It’s no secret that the Hamptons is one of the hottest summertime escapes on the East Coast. And if you’ve ever been to New York’s celeb hideaway, you know that it’s lit — even without Diddy’s now defunct annual all-white party. If you’ve always wanted to go, but are looking for less crowds and more reasonably priced hotel stays, escaping to the Hamptons in the fall is a lovely and lowkey way to spend a weekend.

Especially underrated, the Hamptons in the fall offers vineyards that are still harvesting their last crops and pumpkin patches for family fun. To help you plan your Hamptons fall getaway, we’ve outlined a few must-do experiences — great for time with your boo, your girls or even as a solo escape.


First things first, you’ll want to visit the Hamptons newest property, The Roundtree, Amagansett. This 15-room boutique hotel features 5 stand-alone private cottages perfect for a secluded Hamptons getaway. Book a private BBQ dinner to have The Roundtree team arrange groceries with local ingredients and bring in a private chef to do the grilling. The property just rolled out the Work Remotely at The Roundtree package to make a serene office space away from home with unlimited coffee, snacks and office supplies.

Looking for a touch of luxury? Marram’s 96-room boutique resort is packed with amenities that make it perfect for a fall visit. From guided nature walks, complimentary cruiser bikes, group meditations and s’mores by the fire pit, you’ll want to make this your home away from home during quarantine. Looking for something a little more intimate? Marram’s sister property, Journey is a rustic, contemporary sanctuary in the Hamptons, perfectly situated between the villages of East Hampton and Amagansett.


It wouldn’t be a trip to the Hamptons without a visit to The Lobster Roll — which is also affectionately known as Lunch. Dubbed “the best lobster roll” in the Hamptons, you’ll want to see what all the hype is about and whether it rivals our friends in the Chesapeake Bay. Whether you like a lobster roll cold or hot, smothered in mayo or lightly brushed with butter, this popular lunch spot will do just the trick.

For this past season, Marram’s culinary concept, Mostrador Marram partnered with il Buco to offer Mediterranean fare, with a very specific Montauk feel, which was the brainchild of restaurateur Donna Lennard and Chef Justin Smillie. The East End offering of the celebrated NoHo restaurants Il Buco and Il Buco Alimentari e Vinetari offered house made pizzas, as well as a four-course prix-fixe menu featuring fresh, locally inspired dishes, in a laid-back beach environment.


What can be better than getting into the autumn spirit in the Hamptons? Grab the kiddies and head to Milk Pail’s fields in Water Mill for apple and pumpkin picking galore. Don’t worry — if picking pumpkins isn’t your thing, you’ll at least want to go for the warm apple cider and donuts (because, who can say no to that?). And if you’re looking for more things to do with the kiddies, head to Hank’s Pumpkintown, for an afternoon of activities, such as a corn maze, playground, candy apples and more.

The Hamptons in the fall isn’t just about the kids either. There’s plenty of “adult” activities, and on the East End of Long Island you’ll find plenty of them. With more than 60 wineries, you can sip in delight at your favorite red, white or rose option. And if you’re looking for a bit of adventure, lace up your sneakers for a hike in gorgeous Shadmoor State Park or ride around town with bike amenities at Roundtree, Journey or Marram.


Loading the player...