A Local’s Guide to the Best Things to Do in The Hamptons

The Hamptons, synonymous with being the summer playground for the rich and famous, is an affluent eastern region of Long Island featuring seemingly endless beaches, quaint historic towns and villages, gorgeous wineries, cute farm stands, and high-end art galleries.  

I have lived in the Hamptons for over thirty years, and this stunning New York region never ceases to amaze and inspire me. From the hidden bay beaches and nature preserves to the bountiful farmer’s markets and endless summer events, there is always something new to discover and appreciate. 

Below, I round up some of my favorite things to see and do across the Hamptons, where to stay, eat, shop, and relax, and what to buy during your trip to the South Fork of Long Island. 

Things to Know Before Visiting the Hamptons

Downtown Sag Harbor - The Hamptons NY
Downtown Sag Harbor / Photo Credit: Discover Long Island

Spanning from Southampton through East Hampton out to Montauk, it is about 90 minutes away from NYC by train, bus, or car.

Vacationers that seek out this enchanting region of Long Island encompass a wide range of ages, and the Hamptons readily welcome people from all over the world, with easy access (primarily via the LIRR) from JFK airport.

Though the summer season out east is not only one of the busiest, the demand to visit and experience the Hamptons is high, and the interest only continues to soar year after year. 

With that being said, it is best to plan your trip as much ahead of schedule as possible, and if you can, a midweek visit is ideal during the peak season (Memorial Day to Labor Day weekend). June, for instance, is still relatively calm, with nearly all businesses in full operation. 

Become familiar with the public transportation to and from the Hamptons. This includes the Hampton Jitney and Hampton Luxury Liner buses that run to and from NYC and the LIRR from both Penn Station and Grand Central, with two separate connections in Jamaica, Queens.

The Hamptons villages are very walkable and pedestrian-friendly, though a car is ideal as you travel from town to town. Bicycle paths and lanes are readily accessible on some back roads and along parts of Montauk Highway. 

In addition, seek out Airbnbs as early as possible, and if you are on more of a fixed budget, know that the towns of Riverhead and Brookhaven, about a half hour away from the Hamptons, respectively, offer a wide range of leading hotel chain properties like Marriott and Hilton hotels.

Things to Do in The Hamptons on Vacation

Enjoying the Sun, Sand, and Surf

Sunny Day at Beach with Fenced Off Dunes, East Hampton, NY, US,
Courtesy of Vanessa Gordon

The beaches in the Hamptons are some of the most beautiful in the USA, as regularly noted in Dr. Beach’s annual list and Forbes. In addition to the most popular Cooper’s Beach in Southampton and Main Beach in East Hampton, some of my favorite beaches are Little Plains Beach, close to Cooper’s, Havens Beach in Sag Harbor, and Gerard Beach in the hamlet of Springs in East Hampton. Check each town hall regarding beach passes for the season and day passes. However, you do not need a beach sticker after 5 pm. 

Scenic Delights to Experience in the Hamptons

If I am not at the beach, I walk along the paths throughout East Hampton and Sag Harbor villages. A breathtaking place to hone in on the natural scenery is near David’s Lane in East Hampton Village, also home to Duck Pond.

I love to continue my walk along the path adjacent to Mulford Farm, where you will find two of the region’s historic windmills. And if you visit in late spring or around Memorial Day weekend, you will catch the wisteria growing on the front of the historic home, now a museum. 

Nature-Focused Activities

LongHouse Reserve 2021 Summer Benefit - the Hamptons NY
LongHouse Reserve 2021 Summer Benefit / Photo Credit: Patrick McMullan/PMC

If you love nature and the outdoors, visit the Elizabeth A. Morton National Wildlife Refuge off of Noyack Road in Sag Harbor. At this 187-acre wildlife refuge, you will find many local bird species and wildlife habitats, including painted turtles, white-tailed deer, eastern chipmunks, and green frogs. This also makes for a perfect destination for bird watchers and nature photographers.

In addition, visit the LongHouse Reserve for a relaxing walk-through tour and visit their sculpture gardens, which feature works by Yoko Ono, Willem de Kooning, and many other notable artists. LongHouse Reserve also has rotating annual art exhibitions. 

