Twinkling Lights, Holiday Sights! 

We interrupt your Black Friday shopping scroll to invite you to slow down, relax and book a holiday adventure this holiday season!

Twinkling holiday lights dancing off the water, 18th-century architecture and cobblestone streets draped in bows of garland and holly, and music echoing off the walls of a 300-year-old tavern. Discover this and so much more when you book a winter adventure in Annapolis & Anne Arundel County! Recently named a Top 2022 Christmas Town in the USA by Travel + Leisure magazine, plan your getaway today. 

Midnight Madness

Downtown Annapolis stores along Main and West Streets and Maryland Avenue stay open until midnight giving bargain hunters and last-minute shoppers an incentive to get out and about and shop well into the night. Holiday displays, festive treats, and exclusive discounts make Midnight Madness Holiday Shopping one of the most anticipated holiday events of the year.

Annapolis Chocolate Binge Festival

The Annapolis Chocolate Binge Festival takes over the first block of West Street on Sunday, December 4, from 11 am - 5 pm, in a family-friendly celebration of all things cocoa. 2022 marks the 8th year of the event, and some new activities are coming your way!

Eastport Yacht Club Lights Parade

People travel far and wide to attend the annual Eastport Yacht Club Lights Parade, currently in the running for USA Today's 10Best Holiday Parades in the USA! Spend the weekend and explore the Annapolis Holiday Market while you shop, stroll and dine in the best-preserved 18th-century colonial town in the country and marvel at the lighted boat parade along the shores of the Chesapeake Bay.

The Military Bowl Parade and Festival

The Military Bowl, presented by Peraton, benefitting the USO, will match a team from the Atlantic Coast Conference (ACC) against an opponent from the American Athletic Conference (AAC). The Bowl game begins with a parade up Main Street featuring the Budweiser Clydesdales and a tailgating festival at Navy-Marines Corps Memorial Stadium before kick-off at 2 pm, December 28.

New Year's Eve Celebrations

Kick off 2023 with fireworks and events throughout Anne Arundel County. Book a stay in the Arundel Mills region for gaming and live entertainment at Live! Casino & Hotel Maryland. Traditionally, the City of Annapolis puts on an all-ages fireworks display in the early evening, followed by midnight fireworks at City Dock.

Plan Your Stay!

Magical for Over 300 Years!

Download your Copy of the 2022 Visitor Guide and start planning

your Holiday adventure today!