Annapolis is a waterfront town bathed in history, with a very walkable historic district and suburbs that meander outward, providing ample opportunities for winter holidays adventures. As the capital of Maryland, Annapolis Events embraces the rich history of Christmas in Maryland while showcasing newer traditions that light up the holiday season with dazzling holiday lights. Whether exploring festive decorations or participating in community events, there’s something for everyone to enjoy during this magical time of year.
Any seasonal festivities tend to be permeated with a strong sense of community pride in Maryland’s rich history and seaside economy. So don’t be surprised by some blue crab memorabilia or a few colonial ghosts popping up wherever you go. Whether you like exciting outdoor light shows or cozy musical venues, Christmas in Annapolis Maryland will have the event to start your holidays off right.
Remember, events are always subject to change. It is always a good idea to check the website and call ahead to confirm timing and any special precautions that are in place.
You might be interested to check out Black Santa Claus DC for the holidays.
Winter Blooms in Historic London Town
- Address: Historic London Town and Gardens, 839 Londontown Rd., Edgewater, MD
- Dates: November through mid-December, re-opens in mid-January. (Check the website for updated dates/times.)
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Experience the magic of the holiday season with stunning views of South River on a walk through 10 acres of woodland and ornamental gardens. This flower-centric arboretum places its hardiest winter blossoms, like the bold white, pink, and red Camellias, front and center for a burst of color all year.
Other winter favorites include fragrant evergreens, beautiful holly, and delicate viburnum. The grounds also give visitors a taste of history with reconstructed colonial buildings, including the Lord Mayor’s Tenement, the Carpenter Shop, and the National Historic Landmark William Brown House.
This is a popular site for school trips, with kid-friendly exhibits and staff who are happy to answer questions from students (and their parents).
Get a New View of the City with Holiday Cruises
- Address: Departs from City Dock, Annapolis, MD.
- Dates: Cruises run daily throughout November and December, and special holiday packages are available on weekends in December. (Check the website for updated dates/times.)
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A cruise along Spa Creek past downtown Annapolis is a must for visitors any time of year. But that’s especially true during the holiday season when special tours bring an extra dose of holiday spirit.
Families should check out the Jolly Cruise Express or Captain Santa’s Cruise, both of which feature caroling, sweet treats, and the Big Man himself at the helm! (Where does Santa find the time?)
For those who like some variety in their holiday events, try the Holiday Stroll & Cruise, which starts with a historic tour of Annapolis with a guide in period costume, explaining the colonial traditions of the holiday season. Then visitors board the decked-out Saint Anne for a relaxing 40-minute cruise.
Or check out a Holiday Dinner Cruise with Ken’s Creative Kitchen, featuring beer and wine, dinner on an enclosed deck, and live jazz. Then head to the open-air top deck, enjoying the view of Eastport Yacht Club’s Lights Parade.
Of course, the standard boat rides of Annapolis are just as fun during the holidays as any time of year. For our money, the best bets are the romantic Harbor Lights evening cruise aboard the Harbor Queen, or the “Spirits & Spirits” haunted walk and booze cruise for some ghostly Dickensian fun.
Lights on the Bay for Animal Welfare
- Address: Sandy Point State Park, 1100 East College Parkway, Annapolis, MD
- Dates: Nov.-Jan. (around New Year’s Day) , 5 p.m. – 10 p.m. (Check website for updated dates/times.)
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Enjoy this leisurely drive along the Chesapeake Bay while taking in one of the area’s most enchanting holiday events, featuring more than 60 animated and stationary light displays that are sure to put a smile on every passenger’s face. And don’t forget to pick up 3D glasses at the beginning of the scenic tour for a little extra dose of light show magic!
The event showcases Maryland history and also features a decidedly feline and canine flavor, with all proceeds benefitting the SPCA of Anne Arundel County. In fact, for two nights in mid-November, guests can buy special tickets for the Lights & Leashes event, where dogs and their humans are permitted to park their cars and walk through the brilliant light display.
Small Business Saturday
- Address: Throughout Annapolis and Anne Arundel County
- Dates: Saturday after Thanksgiving
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Downtown Annapolis takes its small businesses seriously, hosting special holiday shopping events like Small Business Saturday to ensure that local shop owners thrive. Supporting these local businesses is a wonderful way to embrace the season, with unique gifts that make holiday shopping feel more personal and meaningful.
Free parking is available all day, and the website provides a complete list of independent shops and what you can find there. We never miss a chance to pop into HERE, a Pop-Up Shop, to see what the owner has curated from artists and makers—items we just have to have!