Wellness Retreats

Shou Sugi Ban House - the Hamptons NY
Yoga Room / Photo Credit: Shou Sugi Ban House

Visit Shou Sugi Ban House in Water Mill for a tranquil spa retreat getaway and Organic Edge, also located in Water Mill, which offers a variety of wellness treatments, including Target Cryotherapy and a relaxing session in their Infrared Wellness Pod.

Art Galleries

For art enthusiasts, head to The Art Barge at the Victor D’amico Institute-Art on the Napeague Stretch in Amagansett. Visitors will discover a variety of workshops and classes for all ages.

Things to Do with Kids in the Hamptons

And if you are traveling with kids in tow, head to the Clubhouse in East Hampton for bowling and arcade games or The South Fork Natural History Museum for hands-on learning activities. 

Luxury Shopping and Unique Finds: The Best Places to Shop in the Hamptons

Sag Harbor - the Hamptons NY
Sag Harbor / Photo Credit: JT-Santini

Sag Harbor offers the most locally diverse shops in the Hamptons, with storefronts ranging from boutique clothing and home goods to antique shops and art supply stores. If you are looking to bring home a housewarming gift or present for that special someone straight from the Hamptons, you will find your best options at any of the shops in Sag Harbor. 

Downtown Sag Harbor The Wharf Shop - the Hamptons NY
Downtown Sag Harbor The Wharf Shop / Photo Credit: Discover Long Island

Some shops I frequent in Sag Harbor are The Wharf Shop for jewelry, Christmas ornaments, and toys, Ryland Life Equipment for men’s and women’s clothing and accessories, and OMO The Apothecary for hemp oils and topicals. 

Off Montauk Highway in Bridgehampton, I frequent Loaves and Fishes Cookshop for kitchen supplies and accessories and Jenni Kayne in Amagansett Square for apparel and accessories. Amagansett Square is where I spend my mornings sipping coffee, meditating, or reading. 

Indulge in the Hamptons’ Culinary Delights: Best Restaurants and Eateries to Try

Carissa's Bakery - the Hamptons NY
Photo Credit: Carissa’s Bakery

When vacationing in the Hamptons, exploring and dining out at some of the region’s most notable restaurants is always a must. Make your reservations early; if some spots do not, take reservations (the popular Estia’s Little Kitchen always comes to mind). It is best to visit on a Wednesday or early in the morning during the week. Head to the new Tutto Caffé in East Hampton Village for a late-morning meetup. This spot has been buzzing since it opened last year and is known for its coffees, pasticcini, and panini sandwiches. Plus, the interior is quite handsome and cozy, perfect for those brisk mornings. 

For grab-and-go, my essential spot is Round Swamp Farm. Their East Hampton and Bridgehampton locations have the best selection of foods, and everything tastes fantastic. My top picks are their Chicken Meatloaf, Fluke Française, Mexican Layer Dip, and Lisa’s Blueberry Peach Muffins. Their selection is so widespread that you will easily find something for everyone on your houseguest list.

Carissa's Bakery the Hamptons, NY
Photo Credit: Carissa’s Bakery

I also love Carissa’s Bakery in Sag Harbor. Their display is gorgeous, with handcrafted pastries and cakes. My essential there is the Salted Soured Picked Rye. They have a secondary location on Pantigo Road in East Hampton. 

An excellent spot for lunch for family members of all ages is the Sip’ n Soda nostalgic luncheonette in Southampton Village. My family loves coming in for burgers and sandwiches, followed by their signature sundaes. We typically visit midweek in the early afternoon as a break from the beach or after camp. 

Sí Sí Mediterranean Restaurant / Photo Credit: EHP Resort & Marina - the Hamptons NY
Sí Sí Mediterranean Restaurant / Photo Credit: EHP Resort & Marina

For some of the most gorgeous sunsets, head to Bell & Anchor in Noyack for local seafood, raw bar towers, sizable pasta dishes, and dreamy desserts. A highly sought-after spot for sunsets in East Hampton outside the village is Sí Sí Mediterranean Restaurant at EHP Resort & Marina. Also on the property is Buongiorno Bakery, an Italian Bakery and Espresso Bar famous for its Nutella croissants and lemon-filled Bomboloni. 

Discover the Best Wineries and Nightlife

Bell and Anchor - the Hamptons, NY
Bell and Anchor / Photo Credit: Jason_Penney

The nightlife scene in Sag Harbor is the most active, followed by Bridgehampton and Amagansett. Murf’s Backstreet Tavern in Sag Harbor Village is where I take all my visiting family and friends for an authentic local night out. The Tavern offers a spacious area in the back for mingling.

