A curated list of notable October events around Annapolis, the Eastern Shore, and nearby areas, featuring community festivals, concerts, sports, theater, fundraisers, family-friendly activities, and more. Event dates may be subject to change.
Photo by Josh Davidson
Annapolis Sailboat Show
Sailors from near and far return to downtown Annapolis for the Annapolis Sailboat Show, taking place October 15th through 18th at City Dock beginning at 10 a.m. each day. The internationally acclaimed show fills the harbor with sailboats from manufacturers around the world, including multihulls, monohulls, cruisers, racers, sailing dinghies, and more. Along the shore, visitors can explore tents featuring the latest nautical gear, electronics, sails, rigging, charter opportunities, educational resources, and sailing clubs. Whether you’re an experienced sailor or simply curious about life under sail, the show offers four days to explore the industry and connect with the sailing community. More info: annapolisboatshows.com
Photo by United States Yacht Shows, Inc.
2026 Annapolis Power Boat Show
Downtown Annapolis transforms into a boater’s paradise when the Annapolis Powerboat Show returns to City Dock October 8th through 11th, beginning at 10 a.m. each day. Floating docks fill Ego Alley and Annapolis Harbor with an impressive selection of new and premiering powerboats, while shoreside exhibitors showcase the latest boating equipment, accessories, apparel, and more. From experienced boaters and anglers to those just discovering life on the water, visitors can walk the docks, explore what’s new in the industry, and experience one of Annapolis’ signature maritime traditions. More info: annapolisboatshows.com
Anne Arundel County Lifeline 100 Bicycle Event
Explore Anne Arundel County on two wheels during the 12th Annual Lifeline 100 Bicycle Event, taking place October 4th at Kinder Farm Park in Millersville. Designed for cyclists of all ages and abilities, the inclusive event offers 15- and 30-mile paved trail rides along with scenic 65- and 100-mile routes featuring water views and historic sites throughout the county. Younger riders can join the fun with a free bike rodeo and family ride, and cyclists with special needs and bikes of all kinds are welcome to participate. Presented by Anne Arundel County Recreation & Parks, Anne Arundel County Police, and Bicycle Advocates for Annapolis & Anne Arundel County, the annual event brings the community together for a day of cycling and outdoor recreation. More info: lifeline100.com
Odenton Fall Harvest Festival
Celebrate the season at the first-ever Odenton Fall Harvest Festival, happening October 2nd through 4th at the Odenton Volunteer Fire Company in Odenton. The weekend kicks off Friday from 5 to 9 p.m., continues Saturday from 10 a.m. to 5 p.m., and wraps up Sunday from 1 to 5 p.m. Families can enjoy kids’ carnival rides, seasonal food and treats, and plenty of fall fun while spending time with the local community. Admission is free, with ride and food prices varying, and proceeds from the festival will benefit the Odenton Volunteer Fire Company. More info: ovfc28.org
Beagle Bash!
