October Events
October 2026 Events in Annapolis & Anne Arundel County
⛵ Annapolis Powerboat Show
📍 Downtown Annapolis, MD
A high-energy waterfront showcase featuring the latest powerboats, marine tech, gear, and on-the-water demos.
⛵ Annapolis Sailboat Show
📍 Downtown Annapolis, MD
An iconic sailing event featuring world-class sailboats, gear exhibits, and a vibrant harbor full of maritime culture.
🎃 The Great Annapolis Pumpkins
📍 Downtown Annapolis, MD
A fall favorite bringing seasonal charm to downtown Annapolis with festive giant pumpkins, family fun, and autumn photo moments.
🌈 Annapolis Pride Parade & Festival
📍 Downtown Annapolis, MD
Annapolis is growing in Pride and Community! Join the Parade and Festival for food and fun for the whole family.
👻 Spooky & Ghostly Tours
📍Downtown Annapolis, MD
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.
🕯️Scarecrow Stroll
📍Downtown Annapolis, MD
Scarecrows will line the streets of downtown Annapolis on West Street, Maryland Avenue and Main Street.
🍁Maryland Ave Fall Festival
📍Downtown Annapolis, MD
The Maryland Ave Fall Festival brings local vendors, food, and community fun to Maryland Avenue in downtown Annapolis. Held rain or shine, the festival is a longtime Maryland tradition featuring shopping, food, and more.
🌽 Maryland Corn Maze
📍 389 Gambrills Road, Gambrills, MD 21054🌽
Get lost in an 8-acre corn maze, then stick around and enjoy a full day of farm fun! This year’s maze theme is Toy Story, bringing all the childhood nostalgia as many celebrate the release of Toy Story 5.
🏰 Renaissance Festival
📍 1821 Crownsville Road, Annapolis, Maryland 21401
One of Maryland’s top seasonal events, the Renaissance Festival runs in Anne Arundel County from late August through October.
🌊 Galesville Maritime Heritage Festival
📍 Galesville Maritime Heritage Festival
Spend the Day in the Waterfront Village of Galesville on Maryland’s West River where Four Centuries of Chesapeake Bay Culture Come Alive.
🐎 Maryland Million Day
📍 Laurel Race Track Rd.
Bring the whole family to enjoy thrilling horse races, interactive games, and local food favorites, all set in the heart of beautiful Maryland.
🦪 Oyster Festival 2026
📍 Captain Avery Museum
Spend a day by the water at Captain Avery Museum, with oysters cooked how you like them, local food, live music and a relaxed festival atmosphere.
🎨 Art @ the Park
📍 Quiet Waters Park
Spend the weekend at Art @ the Park! Enjoy local artists, live music, demonstrations, food trucks, kids’ activities and more at Quiet Waters Park
🚲 Anne Arundel County Lifeline 100 Bicycle Event
📍 Kinder Farm Park
Join the Anne Arundel County Department of Recreation & Parks, Anne Arundel County Police, and Bicycle Advocates for Annapolis and Anne Arundel County (BikeAAA) for the 12th Annual Lifeline 100 Community Bicycle Event!
🏈 USNA Football
📍 Navy-Marine Corps Memorial Stadium
Anyone who’s been to Annapolis in the fall knows the city comes alive on Navy football weekends, when home games bring a surge of fans, energy, and tradition into the heart of town.
