East End Fall Festivals Entertain & Amaze in 2025
Autumn is a great time to be on the East End, especially when it comes to the many fall festivals in the Hamptons and North Fork!
EAST END FALL FESTIVALS 2025
San Gennaro Feast at Lenny Bruno Farms
This spectacular two-day event celebrates Italian-American culture, delicious cuisine, and the beauty of the farm. Admission includes access to a vibrant vendor market and food trucks, where local vendors will showcase their culinary art using the freshest vegetables right from the farm. Guests can immerse themselves in jumbo garden games, taste beer and wine from local breweries and wineries, ride on pedal push tractors for the little ones, and enjoy meet and greets with farm animals. Families with children, as young as toddlers, can play in multiple playground areas designed to keep the little ones entertained and happy throughout the day.
Lenny Bruno Farms, 740 Wading River Road, Manorville. $10. 11 a.m.–6 p.m. Sept. 20-21.
The East End Seaport Museum hosts its 35th annual Maritime Festival, bringing thousands of visitors to Greenport Village’s Mitchell Park for a weekend celebrating the region’s nautical heritage. Among the festival’s biggest draws are the visiting vessels, including tall ships at Mitchell Park Marina, and the historic oyster dredge Ida May, a replica of the first engine-powered dredge built in 1925, will be open for tours throughout the weekend and offer a Saturday evening sunset sail. Other highlights include a parade on Saturday, Coast Guard demonstrations, classic wooden boats, ice boats, the annual Blessing of the Waters and the Merry Merfolk contest.
Mitchell Park, Greenport. Free to enter. 10 a.m. to 5 p.m. Sept. 20-21.
Country Fair is a longstanding tradition at Hallockville, and this year is extra special as they celebrate 50 years as an organization. They will have all the old favorites you have come to love with demonstrations by traditional craftspeople, historic house tours, music, children’s activities and fabulous bake sale. There will also be historical cooking demonstrations, Spirit of Long Island Drill Team horse performances, pony rides, food and beverage trucks, vendors and more! Plus, Long Island Antique Power Association tractor pulls and sawmill demonstrations.
Hallockville Museum Farm, 6038 Sound Avenue, Riverhead. $12. 10 a.m.–4 p.m. Sept. 27-28
The Riverhead Townscape Committee, alongside the Town of Riverhead, presents the 47th Annual Riverhead Country Fair, a cherished fall tradition celebrating the town’s agricultural and community heritage. Set in downtown Riverhead and the Peconic Riverfront, this festive fair features carnival rides, food vendors, artisan booths, agricultural, homemaking, and needlecraft competitions, live music, antique tractors and machinery displays, farm animals with pony rides, and artisan demonstrations. Attendees stroll Main Street between Griffing and Maple avenues, enjoying a lively showcase of local spirit and craftsmanship.
Main St. & Peconic Riverfront, Riverhead. Free admission. 10 a.m.–5 p.m. Oct. 12
Scarecrow Contest and Fall Festival at The Shoppes at East Wind
Visit The Shoppes at East Wind for fall family fun, including the annual Scarecrow Contest and a weekend Fall Festival. Families can build funny, spooky or themed scarecrows, with public voting open Sept. 27–Oct. 26. The contest is free and open to all, with registration due by Sept. 20. All scarecrows will be displayed throughout October, culminating in a grand showcase at the Safe Trick or Treat Halloween event on Oct. 31.
The Shoppes at East Wind, 5768 Route 25A, Wading River. Free. 10 a.m. Sept. 27–Oct. 31.
SouthamptonFest highlights the fall season with family fun, history and the arts, showcasing the Village of Southampton and its many offerings. The celebration features arts and crafts, live entertainment, sidewalk sales, shopping, pumpkins and the popular Chowder Contest.
Southampton Village, Jobs Lane, Southampton. Free. Various times Oct. 4.
Celebrate the season at “The End” of Long Island during the Montauk Chamber of Commerce Fall Family Festival. The weekend features music, local brews, Oktoberfest foods, food trucks, auctions and a full farmers market. Families can also enjoy games, bouncy houses and obstacle courses.
Montauk Village Green, Main Street, Montauk. Free. 11 a.m.–5 p.m. Oct. 11–12.
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