Show Annapolis businesses that you appreciate their personalized attention, unique offerings, and community spirit by choosing to shop local. It’s a perfect way to find one-of-a-kind gifts for everyone on your Christmas list while supporting local businesses that make Annapolis special.
Artist Sunday
- Address: Throughout Annapolis and Anne Arundel County
- Dates: The Sunday after Thanksgiving
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Why not follow up Small Business Saturday with a new Annapolis holiday tradition celebrating independent artists and creators of every stripe? Annapolis, with its multitude of art stores, galleries, and performance venues, shines even brighter during the holiday season, taking an active role in this national festivity.
For a taste of the best holiday lights and holiday happenings, check the annual Facebook event page or the website of your favorite Maryland art space, where you’ll find several discounts and special events throughout the region. These seasonal events offer a fantastic opportunity to support local talent while immersing yourself in the creative spirit of Annapolis during the holidays.
Homestead for the Holidays
- Address: 743 W. Central Ave., Davidsonville
- Dates: Throughout December, there will be live music on weekends. (Check the website for updated dates/times.)
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Enter a truly enchanted wonderland with this home decor store, nursery, and greenhouse as it is decked out with dozens of beautiful Christmas trees of every size and shape. They also offer thousands of ornaments, innumerable lights, and everything you could need to make your own holiday scene.
For more than 30 years, Homestead’s famous model railroad will chug around the greenhouse as guests enjoy a hot chocolate and watch elves hard at work in Santa’s workshop. Live music and talking reindeer delight kids of all ages.
In the outside nursery, a fire pit roars as families pick out their own fragrant evergreens
Parade of Light—Car Parade & Menorah Lighting
- Address: Safeway parking lot, 2635 Housley Rd., Annapolis, MD
- Dates: Evening for the fourth day of Chanukah. (Check the website for updated dates/times.)
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Chabad Anne Arundel County offers entertaining events scheduled throughout Chanukah. But our favorite is the annual Menorah Car Parade on the fourth night of the Festival of Lights. All are welcome to join and even participate in the parade!
Participants should pull up by 5 p.m. to leave from Safeway and drive to the Alex Haley Memorial with fun menorah decorations on their roofs. At 5:45 p.m., event organizers will kindle a giant Menorah and celebrate the miraculous holiday.
Drivers and spectators will receive chocolate gelt (coins), prepackaged latkes, and kits to help celebrate Chanukah (while supplies last).
Annual Kwanzaa Celebration
- Address: Banneker-Douglass Museum, 84 Franklin St., Annapolis, MD
- Dates: December (Check website for updated dates/times.)
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This program is perfect whether you’re a long-time Kwanzaa celebrant or want to learn more about the seven-day African-American festival. Honor the seven principles of Kwanzaa through musical and spoken word performances, a lighting ceremony, an interactive gift-making session, and a discussion on the importance of community and intergenerational engagement.
You’ll also get the chance to meet with representatives of Black-owned businesses.
Midnight Madness Holiday Shopping
- Address: throughout downtown Annapolis
- Dates: The first three Thursdays in December— 4 p.m. – midnight on the first two; third, 4 p.m. – 11 p.m.
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On these special nights, the town is transformed into a winter wonderland as shops stay open late for shoppers who want to shop for unique gifts while supporting local businesses.
The event takes place along Main and West Streets, Maryland Avenue, State Circle, and Dock Street. Pedestrians looking for deals or simply enjoying the lovely night are treated to live outdoor music from carolers and other musicians, refreshments, and other entertainment.
Make sure not to miss Snowflake Alley, the holiday lights canopy, and, of course, the City Christmas tree at Market Space.
Holiday Candlelight Stroll
- Address: Departs from Market House Park, Annapolis, MD
- Dates: Fridays and Saturdays (Check the website for available dates and times)
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A guide in festive period attire leads guests along the centuries-old brick-lined streets of Maryland’s capital city, lit by lanterns and candles and lavishly adorned for the holidays.
Visitors will be enchanted by charming and humorous stories of 18th and 19th-century holiday traditions against the backdrop of colonial mansions, Victorian homes, and quaint shops.
First Sunday Arts Holiday Market
- Address: Whitmore Park and W. Street between Church Cir. & Graduate Annapolis Hotel, Annapolis, MD
- Dates: First Sunday of each month; special holiday markets in Nov. and Dec. (Check website for updated dates/times.)
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The city provides free parking for this cherished Annapolis event, allowing shoppers in search of quirky and unique gifts a leisurely browse through the creations of more than 50 local and regional artisans.
Diverse artists and booths offer everything from customized portraits and delicious-smelling candles to Christmas ornaments with a Maryland flair (plus, visit over a hundred more artists virtually on their website!).
