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.

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.

Annapolis Gingerbread Houses

November 22, 2026 - December 20, 2026

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.

North Pole Lights Walk

November 27, 2026 - December 30, 2026

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.

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.

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.

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

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

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 is Snowflake Alley 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?

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.