Singles Long Island Vineyards ♫ Wine Tasting + Lunch Jamesport
Wine tasting and lunch at Jason's Vineyard in Jamesport for singles of all ages, with live music and staff helping break the ice. The vineyard sits on Main Road along the North Fork wine trail, so you can hit other tasting rooms before or after. Bring your own transportation—it's out east but worth the drive if you're tired of dating apps.
Wine tasting and lunch at Jason’s Vineyard in Jamesport for singles of all ages, with live music and staff helping break the ice. The vineyard sits on Main Road along the North Fork wine trail, so you can hit other tasting rooms before or after. Bring your own transportation—it’s out east but worth the drive if you’re tired of dating apps.
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Read before you go
- town spotlight Sayville Village: A Local's Guide for 2026 Sayville Village — the South Shore walkable downtown that locals refuse to gentrify, with restored 19th-century Main Street, the Sayville Cab Company since 1958, the Sayville Restaurant Group anchors (Casa Luis, Cull House), the Saturday Farmers Market on Foster Avenue, the Fire Island ferry terminal at the harbor, and an annual event calendar that runs from Memorial Weekend Classic Car Show through Holiday Stroll. Walking distance from the LIRR. The slow-paced South Shore village that works.
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- seasonal What We're Tracking: The Long Island Summer 2026 Calendar Takes Shape The Editors' Memorial Weekend reset on what we're tracking for Long Island summer 2026. Programming announcements, venue updates, the new restaurants worth a drive, the festivals that bumped their dates, and the East End rhythm shifts. Updated weekly through Labor Day.