October is when Annapolis and Anne Arundel County begin to show their fall colors. The days get shorter, the air becomes crisp, the foliage starts to peak, and the historic streets are suddenly filled with large pumpkins, scarecrows, festivals, and spooky decor.
It all begins with a trip! Cozy up in your favorite sweater and get away for a while. Experience some of the best events happening in Annapolis and Anne Arundel County this October.
Annapolis Boat Shows
One of Annapolis’ most iconic waterfront events, the Annapolis Boat Shows, returns. First, the Powerboat Show sails into town October 8–11, followed by the Sailboat Show October 15–18. Spend the day wandering the harbor, stepping aboard boats, browsing exhibits, and capturing the beauty of the season near the water.
The Great Annapolis Pumpkins
You’ll know fall has officially arrived when giant pumpkins begin popping up around downtown Annapolis. The Great Annapolis Pumpkins bring seasonal charm to the city with real gourds from the Atlantic region weighing at least 1,000 pounds. Visitors stop by for a seasonal photo op, admire these autumn pumpkins, and return later in the month to watch them being carved. Be sure to stop by the Visitor's Center on Saturday, October 10 for the arrival of our pumpkin and the Fall Fest!
Annapolis Pride Parade & Festival
It may be a different time of year, but the Annapolis Pride Parade & Festival still celebrates the same love, community, and people who make our destination glow. Walk the streets as one, enjoy the festivities, and explore locally vetted, welcoming restaurants around Annapolis.
Spooky & Ghostly Tours
When the sun goes down, the streets of historic Annapolis have a few stories of their own to tell. Spooky season brings ghost tours, witches-and-legends walks, haunted pub crawls, pumpkin crawls, scarecrow strolls, and artistic Halloween performances.
Maryland Avenue Fall Festival
Did you think Maryland Avenue could get any more scenic? It does during the Maryland Avenue Fall Festival. Stroll the brick-lined streets, browse local vendors, enjoy live entertainment, and grab a bite while taking in the autumn charm of Maryland Avenue.
Waterfront Activities
It’s not too late to spend time near the water when you’re in Anne Arundel County. Enjoy a family-friendly outing at the Galesville Maritime Heritage Festival, visit the Captain Avery Museum Oyster Festival, or immerse yourself in art and music at Art @ the Park.
More Things to Do in October
October brings events to Annapolis and Anne Arundel County, from waterfront cruises and live music to historical tours, art festivals, markets, and family-friendly activities.
Waterfront & Maritime
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Galesville, Maritime Heritage Festival – October 3
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Boat Show Cruise – October 9 – October 11
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Mallows Bay & Calvert Brewing - Adventure Paddle – October 10
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DragonFest 2026 – October 17
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Chesapeake Bay Trio: River-Lighthouse-Bridge – October 19
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Bay Lighthouses Cruise – October 24
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Wilma Lee Sunset & Heritage Cruises — select October dates
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Annapolis Darling Sunset Cruise – select October dates
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America's 250 Harbor Cruise — daily
Arts, Music & Entertainment
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CP presents Our Town by Thornton Wilder – October 1
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Resin Art Workshops — Wednesdays–Sundays
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Amanda Milliner's Plein Air Workshop – October 3
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Celebrate Pride at the Visitors Center! - October 3
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Comedian Anthony Rodia: Insanely Funny Tour - October 3
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Annapolis Witches & Legends Walking Tour – October 4
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First Sunday Arts Festival – October 4
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Maryland Witches Pub Crawl – October 9, 11, 23, 29, 31
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Live Arts Maryland Presents A Concert for Peace – October 10
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Open Art Studio Tour - Muddy Creek Artists Guild – October 10, 11
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Maryland Hall Presents: Ailey ll – October 11
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Meet the Author: Rosa Pryor-Trusty – African American Community, History & Entertainment in Maryland – October 24
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Candlelight: 90s Unplugged – October 29
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Anchors + Artisans – October 18
History & Heritage
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Annapolis Tipsy History Tour: 300+ Years of Annapolis Drinking History – Sunday through Friday
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Historic Ghost Tour – select October dates
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Colonial Annapolis & Maryland State House – select October dates
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Colonial Cocktails: Spirits with the Spirits – October 15
Start Planning Your October Visit
Make the most of October in Annapolis and Anne Arundel County with waterfront adventures, local events, live music, history, arts, food, and fall traditions.
Stop by the Annapolis & Anne Arundel County Visitors Center for local recommendations, destination information, and inspiration for your visit. The Visitors Center is open daily from 10 a.m. to 5 p.m.
