Annapolis Christmas Events 2026
Your guide to the best Christmas events in Annapolis and nearby
The Washington D.C. National Christmas Tree Lighting draws visitors from across the region, signaling the start of a beloved holiday season around Annapolis. Local communities embrace the spirit with everything from charming town markets and dazzling light displays to theatrical performances and lively parades along the waterfront.
This year's listings showcase the breadth of seasonal activities, including classic theater productions like Ford's Theatre's A Christmas Carol in the city, or the beloved Nutcracker ballet in Hyattsville. For a truly memorable experience, consider the grand Christmas in St. Michaels festival.
Browse Christmas Near Annapolis by Category
Christmas Markets
Outdoor artisan Kris Kringle market with live community entertainment and dining.
Christmas Shows
Classic holiday ballet reimagined with a 19th-century Annapolis twist.
Christmas Parties
Chocolate tastings, holiday artisan shopping, and live music on West Street
Christmas Lights
Dozens of illuminated boats parade through Annapolis Harbor.
Unique & Unusual Christmas Events
Lantern-led walking tour past historic Annapolis homes and holiday greenery
Editor's Picks
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Lights on the Bay
Two-mile scenic drive with over 70 dazzling light displays
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Midnight Madness
Historic downtown holiday tradition with extended late-night shopping.
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The Nutcracker
Classic holiday ballet reimagined with a 19th-century Annapolis twist.
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Holiday Candlelight Stroll
Lantern-led walking tour past historic Annapolis homes and holiday greenery
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Annapolis Holiday Market
Outdoor artisan Kris Kringle market with live community entertainment and dining.
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Annapolis First Sunday Arts Holiday Market
Holiday market with over 100 artisans and live music
Latest News & Updates
Stay informed about holiday events and activities in Annapolis
- Chef Big Money's Holiday Pies Return to Annapolis Published: Tue, Sep 29, 2026
- Holiday Pie Season Begins at Chef Big Money's Published: Mon, Sep 28, 2026
Annapolis Christmas Events Map
See every Christmas event, light display, and market on one map.
Christmas Events in Nearby Cities
Christmas Events Road Trips & Weekend Getaways
Bigger holiday scenes worth the drive
Annapolis Christmas FAQ
What are the biggest annual Christmas events in Annapolis?
The Grand Illumination tree lighting downtown and the Lights on the Bay drive-through light show at Sandy Point State Park are among the biggest annual Christmas events in Annapolis, drawing locals and visitors alike.
What holiday traditions are unique to Annapolis?
Annapolis is known for its sailboat parade of lights on the harbor, where boats decorated with holiday lights create a magical waterfront display unique to the city’s maritime heritage.
Which neighborhoods are best for Christmas lights in Annapolis?
Neighborhoods near downtown Annapolis and Eastport are popular for their festive neighborhood displays and walking trails, offering a cozy and community-focused holiday experience.
Where can I find Christmas markets and local makers in Annapolis?
Christmas markets and local artisan vendors are primarily found in downtown Annapolis and at community centers near Annapolis, featuring a variety of crafts, gifts, and seasonal food and drink.
What are the best free or budget-friendly holiday activities in Annapolis?
Free activities include attending the Grand Illumination event, exploring neighborhood light displays, and visiting local holiday markets with no admission fees. Many shops also host free seasonal events and late-night shopping nights.
What are good picks for families with kids in Annapolis?
Families can enjoy the Lights on the Bay drive-through event, visits with Santa at local markets, and the sailboat parade. The Grand Illumination event also offers music and performances suitable for children.
Today's Trending Event
One of today's most-visited holiday events from across the country.
Holiday Classic Mansion Tours at Lyndhurst
📍 Tarrytown , NY , United States
Historic mansion adorned with elaborate holiday decorations and rare artifacts.
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