Experience a Picturesque Fall in the Hamptons

With a reputation as a quintessential East Coast summer retreat, New York’s Hamptons still shine easily in any season—but our favorite may just be fall, when the warmer-weather crowds disperse and Mother Nature offers tell-tale signs of cooler temperatures on the horizon. Autumnal hues reveal themselves among the foliage on a leisurely bike ride, or along the banks of a laid-back kayak paddle.

“It’s easier to explore the Hamptons in the fall, when you don’t have the crush of traffic. You can go kayaking, wine tasting on the North Shore—there’s just so much to do that doesn’t involve the beach,” Katie Lee, a television food critic and author, told luxury lifestyle brand DuJour.

An extended stay in the Hamptons—perhaps for the entirety of autumn—can offer a respite that’s both restorative and fun. And it’s now easier to do than ever with Inspirato’s new JauntLiving option, offering long-term stays at our residences, from two weeks all the way up to a year. Read on for Inspirato’s guide to some of the best places to stay, play, and eat on your extended stay in the Hamptons in the fall.

Where to stay

Nestled within the town of Southampton, the Boathouses at Canoe Place Inn offer a sophisticated home base for exploring the Hamptons in the fall. Inspirato’s 18 chic-but-cozy accommodations sit along the picturesque Shinnecock Canal, with views that beg to be enjoyed with a glass of local red—perhaps found on a Canoe Place-curated wine tour.

Depending on whom you’ll be traveling with and how much space you’ll need, the residences range from two to three bedrooms. Private decks and serene canal views will make leaving your unit difficult, but Canoe Place’s top-tier amenities offer a draw of their own. A heated outdoor pool that’s open until mid-September is surrounded by comfortable chaise lounges, while the resort’s outdoor fire pit is the perfect cozy retreat as temperatures start to cool. On-site dining and drinks are available, too. (See more below.)

One of the best parts of an extended stay is the opportunity to unwind that isn’t afforded in our typical day to day. Even if you choose to—or must—work remotely throughout your extended Hamptons vacation, you’ll still have more chance to pamper yourself than you might have at home. And you needn’t even leave the property to do so: An upscale ONDA Spa is just steps from your residence. Indulge in treatments like ice therapy, a 3-in-1 advanced hydra-facial, or a volcanic clay body mask throughout your stay and let the healing effects blossom.

What to do

Between your Care team and the on-site team at Canoe Place, curated excursions are easy to come by—some of the most popular include deep-sea fishing and winery hopping. While the former will leave you in pursuit of marlin, mahi, tuna, flounder, and even shark, the latter will leave you in pursuit of East Coast varietals like merlot, chardonnay, and cabernet franc. Check with your Concierge for outfitter and vineyard recommendations. (Some of our favorite wineries are Wölffer Estate Vineyard and Channing Daughters—both on the East End and a 25-minute drive from Canoe Place.)

On balmier days that still hold tight to the lingering heat of summer, a hike through Shadmoor State Park is a great way to get the heart pumping. The park’s 99 acres offer bluffs with postcard-worthy vistas and freshwater wetlands that’ll have you reaching for your binoculars to spot the bird life that roosts around them. Shadmoor is also home to more than 2,400 feet of oceanside beach, accessible via myriad pathways and hiking trails.

A chillier day, though, offers the perfect opportunity to peruse Parrish Art Museum, a Hamptons mainstay for those who love nothing more than losing themselves within a gallery. Long-standing exhibits includes Another Justice: US is Them in which artist Hank Willis Thomas honors individuals that play a crucial role in our society, but don’t often get recognized or remembered. And on display from fall 2022 into April 2023, Kahlo: An Expanded Body is a multi-gallery exhibition that explores the medical history of the eponymous artist and the lifelong impact it had on her work.

You’d be hard-pressed to find a more autumnal activity than apple and pumpkin picking, and you can do both in the fields of Milk Pail’s farm. Showcasing over 20 varieties of apples and over 60 varieties of pumpkins, gourds, and squash, you’ll feel compelled to grab your basket upon arrival and get straight into plucking your favorites. Don’t leave before stopping in to the on-site market to grab a hot coffee, cider, or fall-inspired treat.

When temperatures finally plummet for the season and winter arrives in full, Buckskill Winter Club provides visitors with the Hamptons’ only NHL regulation-sized ice rink. Take a lesson in figure skating, join in on one of their ice hockey programs, or simply get out on the ice and free skate. After working up a sweat, head inside to the club where you can cozy up by the warm fire, hot chocolate in hand.

And if you’ll be staying for the holidays, Canoe Place Inn offers specially curated holiday experiences. Featured activities include cooking classes such as latke-making and gingerbread house-decorating under the direction of high-end chefs.

Where to eat

With reservations much easier to snag in the shoulder season, the Hamptons’ array of culinary offerings are at your fingertips during the fall. From fresh lobster and Italian food to the perfect cozy takeout meal, some of the most sought-after eateries in the Hamptons are best enjoyed with fewer crowds.

Good Ground Tavern is the closest to home, tucked right within Canoe Place. With Mediterranean fare split among an intimate dining room, tavern-style bar, and cozy patio space, it may easily become your go-to dinner spot throughout your stay.

For more laid-back and quintessentially East Coast fare, the Lobster Roll—known simply and affectionately as LUNCH—is a can’t-miss stop on any Hamptons culinary tour, with its new Southampton location now open year round. Its retro flair and toasty, buttery New England-style rolls are a local staple.

On a more upscale evening, indulge in elevated Italian dishes at Il Buco al Mare. Feast on coastal and seasonal ingredients cooked to perfection by a classic woodburning oven. Or, for more Mediterranean options with a dash of Eastern flair, O by Kissaki offers a lively dining room where you can experience the elegant and unique flavors of Japanese-Italian fusion cuisine.

And if you’d prefer to cozy up and enjoy takeout back at Canoe Place, look no further than Almond, 20 minutes east in Bridgehampton. With a rotating weekly menu of Malaysian, Mediterranean, and Moroccan fare, you’ll be determined to try it all.

Whether you’re looking to get away for a few weeks or a full season, Inspirato’s residences at Canoe Place Inn offer the ideal retreat for a long-term stay in the picturesque Hamptons. Find comfort and well-needed respite in a long, luxury stay and make yourself at home somewhere new with JauntLiving.