Top 25 Things To Do In The Hamptons In The Winter (fun ideas for the Hamptons off-season!)

Winter is a great time to visit the Hamptons, especially if you’re looking for fewer crowds and a quieter experience than summer.

During the colder months you’ll find the traffic isn’t as hectic, the beaches are empty, and the hotel rates are relatively inexpensive.

This is the perfect time of year to hop on the Long Island Expressway and enjoy a Hamptons winter getaway!

Read on for the best things to do in the Hamptons in the winter!

The Best Things To Do In The Hamptons In The Winter

Parrish Art Museum

The Parrish sits just off Montauk Highway in what can only be described as an architectural marvel completely atypical of the Hamptons. 

The museum focuses solely on local artists based on the South and North Forks of Long Island, and offers a picturesque and private backdrop for a truly standalone art experience.

The art museum is open for regular admission, plus public and private tours.

Wine Tasting

Visiting a vineyard is a favorite Hamptons activity no matter the time of year, and Wölffer Estate is the place to kick back and sip vino among the grapevines.

The winery offers a wide variety of wines, ciders (try the dry rose cider!), spirits, and even a few non-alcoholic wines. 

Plan to spend an afternoon enjoying their charcuterie boards, live music, and highly popular rosé in their chic tasting rooms.

Visiting this beloved vineyard is definitely one of the best things to do in the Hamptons in the winter!

Tasting and tour options need to be reserved in advance. 

Check out my guide Best Wineries In The Hamptons for everything you need to know.

Montauk Lighthouse

New York’s oldest lighthouse is probably one of the most famous attractions in the Hamptons.

The picturesque lighthouse, which sits at the easternmost point in New York, is open for tours and visitors are free to walk around the grounds.

The land surrounding the lighthouse consists of sandy and rocky shoreline with sweeping views of the Atlantic Ocean. It’s a really beautiful walk and a good way to spend your time in Montauk.

The grounds are open year-round but will close during inclement weather. 

If visiting during the holiday season don’t miss Lighting the Lighthouse!

Seal Walks At Montauk Point State Park

If visiting Montauk Point State Park in winter, keep an eye out for seals! There are 4 different seals which can be spotted off the shores of Montauk this time of year.

For your best shot of spotting these playful mammals head out on a 1.5 mile hike to Seal Haul Out.

Montauk Point State Park even offers guided seal walks, you can find more information regarding the tours here: Guided Seal Walks.

Be sure to dress warm!

Ice Skating 

Is there anything more charming than a winter day spent at an outdoor skate rink?

Buckskill Winter Club is a favorite choice for ice skating in the cooler months when this East Hampton tennis club turns skate destination. 

With a full NHL regulation-sized ice rink you’ll find tons of space to spread out and enjoy your time on the ice.

Southampton Ice Rink is another popular indoor option, they even offer skate lessons! 

Even if you don’t care to skate, these rinks are a great place to grab a hot chocolate and enjoy some people watching.

Hit The Beach 

The Hamptons are famous for their unspoiled and sprawling white sand beaches.

While winter is far from ideal for sunbathing it’s still a great time to visit, just be sure to bundle up!

The winter months are great for a walk along the shoreline — there’s very few people, untouched seashells, and no parking fees.

For some of the best beaches along the Atlantic Ocean check out: 

• Main Beach (East Hampton)
• Cooper Beach (Southampton)
• Atlantic Avenue Beach (Amagansett) 
• Sagg Main Beach (Sagaponack)
• Ditch Plains Beach (Montauk)
• Cupsogue Beach (Westhampton)

Foster Memorial Beach (also referred to as Long Beach) in Sag Harbor is located on the bay and is the perfect place for seashell hunting. Additionally, the bay’s chilly water is extra clear this time of year.

Live Music At Faraway Sag Harbor

All winter in Sag Harbor Faraway (formerly Baron’s Cove) cranks out live music over stunning views of the harbor. 

The hotel hot-spot known for delicious cocktails and a fun crowd is popular for locals and visitors alike.

No matter the time of year, this is one of the favorite things to do in Sag Harbor!

