When autumn comes to the North Fork, it’s an arrival of not only a new season, but a calendar of events that celebrate the East End’s authentic character, sans crowds. Wineries offer a bevy of activities that take you into the vineyards, to the tasting rooms and beyond, and farm festivals, wine tastings, oyster events and artisan markets carry the spirit of the harvest well into fall. If seaside is your thing, the weeklong Greenport Maritime Festival draws sailors, craftspeople and sea enthusiasts—and “landlubbers”, too!— to the village waterfront in late September. Our annual guide of seasonal events offers compelling reasons to stay beyond Labor Day, return or discover the North Fork for the very first time.
Sept. 11 Though the fall, Suhru & Lieb Vineyards hosts Fridays at the Vineyard with seasonal food, estate-grown wines. 13050 Oregon Road, Cutchogue.
Sept 11 and 12. and weekends through October Wölffer Estate Vineyard hosts Sunset Music at the Wine Stand. Artists include Roses Grove Band, The Fates, Black & Sparrow, Hoodoo Loungers, The Kind Pines. Times vary; check website for details. 139 Sagg Road, Sagaponack.
Sept. 11 and 18. Sustainable Happy Hour at Bridge Lane Wine. Enjoy craft wines in bottle, box, can and keg. 35 Cox Neck Lane, Mattituck.
Sept. 11. Golden Hour at Channing Daughters winery features live music by Lilly-Anne Merat and Chris Befeld. 6 – 8 p.m. 1927 Scuttlehole Road, Bridgehampton
Sept. 12 and 13. Summer Live Music at Bridge Lane Wine, from 2 – 5 p.m. and every weekend through October. Artists include Cassandra House, Nate Charlie, Emy McB, Brandon Gurb, Katt Rardi, Taylor Thomas Lane, Dave March, Dillon Mealy.
Sept. 12. “Scielo in a Bottle” at RGNY. Prepaid reservations for parties of one to 40 includes special tastings of a wine lineup chosen by the winery. $35–$45 pp includes one bottle per two people and snacks. 6025 Sound Avenue, Riverhead.
Sept. 12. Private charter with Bedell on the passenger schooner Bonnie Lynn. 5 – 7 p.m. $220 pp; tickets online.
Sept. 12 and beyond. Live music at Terre Vite North Fork Winery & Vineyard featuring Dorothia Music, Catie Egan, Christiaan Padavan, Deanna Hudson, Jeff LeBlanc, Erin Chase. Reservations recommended for some dates. 1:30 – 4:30 p.m. 250 Manor Lane, Jamesport.
Sept. 13 – 20. Suhru & Lieb holds a weeklong food and wine pairing event for its wine club members at its tasting room in Cutchogue.
Sept. 13. The 20th annual North Fork Foodie Tour includes stops at Castello di Borghese Vineyard, Lenz Winery and Farm wine plus other growers of food and flowers. $35 pp (kids under 12 free). 10 a.m. – 4 p.m. Location map and site list on the website northforkfoodietour.com/2026-locations-speakers.
Sept. 17. Sunset Cocktail Party at Bedell Cellars for Friends of the Southold Free Library. Live music and sustainable wine, local beers, cheeses & charcuterie. 6 – 8 p.m. $60 pp, all proceeds benefit the library. 36225 Main Rd, Cutchogue.
Sept. 17. “The Grapes of Roth” 25th anniversary dinner at the American Hotel in Sag Harbor. The five-course meal featuring a locally inspired menu is accompanied by flights of wine pairings. $250 pp. Limited space; reservations required by calling the hotel (631) 725-3535
Sept. 18. Sunset Wine Cruise with Bedell, featuring Bedell wines and local oysters, $130 per person. Leaves from Greenport, 6 – 8 p.m.
Sept. 18. Annual Harvest Moon Dinner at Sannino Vineyard; 4 courses paired with 4 Sannino Vineyard Estate wines. 6 – 9 p.m. $185 for Wine Club Member; $215 for guests. 15975 County Road 48, Cutchogue.