On the opposite side of the village is the new Kidd Squid Brewing Company, which is also family-friendly. Kidd Squid has an intimate tasting room and lounge featuring local brews on tap or sold by the can. Look out for their ongoing collaborative partnership with Hamptons Raclette, which offers authentic Swiss Raclette experiences. 

Wolffer Estate - the Hamptons NY
Photo Credit: Wolffer Estate

An essential stop and experience during a vacation to the Hamptons is to any wineries, including the breathtaking Wölffer Estate Vineyard. Wölffer hosts events, live music, pop-ups, and much more throughout the summer season and remains one of the best spots for a photo op in the Hamptons. Two other distinctive vineyards include Duck Walk Vineyards in Southampton and Channing Daughters Winery in Bridgehampton, offering tastings and hosting events throughout the season. 

Wolffer Estate - the Hamptons NY
Photo Credit: Wolffer Estate

Not a wine drinker? Just down the road from Wölffer is Sagaponack Farm Distillery. Their tasting room is built in a nearly 100-year-old retired dairy barn. Inside, visitors will find a wealth of local history, including the bar’s footrest sourced from the historic Bridgehampton to Sag Harbor railroad that is no longer in existence. 

For live music featuring a mix of local and live bands, head to The Stephen Talkhouse in Amagansett Village. The Rolling Stones, Paul McCartney, The Velvet Underground, recently Paris Jackson, and many more notable names have performed on their stage. 

For a low-key yet refined spot for grabbing a drink, head to The American Hotel in Sag Harbor, a historic landmark well-regarded by locals and visitors alike. 

Accommodation Options for a Luxurious Getaway

Baker House 1650 - the Hamptons, NY
Photo Credit: Baker House 1650

For a spa getaway, Baker House 1650 on Montauk Highway in East Hampton offers unparalleled luxury in the Hamptons with its indoor private pool and spa, exclusively for guests. A stunning historic property with 17th-century Cotswold-inspired architecture and lush gardens, you would think you instantly stepped foot into the English countryside.

Topping Rose House in Bridgehampton Village is a resorted 19th-century mansion with an onsite Jean-Georges restaurant, wellness programming, and special events and pop-ups held throughout the summer. 

Baron's Cove - the Hamptons NY
Photo Credit: Jennifer Satinsky

Vacationing in the Hamptons with your furry friends is always fun, as there are endless options for pet-friendly activities across South Fork. For pet-friendly overnight stays, Baron’s Cove in Sag Harbor and Mill House Inn in East Hampton Village are excellent selections.

I always recommend these two hotels to friends and family traveling with pets. Mill House Inn, for example, serves its own homemade dog food to pup guests. Plus, save your appetite as their signature breakfast is the best around, and their ‘Nack Bar offers some fun and delicious snacks from cookies and popcorn to your own cheese and charcuterie board. Baron’s Cove offers bicycles to borrow for exploring Sag Harbor Village, and their downstairs lounge is a cozy spot to relax by the fire with a cocktail and listen to live music. 

Experience the Ultimate Hamptons Retreat

Vanessa Gordon the Hamptons
Courtesy of Vanessa Gordon

The Hamptons are one of those rare destinations where you not only find people from around the world returning year after year but also consider the Hamptons a home away from home. Though this East End enclave continues to evolve year after year and draws in a barrage of visitors in summer without hesitation, it still encompasses an abundance of unspoiled seaside beauty and charm that cannot be found anywhere else. 

More Articles From Wander With Alex

This article A Local’s Guide to the Best Things to Do in The Hamptons originally appeared on Wander With Alex.


A Local's Guide to the Best Things to Do in The Hamptons
Vanessa Gordon

Vanessa Gordon is a Hamptons travel and lifestyle expert, and the CEO of East End Taste. She is also the Founder of the Hamptons Interactive Brunch event series. She received her Master of Arts Degree in Teaching English as a Second Language from New York University. She has been featured in The New York Times, Yahoo, Parents Magazine, Reader’s Digest, New York Post, Metro UK, Total Beauty, CNN Underscored, and many more. She lives in the Hamptons with her family. Find Vanessa on Instagram@VanessaPGordon