Grand Illumination

November 30th

Families, friends, and visitors gather in the heart of historic downtown to share the charm of the new season together, at the annual tree lighting near Market House and City Dock. 

Midnight Madness

December 4th, 11th, and 18th

Late-night holiday shopping lights up the streets with twinkling lights, special discounts, seasonal treats, and unique gifts in one of the city’s most festive traditions.

Annapolis Chocolate Binge Festival

December 7th

On the first block of West Street in downtown Annapolis, the Chocolate Festival serves up decadent desserts, warm drinks, family-friendly activities, and holiday arts and crafts for a sweet seasonal experience.

Annapolis Gingerbread Houses

November 23rd - December 19th

Catch the sweet scent of gingerbread at the Visitor’s Center and vote for your favorite house! Local bakers and community creators turned their tasty, whimsical visions into reality.

Eastport Yacht Club Lights Parade

December 13th

A magical waterfront experience awaits in the heart of Annapolis as the harbor sparkles with nautical and Annapolitan-themed holiday lights, presented by the Eastport Yacht Club.

Lights on the Bay

Late November through Early January

There's no better way to get the whole family into the holiday spirit than driving along the shore of the Chesapeake Bay at Sandy Point State Park, where over 70 animated light displays line a stunning two-mile drive along Maryland’s scenic waterfront.

Snowflake Alley

December

A whimsical alley (Cabbage Alley) is lit with twinkling snowflakes, making it a perfect backdrop for holiday posts. Everyone wants a photo here.

FAQS

Looking for the best parking spots for Annapolis holiday events?

Enjoy FREE holiday parking in downtown Annapolis this season at various locations. Additionally, eligible parking meters will be free for the first three hours for everyone between Thanksgiving and New Year's Day. Visit Annapolis Parking for more information.

Are there special seasonal markets, shows, or performances in Annapolis?

Ballet Theatre of Maryland presents The Nutcracker at Maryland Hall on select dates throughout the month of December. The Annapolis Symphony Orchestra performs one of the most beloved traditions in Annapolis, the ASO's Annual Holiday Pops concert at Maryland Hall.

When is Snowflake Alley lit?

Last year (2024) Snowflake Alley lit up in Downtown Annapolis on December 3rd. Stay tuned, these twinkling snowflakes are a sight to see.

Where can I shop in Annapolis and Anne Arundel County during the holiday season?

Downtown Annapolis is the perfect place to start, with charming boutiques along Main Street, Maryland Avenue, and City Dock offering one-of-a-kind finds. Just up West Street, you’ll discover big-name favorites at the Annapolis Town Center and Annapolis Mall. South Forest Drive offers a wide range of retail shops, while Arundel Mills Mall—Maryland’s largest outlet mall with over 200 stores—provides endless options. Plus, wherever you shop, you’ll find plenty of dining spots to refuel in true Annapolis style.

Where can I dine in Annapolis and Anne Arundel County during the holiday season?

Taste our incredible and mouth-watering seafood, unique steak houses, dive bars, pubs, and more! View more options below.

Where to Drop Anchor

Stay in the heart of Annapolis, where historic charm, modern comfort, and luxury meet the city’s holiday festivities.