tab for premium spirits. Don’t forget to check out our Espresso Martini bar! Complementary champagne toast at midnight. ENTERTAINMENT: Dance the night away to music by the always-entertaining DJ! A photo booth will be available for guests to enjoy and capture their night! Enjoy the best view of fireworks from our second floor!
December 31st | 10pm-2am
Join us for an unforgettable New Year’s Eve Black and White Cocktail Party! We will start at 10:00 pm and we will go until the early hours of the new year! Open Bar, delectable bites, live DJ, and the best ambiance, right in downtown Annapolis!
Enjoy the holidays with your friends and families! See you around Annapolis! Stay warm + have fun!
I’ll be updating this list over the next couple of weeks so check back for updates! If I’m missing your favorite holiday event, email it to us at [email protected] to be added to the list.