Escape from New York City to Long Island, renowned for its vibrant must-visit summer spots.

While the Hamptons is always at the top of this list, a visit to these chic shores in the off-season can sometimes be even more picturesque. From top leaf-peeping in the fall to a snowy escape in the winter, the Hamptons on Long Island is much more than just a summer destination.

Here are 6 downtowns worth exploring year-round.


Westhampton Beach

After undergoing an $11 million downtown revitalization project, the village of Westhampton Beach is a reimagined, vibrant, modern, and historic downtown with charming shops, nightlife and proximity to world-class beaches. Check out the Westhampton Beach Performing Arts Center for a robust series of virtual events.

Where to Dine in Westhampton: The newly opened flora by Rooted Hospitality Group delivers a menu driven by the seasons and a mantra of “eat, drink, love.”

What to Do in Westhampton: For an outdoor experience, head to Cupsogue Beach County Park, a 296-acre park, locally known as Dune Road and famed for its white sand beaches and saltwater bass fishing. Camping is also permitted. Finish the day with shopping and art at Good Westhampton + Gallery III. Find unique home décor, design and gifts for the whole family then explore the gallery showcasing local artists and photographers.

Where to Stay in Westhampton: Beaver Dam Creek House or Westhampton Seabreeze Motel

Hampton Bays

The Hampton Bays is a hamlet in the Town of Southampton. This Hampton hamlet gets its name as it is surrounded by three bays, the Peconic Bay to the north, and Shinnecock and Tiana bays to the south. Characterizing this hamlet surrounded by water is the clear blue water views, fresh seafood and outdoor open spaces.

Where to Dine in the Hampton Bays: Cowfish New American Cuisine is a Hampton Bays staple. Head there for Prime Rib Friday or Wine Down Wednesday. Accessible by boat on the Shinnecock Bay, RUMBA Inspired Island Cuisine & Rum Bar, serves up Island-inspired food, handcrafted rum libations paired with reggae and good vibes.

What to Do in the Hampton Bays: Get outdoors at Tiana Beach or Sears Bellows County Park, a 979 acre-park, with bird watching, biking and cross-country skiing weather permitting. Go shopping at Macy's Hampton Bays for clothing, houseware and brand name fashion.

Where to Stay in the Hampton Bays: Bayview Resort or Bowen's by the Bays


Southampton is known for its fabulous art galleries, cultural exhibits, beautiful beaches, and, of course, the iconic and historic Big Duck. Cooper’s Beach is a must experience, which has been rated among the Top Ten Beaches in America by Dr. Beach and has the picturesque backdrop of the luxe mansions that line the shores of the Hamptons.

Where to Dine in Southampton: Local Burger Co. serves up make-your-own or signature burger selections paired with homemade side dishes. A favorite is the hand-spun colorful milkshakes. PLAIN-T is a boutique tea shop with full-leaf, handcrafted teas from around the world. Sip in the T-Loft.

What to Do in Southampton: History comes to life in Southampton! The town is home to the Parrish Art Museum, which has been showcasing the artistic legacy of Long Island’s East End since the 1890s and is one of America’s most vital creative centers. The museum offers a range of different exhibitions, public programs and studio classes throughout the year. The Southampton Cultural Center is also a unique stop for a variety of programming including classes and art exhibitions for children and adults at affordable prices. Currently, the programing includes contemporary dance and country line dancing. The Southampton History Museum consists of 4 separate properties with 14 historic buildings that contain changing exhibits on historic topics, a research center, and educational programs.

Where to Stay in Southampton: Southampton Inn or 1708 House

East Hampton

About 20 hamlets and villages comprise the Hamptons on the East End of the island, but East Hampton is a celebrity in its own right. This town is the original cool kid with its celebrity sightings, upscale shopping and dining, not to mention pristine white beaches. Main Street in East Hampton is a shopping destination with boutique shops, fashion stores and antique finds.

Where to Dine in East Hampton: The 1770 House Restaurant serves up a two-course prix fixe menu for $55 per guest by Chef Michael Rozzi’s crafting refined contemporary American cooking. The property also offers a Tavern for more casual and traditional pub fare. The Palm Restaurant at Huntting Inn serves up the best of land and sea with oysters, crab cakes, steaks and more.

What to Do in East Hampton: Explore art and culture at Guild Hall, LongHouse Reserve and the Pollock-Krasner House. Guild Hall, established in 1931 has 2,400 works in the Permanent Collection showcasing 19th through 21st century works and 8-10 special exhibitions per year. LongHouse Reserve is home to a 16-acre sculpture garden with over 70 contemporary sculpture pieces and a wildlife garden. At Pollock-Krasner House explore the home and exhibit of two leading abstract expressionist artists, Jackson Pollock and Lee Krasner. For a photo-op, head to Gardiners Island Windmill built in 1795.

Where to Stay in East Hampton: Journey East Hampton or The Baker House

Sag Harbor

Originally a whaling port, Sag Harbor is filled with historic attributes that separates itself from the rest of the region. Considered one of the most walkable parts of the Hamptons, this quaint downtown is filled with independently owned businesses rather than the outposts of major retailers. Some of the most talked about stops are Point Surf that sells seasonal sport gear all year long, and Berry and Co., a local bookstore and coffee shop.

Where to Dine in Sag Harbor: Sen Restaurant, a modern Japanese restaurant, serves up next level sushi creations and steamed buns. For more foodie ideas, check out Edible East End.

What to Do in Sag Harbor: Join the Bay Street Theater for a Sip & Sing virtual series and All-Star Comedy hosted online. Also, register for in-person master acting classes. For some outdoor fun, Foster Memorial Beach offers dog walk routs and picnic areas.

Where to Stay in Sag Harbor: Barons Cove or Sag Harbor Inn


Over the last decade Montauk has transformed into a year-round “it” destination. The town’s nostalgic surf-and-fishing driven character set this downtown apart from the traditional Hampton Hamlets. New luxury hotel offerings such as the Marram Montauk, Gurney’s Montauk & Seawater Spa, and Gurney’s Star Island Resort are making waves in the community giving travelers and locals new hot spots to visit while still capturing that chill Montauk vibe.

Where to Dine in Montauk: With panoramic views of the ocean, Scarpetta Beach at Gurney’s Montauk is a dining destination and seaside sister of the Manhattan eatery. Seasonal Italian dishes encompass fresh seafood, pasta, chicken and more. For brews, the Montauk Brewing Co. tasting room offers regionally inspired flavors including the Watermelon Ale and Wave Chaser IPA.

What to Do in Montauk: Fresh air, water views and bluffs await at Shadmoor State Park, Hither Hills State Park and Camp Hero State Park. Fun fact, Camp Hero served as inspiration for the Netflix series Stranger Things. For adventure or family fun, head to Deep Hollow Ranch, the oldest working ranch in the United States. Here, you can take a horseback ride along the beach. For history and picturesque views, don’t miss the Montauk Lighthouse. The Montauk Point Lighthouse is the oldest lighthouse in New York State. The Lighthouse was authorized by the Second Congress, under President George Washington, in 1792.

Where to Stay in Montauk: Gurney’s Star Island or Marram Montauk


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