Every October, just as the summer crowds fade and the light turns golden, the Hamptons International Film Festival (HIFF) transforms our quiet villages into a vibrant celebration of cinema. Whether you’re a seasoned festival-goer or just looking for a special way to experience the Hamptons in the fall, here’s everything you need to know.

The Hamptons has a rhythm all its own. The light shifts, the crowds ebb and flow, and with each new season, the East End reveals a different side of itself. Over the years, we’ve found that some of our most treasured memories weren’t made in the height of summer, but in the quiet, in-between moments — a golden hour walk through empty streets, a chilly sunset at the beach with blankets in tow, the first fire crackling in the fireplace.

Fall in the Hamptons is a season unlike any other. The crowds thin out, the leaves turn golden, and the East End comes alive with community traditions that bring locals and visitors together. From wine harvests to Halloween parades, these events are the heart of autumn out East. If you’re looking for things to do in the Hamptons this fall, here are the traditions we look forward to most.

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.

This summer, my 100 Hidden Gems & Must-Visit Places in the Hamptons series took off in a big way — and so many of you joined in on the adventure. From iconic beaches to buzzy new restaurants, certain reels went viral and became the places everyone was talking about.

Block Island might only be a short ferry ride from Montauk, but it feels like another world. Charming, walkable, and packed with classic New England summer vibes, it’s one of our favorite family getaways. On our most recent trip, we brought the kids along for the first time — and it was surprisingly easy. Here’s how we spent two days on Block Island, plus our best tips for making the most of your visit.

On Friday, August 15 at 5:30 PM, the fields of Amber Waves Farm in Amagansett will come alive with the sound of music, the smell of sizzling food, and the buzz of friends gathered under the summer sky. This isn’t just any Friday night — it’s the Amber Waves Hoedown, a one-night celebration of community, flavor, and the future of local farming.

Five experiences to savor before the season fades

Somehow, it’s already August, and summer in the Hamptons is doing that thing it always does—flying by. Before you trade beach bags for blazers, here’s a short and sweet bucket list of local adventures to squeeze in while the days are still long and the water’s still warm.

Montauk isn’t short on places to relax, but there’s a new spot that’s raising the bar for self-care on the East End: Omayo Studios.

Right in the heart of Montauk, this polished, sunlit space has quickly become the go-to for locals and in-the-know visitors looking to move, recover, and recharge—all without bouncing between multiple locations.

There’s something special about September in the Hamptons.

The summer crowds have thinned, but the magic hasn’t gone anywhere. In fact, some of the best days of the season happen after Labor Day—when the energy slows, the beaches stretch out quiet and golden, and the mornings carry just enough crispness to remind you fall is on its way.

If August is a celebration, September is a sigh of relief—in the best possible way.

If you’ve spent any time in the Hamptons, you already know: the chicken salad from Round Swamp Farm is iconic. It’s creamy, herby, just the right amount of tangy—and somehow always gone before you even think to portion it out.

But when I need a lot of it—like for a beach picnic, a backyard lunch, or a crowd of hungry kids—I make it at home. This version is inspired by the original, with the same smooth texture and summer-perfect flavor. It’s not a replacement (we’re still loyal to Round Swamp forever), but it’s the next best thing when you need enough to go around.

There’s something about a Hamptons sunset—it stops you in your tracks and makes life feel slower, softer, a little more magical. Here are five favorite spots where locals go to soak it all in:

You might think everyone knows Wölffer Estate—it’s the most famous vineyard on the East End, after all. But even after years in the Hamptons, we still meet clients trying to navigate this sprawling, sun‑drenched property and figure out the difference between the main estate and the wine stand. Here’s your guide so you can do Wölffer like a local.

Not every spot that blows up on TikTok or Instagram is worth your time—or your money. But these three? They’ve earned their reputation… with a few ground rules. Here’s how to experience them like a local, skip the tourist traps, and actually enjoy what makes them special.

If you’ve ever found yourself inching through traffic on Montauk Highway or waiting an hour for a table in East Hampton, you’re not alone. While summer weekends in the Hamptons are full of magic, they can also be full of… people.

So what do we do when it’s all a little too much? We skip the scene and head to these relaxed, local-favorite spots—places where the food is incredible, the vibe is low-key, and you don’t need a reservation three weeks in advance.

Here are three of our go-to escapes when the weekend chaos hits:

Crafted exclusively for our golden hour gathering by Paper Plane Cocktail Club, The Quiet Luxury is a tropical-meets-elevated cocktail that perfectly captures the Hamptons in a glass. Elegant, surprising, and just a touch indulgent—exactly how we like it.

There’s nothing quite like golden hour in the Hamptons, and last week’s cocktail party at the FreshDirect Summer House captured that magic perfectly. Together with our clients, collaborators, and friends, we welcomed summer in style—surrounded by blooms, cocktails, lobster rolls, and that unmistakable coastal glow.