12 Things to Do in Montauk & The Hamptons

A hugely popular summer haunt with wealthy New Yorkers, The Hamptons is a string of coastal towns on the Long Island peninsula, a couple of hours east of Manhattan. The area is characterised by vast stretches of beach, verdant farmland, and charming towns and villages, while high-end restaurants and designer boutiques offer ample chance for more material pursuits. And among the Hamptons’ most popular spots is the village of Montauk, perched at the eastern most tip of Long Island.

Whether it’s retail therapy, gourmet dining, rest and recuperation, or connecting with nature, The Hamptons and Montauk offer a wealth of opportunity. If you’re planning a visit in the near future and are looking for some inspiration, we’ve picked out 12 of the best things to see and do here.

1. Admire art and nature at LongHouse Reserve

This is a tranquil place where visitors come to relax, unwind and admire exceptional works of art of every type. Spread over 16-acres of East Hampton Township’s great Northwest Woods, LongHouse Reserve exemplifies the region’s idyllic natural scenery. Art is at the heart of daily life here, with a dedicated sculpture garden playing host to a regularly changing assortment of artwork and installations, ranging from ethnographic works and handcrafts to modern art, glass, ceramics and bronzes.

2. Attend a fine arts festival

Providing an opportunity for the general public to meet and engage with some of the region’s most gifted artists, the annual outdoor Amagansett Fine Arts Festival attracts large numbers of visitors each year for a full weekend of exhibitions. Diverse art work including paintings, photography, drawing, sculpture, jewellery and mixed media by some 40 artists are showcased here, demonstrating the artistic expression of the Hamptons’ most creative communities, all under the area’s famous summer sunshine.

3. Sample some world class rosé at Wolffer Estate

A Hamptons winery with a distinctively European character, Woffer Estate is nestled among the expensive real estate and luxurious summer retreats of Long Island’s East End, with production focussing heavily on rosé wine. The venue is open to visitors throughout the year, with a dedicated tasting room welcoming you into a rustic-modern space perched on a rise overlooking the lush vineyards and gently rolling Hamptons landscape. Also located here are the Wölffer Estate Stables offering equestrian facilities for hunters, jumpers, and dressage.

4. Join a fully guided Hamptons Day Tour

A great way to explore the riches of the Hamptons is by joining an organised tour. Hosted by Tour the Hamptons, this full-day adventure from New York City invites you to take in some of the area’s most desirable attractions and places of interest. You’ll travel through neighbouroods where the rich and famous reside, before visiting the village of Southampton for some retail therapy, continuing on to the quaint fishing village of Sag Harbor for lunch and more shopping. On your way back to NYC you’ll have the option of stopping for a wine tasting at the South Forks famous Duck Walk Vineyards.

5. Take in local artwork at Parrish Art Museum

The Hamptons certainly aren’t short of distinguished arts venues and one of the most renowned is this museum in the pretty hamlet of Water Mill. Inspired by the natural setting and artistic life of its surroundings, the museum offers a wide range of exhibitions, educational initiatives and other programmes focusing heavily on work by artists from the artistic colony of the South and North Shores of Long Island.

6. Get a valuable history lesson at the Shinnecock Nation Cultural Center

If you’re interested in learning more about Native American history, this acclaimed cultural centre and museum in Southampton is the place to come. Dedicated to honouring the ancestral and living history of the Shinnecock Indian Nation, the venue is fully owned and operated by Native Americans and attracts thousands of visitors each year thanks to its vast collection of artefacts, documents, and other material related to Shinnecock history and culture.

7. Take to the high seas with Sail Montauk

The Atlantic waters that surround the Long Island peninsula offer ample opportunity for sailing enthusiasts. Sail Montauk host a wide range of affordable cruising adventures off the shores of Montauk, including sailing charters for small and large groups. Or why not book onto a sailing lesson so you can learn the tricks of the trade for yourself? For something altogether more sedate and seductive, private sunset cruises invite you to enjoy an evening in the Hamptons on a private sailboat, complete with Bluetooth speakers so you can enjoy your own playlist under the stars.

8. Catch a flick or three at Hamptons Film Festival

Movie lover who are visiting the Hamptons in October are in for a treat thanks to the annual Hamptons International Film Festival. Founded to celebrate independent film-making of every length and style, the festival has grown to become a major event on the East Coast’s cultural calendar. Whether it’s long, short, fiction or documentary films that float your boat, you’re likely to find something to please you, with a wide range of screenings by local, national and international movie-makers.

9. Taste the local amber nectar at Montauk Brewing Company

Founded by a trio of friends in 2012 as a basement brewing operation, Montauk Brewing Company has grown to become one of the region’s finest purveyors of locally produced beer. Located just steps from the surf, the brewery is a popular attraction with visitors to Montauk and plays host to tastings sessions on most days of the week,where you can sample perennial favourite such as Summer Ale and Wave Chaser IPA.

11. Become a cowboy for the day at Deep Hollow Ranch

Founded as a cattle ranch in 1658, America’s oldest working ranch lays claim to being the birthplace of the American cowboy, and is a popular attraction with visitors to Montauk looking for an authentic local experience. The ranch plays host to regular pony and horseback tours, as well as hayrides, that take guests across 3,000 acres of beaches and countryside.

10. Explore majestic scenery at Montauk Point State Park

Montauk’s natural landscape is something to behold, and perhaps the jewel in its crown is Montauk Point State Park. Home to New York State’s oldest lighthouse, the heavily wooded 862-acre park is awash with hiking trails, ski-slopes, surf-fishing sites and stunning views of the Atlantic Ocean where it meets the Block Island Sound. It is also a popular area for small game and waterfowl hunting.

12. Immerse yourself in experiential shopping at Room 09

For a unique shopping experience in Montauk, head to this upscale retail concept housed within a reconfigured guestroom at Haven Montauk, a boutique hotel in the heart of the city. The store offers a wide range of exclusive products from both emerging and established brands, including a curated luxury vintage selection, design pieces and household necessities. The space also hosts a busy programme of summer events including pop-ups, installations and live musical performances.

By Paul Joseph