Get set for a holiday adventure in Annapolis with our guide. Discover all the exciting festive happenings. Whether Annapolis is your permanent address or your temporary haven, this guide helps you embrace the spirit of the season.
Popular events include the enchanting Lights on the Bay, where you can drive through a dazzling display of holiday lights along the Chesapeake Bay. With intricate designs and festive themes, this event brings joy to families and friends alike. The Military Bowl, a celebration of college football, adds a spirited touch to the holidays, featuring teams competing in an exciting showdown. And the New Year’s Eve Fireworks is something you definitely don't want to miss, offering a spectacular display that lights up the waterfront. See more details on these and other fun events and activities below!
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Top Holiday Events In and Around Annapolis
- New Year’s Eve Fireworks
- Military Bowl
- Lights on the Bay
- Miracle on Annapolis Street Clydesdale Parade
- Midnight Madness
- Annapolis Chocolate Binge Festival
- Downtown Annapolis Grand Illumination
- First Sunday Arts Holiday Market
- Annapolis Town Center Annual Christmas Tree Lighting
- Eastport Yacht Club Lights
See these and even more events listed below!
Annapolis Holiday Light Displays
Downtown Annapolis Grand Illumination
What to Expect:
Annual tree lighting ceremony with local kids' decorations.
Description:
The Downtown Annapolis Grand Illumination is a festive holiday event held near the Market House on the Sunday after Thanksgiving. It features dancing and carols by local groups, an annual Christmas Tree lighting ceremony with carolers and music, and general merriment. The event is free and open to the public, with Santa, Mrs. Claus, and Elfie lighting the tree. This year's tree decorations are designed by local kids and sponsored by the Annapolis Symphony Orchestra.
Where: Annapolis | More Info: Downtown Annapolis Grand Illumination
Lights on the Bay
What to Expect:
Scenic drive with 70 animated and stationary light displays.
Description:
Drive through a two-mile illuminated display along the Chesapeake Bay featuring over 70 animated and stationary lights, sponsored by the SPCA of Anne Arundel County.
Where: Annapolis | More Info: Lights on the Bay
Eastport Yacht Club Lights
What to Expect:
Boats illuminated with thousands of colored lights.
Description:
The Eastport Yacht Club Lights Parade is an annual event where boats in Annapolis Harbor are decorated with thousands of colored lights, creating a spectacular display of holiday cheer.
Where: Annapolis | More Info: Eastport Yacht Club Lights
Annapolis Holiday Markets and Shopping
Midnight Madness
What to Expect:
Holiday shopping event with live entertainment and decorated streets.
Description:
Downtown Annapolis transforms into a holiday shopping paradise with Midnight Madness, featuring decorated streets, holiday decorations, and live entertainment. Residents and visitors can stroll along Main Street, West Street, Maryland Avenue, State Circle, Market Space, and Dock Street to support local businesses and enjoy refreshments and sales.
Where: Annapolis | More Info: Midnight Madness
Annapolis Chocolate Binge Festival
What to Expect:
Unique chocolate tour and holiday market.
Description:
The Annapolis Chocolate Binge Festival is a family-friendly event celebrating all things chocolate. It features a chocolate tour along West Street with various vendors selling chocolate specialties, a holiday market with local artisans, and live music and entertainment. Admission is $5 when purchased online, and the event includes a festive West Street Holiday Light Canopy.
Where: Annapolis | More Info: Annapolis Chocolate Binge Festival
First Sunday Arts Holiday Market
What to Expect:
Monthly street festival with local artisans and live entertainment.
Description:
The First Sunday Arts Holiday Market in Annapolis features over 100 vendors selling handmade crafts, artwork, and local goods, accompanied by live music and café dining.
Where: Annapolis | More Info: First Sunday Arts Holiday Market
Annapolis Holiday Shows and Entertainment
Annapolis Town Center Annual Christmas Tree Lighting
What to Expect:
Free ornaments for the first 500 families.
Description:
Join Annapolis Town Center for the Annual Christmas Tree Lighting on Friday, November 17, from 7 PM to 8 PM. The first 500 families to arrive will receive a 1st Annual Annapolis Town Center Ornament. Enjoy DJ music, games, fireworks, and a visit from Santa, all located near P.F. Chang’s and the East Village Boathouse.
Where: Annapolis | More Info: Annapolis Town Center Annual Christmas Tree Lighting
Annapolis Other Holiday Activities
Military Bowl
What to Expect:
Post-season college football game with parade and festivities.
Description:
The Military Bowl is a prestigious NCAA Division I college football bowl game held annually in Annapolis, Maryland, featuring teams from the ACC and American Athletic Conference. The event includes a parade, live music, and festivities, making it a significant part of the holiday season.
Where: Annapolis | More Info: Military Bowl
Miracle on Annapolis Street Clydesdale Parade
What to Expect:
Budweiser Clydesdales and festive activities.
Description:
The Miracle on Annapolis Street features the Budweiser Clydesdales, food trucks, vendors, games, and activities for adults and children.
Where: Annapolis | More Info: Miracle on Annapolis Street Clydesdale Parade
New Year’s Eve Fireworks
What to Expect:
Exclusive yacht cruise with DJ, dancing, and fireworks.
