From a ‘little drinking village with a fishing problem’, to one of the trendiest summer destinations in the country—Montauk has undergone some identity shifts on the surface, but what remains tried and true is its soul, filled with breathtaking natural beauty, a family friendly vibe, and an adventurous spirit. Experiencing Montauk like a local is all about getting outside, exploring, and seeking out authentic experiences to share with friends and family. Come with us to find the freshest seafood, big waves, rocky cliffs, winding trails, live music, and the chillest, most local-centric vibe possible.

RISE AND SHINE

Morning is the time for a coffee and a beach walk—combing the shores for shells and beach glass is how we like to start the morning. Leallo staffer Chelsea is a born-and-bred Montauk girl, and her first morning stop is always Left Hand Coffee. “I’ll go early in the morning to beat the crowds and grab a vanilla oat milk latte before walking the beach.” The ocean is only a block away! All their coffee is organic, fair trade, shade grown, direct trade and Rainforest Alliance Certified.

SURF AND SAND

Hands down, our favorite beach for a stay-all-day adventure is Ditch Plains. Go for the picturesque cliff views, to swim or surf the perfect waves, to watch surfers, or just to snack and nap all day, but always go as early as you can. Chelsea says, “grab your beach chairs, umbrella, and cooler and head down early to get a spot because it gets crowded, but it’s so worth it.” The Ditch Witch is arguably the most iconic food truck on the East End too, so it’s a must for breakfast or lunch. “Try the sesame noodles, they’re the best you’ll ever have” says Chelsea. Just be sure to have your East Hampton Town Resident Beach Sticker if you want to park in the lot.

THE FRESHEST SEAFOOD

Some of the freshest seafood in the world can be found all over Montauk, but for us it’s also about finding the perfect spot with great water views, reasonable prices, and a chill local vibe. Julia and Chelsea both love the upstairs deck at The Inlet. “During lunch you can watch all the local fishermen coming in and out of the harbor, and during dinner you’ve got the most incredible sunset views.” says Chelsea. “The calamari is top-tier and the fluke piccata is 10/10” says Julia. Chelsea’s go-tos are the Spicy Girl and the Lady Slipper sushi rolls. The Inlet has been locally owned by commercial fishermen since 2006, and their motto is “Respect the ocean, harvest the bounty, feed the people.” Perfect.

LAZY AFTERNOONS

From the Inlet, just drive around Lake Montauk to Gosman’s Dock (est. 1943) where staffers Chelsea and Hannah both had some of their favorite childhood experiences. “Walk around the little shops, play in the toy stores, grab some ice cream, and look for crabs over the dock” says Chelsea, “they do free live music in the summer too, bring your chairs and a blanket and get comfy, the kids will love dancing around and letting loose!”

THE GREAT OUTDOORS

There’s no shortage of trails to explore in Montauk—Camp Hero, the Point, Money Pond, Hither Hills, Big Reed Pond Loop. You can see seals, whales, sweeping vistas, dense forests, ruins, dunes, cliffs, and all sorts of wildlife. Meg’s favorite is the trail at Shadmoor State Park. “It’s a gorgeous walk along the dunes that brings you down to the beach.” The overlook at Shadmoor is breathtaking, but keep your little ones close, there’s no fencing in certain areas along the edge. Hannah also loves the Walking Dunes trails off Napeague stretch, “it feels you’re on another planet out in the sprawling dunes, and the kids love to roll down them, but don’t forget your tick/insect repellant at any of the trails in Montauk, especially in the summer!” Local brand 3 Moms Organics, based in East Hampton, makes a really great organic spray for the whole family.

THE MONTAUK EDIT

Compliment the Montauk seascape in breezy 100% pima cotton, in soft summer neutral colors, with pockets for a functional, cool, classic adventure vibe. Pair with walking sandals with arch support and a simple cross-body belt bag and you're ready for anything.

THE MOLLY DRESS WITH POCKETS (SHOWN IN NAVY)

THE SAMANTHA TEE IS CUT LOOSE IN THE BODY

THE SAMANTHA PAIRS PERFECTLY WITH THE CHRISTINE SHORT (WITH POCKETS)

THE POPPY JUMPSUIT IS SUCH A MONTAUK VIBE

BELLA DRESS IS THE BREEZIEST

PAIR THE CASHMERE BEACH LANE HOODIE WITH EVERYTHING