The Hampton Classic has come and gone, unofficially signaling the end of summer out East—and the start of Hamptons fall fun. The Hamptons is home to some of the most serene trails, burgeoning art scenes and delicious dining destinations. As the heat and humidity whisks away, it’s prime time to enjoy all the beauty tucked away on the South Fork.
White Fences Inn, Water Mill
This Long Island inn is a luxurious home away from home situated between Water Mill’s chic boutiques and Southampton’s museums and beaches. Get cozy in one of their modern suites with gas fireplaces and heated bathroom floors as the temperature starts to cool down. The ever-changing homemade breakfast menu always offers something savory with a hearty kick. Think berry baked oatmeal or Nutella banana nut muffins for the ultimate pick-me-up. Go.
The Mill House Inn, East Hampton
The Mill House Inn is a B&B that puts an emphasis on R&R. Pick up one (or more) of the curated cheese and charcuterie plates or snickerdoodle cookies at the ‘Nack Bar and bring it back to a uniquely designed room with stunning views of Old Hook Mill. Bonus: Dogs are welcome, meaning your super-busy pals can come along for the ride without having to worry about finding a petsitter for a few days. Go.
Union Cantina, Southampton
Approachable, everyday cuisine with a Mexican flare comes with the territory at Union Cantina. Try Chef Scott Kampf’s deconstructed enchiladas for the ultimate comfort dish. Crunchy corn tortillas are stacked with three layers of fresh corn, chicken, black beans and herb-infused spices. Kampf tops the tower with a scoop of pico de gallo and a chunky guacamole spread to extinguish some of the initial blaze. Go.
Swallow East, Montauk
New American small plates are the signature style of this hip eatery. Entrées like butternut squash cappuccino soup, mac & cheese with orzo, coconut curry mussels and Angus sliders with tomato jam scream relief on a chilly evening. Go.
Wölffer Estate Vineyard, Sagaponack
The 55-acre vineyard is a must-stop on the Hamptons wine trail. Wölffer grows Cabernet Franc, Cabernet Sauvignon, Chardonnay, Merlot and small lots of Trebbiano, Pinot Noir and Vignole. Winemaker/Partner Roman Roth uses only estate-grown or locally sourced fruit for his wines, and New York State apples from Halsey Apple Orchard for the ciders you’ll be tasting this fall. Go.
Dockers Waterside Marina & Restaurant, East Quogue
Fish lovers rejoice—this nearly 30-year-old Hamptons mainstay boasts sea-to-table service. Treat your taste buds with an order of the fish tacos that are made with swordfish in a hard shell or the ahi tuna BLT as you dine at one of the two waterside living rooms or three bars. Go.
Quogue Wildlife Refuge, Quogue
Relish in the crisp autumn air by strolling through the 305-acre nature preserve that is home to bobcats, owls, falcons, eagles and other native New York animals. It is the quintessential setting for downtime and reflection overlooking Pine Barrens, bogs, wetlands and a tidal estuary. Go.
The Watermill Center, Water Mill
Broaden your horizons in the Hamptons and attend some of the talks and lectures by leading voices in the arts, sciences and humanities. There are also special exhibitions inspired by a key proponent in the world of experimental theater, founder Robert Wilson, that share emerging artists work with the community through open rehearsals. Go.
Camp Hero State Park, Montauk
Keep it simple at The End with early sunsets, warm tea and big sweaters. Camp Hero is a 415-acre park that is home to maritime forests, an extensive piece of beachfront along the Atlantic Ocean and a historic military installation. Immerse yourself in the sweeping system of trails available for hiking, biking and horseback riding. Go.