A Guide to the East End: Long Island’s Go-to for Fun in the Sun

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With winter behind us and the summer sun on the horizon, it’s time once again for the East End to come out of hibernation and return to its rightful place as a premier destination for food, shopping, culture, and warm-weather recreation on Long Island. It’s not just a playground for celebrities, artists, and the ultra-wealthy, either; there’s something for everybody out east. 

The five towns that comprise this storied section of the Long Island map certainly share some characteristics, but each one of them carries their own special charm. There are flourishing downtown areas and posh villages, artsy shops and upscale boutiques, bustling beaches and secluded trails, family-owned delis and world-class dining, and much more.

Here are some tips to help you make the most out of your time on Long Island’s East End this season.


A Guide to the East End: Long Island’s Go-to for Fun in the Sun

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A row of vines and wine grapes growing in a vineyard on the North ForkGetty Images


The East End’s main entrance has been undergoing a transformation in recent years, becoming hipper, more bustling, and a lot more fun, particularly in its downtown area. If you’re spending any recreational time in Riverhead, you’ll more than likely want to spend it there.

If you’re looking to grab a bite to eat in Downtown Riverhead, you’ve got many options at your disposal. Maple Tree BBQ (820 W. Main St., 631-727-2819, www.mapletreebbq.com) and Dark Horse Restaurant (1 E. Main St., 631-727-7606, www.darkhorserestaurant.com) are two local favorites.

For some of the area’s best breweries, check out  übergeek Brewing Company (400 Hallett Ave., 631-381-0848, www.ubergeekbrewing.com) and North Fork Brewing Co. (24 E. 2nd St. Suite A, 631-591-1191, www.northforkbrewingco.com), the latter of which shares a building with another great spot for a quick craft drink, Montauk Distilling Co. (24 E. 2nd St. Suite B, 631-727-6326, www.montaukdistillingco.com).

Where to Eat on the East End

Maple Tree BBQ (820 W. Main St., Riverhead, 631-727-2819, www.mapletreebbq.com)

Commander Cody’s Fish Shoppe (41 Smith St., Shelter Island, 631-749-1851)

Flora (149 Main St., 631-998-9600, www.florawhb.com),

75 Main (75 Main St., Southampton, 631-283-7575, www.75main.com)

Love Lane Kitchen (240 Love Lane, Mattituck, 631-298-8989, www.lovelanekitchen.com)


Southold and its constituent towns make up a majority of the serene and bucolic North Fork. The East End’s road less traveled offers a decidedly different experience from its more outwardly opulent southern sibling, with fewer crowds, more country, and a whole lot of wine. 

The North Fork is internationally lauded for its wine, and there are countless vineyards, like Sannino Vineyard (15975 County Rd. 48, Cutchogue, 631-734-8282, www.sanninovineyard.com) and Mattebella Vineyards (46005 NY-25, Southold, 631-655-9554, www.mattebella.com),  where you can learn how the area earned its accolades. 

Mattituck’s Love Lane is among the most charming downtown areas on the entire East End, and brunch or lunch at Love Lane Kitchen (240 Love Lane, Mattituck, 631-298-8989, www.lovelanekitchen.com) is a great way to experience it, particularly if you dine outside.  

One of the most popular destinations in the Town of Southold is the Village of Greenport. There you’ll find great breweries like Greenport Harbor Brewing Company (234 Carpenter St., 631-477-1100, www.greenportharborbrewing.com), intriguing eateries like Pearl Restaurant and Bar (409 Main St., 631-333-2888, www.pearlrestaurantbargreenport.com), and eclectic shopping experiences like the hot sauce shop Greenport Fire (125 Main St., 631-333-2233, www.feelthefireny.com), which has its ceiling and walls covered in 45-rpm vinyl records.

Shelter Island Comprehensive Guide
A full moon rises over the ferry on the cover of Shelter Island Comprehensive Guide, a book detailing all there is to do in the East End community.

Shelter Island

Resting peacefully out in the bay between the North and South forks is one of Long Island’s most beautiful and somewhat unsung destinations. Shelter Island is a place out of time that seems to be a shared vision between Steinbeck, Fitzgerald, and Rockwell. The island is far more suited to relaxation than jubilation, but those interested in the former should find it there in great abundance.

Some key itinerary items for a visit to Shelter Island:

Spend the day on Wades Beach (114 S Midway Rd).

Have dinner at Commander Cody’s Fish Shoppe (41 Smith St., 631-749-1851) or Maria’s Kitchen (55 N. Ferry Rd., 631-749-5450, www.mariaskitchenshelterisland.com).

Explore the expansive and beautiful Mashomack Preserve (79 S Ferry Rd., 631-749-1001). 

Spend a night at The Pridwin Hotel and Cottages (81 Shore Rd., 631-749-0476, www.caperesorts.com/pridwin), the newly renovated historic resort overlooking Peconic Bay. They’ve also got The Terrace, their own waterfront restaurant with a menu focused on locally sourced, high-quality ingredients. 