Outdoor café seating and live music are provided for shoppers who need to take a break. It’s also a perfect day to visit the galleries and art shops of West Street, many of whom take part in the market with special events and deals.
A Celebration of Christmas
- Address: Maryland Hall, 801 Chase St., Annapolis, MD
- Dates: Friday in December, 8 p.m. (Check website for updated dates/times.)
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Each year, tickets sell out early for this enthralling evening featuring the Annapolis Chorale and Chamber Orchestra. Joining together in a one-night-only show to perform dozens of seasonal favorites that often end in standing ovations.
Ballet Theatre of Maryland presents The Nutcracker
- Address: 801 Chase St., Annapolis, MD
- Dates: Nov/Dec., Saturdays at 7 p.m., Sundays at 1 p.m. and 4:30 p.m. (Check website for updated dates/times.)
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This cherished holiday tale of a girl’s adventure alongside her unusual Christmas present is performed by the top-tier dancers of the prestigious Ballet Theatre of Maryland. Annapolis is a great place to catch this classic production, filled with holiday happenings that bring festive cheer to the entire family. Let the spellbinding music of Tchaikovsky and the athleticism of the graceful dancers whisk you away to the whirling Kingdoms of Snow and Sweets, where every scene radiates the magic of the season.
Find more performances of The Nutcracker Ballet in Washington DC.
Handel’s Messiah at St. Anne’s
- Address: St. Anne’s Episcopal Church, 199 Duke of Gloucester St., Annapolis, MD
- Dates: Check site for December date
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Live Arts Maryland presents one of the world’s best-loved and most popular musical works, performed many times each Christmas since its completion in 1741.
This cherished Annapolis holiday tradition, set in one of the city’s most beloved and iconic buildings, invites you to experience world-class soloists, the Chamber Orchestra, and the Annapolis Chorale in a powerful holiday celebration. When you visit Annapolis during the holiday season, don’t miss this event, where guests can even join in singing some holiday carols, making it a family-friendly and festive highlight of the season.
Annapolis Symphony Orchestra – Holiday Pops
- Address: Maryland Hall For The Creative Arts, 801 Chase St., Annapolis, MD
- Dates: One night each December
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This popular seasonal program features nearly two hours of holiday favorites by the Annapolis Symphony Orchestra. Fun for the whole family, the tickets sell out every year. Buy now!
Historic Annapolis Holiday Wreath and Gift Sale
- Address: 1 Martin St., Annapolis, MD
- Dates: November dates (Check website for updated dates/times.)
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Place your orders early for festive holiday greens, tabletop trees, and a special hand-painted ornament for each year, along with a curated selection of pre-wrapped gifts with a touch of Maryland charm.
During the holiday season, Historic Annapolis comes alive with beautiful holiday decorations and holiday displays that capture the essence of a traditional Annapolis celebration. Each wreath and tree is crafted by Historic Annapolis volunteers using greenery and plants from the William Paca Garden. Purchases support Historic Annapolis’ mission to educate and preserve the area’s colorful past, making these gifts as meaningful as they are charming.
Military Bowl
- Address: Navy-Marine Corps Memorial Stadium, 550 Taylor Ave., Annapolis, MD
- Dates: Late December (typically a 2 p.m. kickoff)
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For some, it’s a winter tradition as cherished as Thanksgiving or Christmas: The Military Bowl. This exciting holiday event, benefitting the USO of Metropolitan Washington-Baltimore, pits two college football teams head-to-head—the Atlantic Coast Conference against the American Athletic Conference—in an outstanding display of athleticism and holiday spirit.
The holiday season fun begins before kickoff with a parade through historic downtown Annapolis, featuring musical acts, civic and youth groups, and the world-famous Budweiser Clydesdales. Grab some concessions and take your seat for an energetic game sprinkled with special holiday events to salute the military and their families.
Mus Read: Christmas Concerts Baltimore
The Grand Illumination
- Address: City docks near the Market House, Market Space, Annapolis, MD
- Dates: The Sunday after Thanksgiving, 5:15 p.m., festivities begin at 4 p.m. (Check website for updated dates/times.)
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Annapolis makes a big party out of the annual lighting of the city’s Christmas tree, and it’s a must if you’re in town for the holiday season. This beloved Annapolis holiday event includes a lively show of carols and dancing, warm drinks and candy canes, and the arrival of Santa Claus to light the tree himself, filling the night with holiday lights and festive cheer.
Children will enjoy decorating ornaments, and holiday decorations add a magical glow throughout the area. The Annapolis Jaycees will also be on-site, collecting toys and non-perishable foods to donate to families in need, ensuring the holiday spirit reaches everyone in the community.