Visit A Library Or Bookstore

Another relaxing winter activity is to browse a local bookstore.

Scan the latest releases or get lost in an all-time classic — there’s no better way to spend a chilly day than in a bookshop! 

Curl up with a good book from one of these local bookstores:

• Book Hampton (East Hampton)
• Harper’s Books (East Hampton)
• Homeport (home good and bookstore in Montauk)
• Sag Harbor Books (Sag Harbor)

If you prefer to check out a library, you may like East Hampton Library, John Jermain Memorial Library in Sag Harbor, or Hampton Library in Bridgehampton to name a few.

Most have free programs and classes for locals throughout the year. 

Bowling At The Clubhouse

For a fun night indoors check out The Clubhouse in East Hampton. They have bowling lanes, pool tables, darts, and a full bar. 

A family-friendly addition to the Hamptons lifestyle, the Clubhouse has everything you’d need to entertain anyone young or old during a cold or rainy day. 

Plenty of TVs, live music and events, a well-thought cocktail list, plus games and contests, even us adults can have a blast here.

This is definitely one of the best things to do in the Hamptons in the winter if it’s too cold for outdoor activities.

Visit Shelter Island

Shelter Island prides itself on its privacy and its history, making no apologies for its hard-to-get-to approach and lifestyle. 

In reality though, the ferry ride to get here is both simple and entertaining.

Once on the island it’s hard to ignore the charm, solitude, and simple nature of the place.  

Take a drive through the gorgeous neighborhoods on Ram Island, the marina at Dering Harbor, and if the weather permits, take a hike through Mashomack Preserve.  

Tate’s Bake Shop 

The Hamptons’ most famous bakery is a must-visit during your time on the South Fork of Long Island. 

The 20+ year old bake shop is much-loved for its thin, crispy chocolate chip cookies but you’ll find tons of additional options at their bake shop.

They even have vegan and gluten free goodies for the dietary restriction crew. 

This is definitely a top choice among winter activities in the Hamptons.

Stephen Talkhouse

Stephen Talkhouse is a no-frills live music venue that’s hosted everyone from Billy Joel and Bon Jovi to Coldplay and The Killers.

Most weekend nights see crowds of locals and weekenders rubbing elbows while sipping from plastic cups in this small but iconic music venue.

Did You Know? Stephen Talkhouse is named for Montaukett Native American Stephen Taukus “Talkhouse” Pharaoh who lived and worked in the region in the mid 1800’s. 

Pollock-Krasner House

As the name suggests, this was the home of artists Jackson Pollock and Lee Krasner, who painted many of their now world-famous works within the home. 

Situated in one of the more remote areas of the Hamptons in Springs, you’ll quickly realize why this peaceful enclave was a favored workplace of both artists.

Off-season visits are available by reservation only.

Hamptons Museums (usually) Open In Winter

There are a number of great museums throughout the Hamptons, a handful of which remain open during winter.

Below are a few of my favorite options, just be sure to double check opening hours before heading out!

• Southampton History Museum
• South Fork Natural History Museum & Nature Center (Bridgehampton)
• Guild Hall (East Hampton)
• East Hampton Historical Society 
• Southampton Arts Center
• Montauk Indian Museum 

Watch The Sunset

No matter the time of year, the Hamptons is one of the best spots to catch a sunset.

Head to the north end of the South Fork for the best vantage points.

My personal favorites are Long Beach in Sag Harbor and Gosman’s in Montauk — or you can watch the moonrise over the southeast-facing Atlantic Ocean.

Go For A Hike

Wildlife, solitude, and the sound of crunchy leaves under your feet can all be found on hiking trails throughout the Hamptons in the winter. 

It will be cold, yes. But the ticks are dormant, and honestly, that alone makes this one of the best times of year to hike in the Hamptons. 

Some of my favorite hiking areas in the Hamptons include:

• Walking Dunes at Hither Hills State Park (Montauk)
• Mashomack Preserve (Shelter Island)
• Shadmoor State Park (Montauk)
• Elizabeth A. Morton National Wildife Refuge (Noyac near Sag Harbor)
• Quogue Wildlife Refuge (Quogue near Westhampton)
• Cedar Point County Park (East Hampton)
• Montauk Point State Park (Montauk)

As far as Hamptons winter activities go, this is definitely a favorite for me!