Celebrate 25 years of Beagle Rescue of Southern Maryland at Beagle Bash, taking place October 4th at Crownsville Canine in Crownsville. The anniversary celebration will bring together more than 100 BRSM alumni and honorary beagles for a day dedicated to the dogs, volunteers, and supporters who have helped the organization find homes for more than 2,600 beagles. Guests can enjoy a bake sale with treats for people and pups, raffle prizes, a photo booth and photos with Snoopy, adoptable dogs, food, goodie bags, and more. This year’s celebration will also honor the memory of longtime BRSM supporter Doug Labant, who passed away last year. More info: beaglemaryland.org
Hoedown on the Farm
Spend a fall evening on the farm at Maryland Therapeutic Riding’s Hoedown on the Farm, happening October 3rd from 4 to 7:30 p.m. in Crownsville. This family-friendly celebration features BBQ, live music and dancing, games, activities, and plenty of opportunities to enjoy the farm with family and friends. Proceeds benefit MTR’s equine-assisted services, which use the healing power of horses to support children and adults of all abilities, veterans, active-duty military members, first responders, and their families. More info: horsesthatheal.org
You’re a Good Man, Charlie Brown
Join Charlie Brown and the entire Peanuts gang for You’re a Good Man, Charlie Brown, coming to Annapolis Mall October 2nd through 4th. Based on the beloved comic strip by Charles Schulz, the award-winning musical follows Charlie Brown, Snoopy, Lucy, Linus, Sally, and Schroeder as they tackle life’s big questions through baseball games, homework struggles, crushes, songs, and the simple joys of friendship. October performances are Friday, October 2nd at 7:30 p.m.; Saturday, October 3rd at 2 and 7:30 p.m.; and Sunday, October 4th at 2 p.m. With music, humor, and familiar characters, the production offers a nostalgic experience for longtime Peanuts fans while introducing a new generation to the gang. More info: compassrosetheater.org
Porchfest Annapolis 2026
Experience Annapolis one porch at a time during Porchfest Annapolis, returning October 24th from 11 a.m. to 3 p.m. across various neighborhoods throughout the city. The free community music festival transforms porches, stoops, driveways, and front yards into neighborhood stages where local musicians perform as attendees stroll from one stop to the next. After debuting in the Germantown-Homewood neighborhood in 2025, this year’s event will expand its focus to showcase more of Annapolis while bringing neighbors together through local music and community connection. A rain date is scheduled for October 25th. More info: porchfestannapolis.com
2026 Walk to End Alzheimer’s
Join the community in the fight against Alzheimer’s at the 2026 Walk to End Alzheimer’s, taking place October 18th at Sandy Point State Park in Annapolis. Registration begins at 11 a.m., followed by the opening ceremony and walk at noon, bringing together families, friends, caregivers, and supporters to raise awareness and funds for Alzheimer’s care, support, and research. Participation is free, though registration is required and donations and fundraising are encouraged. Every step helps support the Alzheimer’s Association’s work toward a future without Alzheimer’s and other dementias. More info: act.alz.org
2026 Business Hall of Fame Awards Dinner
Celebrate the people shaping Anne Arundel County’s business community at the 2026 Business Hall of Fame Awards Dinner, taking place October 15th from 5:30 to 8:30 p.m. at the DoubleTree Annapolis. Hosted by the Anne Arundel Chamber of Commerce, the evening will recognize this year’s Hall of Fame inductees Paul Gable, Sherry B. Perkins, Raymond Crosby, and Michael N. Russo Jr., along with Lifetime Achievement honoree Richard “Dick” Franyo and Business Leader of the Year Brendan “BK” Kelly. The annual dinner brings the local business community together to recognize leadership, achievement, and lasting contributions throughout the region. More info: annearundelchamber.org
A Toast to History
Step back into Annapolis-area history as Historic London Town & Gardens commemorates the nation’s 250th anniversary with a special evening on October 8th from 5 to 8 p.m. at its waterfront campus in Edgewater. Guests can explore the historic site and gardens while experiencing London Town’s colonial past through living history interpreters, colonial cocktail history talks, live music, interactive photo opportunities, and immersive programming. Heavy hors d’oeuvres, a cash bar, wine pull, and more round out the evening, with general admission and an enhanced VIP experience available. Proceeds from the event support Historic London Town & Gardens’ mission to preserve and share the stories that have shaped the community. More info: historiclondontown.org
Art @ The Park
