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!
Happy Holidays!
Top Events Events In and Around Annapolis
- Midnight Madness
- Grand Illumination of the Annapolis Tree
- Annapolis Holiday Market
- Annapolis New Year's Eve Fireworks Cruise
- Jolly Express Cruise
- Eastport Yacht Club Lights Parade
- Annapolis Chocolate Binge Festival
- First Sunday Arts Holiday Market
- Lights on the Bay at Sandy Point State Park
- North Beach Christmas Parade (North Beach)
🎃 Explore all 10+ featured events below!
Annapolis Events Events
Midnight Madness (Annapolis) • 0.1 miles
Historic streets transformed into a winter wonderland with live entertainment.
Grand Illumination of the Annapolis Tree (Annapolis) • 0.1 miles
Annual tree lighting ceremony with Santa and festive performances
Annapolis Holiday Market (Annapolis) • 0.3 miles
Over 100 artisans and specialty food vendors
Annapolis New Year's Eve Fireworks Cruise (Annapolis) • 0.3 miles
Luxury yacht cruise with DJ and fireworks
Jolly Express Cruise (Annapolis) • 0.3 miles
Festive 45-minute holiday cruise with Captain Santa or Mrs. Claus.
Eastport Yacht Club Lights Parade (Annapolis) • 0.7 miles
Illuminated boats parading on the water
Annapolis Chocolate Binge Festival (Annapolis) • 1.2 miles
A chocolate lover's paradise with over 40 vendors and a holiday market.
First Sunday Arts Holiday Market (Annapolis) • 1.2 miles
Over 100 vendors and live music stages
Lights on the Bay at Sandy Point State Park (Annapolis) • 5.4 miles
Two-mile drive-through holiday light display along the Chesapeake Bay
North Beach Christmas Parade (North Beach) • 19.0 miles
Annual holiday parade celebrating the season
Eastern Shore Sea Glass and Coastal Arts Festival (Saint Michaels) • 19.5 miles
Nearly 100 exhibitors selling coastal art and sea glass treasures
Easton's Christmas Tree Lighting Ceremony (Easton) • 26.4 miles
Santa's arrival and tree lighting ceremony
Breakfast with Santa at Tidewater Inn (Easton) • 26.5 miles
Historic inn hosts Santa for a festive breakfast
Waterfowl Festival (Easton) • 26.6 miles
A three-day celebration of Eastern Shore heritage, art, and conservation.
Oxford Holiday Market (Oxford) • 26.8 miles
Artisan gifts, holiday music, and special guests.
Santa 5K Fun Run & Walk (Easton) • 26.9 miles
Festive 5K run/walk benefiting Talbot Hospice.
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With 20 years of experience, we use AI technology to build the most comprehensive list of events events.
Our goal is complete coverage—from major festivals to small community celebrations, ensuring you never miss anything happening in your area.
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