Seasons · 5 min read
What's Happening on the Long Island Wine Trail in September
September is the best month to taste on Long Island. Period. Harvest East End anchors the calendar, the crush pads are alive, and the weather is the year's most reliable.
What's happening on the wine trail in September
_By Hollis Cooper — updated for the September 2025 season._
September is the best month to taste on Long Island. Period. Harvest East End anchors the calendar, the crush pads are alive, and the weather is the year's most reliable.
Below are the 2–3 things actually worth driving out for this September, broken out by region. Dates and lineups change year to year — confirm on each winery's site before you book — but these are the recurring events and seasonal pours I plan my own September around.
North Fork
- Harvest East End (typically the second Saturday) — the region's marquee annual benefit, hosted at a rotating North Fork winery; the single best night to taste across producers in one place.
- Crush-pad visits — every North Fork winery is bringing in fruit; Macari, Bedell, Lenz and Paumanok will all show you the sorting line if you ask.
- September shoulder midweek — Tuesday/Wednesday after Labor Day through end of month is the best tasting window of the year.
For September North Fork itineraries, see the North Fork day trip guide and the first-time visitor's guide. Browse the wineries directory to build your own route.
The Hamptons
- Channing Daughters harvest tastings — the cellar is busiest and the small-lot conversation is at its best.
- Wölffer Estate harvest dinners — paired-wine dinners typically run on select September weekends.
- Hamptons International Film Festival kickoff — late-September dinners at The American Hotel and Nick & Toni's are bookable but tight.
For September Hamptons planning, see the Hamptons wineries overview and the hotels & stays guide for nearby rooms.
How I'd plan a September weekend
If you're putting together a single weekend on the East End this September, the move is to anchor Saturday on one fork and Sunday on the other. North Fork Saturday lets you string together three winery visits at a comfortable pace — start at one of the producers listed above, break for lunch in Greenport or on Love Lane, and finish at a Sound-side tasting room for the late-afternoon light. Sunday in the Hamptons is best built around one major Wölffer or Channing Daughters visit plus a long lunch in Sag Harbor before the drive home.
Reserve every tasting in advance. Even in the shoulder months the better seated experiences fill up by Thursday. And if you're staying over, book the room before the tasting — the hotels guide has the full lineup by town.
What's next
Next month's edition will cover the events and seasonal pours worth planning around in the following weeks. In the meantime, the Long Island wine events calendar tracks the bigger dated happenings, and the seasonal guide collects every month-by-month edition in one place.