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Last updated: November 11, 2024

Get set for a holiday adventure in Annapolis with our guide. Discover all the exciting festive happenings. Whether Annapolis is your permanent address or your temporary haven, this guide helps you embrace the spirit of the season.

Popular events include the enchanting Lights on the Bay, where you can drive through a dazzling display of holiday lights along the Chesapeake Bay. With intricate designs and festive themes, this event brings joy to families and friends alike. The Military Bowl, a celebration of college football, adds a spirited touch to the holidays, featuring teams competing in an exciting showdown. And the New Year’s Eve Fireworks is something you definitely don't want to miss, offering a spectacular display that lights up the waterfront. See more details on these and other fun events and activities below!

Contact information and details below.

Annapolis Holiday Light Displays

What to Expect:

Annual tree lighting ceremony with local kids' decorations.

Description:

The Downtown Annapolis Grand Illumination is a festive holiday event held near the Market House on the Sunday after Thanksgiving. It features dancing and carols by local groups, an annual Christmas Tree lighting ceremony with carolers and music, and general merriment. The event is free and open to the public, with Santa, Mrs. Claus, and Elfie lighting the tree. This year's tree decorations are designed by local kids and sponsored by the Annapolis Symphony Orchestra.

Where: Annapolis | More Info: Downtown Annapolis Grand Illumination

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What to Expect:

Scenic drive with 70 animated and stationary light displays.

Description:

Drive through a two-mile illuminated display along the Chesapeake Bay featuring over 70 animated and stationary lights, sponsored by the SPCA of Anne Arundel County.

Where: Annapolis | More Info: Lights on the Bay

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What to Expect:

Boats illuminated with thousands of colored lights.

Description:

The Eastport Yacht Club Lights Parade is an annual event where boats in Annapolis Harbor are decorated with thousands of colored lights, creating a spectacular display of holiday cheer.

Where: Annapolis | More Info: Eastport Yacht Club Lights

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Annapolis Holiday Markets and Shopping

What to Expect:

Holiday shopping event with live entertainment and decorated streets.

Description:

Downtown Annapolis transforms into a holiday shopping paradise with Midnight Madness, featuring decorated streets, holiday decorations, and live entertainment. Residents and visitors can stroll along Main Street, West Street, Maryland Avenue, State Circle, Market Space, and Dock Street to support local businesses and enjoy refreshments and sales.

Where: Annapolis | More Info: Midnight Madness

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What to Expect:

Unique chocolate tour and holiday market.

Description:

The Annapolis Chocolate Binge Festival is a family-friendly event celebrating all things chocolate. It features a chocolate tour along West Street with various vendors selling chocolate specialties, a holiday market with local artisans, and live music and entertainment. Admission is $5 when purchased online, and the event includes a festive West Street Holiday Light Canopy.

Where: Annapolis | More Info: Annapolis Chocolate Binge Festival

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What to Expect:

Monthly street festival with local artisans and live entertainment.

Description:

The First Sunday Arts Holiday Market in Annapolis features over 100 vendors selling handmade crafts, artwork, and local goods, accompanied by live music and café dining.

Where: Annapolis | More Info: First Sunday Arts Holiday Market

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Annapolis Holiday Shows and Entertainment

What to Expect:

Free ornaments for the first 500 families.

Description:

Join Annapolis Town Center for the Annual Christmas Tree Lighting on Friday, November 17, from 7 PM to 8 PM. The first 500 families to arrive will receive a 1st Annual Annapolis Town Center Ornament. Enjoy DJ music, games, fireworks, and a visit from Santa, all located near P.F. Chang’s and the East Village Boathouse.

Where: Annapolis | More Info: Annapolis Town Center Annual Christmas Tree Lighting

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Annapolis Other Holiday Activities

What to Expect:

Post-season college football game with parade and festivities.

Description:

The Military Bowl is a prestigious NCAA Division I college football bowl game held annually in Annapolis, Maryland, featuring teams from the ACC and American Athletic Conference. The event includes a parade, live music, and festivities, making it a significant part of the holiday season.

Where: Annapolis | More Info: Military Bowl

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What to Expect:

Efficient waste management system with interactive route maps and reporting options.

Description:

The City of Annapolis provides comprehensive residential solid waste collection services, including refuse, recycling, and yard trim. Residents can find their collection routes and days using the Residential Collection Route PDF map or visiting DPW Services by Street List. Issues can be reported by calling 410-263-7949 or using the TextMyGov service.

Where: Annapolis | More Info: Refuse and Recycling Collection Adjustments

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What to Expect:

Intimate holiday cruise with hot cocoa and holiday music.

Description:

Embark on a 45-minute holiday cruise aboard Miss Anne, adorned in reindeer spirit, featuring hot cocoa, holiday music, and good cheer. Captain Santa leads this festive evening ride along Spa Creek, with blankets available to stay warm and cozy.

Where: Annapolis | More Info: Jolly Express cruise

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What to Expect:

Guided candlelight tour focusing on historical medical practices and mourning rituals.

Description:

Explore the historic William Paca House through a candlelight tour, delving into the past's sickness treatments, mourning rituals, and superstitions.

Where: Annapolis | More Info: Candlelight history tours

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What to Expect:

World-class art exhibition and wildlife conservation events.

Description:

The Waterfowl Festival is a three-day celebration on the Eastern Shore, featuring 350 artists and vendors, live demonstrations, and activities for all ages, including fly-fishing, retriever dog demonstrations, and the World Waterfowl Calling Championship.

Where: Easton | More Info: Waterfowl Festival

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