At first it was mostly fishermen who headed out to “the End,” unassumingly bringing in their catch of the day a few mere miles from the posh and the famous in the Hamptons. Then came the surfers, bringing a laidback, bohemian air to the relatively secluded tip of the island. Today, Montauk is shared by an eclectic mix of colonizers, blending the best of dive bars, lobster shacks, boutique hotels, indie concerts, foodie spots, cocktail scenes and nature preserves.
It still exudes a more relaxed, gritty style than its neighboring high-end towns, but some of that money and scene has made its way to this eastern retreat. While it may no longer be a completely hidden gem, there are likely a few more years (or decades, if we are all so lucky) of Montauk living in the balance of charm, tasteful indulgence and remote haven. Here’s a head start:
The Crow’s Nest – This isolated spot has the ideal set up: removed from the rest of town, aesthetically furnished rooms, its own small spot on the water, and a respectable food and beverage offering if you decide not to leave the property.
The Surf Lodge – If you don’t mind the “scene” and you want a guaranteed spot for one of their notable summer concerts, this is where you’ll want to stay. Otherwise, you can get a more relaxed experience at this famed spot for brunch, lunch or an afternoon drink.
Solé East – For a low-key spot that still has a touch of beach-vibe luxury.
Eat & Drink
Ruschmeyer’s – A summer camp for grownups, this place offers one of the best meals in Montauk. Stick around after dinner as their large outdoor area, complete with hammocks, lanterns, ping-pong tables and Adirondack chairs, turns into a vibrant nightlife.
South Edison – A standout for many foodie visitors, the informal atmosphere is only surprising in comparison to the superb quality of their menu.
Joni’s Kitchen and Montauk Bake Shoppe – Two very different experiences and menus, but depending on your mood/diet (or if you don’t beat the crowd to Joni’s) both can take care of your breakfast needs.
The Dock – This no-nonsense fishermen and locals dive bar is a step back in time compared to some of the more recently established, trend-setting spots. Enjoy some of the best mussels, beer and old-timer conversations at the bar.
Cyril’s – Home of the mandatory BBC drink that you’ll have at least once during your visit.
La Brisa – Traditional and creative tacos in a casual, well-designed spot in the heart of town.
Melet Mercantile – An outpost of the vintage king, Bob Melet, here you’ll get a sense for the past and the present cultures of Montauk.
Montauk Point Lighthouse – A climb to the top of the fourth-oldest lighthouse in the U.S. gives you an incredible view of the sea, cliffs and boats at the point of the island.
Ditch Plains Beach – The celebrated surfer spot is known for its offshore break and secluded beach. Get a beach parking pass and retreat from the crowds at the in-town beaches.
The Montauket – Grab a drink and watch the sun set over the water.
On your drive out to Montauk, there’s plenty to explore in the Hamptons, but a few distractions to break up the trip would include Tenet in South Hampton; the RRL store in East Hampton (one of the most idyllic rustic spaces); and Pilgrim Surf + Supply and Jack’s coffee shop in Amagansett.