The sleepy town of Montauk is 120 miles from New York City, on the easternmost end of Long Island. Long hailed as the “anti-Hamptons”, the chichi-ness of the Hamptons is slowly creeping in—but nonetheless, the fishing town still maintains its rough, rustic charm. Affectionally known as “the end of the world,” Montauk is home to more than 5,000 acres of parks and beaches, each with a surprising amount of hiking trails and hidden gems. Though the secret’s out on summer weekends in Montauk, we wanted to create an off-season guide for exploring Montauk during fall, when the water is still warm, the beaches are empty, and visitors can enjoy its longtime establishments and its fishing-town roots.

We recently headed out to Montauk to hang out with the folks at Clif Bar for a post-Labor Day getaway they branded a “Watermans Weekend.” To celebrate the release of some new products, the Clif Bar team rounded up some of their favorite photographers and bloggers for a water-sports themed, two-day event. Our group of eight learned to stand-up paddle board, surf, toured an oyster farm, and went for a sunset sail around the harbor. (Not to mention, we also also put in some serious pool time.) After the event was over, we stayed a couple extra days to continue exploring on our own, rounding our our experience and creating  an off-season guide to one of New York’s most beautiful places.

Where To Stay in Montauk: From the Chicest to the Cheapest


We stayed at the laid-back and beachy Solé East Resort, whose location is set back far enough from the main strip to feel like a real getaway. It’s only a ten minute walk into town or the beach, or an even shorter ride down using the hotel’s rental bikes. The 60-room hotel is housed in a landmark American Tudor building with open, bungalow-like rooms; the bathroom is modern and spacious. Larger accommodations include seven garden cabana suites. The big draw here to Solé is its lively outdoor space: with a heated saltwater pool as the centerpiece, encircled by comfy loungers, and a full-service bar and restaurant. At night, bonfires are lit as bands and DJs play poolside, turning the bar into a lively, but laid-back scene. Solé East is open April 1-October 31; other similar seasonal hotels include The Surf Lodge and the Crow’s Nest.

Year-round options are sparse, but certainly not impossible. At the luxurious end of the scale, Gurney’s is stunning. It’s 146 beautifully appointed rooms comes in all shapes, sizes, and prices. For convenience, the property has five dining/drinking venues with an array of foods and beverages; most are open year-round. Aside from the rooms, the highlight is the indoor pool, which is ocean-fed and whose windows overlooks the Atlantic. Taking a dip in the ocean has never been so easy, and the pool is the only one of its kind. If a trip to Gurney’s spa or pool sound enticing, but you stay elsewhere, consider purchasing a spa pass, which is available in the off-season only. Passes include access to the pool, Roman bath, Finnish rock sauna, Russian steam room, and Swiss shower. For more budget-friendly, year-round accommodations, check out Montauk Bungalows, Dune Resorts, Daunt’s Albatross Motel, Sands Motel, Born Free Suites, and Ocean Resort Inn.

What To Do in Montauk: Year-Round Watersports, Hike to the Creepy Military Base That Inspired Stranger Things, Shop For Nautical Vintage Treasures


Even though many hotels and restaurants shut down for the winter season, surprisingly, the water sports continue year-round. We learned to surf (ahem, we both managed to stand up on our boards before wiping out) with Corey’s Wave, whose super-friendly, totally non-judgemental staff gives lessons straight through winter. The website even raves about surfing as a winter spot, comparing the scenic backdrop of winter surfing as “akin to magic.” We wouldn’t imagine it otherwise. Clearly on the same wavelength, Evelyn ODoherty of Mind Body Excursions swears by the off-season too. She offers stand-up paddleboarding excursions year-round, as well as surfing and SUP yoga. For a more passive water experience, check out the sunset boat charter offered by Grey Lady. Split the cost with friends and enjoy a private 39′ yawl ride with your choice of beverages.

Continuing the theme of the outdoors, you might not guess it, but this traditional beach destination has tons of hiking. Check out Hither Hills State Park, which has 10+ miles of trails offering stunning water views from beaches and bluffs. Its trails and sandy paths pass through woodland made of olive, oak, shad and pine trees. A highlight at Hither Hills State Park are the Walking Dunes, where a short trail opens up into a vast expanse of sand dunes reaching up to 80 feet tall. The sand dunes, created by winds carrying sand from the nearby beach, have been slowly creeping over Montauk’s forest and wetlands for hundreds of years and are an extraordinary sight. After the hike, have a picnic at the secluded beach across from the trailhead.

Another must-see for outdoor enthusiasts is Camp Hero State Park. The park sprawls for 425 acres, through heavily wooded areas, beaches and bluffs that are reminiscent of Big Sur. Plus, its also the home of the historic military installation that inspired Netflix hit Stranger Things. (Read: Montauk Project.) From the parking lot, take the trails to the right to get to the radio tower, which looms in the distance. There aren’t many markers, but if you head in the direction of the tower, you’ll eventually get there. A trail on the other side of the parking lot will take you to Montauk Lighthouse. The historic landmark is New York State’s oldest lighthouse, dating back to 1796. To avoid crowds and parking fees, check out Camp Hero after 4 p.m.

