A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of October. Event dates may be subject to change.
Photo by Eastport Yacht Club
Party in the Port
Eastport Yacht Club’s legendary waterfront bash returns on Saturday, October 12, with an unforgettable night of live music, food, and celebration. Headlining the stage is Misspent Youth, the powerhouse cover band known for their high-energy performances of dance rock hits from the ’80s to today. This year’s party also honors the 10th anniversary of the Valhalla Sailing Project, which has empowered veterans through the healing power of sailing. Enjoy delicious food, EYC’s famous drinks, and an electric atmosphere that captures the true spirit of sailing and community. More info: eastportyc.org/party
The Walk to End Alzheimer’s
Join the region’s largest event dedicated to raising awareness and funds for Alzheimer’s care, support, and research. The Walk to End Alzheimer’s is a free, family-friendly gathering at Sandy Point State Park on October 19 that brings communities together to honor those affected and take steps toward a future without the disease. Walk, connect, and be part of a powerful movement of hope and support for families everywhere. More info: alz.org/walk
Photo by Michael G. Stewart
Naptown Philharmonic: Halloween Spooktacular!
Naptown Philharmonic’s annual Halloween Spooktacular takes the stage on Sunday, October 19, at St. John’s College Key Auditorium. This family-friendly concert is a community favorite, blending classical music with festive fun. Orchestra members perform in costume, and audience members are encouraged to join in the tradition and compete in a lively costume contest. With local personality Michael Hughes as master of ceremonies, it’s the perfect way to introduce younger audiences to the joy of orchestral music in a playful, seasonal setting. More info: naptownphil.org
Lifeline 100 Bicycle Event
The 11th annual Lifeline 100 Community Bicycle Event rolls out on Sunday, October 6, across Anne Arundel County. Riders of all ages and abilities can choose from scenic 65- and 100-mile county tours with waterfront views and historic stops, or shorter 15- and 30-mile paved trail options. Families can enjoy a free bike rodeo and kids’ fun ride, making it a true community celebration. Since its start, the event has raised more than $350,000 for local nonprofits while promoting cycling, safety, and the beauty of Anne Arundel’s trails and roadways. More info: lifeline100.com
CCA Annapolis Chapter Annual Fundraising Banquet
Enjoy an evening of oysters, dinner, open bar, live music, raffles, and both silent and live auctions at the annual Annapolis Chapter Fundraising Banquet hosted by Coastal Conservation Association Maryland. This celebration of conservation and Chesapeake Bay culture brings together anglers, boaters, and community members to support the health and sustainability of local marine resources. Proceeds benefit CCA Maryland’s mission to conserve, promote, and enhance the Bay for future generations. Join fellow supporters for great food, lively entertainment, and a shared commitment to protecting the Chesapeake. More info: ccamd.org
2025 Every Step Counts Autism Walk & 5K
The Autism Society of Maryland hosts its annual Every Step Counts Autism Walk & 5K Run on Saturday, October 4, at Centennial Park in Ellicott City. This year’s superhero-themed event invites participants of all ages and abilities to run the 5K, walk the 4K, or enjoy the 1K stroll, all while supporting thousands of individuals and families across Maryland. It’s a day of community, connection, and celebration designed to raise awareness and funds for autism programs throughout the state. More info: autismsocietymd.org
2025 Autumn Reggae Wine & Music Festival at Linganore
Linganore Winecellars hosts its annual Autumn Reggae Wine & Music Festival on Saturday and Sunday, October 11–12, in Mount Airy. As the East Coast’s longest-running reggae festival, it’s a weekend of live performances, authentic island cuisine, artisan vendors, and unlimited wine sampling from Linganore Winecellars. Guests can enjoy two live bands each day, plus a lively DJ to keep the energy high. General admission includes a souvenir wine glass and tastings of 20-plus wines, with VIP tickets offering exclusive perks and indoor amenities. More info: linganorewines.com | 301-831-5889
Photo by Josh Davidson
Annapolis Powerboat & Sailboat Shows
Each October, Ego Alley and Annapolis Harbor transform into a boater’s paradise as floating docks create a bustling temporary marina. The Annapolis Powerboat Show, held October 2–5, and Annapolis Sailboat Show, held October 10–14, bring together the newest boats making their debut alongside cutting-edge accessories, equipment, and apparel. Whether you’re a seasoned captain, an avid angler, or simply curious about life on the water, this iconic event invites you to stroll the docks, explore the latest in boating, and connect with fellow enthusiasts in the heart of downtown Annapolis. More info: annapolisboatshows.com | 410-268-8828
GiGi’s Playhouse Pickleball Tournament
Grab your paddle and join GiGi’s Playhouse Annapolis for a fun-filled Pickleball Tournament on Sunday, October 5, at 9 a.m. Hosted at The PutAway Severna Park in Millersville, this community event brings players together to compete, connect, and support GiGi’s Playhouse programs for individuals with Down syndrome. Whether you’re a seasoned player or new to the sport, it’s a great way to get involved in a cause that inspires and empowers. More info: gigisplayhouse.org/annapolis/pickleball-tournament
World Is Your Oyster Fest 2025!
