The Chesapeake Bay region sparkles with holiday magic, blending timeless traditions with waterfront charm. From Annapolis to Maryland’s Eastern Shore, this area is a perfect destination for celebrating the season—and discovering why it’s ideal for your forever home or weekend retreat. Here are five must-see holiday events to enjoy this year.
1. First Night Talbot in Easton, MD
When: December 31, 2024 | Where: Downtown Easton
Ring in the New Year with the family-friendly festivities of First Night Talbot in historic Easton. This alcohol-free event features live music, performances, and fireworks to cap the evening. Wander the beautifully lit streets and experience the small-town charm that makes Maryland’s Eastern Shore an idyllic place to call home.
First Night in Talbot, revelers enjoy parades and events before the infamous Crab Drop!
2. New Year’s Eve Fireworks in Downtown Annapolis
When: December 31, 2024. 9:00 PM | Where: City Dock, Annapolis
Celebrate New Year’s Eve in the heart of Annapolis with a dazzling fireworks display over the waterfront. City Dock transforms into a lively gathering spot, with live entertainment and festive energy. Watching fireworks light up the Chesapeake Bay is the perfect way to imagine yourself living amidst this vibrant, coastal lifestyle.
Fireworks over the harbor in downtown Annapolis on New Year's Eve are a must!
3. Midnight Madness in Historic Downtown Annapolis
When: December 12 & 19, 2024 | Where: Main Street, Annapolis
Get swept up in the holiday spirit during Midnight Madness, a beloved Annapolis shopping event. Historic Main Street comes alive with twinkling lights, live music, and extended shop hours. It’s the perfect chance to pick up unique gifts while exploring the walkable charm of Annapolis—a town as inviting during the holidays as it is year-round.
Stop by Snowflake Alley off Main Street in Annapolis for your winter selfie!
4. Eastport Yacht Club Lighted Boat Parade
When: December 14, 2024 | Where: City Dock, Downtown Annapolis
Add some holiday fun to your schedule with the annual Lights Parade along the Annapolis waterfront. Boaters decorate their powerboats and sailboats with lights, lasers, and sometimes Santa himself for this parade of lights, which was recently voted as a top Christmas Parade in the nation by USA Today. The event reflects the community spirit of this waterfront city, known as America's Sailing Capital, making it a place you’ll want to call home.
It's not Christmas in Annapolis, MD without the Eastport Yacht Club Lights Parade!
5. Christmas in St. Michaels
When: December 13–15, 2024 | Where: St. Michaels, MD
This iconic celebration features a weekend of events, including a holiday parade, a festive marketplace, and a tour of beautifully decorated homes. Don’t miss the lighted boat parade, showcasing the maritime heritage of this picturesque Eastern Shore town. St. Michaels’ warmth and history make it an enchanting holiday destination—and a dream location for a waterfront retreat.
Charming and walkable, there are so many things to see and do in quaint St. Michaels, MD during the holidays!
The holidays in Annapolis and Maryland’s Eastern Shore are a testament to the region’s bespoke charm. From festive parades to stunning fireworks, every event highlights the unique blend of history, waterfront living, and community spirit. This is more than a holiday destination—it’s a lifestyle.
Ready to find your forever home in Annapolis or Maryland’s Eastern Shore? Discover why so many choose to call this magical region home with Brad Kappel, Maryland’s #1 waterfront real estate expert.