Unfortunately most shopping closes in Montauk in the off-season, with few exceptions. But should you find yourself there pre-Labor Day, there’s a handful of shops that stand out from the rest. First up, vintage lovers should check out Melet Mercantile. Owner Bob Melet oversaw vintage buying for Ralph Lauren for years; nowadays, his warehouse sells vintage clothing, accessories, books, maps, and everything else under the sun. Deep Blue Vintage is another great vintage shop, filled with a highly curated selection of womens apparel, ranging from surfer to workwear. Owner Christina says she’ll be open regular hours through October, then the first two weekends of November; it’s all weather-permitting, as the shop is housed in an old garage. Last, check out Whalebone Creative, founded by Jesse Joeckel: surfer, designer, and Montauk native. The Whalebone shop carries apparel, art and surf-related accessories; but they also have a lifestyle magazine, with six issues going to print each year. The shop and magazine come together to create a really cool, approachable lifestyle brand embodying both the “old” and “new” Montauk.

Where To Eat & Drink in Montauk: The Perfect Oyster, Lowbrow Clam Bar to Highbrow Farm-to-Table Italian


Montauk is the biggest commercial port in New York State, and fresh, local seafood is in abundance. We were fortunate enough to tour the Montauk Shellfish Company, the exclusive growers of Montauk Pearl Oysters. At the underwater farm, oysters are grown in their natural habitat then harvested after about two years. If you see them, try ’em! Even if seafood isn’t your thing, Montauk also offers pretty much everything on the spectrum when it comes to food—from low-key food trucks to extremely fine dining. Most restaurants are keen to the whole farm-to-table movement, with menus centered around local ingredients, especially during the height of summer. From year-round to seasonal, here’s some of the best food we could get our hands on.

During summer, there’s nothing quite like breakfast on the beach at Ditch Plains, whose landscape is gorgeous and absolutely packed with surfers. Before you hit the waves, fuel up with a breakfast sandwich at Ditch Wich, a food truck parked just feet from the beach. It offers yummy sandwiches, wraps and patties without the attitude or astronomical prices you’ll see elsewhere in Montauk. Back on the main drag, another great breakfast spot is Mr. John’s Pancake House, offering up your standard greasy spoon fare; bonus points for being open year-round! For lunch, check out Navy Beach, especially if the weather is cooperating. There’s indoor seating, but the outdoor seating is on the beach at this laid-back joint, serving up family-style meals. Clam Bar is another total gem, a little bit outside of town close to Hither Hills State Park, and is completely outdoors. Stick to the specials menu and try the chowder. The Hideaway is a solid option too, whose menu is mostly authentic Mexican, with BBQ available as well. Food is counter-service and complimented nicely with a margarita… or five. Unfortunately both Clam Bar and The Hideaway are seasonal, but have a longer season than most, lasting from April through November.

For dinner, there’s endless options, though most Montaukians we spoke to had similar favorites. Nearly everyone we spoke to recommended Harvest on Fort Pond, who serves farm-to-table rustic Italian fare year-round. It ain’t cheap, but the portions family size and delicious; it’s definitely worth the splurge for a memorable night out. Grey Lady is another top-notch restaurant, with great food, a beautiful interior, and incredible views from their patio. Don’t pass up their daily specials, where seafood was likely caught the same day. Last, you can find some of Montauk’s finest seafood at Inlet, including the famous Pearl Oysters from Montauk Shellfish Company. It’s not open year-round, but it is open through the end of November, re-opening President’s Day weekend in February.

Last, Montauk has some serious institutions when it comes to bars. Our favorite spot was Liar’s Saloon, whose Friday night karaoke plays host to every type of local you could imagine: from the super-preppy, to the surfy-boho hipsters, to long-time locals. Before you go, know that the bar is cash only, with no ATM, and you can expect a line when you get there; capacity is small and it’s a one-out, one-in policy. The mudslide alone makes it worth the wait. If this sounds a little too arduous, head to laid-back tavern The Dock—but don’t let them catch you on your cellphone. Bar rules are as posted: no checks, no yapping mutts, no sensitive drunks, no cell phones, no strollers, no public restrooms, no dirt bags, and no wimps or chickenhawks. So follow the rules, belly up to the bar, and actually say hello to someone. Shagwong is another local establishment, whose location on main street make it a somewhat annoyingly popular spot during high season… But post-Labor Day, it’s a cool place to have a beer and take in the old “man dive bar” decor, which is made up of taxidermy and nautical themed relics. Last, enjoy sunset drinks at Montauket, a restaurant and bar housed in an old 1960’s fishing lodge. To grab a good spot, head over about an hour early or watch from inside, where the wall behind the bar is entirely windows. The spectacular views from this Montauk institution reach across the beautiful Fort Pond Bay—something that no amount of Hamptons money can buy.