November brings a little bit of everything to Annapolis and Anne Arundel County. From the final days of fall foliage, waterfront adventures and the first signs of holiday magic, there's plenty to experience before winter arrives. Discover the events and experiences worth planning a November getaway around.
Bay Bridge Run
The annual Bay Bridge Run gives runners and walkers a rare opportunity to experience the iconic bridge without vehicle traffic on its eastbound span. Take in sweeping views of the Chesapeake Bay during this unforgettable 10K experience.
Tasting & Tunes - Wine & Beer Fest on West
Head to West Street in downtown Annapolis for Tasting & Tunes – Wine & Beer Fest on West, featuring bites from eight local restaurants, regional wines, craft beers, and live entertainment.
Annapolis Jazz & Roots Festival
The Annapolis Jazz & Roots Festival brings a mix of jazz, roots music, and live performances to venues throughout Annapolis. It's the perfect excuse to discover the city's vibrant music scene and make a night of it.
Lights on the Bay
Lights on the Bay transforms Sandy Point State Park into a dazzling drive-through holiday light display. Pack up the car, bring your favorite people, and enjoy a festive evening along the waterfront.
The Great Annapolis Gingerbread Houses
Something sweet is happening in downtown Annapolis! Stop by the Annapolis Visitors Center to admire The Great Annapolis Gingerbread Houses, a festive display of creatively crafted gingerbread houses that celebrates the beginning of the holiday season.
North Pole Lights Walk
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.
Grand Illumination
On 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.
The Best Holiday Plans Deserve a Weekend Stay
With so many holiday festivities happening back-to-back, why not stay a little longer? Make the most of the season, enjoy every festive moment, and fill your camera roll with memories worth keeping. Wondering where to stay? Explore cozy accommodations in the heart of the holiday magic or find a peaceful stay nearby if you prefer to escape the crowds. Find your perfect stay and start planning!
Looking for more inspiration?
Find more things to do in November.
Waterfront & Maritime
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Private Afternoon Charter – select November dates
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Sunset Cruise – select November dates
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Bay Lighthouses Cruise – November 7
Arts, Music & Entertainment
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Rams Head on Stage – various shows on select November dates
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CP presents The Legend of Sleepy Hollow – November 1, 5, 6, 7, and 8
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Miguel Braceli: UNBURIAL (exhibition) - November
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Resin Art Workshops – Select November dates
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Folk Garden Ramble @ Historic London Town & Gardens – November 4
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DoArt Workshop – Weave a Wall Hanging – November 8
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USNA Masqueraders presents POE'S DARK CARNIVAL OF TALES – November 13 – 21
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Historic Annapolis Book Club – November 19
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Fiber Options 2026 Closing Reception – November 21
History & Heritage
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Scandalous Annapolis – select November dates
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Weird, Wacky, & Unusual History of Annapolis Tour – select November dates
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African American Heritage Tour – select November dates
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Holiday Candlelight Stroll – November 27 and 28
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Christmas in the Capital: Annapolis Traditions and State House Trees – November 28 and 29
Start Planning Your November Visit
Turn your favorite November events into a getaway with a cozy overnight stay, waterfront dining, and a little extra time to explore Annapolis and Anne Arundel County.
Arriving at BWI Airport? Visit our new Welcome Center located at Terminal A baggage claim area between doors 2 & 3, near Starbucks. Get insider tips, destination inspiration, and everything you need to start exploring Annapolis and Anne Arundel County.
On 26 West Street, The Annapolis & Anne Arundel County Visitors Center is perfect for local recommendations, destination information, and inspiration for your visit. The Visitors Center is open daily from 10 a.m. to 5 p.m. unless otherwise disclosed.
