Seasons · 5 min read
What's Happening on the Long Island Wine Trail in May
May is when the season truly opens. Cab Franc Day on the 4th, rosé brunches all month, and a final shoulder window before the Hamptons crowd arrives in earnest.
What's happening on the wine trail in May
_By Hollis Cooper — updated for the May 2025 season._
May is when the season truly opens. Cab Franc Day on the 4th, rosé brunches all month, and a final shoulder window before the Hamptons crowd arrives in earnest.
Below are the 2–3 things actually worth driving out for this May, 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 May around.
North Fork
- Mother's Day rosé brunches — Macari, Bedell and Pellegrini all run reservation-only Mother's Day services; book by mid-April.
- Cabernet Franc Day (May 4) — North Fork wineries collectively pour their Cab Francs by the glass; the best day of the year to taste through the region's signature varietal in one afternoon.
- Memorial Day weekend kickoff — by Sunday the tasting rooms are full; midweek visits May 27–30 are the sweet spot.
For May 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
- Wölffer's rosé season hits full stride — the lawn at Sagaponack is open and full by mid-month.
- Channing Daughters orange-wine flights — extended Saturday hours and the new vintage skin-contact lineup.
- Sag Harbor Memorial Day brunch — The American Hotel and Tutto il Giorno both pour Long Island whites with the holiday menu.
For May Hamptons planning, see the Hamptons wineries overview and the hotels & stays guide for nearby rooms.
How I'd plan a May weekend
If you're putting together a single weekend on the East End this May, 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.