When most people think of the Hamptons, they picture long summer days at the beach. But locals know: fall in the Hamptons is when the East End slows down, the light turns golden, and the crowds thin out. It’s one of the most magical times of year to visit.
If you only had one day to experience autumn here, this Hamptons fall itinerary is exactly how to spend it.
Morning in the Hamptons: Coffee, Donuts & a Beach Walk
Start your morning at Grindstone Coffee & Donuts (https://www.grindstonedonuts.com/) (locations in Sag Harbor and East Hampton). A seasonal pumpkin latte and one of their famous warm donuts are the perfect start to a crisp fall day.
Take your coffee to go and head straight to the beach. In autumn, the shoreline is quiet and serene, with golden light and cooler air that makes the ocean feel even more striking. If you’re lucky, you might even spot dolphins or whales offshore.
👉 Looking for more local beaches? Check out our Hidden Gems guide to the Hamptons (#).
Late Morning: Apple & Sunflower Picking in Water Mill
Fall wouldn’t be complete without a trip to an orchard. Head to Seven Ponds Orchard (https://www.sevenpondsorchard.com/) in Water Mill for apple picking and sunflower fields. It’s family-run, relaxed, and ideal for both families and couples who want a true Hamptons autumn experience.
If you’re planning your trip with kids, explore our Family-Friendly Hamptons Mini Guide (#) for more ideas.
Afternoon: Vineyard Lunch at Wölffer Estate
No fall trip to the Hamptons is complete without a stop at Wölffer Estate Vineyard (https://www.wolffer.com/) in Sagaponack. In October and November, the vines turn shades of gold and amber, creating a picture-perfect backdrop.
Order a crisp white or their iconic rosé and pair it with light bites on the terrace. Sitting among the vines with the autumn sun overhead is pure Hamptons magic.
Evening: Shopping, Cocktails & Cozy Dinner in Sag Harbor
Spend the late afternoon strolling through Sag Harbor Village. Its charming shops, boutiques, and historic streets are even prettier framed by fall leaves.
As the sun begins to set, head to Baron’s Cove for happy hour cocktails around the fire pits. Overlooking the harbor, it’s one of the coziest spots in town this time of year.
When it’s time for dinner, book a table at Tutto il Giorno in Sag Harbor. With candlelight, rustic Italian dishes, and an inviting ambience, it’s one of the best restaurants for a cozy Hamptons fall dinner.
Nightlife: Music & Dancing at The Stephen Talkhouse
End your day with live music in Amagansett at The Stephen Talkhouse . This legendary venue is known for its intimate atmosphere, energetic crowds, and local vibe.
There’s no better way to experience Hamptons nightlife in the fall than dancing and singing along to live music here — a tradition locals swear by year-round.
Final Thoughts: Why Fall in the Hamptons Is Worth the Trip
The Hamptons in fall offers the perfect blend of seasonal activities, cozy dining, and coastal charm. From apple picking and vineyard lunches to firelit cocktails and live music, this itinerary captures the very best of the East End in autumn.
Whether you’re visiting for the first time or returning after summer, one thing’s certain: fall might just be the most magical season in the Hamptons.
For more inspiration, explore our 100 Hidden Gems & Must-Visit Places in the Hamptons series on Instagram and stay tuned for our upcoming Fall Guide to plan your perfect East End getaway.