Your Fall Guide to Montauk Starts Here

TRENDY: Once an Irish dive bar in the heart of Montauk, The Surf Lodge, now one of the area's hottest spots, stays true to its rustic legacy, but with a nautical twist. The property, scattered with hammocks, surf boards, and sandy outdoor lounges is overrun by Manhattan scenesters in summer, but a peaceful refuge come fall. It’s only a short drive from town (you could walk it on a cool fall day), and concierge drivers will take you and pick you up in the house Lincolns on weekends through early September.

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LUXE: One of the few hotel options open year-round, Gurney's Montauk Resort & Spa is set on a 2,000-foot stretch of private beach with rooms overlooking the water. Take a dip in the indoor seawater pool, catch up on R&R at the spa—complete with Roman baths, rock saunas, and Russian steam rooms—or hang by the fire pit with a cocktail from the on-site Regent Cocktail Club.

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CULTURE FIX: Visit the homestead and studio of renowned abstract expressionist Jackson Pollock and wife Lee Krasner, who called the East End home. Artworks that have been acquired by the museum for more than 30 years (including pieces by Pollock and Krasner) are on display until late October.

NATURE FIX: Located on the very eastern tip of Long Island, Montauk State Park stretches 862 acres, all of which are especially beautiful come fall. Watch the sunrise or sunset over the Montauk Lighthouse, get a peak at Montauk surfers catching waves, and take a not-too-strenuous hike on the park’s grounds. If you're feeling extra, you can explore the beach on horseback at Deep Hollow Ranch, where ranch hands will guide you through the sandy beaches of the coastline. Hither Hills State Park has a more intense 10+ mile trail, if you're up for that.

FALL FIX: Open Labor Day weekend through October, visit Milk Pail Market & U-Pick, a family farm and orchard that dates back to 1640. Go apple picking straight from their trees or pick pumpkins and squash from their vines. Stop by the fresh market for homemade pies, honey, and jams.

FOR EARLY EATS: Head over to homey breakfast spot Mr. John’s Pancake House. In the summer months there's a line out the door, but fall should ensure a shorter wait. Order the hot apple flapjacks or the crepe suzettes with strawberry jam and signature Cointreau suzette sauce.

FOR DINNER: Hit up Harvest on Fort Pond, a favorite for rustic Italian fare inspired by fresh Montauk seafood and homegrown produce from their veggie and herb garden. Order the endive salad with gorgonzola, apples, pecans, and red wine vinaigrette along with the swordfish piccata. Since you are by the beach, another great option is fisherman owned Inlet, which specializes in fish and shellfish and freshly prepared sushi. For super fun vibes, eat at the Surf Lodge's on-site restaurant, serving up dishes featuring sustainable and local ingredients from farms throughout the North and South Forks. Order a ½ dozen oysters from the raw bar (oysters peak in autumn), a market salad with shaved local veggies dressed with lemon-marjoram vinaigrette, and the trumpet pasta with green beans, sun-dried tomatoes, and fresh grated cheese. You won't be disappointed.

FOR THE BEER LOVER: Montauk Brewing Company, situated in a red brew barn just steps from the beach, is a laid-back spot started by longtime buddies that's open year-round. Visit the tasting room, then hang out on the dog-friendly outdoor patio while sipping on one of the seasonal beers on tap, like the newly released Montauk Pumpkin Ale, studded with spices and subtle hops, Driftwood Ale with malty, nutty, and toasty notes, or the classic, clean, crisp Brew Barn Pale Ale.

FOR THE WINE LOVER: Visit Wölffer Estate's 30-year-old sustainable vineyard, wine stand, and tasting room and try the newly released No. 139 red cider. If you happen to be traveling on the weekend of October 5th, partake in Wölffer’s Annual Harvest Party. The shindig, now in its 26th year, is held on the lawn of the estate and features live music, pony rides, and seasonal dishes. All of Wölffers wines are made with locally-sourced or home-grown fruits, while ciders are crafted using apples from nearby orchards.

FOR THE COCKTAIL ENTHUSIAST: To carry good summer vibes into fall, order up some fun umbrella drinks at Lynn’s Hula Hut, a waterside tiki bar with a bohemian vibe. Chill out in the hammock garden—cocktail in hand, of course—made from naturally infused liquors and matched with ingredients from East End farms, the onsite herb garden, and tropical fruit and spice combos. For a sunset sip, head over to the Montauket, a cliffside restaurant with some of the best views in the East End and a local watering hole year-round. Come for the drinks but stay for the sunsets, said to be some of the best in the area.