Art and nature come together for the 36th annual Art @ the Park, returning to Quiet Waters Park in Annapolis on October 17th and 18th from 10 a.m. to 4 p.m. each day. Set against the park’s scenic fall surroundings, the two-day fine arts festival features unique works of art, live music, artist demonstrations, food trucks, and free activities for kids. Visitors can spend the day browsing art while enjoying the beauty of one of Annapolis’ favorite outdoor spaces, and leashed dogs are welcome in outdoor areas. Admission to the park is $8 per vehicle. More info: fqwp.org
Photo by St. Michaels Tourism
Fall Into St. Michaels
Celebrate the season on the Eastern Shore during Fall Into St. Michaels, returning October 17th and 18th throughout the historic waterfront town of St. Michaels. This weekend-long celebration brings the community together with seasonal fun, festive flavors, and plenty of small-town charm around every corner. Visitors can stroll through town, explore local businesses, and enjoy the sights and spirit of autumn during one of St. Michaels’ signature fall weekends. No tickets are required, making it an easy way to spend a crisp October day enjoying everything the town has to offer. More info: stmichaelsmd.org
Easton’s Fall Kickoff
Welcome fall in downtown Easton during the Fall Kickoff, taking place October 2nd and 3rd with two days of seasonal activities, entertainment, shopping, and dining. On Friday, stroll the giant pumpkin trail, enjoy live music from the Quinn Parsley Trio and DJ E Shore from 4 to 7 p.m., catch juggling performances from Cascading Carlos, explore the First Friday Gallery Walk, decorate pumpkins at the Academy Art Museum, and settle in for a free outdoor screening of Hotel Transylvania. The festivities continue Saturday with live music from Honey Sol from 11 a.m. to 3 p.m., family activities, pumpkin decorating, glassblowing demonstrations, the Easton Fall Craft Fair featuring more than 30 local artisans, and the Hot Rods and Hose Car Show. Throughout the weekend, downtown shops, galleries, and restaurants will offer seasonal specials and plenty of opportunities to celebrate autumn on the Eastern Shore. More info: discovereaston.com
Talbot County Young Life Charity Golf Tournament
Tee off for a good cause at the Talbot County Young Life Charity Golf Tournament, taking place October 17th from 9 a.m. to 2 p.m. at Hog Neck Golf Course in Easton. Golfers can enjoy a fall day on the course with an 18-hole scramble, lunch, contests, and prizes, all while supporting programs for local young people. Proceeds benefit Talbot County Young Life and its work providing mentorship, meaningful experiences, and opportunities that help middle and high school students, as well as young adults with disabilities, build confidence, connection, and a sense of belonging. More info: talbotcounty.younglife.org
Chesapeake Film Festival
Celebrate the art of independent storytelling at the 19th annual Chesapeake Film Festival, taking place October 8th through 10th at venues throughout historic downtown Easton. This year’s festival will showcase as many as 50 environmental, narrative, documentary, and short independent films, with screenings and special events held at the Ebenezer Theater, Academy Art Museum, and Talbot County Free Library. Beyond the screen, festivalgoers will have opportunities to connect with filmmakers, artists, community leaders, and fellow film enthusiasts through receptions and filmmaker events, making for three days dedicated to creativity, conversation, and cinema on the Eastern Shore. More info: chesapeakefilmfestival.com
Neko Case
Grammy-nominated singer-songwriter Neko Case brings her genre-defying sound to the Avalon Theatre in Easton on October 25th at 7:30 p.m., with doors opening at 6:30 p.m. Known for her distinctive voice, poetic songwriting, and fearless approach to music, Case takes the stage following the release of her ninth album, Neon Grey Midnight Green. The evening will also feature Destroyer, making for a standout night of live music on the Eastern Shore. Tickets range from $51 to $91, with $1 from every ticket supporting Peer Solutions and its youth leadership and development programs. More info: avalonfoundation.org
Mid-Atlantic Small Craft Festival XLIII
Celebrate the craftsmanship and tradition of small boats at the 43rd annual Mid-Atlantic Small Craft Festival, returning to the Chesapeake Bay Maritime Museum in St. Michaels October 2nd through 4th. One of the nation’s largest gatherings of its kind, the waterfront festival brings together dozens of sailing skiffs, rowing shells, kayaks, canoes, paddle boats, prams, and one-of-a-kind vessels along the Miles River. Throughout the family-friendly weekend, visitors can enjoy demonstrations, workshops, guest speakers, children’s activities, boat judging, and more, with Saturday’s sailing and rowing races offering a chance to watch competitors take to the water and vie for bragging rights. More info: cbmm.org
