September – November · Seasonal guide
Fall on Long Island wine country
Harvest, foliage, and the most cinematic season on the East End. Fall is the peak season for Long Island wine country: harvest in the vineyards, pumpkins on every farm stand, and Route 25 lit up in red and gold. Weekends are crowded but worth it — and weekdays in October are arguably the single best time of year to visit.
A weekend in fall
- Friday: Arrive late, harvest dinner at a vineyard.
- Saturday: Three harvest tastings + Riverhead pumpkin/apple stops.
- Sunday: Slow foliage drive down Route 25 to Greenport, ferry-watching and home.
Suggested stops
- Harvest tastings — Watch fruit come in while you sip.
- Riverhead farm stands — Pumpkins, cider, apple-picking.
- Greenport finish — Foliage, harbor and an oyster lunch.
FAQ
When is harvest on Long Island?
Long Island grape harvest typically runs from early September through mid-October, depending on varietal and vintage.
When does Long Island fall foliage peak?
Peak color along the North Fork usually lands in the last week of October and first week of November.