LongHouse Reserve

If a “hike” through a garden is more your speed you’ll love LongHouse Reserve.

16 acres of gardens, ponds, and paths — intermingled with sculptures from contemporary artists such at Yoko Ono and Dale Chihuly — form LongHouse Reserve. 

It’s easy to spend an entire afternoon exploring the many hidden gems throughout this sculpture garden.

Tip: For less sculptures and more gardens, check out Bridge Gardens in Bridgehampton or Halsey House & Gardens in Southampton. 

Spa Day

If a mud body wrap and seaweed facial, followed by a dip in an indoor seawater pool overlooking the Atlantic Ocean, sounds dreamy to you (um, duh), you’ll want to head on over to Gurney’s Montauk Resort Seawater Spa. 

A day spent relaxing here is the perfect form of cold weather self-care.

Each hamlet offers a high-quality spa or two but Gurney’s in Montauk definitely takes the cake for best spa experience in the Hamptons.

Shop & Browse The Village Main Streets 

Imagine stylish boutique and antique shops mixed in with supermarkets and hardware stores and you’ve got shopping in the Hamptons.

While many businesses close their doors in the winter months, a number stay open for year-round visitors.

In fact, this is often a great time to snag a deal on normally high-priced goods.

Check out East Hampton for designer fare, Montauk for a surf-vibe, and Sag Harbor for simple boutiques and antique shops.

Bridgehampton, Water Mill, Westhampton, and Amagansett (check out Innersleeve Records) also have charismatic Main Streets worth browsing.

Tip: If you’re visiting over the holiday season, be sure to check out flying Santa on Southampton Village’s Main Street!

Go To The Movies

A day at the movies is an ever-exciting family adventure and perfect cold-weather activity. Luckily there are several excellent choices within the Hamptons! 

Sag Harbor Cinema is a favorite thanks to its historic charm. The 100+ year old theatre was lovingly remodeled following a fire a few years back and now offers a well composed combination of charm and modern amenities.

They present current feature films, along with their more standard approach of older classic films.

Don’t forget to grab a bag of popcorn from Billy Joel’s popcorn machine or a cocktail from the rooftop bar!  

Also consider East Hampton’s movie theater, Regal UA, it sits right on the main drag making it a simple addition to a day of exploration. 

Grab A Coffee

If you find yourself wondering what to do on a cold winter day in the Hamptons, I’d say start with a coffee. Relaxing in a cafe is a favorite option among locals and visitors alike this time of year.

There’s also lots of good breakfast spots and bagel shops worth popping into.

Each hamlet has an array of options, most of which are excellent, here are a few of the top picks:

• Sagtown Coffee (Sag Harbor)
• Grindstone Coffee & Donuts (Sag Harbor & East Hampton)
• Jack’s Stir Brew Coffee (Sag Harbor & Amagansett)
• Beach Bakery & Grand Cafe (Westhampton)
• Krieg’s Bakery (Hampton Bays)
• Montauk Bake Shoppe (Montauk)
• Left Hand Coffee (Montauk)
• Stars Café (Shelter Island)
• Golden Pear Cafe (locations throughout the Hamptons)
• Carissa’s The Bakery (locations throughout the Hamptons)
• Hampton Coffee Company (locations throughout the Hamptons)
• Goldberg Bagels (locations throughout the Hamptons)

There is something so perfect about coffee and cold day. 

See A Show

There are a number of performing art centers around the Hamptons. Each with live performances in a variety of categories such as musicals, plays, comedy, and so on.

No matter your taste, you’re sure to find something you enjoy!

Check out the following performing art venues in the Hamptons:

• Guild Hall in East Hampton 
• Bay Street Theater in Sag Harbor
• Southampton Arts Center
• Westhampton Beach Performing Arts Center

Go Out To Eat

The Hamptons have numerous local restaurants throughout the villages and hamlets.