Raise your glass—and a half shell—on Thursday, October 2, from 5:30 to 9 p.m. at the B&O Railroad Museum in Baltimore. This 21-plus celebration features the Bay’s best oysters and seafood, handcrafted cocktails, a lively vendor village, and the Tito’s Handmade Vodka Shucking Competition. Learn to “Shuck Like a Pro,” enjoy live music, and discover how oysters are helping to restore the Chesapeake Bay. More info: oysterrecovery.org | 410-990-4970
U.S. National Oyster Festival
The Annual U.S. Oyster Festival returns to the St. Mary’s County Fairgrounds in Leonardtown on Saturday and Sunday, October 18–19. Hosted by the Rotary Club of Lexington Park, this weekend tradition serves up fresh local oysters every way imaginable—raw, fried, grilled, steamed, and more. Highlights include the exciting oyster shucking competition, plus live music, artisan vendors, and family-friendly activities throughout the fairgrounds. With over 500 miles of shoreline to celebrate, this Chesapeake tradition is a must for seafood lovers of all ages. More info: visitstmarysmd.com/usoysterfestival
Art @ The Park’s 35th Anniversary
Celebrate 35 years of creativity at Art @ the Park, held Saturday and Sunday, October 11–12, from 10 a.m. to 4 p.m. at Quiet Waters Park in Annapolis. This beloved festival showcases ceramics, woodwork, photography, jewelry, paintings, and more, alongside live music, performances, artist demonstrations, and family activities. Food trucks keep the energy high, and leashed pets are welcome to join in the fun. Admission is just $6 per vehicle, rain or shine, making it the perfect autumn outing for art lovers of all ages. More info: fqwp.org
Chesapeake Film Festival
The Chesapeake Film Festival takes place October 10–12 in historic downtown Easton. The Festival’s top screenings will take place at the beautifully renovated Ebenezer Theater, the Academy Art Museum, and the Talbot County Free Library. For the full list of feature films, shorts, tickets, and more information visit the website. More info: chesapeakefilmfestival.com
100 Plates Dinner
Join Haven Ministries on Saturday, October 4, from 5 to 9:30 p.m. at the Four Seasons Community Clubhouse in Chester for an inspiring evening to combat hunger. Enjoy a thoughtfully crafted dinner while supporting Haven Ministries’ vital programs—shelter, food, clothing, education, and resources. Sponsorships begin at $250, and guests are encouraged to contribute to the silent auction with experiences, sports tickets, art, spirits, or wine. More info: event.auctria.com
OysterFest
The Chesapeake Bay Maritime Museum hosts its annual OysterFest on Saturday, October 25, from 10 a.m. to 4 p.m. in St. Michaels. This fall favorite celebrates the Bay’s beloved bivalve with oysters prepared every way imaginable, plus other local fare, craft beer, and spirits. Guests can enjoy live music, children’s activities, and a full schedule of demonstrations and presentations. Highlights include the popular oyster stew competition, an oyster slurp-off contest, and plenty of Chesapeake delicacies from local vendors. With fun for all ages, OysterFest is a can’t-miss celebration of Bay culture and cuisine. More info: cbmm.org
Mid-Atlantic Small Craft Festival XLII
The Chesapeake Bay Maritime Museum hosts the 42nd annual Mid-Atlantic Small Craft Festival from Friday–Sunday, October 3–5, in St. Michaels. This family-friendly gathering features dozens of unique vessels, from sailing skiffs and rowing shells to kayaks, canoes, and one-of-a-kind boats, with many displayed on the water. Guests can stroll the waterfront, meet boat owners and builders, and cheer during the lively Saturday race on the Miles River. Festival admission includes access to vote for the People’s Choice Award, with winners announced Saturday evening. More info: cbmm.org