Sept 19. The Como Brothers perform at Jason’s Vineyard 1 – 5 p.m., part of the ongoing free concert series through September. (1785 Main Road, Jamesport) and at Kontokosta Winery, Sept. 27 at 2 p.m. 825 North Road, Greenport.
Sept. 25. Macari hosts a five-course “Vine and Tide” tasting dinner of local seafood paired with small-batch wines from its Meadowlark North Fork winery. 5 – 8 p.m. $195 pp. 24385 Main Rd, Cutchogue,.
Sept. 25. Kick-off date for the Greenport Maritime Festival, a weekend-long, village-wide celebration of maritime culture, local craftsmanship, food, music. Event schedule is online and includes an oyster shucking contest, the Classic Boat Regatta, Cardboard Boat Races and a Maritime Parade, Pie Eating Contest and other family-friendly activities.
Sept. 27. Candlelight Concert with Lumos in the Bedell vineyards. candlelight string quartet concert with a tribute to ABBA. Wine bar starts at 6 p.m.; concert seating at 7 p.m.
Oct. 1. Music, Vines & Paws, a charity fundraiser featuring live music, wine, and food trucks at Bedell Cellars in Cutchogue, with proceeds supporting the North Fork Animal Welfare League. 5 p.m.
Oct. 4. RGNY’s annual Stomp Party features grape stomping, live salsa music and flowing wine, featuring lunch by Ammiratis on Love Lane and eats by Dos Ositos Paletas! $38.10 – $97.87 pp. 12 – 3 p.m.
Oct. 4. Stomp Party at Bedell. Crush grapes, drink wine and have lunch by Lombardi’s Love Lane. Live music on the pavilion. $75 pp ($55 for wine club members)
Oct. 4. Local Oyster Showcase at Sparkling Pointe, a walk-around tasting experience of six Sparkling Pointe wines paired with live-shucked local Long Island oysters grilled, roasted and fried on site. 3 p.m. $115 pp includes six wines and two dozen oysters. 39750 County Road 48, Southold.
Oct. 8. The Halyard in Greenport hosts its monthly dinner series featuring local wineries and farms. Upcoming parings include RGNY & Hog Farm (Oct 8), and Macari and Deep Roots (Nov. 12). 6 – 9 p.m. $95 pp for five courses.
Oct. 9. Suhru & Lieb’s Friday Night Music Series featuring local talent Artists including Abby Scharff, Julian Love, Paris Ray, Emy McB, Jesse Barnes, Jeff LeBlanc, Cassandra House. 5 – 7:00 p.m. on Fridays through Dec. 18.
Oct. 24. RGNY’s “Help us Harvest” party in two sessions at 10 a.m. and 2 p.m. Learn about sustainable winemaking while picking grapes; enjoy wine, brunch and pro coaching on your picking technique. $87 pp.
Oct. 25. Race for the Greenway 5K race/walk hosted by Long Island Wine Country through Hallock State Park, passing vineyards and the Long Island Sound. Afterward, a wine trail party includes wine samples and other offers. Proceeds go towards the Long Island Greenway Trust for Public Land. 8:30 a.m. Adults entry: $39.48 (increases after Oct. 24) and $13.78 for kids’ “Fun Run.”
Oct. 6. Chefs Against Hunger: Macari Wine Dinner with The Halyard at Tellers Next Door. Newly released wines paired with a chef-crafted multi-course menu. Proceeds to benefit the Long Island Cares food bank. 599 Main St., Islip.
Oct. 31. Paws and Pours Halloween Party at Bridge Lane Wine Tasting Room, 2 – 5 p.m. Every pup dressed in costume (and on a leash), their owner will receive a complimentary glass of wine.
Nov. 7. Día de los Muertos celebration at RGNY. An evening of music, ceremonial fire, wine and tradition. Entertainment by House of Yes $163.13 per person.
