October in Annapolis and Anne Arundel County is full of fall magic, from crisp Bay breezes and colorful leaves to festivals, boat shows, cozy cafés, and family‑friendly adventures.
☕ Café Diem: The Annapolis Coffee Crawl
September 28th – October 5th
Calling all coffee lovers! Café Diem: The Annapolis Coffee Crawl is brewing now through October 5. Timed around National Coffee Day, the crawl takes you on a flavorful journey through Annapolis’ vibrant café scene.
⚓ The Annapolis Boat Shows
October 2nd – October 5th & October 9th – October 12th
It’s not October in Annapolis without the world-famous Annapolis Boat Shows. First up: the Powerboat Show (Oct. 2–5), followed by the Sailboat Show (Oct. 9–12). City Dock becomes a floating marina where you can step aboard luxury yachts, sleek performance boats, and the latest in marine gear.
🏇 Maryland Million Day
October 11th
Celebrate 40 years of Maryland Million Day at the Races at Laurel Park. Expect thrilling horse races, family fun, and a festive atmosphere celebrating the state’s Thoroughbred tradition.
🌈 Annapolis Pride Parade & Festival
October 18th
A lively parade winds through downtown before the festival kicks off at Maryland Hall and Wiley Bates Athletic Complex. With music, food, vendors, and a powerful theme, “Growing in Pride, Growing in Community”.
🎨 Fall Family Fun Day
October 19th
Bring the whole crew to the Visit Annapolis & Anne Arundel County Visitors Center (26 West Street) for a festive Fall Family Fun Day on Sunday, October 19, 10 a.m.–2 p.m. Enjoy face painting, crafts, seasonal treats, and insider tips from local experts to help plan your autumn adventures. Make it a full day by wandering over to the Maryland Avenue Fall Festival nearby.
🎃 The Great Annapolis Pumpkins
October 6th and Beyond
Downtown Annapolis transforms into pumpkin town starting October 6, when giant orange gourds take over the historic streets. As Halloween nears, local artists carve them into giant jack-o’-lantern masterpieces, adding a magical Annapolis twist to the season.
👻 Spooky & Ghostly Tours
October nights in Annapolis come with a side of goosebumps. Ghost tours and haunted history walks dive into colonial legends, eerie lore, and paranormal tales that make the city’s cobblestone streets feel spooky. Options range from “Witches & Legends” to ghostly pub crawls, perfect for thrill-seekers.
🍂 All the Fall Things – Festivals, Art, & Farmers Markets
From artisan markets to oyster festivals, October is basically one big fall bucket list. Highlights include:
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Oct. 4: Chesapeake Arts in the Park
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Oct. 5: First Sunday Arts Festival
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Oct. 11 & 12: Quiet Waters Art @ the Park
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Oct. 18: Captain Avery Museum Oyster Festival
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Oct. 19: Fall Foliage Bay Lighthouse Cruise
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Oct. 31: Annapolis Opera presents Don Giovanni
…plus farmers markets every weekend, seasonal concerts, and more.
🍁 More October Happenings
Navy football games, lighthouse cruises, art tours, live performances, and historic celebrations fill the calendar all month long. From oyster shucking to spooky concerts, Annapolis in October is buzzing with energy.