Each offers its own variety of upscale and casual options with cuisines ranging from Italian to Mexican, and of course, seafood. It’s easy to find something everyone can enjoy.

Some restaurants close for the winter season. But quite a few remain open, offering a special seasonal menu for winter visitors and year-round locals. 

Tip: Missing the iconic “LUNCH” spot, Lobster Roll, in Amagansett? They offer a year-round menu at their second location in Southampton.

Visit The North Fork 

The North Fork is a great place to explore during the winter months!

Enjoy one of their 40 vineyards or spend a day exploring the North Fork’s towns.

Greenport is one of my favorite spots here, you can sip wine at a vineyard, go antiquing, dine on the picturesque waterfront. Or see how oysters are raised at Widow’s Hole Oyster Farm.

For more ideas of what to do in Greenport check out The Best Things To Do In Greenport.

Looking for more East Coast winter vacation ideas? You may like The Best East Coast Winter Vacation Destinations

Where To Stay In The Hamptons During Winter

There’s a number of beautiful hotels around the Hamptons, most of which are of the boutique variety, you won’t find any chains out here!

As mentioned before, you’ll find guest rooms at much lower prices than during the high season — definitely one of the large perks to visiting during winter!

A few popular hotels in the Hamptons include:

• Southampton Inn (Southampton)
• Topping Rose House (Bridgehampton)
• The Baker House 1650 (East Hampton)
• Faraway Sag Harbor (Sag Harbor)
• The American Hotel (Sag Harbor)
• Gurney’s Montauk Resort & Seawater Spa (Montauk)
• Montauk Yacht Club (Montauk)
• The Roundtree (Amagansett)
• Ram’s Head Inn (Shelter Island)
• The Quogue Club (Quogue near Westhampton)

You May Also Like: Where To Stay In The Hamptons

Getting To The Hamptons In Winter

By Car

The Hamptons are located at the tip of Long Island’s South Fork, a straight shot from New York City.

The drive normally takes about 2+ hours (about 100 miles).

Luckily, winter sees fewer crowds and therefore less traffic, However, I’d still plan for slight delays if visiting over the weekend in winter.  

Tips: Gas stations are a bit of a pain in the Hamptons, grab gas before you get off the Long Island Expressway. Also, cell service is spotty the further east you go so have your directions downloaded ahead of time!

By Bus

One of the most convenient ways to get across Long Island is via the Hampton Jitney.

These are luxury buses with cozy seats, WiFi, restrooms, even an attendant, and yes, they run year-round. 

Tip: For even more space check out their luxe option, the Hampton Ambassador. 

By Train 

The Long Island Railroad (LIRR) combines convenience and affordability.

The route takes 3 hours so this is especially a great option during summer months when the roadways are jammed with cars. But even in winter it can be an enjoyable way to get across Long Island.

The train takes you from Penn Station to Montauk with a transfer at Jamaica Station or there’s an express option that’ll take you direct (the fast train is seasonal only). 

Stops in the Hamptons, in order from west to east, include: Speonk, Westhampton, Hampton Bays, Southampton, Bridgehampton, East Hampton, Amagansett, and Montauk.

By Air

For the quickest (and least affordable) option, BLADE offers helicopter service into East Hampton.

Think Uber gone helicopter, it may be pricey but it’ll get you to the East End in a fraction of the time.

For lots more information check out How To Get To The Hamptons.

While winter in the Hamptons is certainly a lot quieter than summer, there’s still plenty of fun things to do this time of year! 

I hope you enjoy your time on the east end of Long Island this winter.

Any questions? Please leave a comment below or reach out on social media.

Looking for more ideas? Head on over to my Hamptons and New York guides below!

More Information For Your Hamptons Vacation:

• Christmas In The Hamptons: Top Things To Do
• Hamptons Travel Guide (everything you need to know!)
• Amagansett Guides
• East Hampton Guides
• Montauk Guides
• Sag Harbor Guides
• Southampton Guides
• All Hamptons Guides

More Information For Your Trip To New York:

• North Fork Guides
• Long Island (Central) Guides
• New York City Guides