You may know The Hamptons for Lamborghinis, mega-mansions and polo, but sleepy Montauk, at the far eastern edge of the South Fork, came a little late to the party. For years the beach town remained under the radar, but the secret's out now, and it's a popular escape for New Yorkers. In fact, Montauk draws plenty of comparisons with NYC - it is to The Hamptons what Brooklyn has been to Manhattan, drawing regular visitors away from more established Hamptons hotspots. But even though celebrities including Julianne Moore and Robert De Niro own properties in Montauk, it still retains a distinct atmosphere as a bohemian surf spot.
Montauk is one of our new holiday destinations, which reflect a newfound desire for more outdoorsy, slower-paced destinations over big-city jet setting. And if you’re looking for accommodation, our holiday rental homes are vetted by professionals who make sure only the top 3% make it into our listings. So you know you’re in for a luxurious and stress-free stay in an exclusive Plum Guide home. (Tip: you’ll probably want to book a property with a pool here). And now, without further ado, here's our expert-curated list of the top things to do in Montauk.
Book a table at The Surf Lodge
With seafood fresh off the boats in Montauk Harbour and the occasional residence with Michelin-star chefs (Shaun Hergatt came down from NYC last year), The Surf Lodge is one of Montauk's hottest restaurant venues. Expect live music - it could be Solange or Janelle Monaé, if you’re lucky - and highly probable celebrity sightings under the canopy of woven fishing-style baskets.
The Captain's House, Plum Guide home in New York
Hit the waves at Ditch Plains Beach
One of the best things to do in Montauk is to make the most of its spectacular surf, and the famous Ditch Plains, also known as ‘The End’, have some of the top waves. But even if you’re not here to surf, there’s bodyboarding and stand-up paddle boarding here too (with the breaks here making it that little bit more of a challenge). If you're too fancy for water sports, grab a spot on the golden sand and watch it all happen.
Architectural Voices, Plum Guide home in East Hampton
Climb up Montauk Lighthouse to see the views
The historic Montauk Lighthouse was commissioned by George Washington in 1792, making it New York State's oldest. Inside, there’s a museum covering the history, but best of all, if you commit to climbing the 137 stairs to get up the tower, you’ll be rewarded with views out across the ocean and coast from the picturesque easternmost point on Long Island.
The Whaler's Cottage, Plum Guide home in The Hamptons
Hike through the Montauk Point State Park
Hither Hills State Park, Montauk
Once you’ve seen the lighthouse, head to Montauk Point State Park for a clifftop walk along rugged Atlantic coastline. As well as coastal hiking along impressive bluffs, this is also a top spot for stand-up paddle boarding, windsurfing and spotting seals on the rocks offshore. Plus, Montauk Music Festival is also held here each May, supporting acts spanning the genres from pop and hip-hop to jazz, bluegrass and folk.
Long Point, Plum Guide home in The Hamptons, USA
Go for dinner at The Crow’s Nest
Don’t expect super-swanky dining at Montauk’s best restaurants: The Crow’s Nest is way up there, but it keeps its character with wooden tables, mismatched crockery and an obvious design commitment to the beach location. Expect local sea bass, organic salads, artisanal cheeseboards and a cocktail menu that’ll appease most committed New York City bar-hoppers.
Explore the Montauk Country Park
Montauk Coastline, The Hamptons
Montauk Country Park is all hiking trails, grassy sand dunes and beaches that trail into the distance. Explore this tranquil area on horseback via Deep Hollow Ranch, the oldest working ranch in the US, established in 1658.
Relax at Gurney’s Star Island Resort & Marina
If you didn't stretch to a property with a swimming pool when booking a stay in the Hamptons, all isn’t lost: snag a lounger by the pool at Gurney’s Star Island beach club, with its chic white loungers and location right beside the water. A menu of oysters, Sriracha lobster rolls and fish tacos will have you wanting to stay forever. Well, you can certainly prolong your stay with a treatment in the spa.
Take a trip to Duryea’s Lobster Deck
Finally, rounding off our list of things to do in Montauk, we have Duryea's Lobster Deck. This 80-plus-year-old seafood institution used to be much more… basic, but Duryea’s has been given a simple-yet-chic, gently Balearic-style reinvention with white cushioned benches and a sail-like canopy. Admittedly, it's not hard to make a place look good with these ocean views as a backdrop, and the fresh seafood dishes still do most of the hard work anyway: think lobster rolls, chips and champagne, and platters of fresh-caught shellfish to share.
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