Annapolis is a charming and romantic city that’s dense with historic buildings, and fun traditions that are especially uplifting around the holidays. From elaborate lighting exhibitions to shopping extravaganza and historic tours, here’s a brief guide for travelers visiting Annapolis for the holidays. 

Midnight Madness 

Every year on the first three Thursdays of December, Midnight Madness marks a shopping extravaganza in Downtown Annapolis. From 4 pm until Midnight (and until 11 pm on the third Thursday), shops will stay open with special deals and more. The streets will also be filled with carolers and street musicians, and a large tree will stand at Market Space. 

Midnight Madness. December 1st, 8th, and 15th. Downtown Annapolis, MD 

Lights On The Bay 

Don’t miss Lights on The Bay, which will feature an epic lighting display along the shore of the Chesapeake Bay. This drive-through experience cuts through Sandy Point State Park and it will feature more than 60 animated and stationary displays along the way. 

Lights on the Bay. Sandy Point State Park. November 20th-January 2nd

Holiday Candlelight Stroll

Annapolis maintains its Revolutionary-era charm with historic buildings and traditions such as the Holiday Candlelight Stroll. Featuring tour guides in period attire, the tour leads you around town by lantern. See colonial mansions and Victorian homes while hearing tales of local holiday traditions. 

Holiday Candlelight Stroll. November 25th-December 23rd

Jolly Express Cruises

Watermark Holiday Cruises is reviving one of its favorite traditions during this season. Their boat Miss Anne will be turned into a reindeer for 45-minute “sleigh-ride” excursions. These fun outings on the water are family-friendly and include not only hot cocoa and holiday music but also a Captain Santa to lead the way along Spa Creek. 

 Jolly Express Cruises. November 25th-December 30th

Eastport Yacht Club Lights Parade

This year will mark the 40th anniversary of the Eastport Club’s Lights Parade. Taking place every year on the second Saturday in December, this show features boats illuminated by thousands upon thousands of colorful lights taking to Annapolis Harbor for a two-hour display. 

Eastport Yacht Club’s Lights Parade. Eastport Yacht Club. December 10th

AMFM Presents an Annapolis Christmas

Head to one of the city’s most prized music venues for one of two nights of holiday jamming at the AMFM Presents an Annapolis Christmas. This show is an annual tradition that’s over 23 years old, and it is run by the Annapolis Musicians Fund for Musicians. It will feature a lineup of local acts, some of which include Meg Murray, the Geckos, and SwampCandy. 

AMFM Presents an Annapolis Christmas. Rams Head On Stage. December 12-13th.