Description:
Celebrate New Year's Eve with a luxurious yacht cruise in Annapolis, featuring a DJ, dancing, and fireworks.
Where: Annapolis | More Info: New Year’s Eve Fireworks
NapTown Anti-Dope Move(meant) Health Fair
What to Expect:
Interactive health and wellness resources.
Description:
Join NapTown Anti-Dope Movement at the Health and Wellness Resource Fair in Peoples Park, Annapolis, Maryland, for an informative and engaging event featuring health and wellness resources.
Where: Annapolis | More Info: NapTown Anti-Dope Move(meant) Health Fair
Recreation and Parks Holiday Closures
What to Expect:
Temporary suspension of regular activities for holiday observance.
Description:
The Recreation and Parks Holiday Closures include various events and activities that are temporarily suspended due to holidays, ensuring a well-planned and organized schedule for all participants.
Where: Annapolis | More Info: Recreation and Parks Holiday Closures
Refuse and Recycling Collection Adjustments
What to Expect:
Efficient waste management system with interactive route maps and reporting options.
Description:
The City of Annapolis provides comprehensive residential solid waste collection services, including refuse, recycling, and yard trim. Residents can find their collection routes and days using the Residential Collection Route PDF map or visiting DPW Services by Street List. Issues can be reported by calling 410-263-7949 or using the TextMyGov service.
Where: Annapolis | More Info: Refuse and Recycling Collection Adjustments
Jolly Express cruise
What to Expect:
Intimate holiday cruise with hot cocoa and holiday music.
Description:
Embark on a 45-minute holiday cruise aboard Miss Anne, adorned in reindeer spirit, featuring hot cocoa, holiday music, and good cheer. Captain Santa leads this festive evening ride along Spa Creek, with blankets available to stay warm and cozy.
Where: Annapolis | More Info: Jolly Express cruise
Candlelight history tours
What to Expect:
Guided candlelight tour focusing on historical medical practices and mourning rituals.
Description:
Explore the historic William Paca House through a candlelight tour, delving into the past's sickness treatments, mourning rituals, and superstitions.
Where: Annapolis | More Info: Candlelight history tours
Waterfowl Festival
What to Expect:
World-class art exhibition and wildlife conservation events.
Description:
The Waterfowl Festival is a three-day celebration on the Eastern Shore, featuring 350 artists and vendors, live demonstrations, and activities for all ages, including fly-fishing, retriever dog demonstrations, and the World Waterfowl Calling Championship.
Where: Easton | More Info: Waterfowl Festival
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- Arnold (4 miles)
- Severna Park (7 miles)
- Pasadena (11 miles)
- Crofton (11 miles)
- South Gate (13 miles)
- Bowie (13 miles)
- Odenton (13 miles)
- Glen Burnie (15 miles)
- Severn (16 miles)
- Dundalk (19 miles)
- Hanover (19 miles)
- West Elkridge (20 miles)
- South Laurel (20 miles)
- Greenbelt (21 miles)
- Laurel (21 miles)
- Landover (22 miles)
- Arbutus (22 miles)
- Baltimore (22 miles)
- Essex (23 miles)
- Ilchester (24 miles)
- College Park (24 miles)
- Catonsville (24 miles)
- Middle River (25 miles)
- Scaggsville (25 miles)
- Suitland (25 miles)
- Suitland-Silver Hill (25 miles)
- Ellicott City (26 miles)
- Fairland (26 miles)
- Columbia (26 miles)
- Clinton (26 miles)
- Gwynn Oak (27 miles)
- Chillum (27 miles)
- Woodlawn (27 miles)
- Parkville (28 miles)
- Lochearn (28 miles)
- Silver Spring (29 miles)
- Carney (29 miles)
- Oxon Hill-Glassmanor (29 miles)
- Milford Mill (30 miles)
- Towson (30 miles)
- Washington (30 miles)
- Pikesville (30 miles)
- Perry Hall (30 miles)
- Wheaton (31 miles)
- Randallstown (31 miles)
- Aspen Hill (32 miles)
- Alexandria (32 miles)
- Edgewood (32 miles)
- Bethesda (33 miles)
- Olney (33 miles)
- Arlington (34 miles)
- North Bethesda (34 miles)
- Owings Mills (34 miles)
- Fort Washington (34 miles)
- Waldorf (34 miles)
- St. Charles (35 miles)
- Saint Charles (35 miles)
- Baileys Crossroads (35 miles)
- Cockeysville (36 miles)
- Rose Hill (36 miles)
- Rockville (36 miles)
- Lincolnia (37 miles)
- Hunt Valley (37 miles)
- McLean (37 miles)
- Bel Air South (38 miles)
- West Falls Church (38 miles)
- Eldersburg (38 miles)
- Reisterstown (39 miles)
- Potomac (39 miles)
- Woodlawn (39 miles)
- South Bel Air (39 miles)
- Annandale (39 miles)
- North Bel Air (39 miles)
- Springfield (40 miles)
- Gaithersburg (40 miles)
- Montgomery Village (40 miles)
- Bel Air North (40 miles)
- West Springfield (42 miles)
- North Potomac (42 miles)
- Burke (44 miles)
- Oakton (44 miles)
- Fairfax (45 miles)