10 Favorite Holiday Events & Festive Spots in Downtown Annapolis
Regularly recognized by Travel + Leisure Magazine as one of America's best Christmas towns, Annapolis is a must-visit during the holiday season! This already charming town comes alive with stunning lights, decorations, and plenty of entertaining events and festivities.
One of the best ways to experience the holiday magic is to explore downtown Annapolis on foot. Once downtown, you can stroll to any of these locations easily! Enjoy walking past the beautifully decorated buildings, charming local shops and lit-up waterfront area.
Whether you're planning a festive outing with friends, a romantic date night, or a day exploring Maryland's historic capital, these 10 downtown Annapolis holiday events and experiences are worth putting on your list. From the season's kickoff with the Grand Illumination and the lighted boat parade, to seasonal drinks and my own Christmas Lights Trail, here's how to make the most of the season — one festive stroll at a time.
10 Favorite Downtown Annapolis Holiday Events
Jump to your favorite festive experience:
Grand Illumination
Date: Sunday, November 29, 2026 3:00pm - 5:30pm (Tree Lighting at 5:15pm)
Location: Market Space near the Annapolis Market House & City Dock
Annapolis kick's off the holiday season annually with this free tree lighting event on the Sunday after Thanksgiving. The Grand Illumination features family-friendly entertainment, holiday music, and typically includes a visit from Santa, Mrs. Claus and Elfie by firetruck.
Snowflake Alley
Date: Lit First Week of December - Beginning of January
Location: Cabbage Alley - off of Main Street, across from Chick & Ruth's Deli
Snowflake Alley is one of the prime photo spots in downtown Annapolis during the holidays. Its magical appearance provides the perfect back drop for a selfie or group photos!
This alley is quite popular, so be prepared to wait in line to snap a pic at this festive location during busy evenings downtown.
Midnight Madness (Late Night Shopping & Dining)
Date: December 3 & 10 4pm - Midnight, December 17 4pm - 11pm
Location: Main Street, West Street & Church Circle, Maryland Ave, State Circle, Market Space & Dock Street
Alpacas at Midnight Madness in Annapolis Annapolis Midnight Madness is a super fun late-night holiday shopping tradition held on the first three Thursdays of December in the historic downtown area of Annapolis. During this time, the charming streets of Annapolis come alive with holiday cheer and community festivities, turning the downtown into a winter wonderland. Many of the shops offer discounts, provide free festive refreshments and even host live music. There are strolling carolers, musicians and even live alpacas entertaining shoppers on the bustling streets. If you're in town during one of these Midnight Madness events, be sure to make your way to this outdoor holiday party!
Eastport Yacht Club Lights Parade Festive Boat in Lights Parade in Annapolis
Eastport Yacht Club Lights Parade
Date: Saturday, December 12, 2026 6:00pm
Location: Annapolis Harbor
The Eastport Yacht Club Lights Parade is another Annapolis holiday tradition that can't be missed! Since 1988, the Annapolis Harbor has come alive with sailboat and powerboats parading along the waterfront in holiday style. USA Today ranks this as one of the top 10 holiday parades in the country and it definitely is.
You can watch the parade from many locations including Annapolis city front, Spa Creek Bridge, and various pocket parks or streets that lead to the water in Annapolis and Eastport. Be sure to bundle up and bring your warm beverages to enjoy watching these magical boats as they sail by.
Annapolis Visitors Center Great Annapolis Gingerbread Houses
Date: November 22 - December 19, 2026
Location: Annapolis Visitors Center, 26 West Street Annapolis
Maryland State House Gingerbread House Holiday Gingerbread Decorating Contest - Annapolis
Every year Inner West Street Association holds a gingerbread house decorating competition. Anyone can participate and the houses are displayed at the Annapolis Visitors Center. All visitors are encouraged to vote on their favorite creation. The winner of the contest is announced at the Annapolis Chocolate Binge Festival on November 7th.
I always enjoy seeing the fantastic gingerbread houses. Annapolis is home to some truly creative and talented individuals! Be sure to check them out the next time you are walking down West Street and cast your vote.
Sip a Festive Egg Nog at Galway Bay
Date: Everyday! Location: Galway Bay Irish Restaurant & Bar, 63 Maryland Ave, Annapolis Galway Bay is one of our favorite spots any time of year, the food is delicious and the vibe is cozy and inviting. But visiting during the holidays is extra special. They definitely don't scrimp when it comes to the decor - check out the ceiling in the bar area below!
Galway Bay Holiday Bar Known for its handcrafted eggnog and offering an extensive menu with different eggnog flavors everyday, Galway Bay is the perfect place to take a break from holiday sightseeing and shopping. I bring all of my friends and family here to soak up the holiday atmosphere.
Government House Holiday Open House
Date: TBD (usually held mid-December)
Location: Government House, 110 State Circle, Annapolis
Each year, Governor Wes Moore and First Lady Dawn Moore host a holiday open house at their residence. This free event welcomes the public to tour this stunning historic Georgian-style mansion. Simply bring an ID for admittace.
When I visited, the house was beautifully decorated for the season, featuring several gorgeous Christmas trees throughout. A choir was performing Christmas carols, and as you departed, you received homemade cookies and a Maryland Christmas ornament.
Government House Entry for the Holidays Governor's Mansion Sitting Room with Holiday Decor
The date is typically announced through a press release in early December. Once the date is determined, I will update this post with the details.
A Drink with a View at Harry Browne's
Date: Any Time
Location: 66 State Circle, Annapolis
Harry Browne's Restaurant on State Circle Harry Browne's Upstairs Bar
For more than 45 years, Harry Browne's Restaurant has been an Annapolis staple for upscale dining. Located across from the state house, it's known to serve legislators, lobbyists, and governors delicious meals for decades.
I recently discovered Harry Browne's Upstairs Bar - and I love it! For a relaxed, cozy tavern vibe, head up the steep staircase to the upstairs bar. Here you can enjoy lighter pub-style fare. Plus the view is amazing, especially during the holiday season!
Take a Jolly Express Cruise
Date: Fridays, Saturdays & Sundays, November 27 - January 3
Location: The Piers at 1 Prince George Street
The Jolly Express Cruise offers a great way to celebrate the holidays on the water - after all isn't that what Annapolis is all about? The Queen Anne tour boat is transformed into Santa's sleigh on the bay. This 45-minute boat tour cruises along Spa Creek, providing hot cocoa and blankets to keep you cozy and warm.
Adult tickets are $28, while children's tickets cost $15. It's recommended to purchase tickets in advance due to limited availability for walk-up sales. Visit the Watermark website for further details.
Annapolis Christmas Lights Trail
Date: November 29 - January 3, 2026 Location: Historic Downtown Annapolis
One of the best ways to experience the magic of the holidays is to explore historic downtown Annapolis on foot after dark. Colorful lights, decorated storefronts, and charming historic streets create the perfect setting for a festive evening stroll.
I've created my own Annapolis Christmas Lights Trail, a self-guided walking route that lets you enjoy the holiday decorations at your own pace, with plenty of opportunities for photos, shopping, and a festive drink along the way.
Discover my easy-to-follow Annapolis Christmas Lights Trail walking guide. This 1.5-mile loop is perfect for viewing the best holiday lights Annapolis, MD has to offer.
I hope you enjoy these 10 stops as much as I do! It's hard to beat the charm of Annaplis during the holidays.
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