Discover Holiday Events

Explore our guide to local favorite holiday events and start planning your winter getaway to Annapolis and Anne Arundel County.

Annapolis Gingerbread Houses

November 21, 2026 - January 6, 2027

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.

Photography by Jarvin Hernandez.

Lights on the Bay

November 23, 2026 - January, 3, 2027

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.

Photography by Jarvin Hernandez.

North Pole Lights Walk

November 28, 2026 - December 28, 2026 (select dates)

Let a North Pole Fairy walk you through a garden of flowers and arctic animals to the North Pole Palace. New scenes are added every year along the Willow Oak Flower & Herb Farm.

Photography by Jarvin Hernandez.

Historic Annapolis

November 27, 2026 - December 26, 2026 (select dates)

Step back in time this holiday season with Historic Annapolis! Experience the magic of holidays past at 1776: Yuletide in Revolutionary Annapolis on December 5, 2026. Or discover the holidays past at Christmas Traditions by Candlelight at the William Paca House, running November 27 through December 26, 2026. Both event brings history to life through festive traditions and holiday storytelling.

Image courtesy of Historic Annapolis.

Grand Illumination

November 29, 2026

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. 

Photography by Albert Ewing.

Snowflake Alley

December 2026

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

Photography by Makayla McKoy.

Annapolis Holiday Market

December 4 - 6, 2026 and December 11 - 13, 2026

The Annapolis Holiday Market returns with 100 artisans, specialty holiday food vendors, festive entertainment, and will be located at the Annapolis Mall.

Midnight Madness

December 3, 10, and 17, 2026

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.

Photography by Jarvin Hernandez.

 

 

Annapolis Chocolate Binge Festival

December 6, 2026

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.

Eastport Yacht Club Lights Parade

December 12, 2026

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.

Photography by Katie Krause.

Santa Speedo Run

December 12, 2026

Photography by Jarvin Hernandez.

The Santa Speedo Run in downtown Annapolis is holiday spirit at its funniest. Locals and dash through the streets in festive costumes, sometimes with more tinsel than fabric, all to collect toys over the tears for less fortunate children. Whether you run or cheer, it’s pure Annapolis holiday energy. 

More Events To Consider

If you're looking for something a little more intimate, discover smaller-scale events that bring art, history, and entertainment to life this holiday season in Annapolis and Anne Arundel county.

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.

When will Snowflake Alley be lit?

Snowflake Alley usually lights up in Downtown Annapolis the first week of December. Stay tuned, these twinkling snowflakes are a sight to see.

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

Find thoughtful gifts in downtown Annapolis boutiques, shop your favorite brands at Annapolis Town Center, or discover deals at Arundel Mills.

Where should I stay?

Stay in downtown Annapolis with its historic attractions, waterfront restaurants, shopping, and nightlife, or choose a quaint stay in the countryside and surrounding neighborhoods. Hotels near BWI Thurgood Marshall Airport also offer convenient access to Annapolis, Baltimore, and Washington, D.C.

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.