A Colonial Yuletide
- Address: William Paca House & Garden, 186 Prince George St.; Hogshead, 43 Pinkney St. George St., Annapolis, MD
- Dates: First Saturday in December, 2 p.m. – 6 p.m.
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Always a fun trip for visitors and residents, this Georgian red-brick mansion is preserved as it would have been in the 18th century when William Paca signed the Declaration of Independence and served as Maryland’s third governor.
During the holiday season, celebrate the magic of an Annapolis holiday as William, Mary, and the household servants decorate the home and prepare for a traditional colonial Christmas. The festive holiday light decor and seasonal touches make this one of the area’s most beloved holiday experiences.
With reservations, a docent will lead you through the first floor of the house and the 2-acre William Paca Garden, where you’ll take in authentic holiday decorations that capture the spirit of the past. Then, continue the good cheer at Pinkney Street’s “Hogshead Tavern” and party like it’s 1774! These moments are sure to become some of your most beloved memories of an Annapolis holiday.
The tour includes both sites. Timed entry is offered hourly 2 p.m. – 5 p.m. Walk-ups will be accommodated as space permits. Reservations recommended.
Eastport Yacht Club Lights Parade
- Address: Annapolis Harbor and Spa Creek, Annapolis Waterfront
- Dates: Second Saturday in December, 6 – 8 p.m.
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Spectators gather each year to watch more than 30 brightly lit boats bedecked for the holiday season as they parade through the Annapolis Harbor during this beloved annual event. The Annapolis holiday spirit shines bright with thousands of lights crafted into some very creative displays. Stalwart boat crews and a crowd of jolly revelers make this a fun Christmas tradition for the entire family, showcasing the best of local holiday events. Don’t miss this festive gathering that beautifully captures the essence of the season!
Inside tip: if you bring some non-perishable food to donate, you can get onto the Harbor Queen cruise ship for free to watch the show in style!
Dining with the Loockermans
- Address: Hammond-Harwood House, 19 Maryland Ave., Annapolis, MD
- Dates: Mid-December (Check website for updated dates/times.)
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The curator and food historian of this William Buckland-built estate discusses the cooking and dining traditions of the house’s 19th-century residents, both free and enslaved.
Visitors are able to savor some historically accurate treats during the hour-long tour through the stately home’s kitchen, breakfast area, and dining room. Reservations are required, and often visitors can pick a daytime or evening candlelight tour.
Jane Austen Tour
- Address: Hammond-Harwood House, 19 Maryland Ave., Annapolis, MD
- Dates: Mid-December (Check website for updated dates/times.)
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The book lover in your group will adore this spotlight tour of the historic, Christmas-decorated Hammond-Harwood House, which compares the customs and social graces of the Loockerman family (residents of the red-brick mansion during the early 19th century) with those in Jane Austen’s novels.
It’s a surprisingly affordable way to spend a holiday afternoon feeling posh and proper.
Lights Parade Dinner & Dessert Cruise
- Address: Begins at Severn Inn, 1993 Baltimore Annapolis Blvd., Annapolis, MD
- Dates: Mid-December (Check website for updated dates/times.)
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Dine in style at the Severn Inn before enjoying a dessert aboard Watermark’s luxury yacht, Catherine Marie, as you watch the spectacular annual Eastport Yacht Club Lights Parade on the water. This event is one of the highlight holiday events of the winter holidays, showcasing dazzling holiday lights that illuminate the Annapolis waterfront.
The yacht offers two levels, with double the bar service and convenient buffet-style desserts, allowing your family to appreciate the parade in comfort. Tickets include a starter, entrée, dessert, and a glass of champagne, ensuring a memorable evening that combines fine dining with the festive spirit of the holiday season. Don’t miss this chance to create cherished memories during the holidays!
Santa Speedo Run
- Address: O’Brien’s Oyster Bar & Seafood Tavern, 113 Main St.Annapolis, MD
- Dates: One Saturday in December, 11 a.m. – 3 p.m. (Check website for updated dates/times.)
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Get in your holiday-style skivvies for this fun run/stroll through Annapolis, a festive event that embodies the spirit of the holiday season. With a mission to spread holiday cheer and help local charities, this is one of the most delightful holiday events you can participate in.
Participants should register early to secure a spot and t-shirt. Bring your donated toy(s) at 11:00 a.m., then gather out front for caroling, pictures, and the start of the event. The after-party kicks off at 12:30 p.m. with live music, making it a perfect way to celebrate holiday traditions while supporting a good cause. Don’t miss this joyful celebration that brings the community together during the most wonderful time of the year!
Additional reporting by Shannon K. Pennell and Heather Mundt
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