Fall Weekend in Montauk

Where to stay:

Gurney’s Montauk Resort & Seawater Spa - Gurney’s is a Montauk icon with a beachy, yet cozy vibe. This up-scale hotel features rooms that overlook the Atlantic Ocean. Even after the summer crowd leaves for the season, Gurneys still has so much to offer with an indoor heated seawater pool and spa. Our favorite part about Gurney’s is The Firepit, which is an outdoor lounge with views of the ocean and a menu that offers light bites. There are actual fire pits at most tables and the cocktail list does not disappoint.

The Surf Lodge - If you’re planning a Montauk getaway after the peak summer season but before mid-October, The Surf Lodge is a super cool and fun choice. Even in the off-season, TSL is known for its lively flare and always has something going on. It offers a beautiful aesthetic, spacious rooms & a breathtaking sunset view on Fort Pond. The friendly staff will be happy to give recommendations on what to do & where to go. No wonder they call themselves “your home away from home”.

(*The Surf Lodge Restaurant closes for the season by the end of September.)

Solé East - For a laid back and relaxing experience, stay at Solé East, a hotel housed in a landmark American Tudor building. It’s off the main strip in a secluded location, but only a 10-minute walk to the main town. The best part about Solé in the chillier months is its beautiful outdoor garden space with a wood-burning fire-pit. They also have bike cruisers available for rent and a heated outdoor swimming pool if you happen to be there on a warmer fall day.

What to do:

Montauk Point State Park - For the most photographed spot on the East End, head to Montauk’s Point State Park where you can visit the oldest lighthouse in New York State. It offers stunning & scenic views with great photo ops. Even though the Lighthouse Tower is currently closed, the grounds and museum are still open. A fall visit will also allow you to beat the summer crowds.

(*Be prepared to pay an $8 parking fee, along with a separate entrance fee to enter the lighthouse).

Deep Hollow Ranch - If you’re looking for a fun, scenic activity while you’re in Montauk, head to Deep Hollow Ranch, the oldest working ranch in the U.S. The ranch offers a beautiful and peaceful horse ride on a beautiful trail that brings you along the beach.

Wölffer Estate Vineyard - One of our favorite places to spend the afternoon is at the very chic and upscale Wölffer Estate Vineyard. Choose between their indoor tasting room, outdoor terrace, or lawn to enjoy a great selection of wines, including their own famous rosé  “Summer in a Bottle”. We personally enjoy reserving a private table right in between the vines while snacking on yummy meats & cheeses.

The Milk Pail - If you’re visiting between Labor Day and the end of October, head to the Milk Pail Market and U-Pick, a family farm and orchard that has been in business since 1640.  It’s the perfect place for apple and pumpkin picking. Sip hot cider or coffee and check out the market where they sell pies, donuts, homemade ice cream, and more.

Left Hand Coffee - Left Hand is our favorite coffee shop in town. The coffee shop has a rustic-chic vibe and it is the best coffee in Montauk! With an extensive variety of coffee and espresso drinks, you’re sure to get your caffeine fix here!

Where to eat:

Scarpetta Beach at Gurney’s - If you have one night to splurge on dinner, it’s at Scarpetta, located at Gurneys Montauk. Scarpetta is Italian cuisine that is upscale and sophisticated. The restaurant delivers Scarpetta’s signature classics as well as some seasonal dishes and fresh seafood selections. The outdoor deck is beautiful with a panoramic view of the ocean.

Harvest on Fort Pond - The Italian inspired Harvest on Fort Pond is one of Montauk’s top Zagat-rated restaurants and has some of the best seafood out east. The Harvest offers creative cocktails, garden dining, and sunsets over Fort Pond. The portions are family style so come hungry!

Navy Beach - If you make it to Montauk before mid-October, head to Navy Beach for the ultimate beachfront sunset experience. This casual-chic restaurant offers both indoor & outdoor seating, making you feel like you’re on a colorful, luxury yacht. Enjoy some delicious seafood, along with one of their fabulous cocktails or a glass of their specialty rosé. It is surely one of the top five water-view dining spots on the East End. 

(*Navy Beach closes for the season after Columbus Day weekend.)

South Edison - South Edison is a casual restaurant with modern and colorful decor that resembles a beach house. It has a delicious seafood menu and one of the best raw bars in town which includes oysters, shrimp, clams, shrimp, jumbo lump crabmeat, and more. Try their various fish tacos and if you’re pickle obsessed like us, try their signature Pickle Martini.

Where to chill:

Montauk Beach House - The Montauk Beach House is a hotel situated in the heart of downtown Montauk. The hotel describes themselves as having a laid-back East Coast vibe and we agree that their backyard is the *most chill* spot to be at all summer and even into the fall months. The backyard has an outdoor bar with a poolside fire lounge where you can grab a drink and cuddle up with your beau. The best part is it's not limited to hotel guests.

Lynn’s Hula Hut - Stop at Lynn’s Hula Hut for amazing cocktails that will make you feel like you’ve been transported to French Polynesia. A repurposed office trailer, this bamboo bar has a beautiful ambiance with a hammock garden and a view of the marina. Try the Hula Juice which is rum, pineapple, a drizzle of Gosling’s Dark Rum, and a squeeze of lime. No matter what you choose, you will not be disappointed!

Montauk Brewing Company - You’ll know it’s fall in Montauk when the pumpkin-flavored ale is added to the menu. Located in its well-known red barn, the MBC has a delicious selection of brews, along with a very relaxed vibe. Their tag line, “come as you are” embraces the fact that people from all over the world come to visit the brewery. Stop by and be a part of the cool experience!