Roughly a 1.5-hour drive from Dulles, Annapolis makes for an ideal day trip or weekend getaway, especially during the holidays. Here are six sensational reasons to visit Maryland’s capital city this November and December.
Annapolis Gingerbread Houses
November 22 through December 19
Sponsored by Visit Annapolis & Anne Arundel County, this annual contest invites bakers, artists, families, and businesses to showcase their edible creations. Public voting is open through December 7, and winners in multiple categories receive cash prizes. The finalists will remain on display at the Visitors Center through December 19. Annapolis Visitors Center: 26 West St., Annapolis, free
Lights on the Bay
November 23 through January 1, 2026
This popular drive-through holiday light show spans 2 miles along the scenic shores of the Chesapeake Bay. Hosted by the SPCA of Anne Arundel County, it features more than 70 animated and stationary displays, and proceeds help support animal welfare. Special theme nights include pet-friendly walk-throughs, scavenger hunts, and visits from Santa. Sandy Point State Park: 1100 E. College Pkwy., Annapolis, $20 per car, $30 for large vans, $50 for buses
Grand Illumination
November 30, 3 p.m. to 5:30 p.m.
The Grand Illumination Tree Lighting near Market House and City Dock features dancing and singing performances by local groups, including the Annapolis Symphony Orchestra Duet. Families will also enjoy free storytimes and treats provided by nearby shops before joining Santa and Mrs. Claus for the tree lighting.
Midnight Madness
December 4, 11, and 18, 4 p.m. to midnight
Enjoy late-night shopping at this downtown Annapolis holiday tradition. Stop by for an Instagrammable pic at Snowflake Alley on your way — the Main Street passageway is decorated with twinkling snowflakes. Then, enjoy music from carolers and choirs as well as festive holiday decorations as you shop. Stores will offer refreshments and special sales, and you can also shop the Annapolis Holiday Market on the City Dock.
Annapolis Chocolate Binge Festival
December 7, 11 a.m. to 4 p.m.
Held under a twinkling canopy of lights, start the holidays off on a sweet note at this festival. Enjoy live music and entertainment as you sample and shop the selection of chocolate truffles, caramels, bars, fudge, cookies, cakes, martinis, French macarons, cupcakes, pies, and brownies. The event also features local artisans selling handmade jewelry, pottery, candles, wood turnings, ornaments, and clothing. First block of West Street, $5, free admission for 12 and under
Eastport Yacht Club Lights Parade
December 13, 6 p.m. to 8 p.m.
Bundle up and enjoy this free annual Annapolis maritime tradition. For 40 years, Eastport Yacht Club members have been decking out their boats with holiday lights and music. You can book a boat tour to watch the action or find a vantage point along the Annapolis Harbor, Spa Creek, Eastport, or Murray Hill — or at any of the downtown streets that end at the water.
Feature image courtesy Jarvin Hernandez