Bear in mind that in order to get to Shelter Island, you’ll need to take a ferry either from the north (Greenport) or the south (North Haven). 

Where to Stay on the East End

The Pridwin Hotel and Cottages (81 Shore Rd., Shelter Island, 631-749-0476, www.caperesorts.com/pridwin)    

Baron’s Cove (31 W. Water St., Sag Harbor, 844-227-6672, www.caperesorts.com).

The Menhaden (207 Front St., Greenport, 631-333-2777, www.themenhaden.com

Gurney’s Montauk Resort & Seawater Spa (290 Old Montauk Hwy., 631-668-2345, www.gurneyresorts.com/montauk)


The first bit of Hamptons you’ll find as you head eastbound down route 27 may be looked at as the lesser sibling by some, but rest assured that there are more than a few spots in the seven incorporated villages which Southampton is comprised of that can give the best of the best in East Hampton a run for its money. 

Westhampton Beach has a recently reimagined downtown area full of unique little shops to wander through just before you hit Rogers Beach (101-105 Dune Rd., Westhampton Beach, 631-288-1654) for the day.

You can grab brunch at Flora (149 Main St., 631-998-9600, www.florawhb.com), check out one of the many Main Street boutiques like NIBI (126 Main St., 631-483-5139, www.nibimtk.com) or Mint (83B Main St., 631-288-0743, www.shopmint.com) or stop by one of the town’s newer commercial residents, Red Jacket Books (77D Main St., Westhampton Beach, 631-533-5580, www.redjacketbooks.com) to grab a breezy beach reader for your day on the sand. 

“A few years ago, [the local] bookstore closed, and Westhampton Beach Village was without a bookstore for the first time in over a decade.,” owner Ben Vengroff tells us. “As I’ve told many customers, every good town deserves a bookstore, so I decided it was the perfect place to set up shop.”

In addition to selling books, Red Jacket also hosts various events, including author signings, two book clubs, short story contests, and more. 

The Village of Southampton has its own beautiful Main Street that’s full of boutiques like TENET (91 Main St., 631-377-3981, www.tenetshop.com), funky gift shops like Aloof Icon (87 Jobs Ln., 631-488-4111, www.alooficon.com), and beloved local eateries like 75 Main (75 Main St., 631-283-7575, www.75main.com) and Sip ‘n Soda (40 NY-27A, 631-283-9752, www.sipnsoda.com). 

Bridgehampton is among the more overlooked of all of the Hamptons areas. This little hamlet is relatively quiet and quaint, but it has both a taste of everything the East End is loved for and some more unique treasures.

Two great examples of those unique treasures are the Children’s Museum of the East End (376 Bridgehampton-Sag Harbor Tpke., 631-537-8250, www.cmee.org) and the South Fork Natural History Museum (377 Bridgehampton-Sag Harbor Tpke, 631-537-9735, www.sofo.org).

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A typical beautiful sunset in East Hampton, NY. (Photo by Taber Andrew Bain)

East Hampton

The most internationally recognized area on all of Long Island is unsurprisingly full of interesting things to see and do. East Hampton’s exceedingly high profile means it can be absolutely packed with people, of course, but there are several good reasons why the area is renowned enough to attract so many tourists.

East Hampton is known primarily for its pristine beaches, like Main Beach (101 Ocean Ave., 631-324-0074) and the opulent shopping experience you’ll enjoy on the village’s Main Street, but the area is also teeming with history and interesting little landmarks.

Stop by the LongHouse Reserve (133 Hands Creek Rd., 631-329-3568, www.longhouse.org) to explore a 16-acre garden that is home to an eclectic array of plants and more than 70 sculptures.  

Go to Cedar Point County Park (5 Cedar Point Rd., 631-852-7620) for another beautiful outdoor experience. The park is comprised of 607 acres of beautiful untouched land overlooking Gardiners Bay.  

If you’re looking for an amazing live music experience in a historic venue, check out Stephen Talkhouse (161 Main St., Amagansett, 631-267-3117, www.stephentalkhouse.com). For an idea of the building’s history, just take a look at the photographs decorating the walls to find countless images of all the legendary musicians who have taken the stage there. 

The Village of Sag Harbor offers plenty of unique shopping, beautiful historic buildings, and fantastic food, as well as the newly constructed John Steinbeck Waterfront Park (www.johnsteinbeckwaterfrontpark.org) on its northern end. The park is named in honor of the beloved American author, who called Sag Harbor home in his twilight years.

For another local landmark that’s associated with iconic authors, book a night at Baron’s Cove (31 W. Water St., 844-227-6672, www.caperesorts.com). The luxury resort is celebrating its 65th anniversary this year.  

“[We’ll be looking] back at the history of Baron’s Cove a bit, with some amazing new photos,” Scott Currie, a representative of the resort, tells us. “It was famously one of the regular haunts on the East End where Truman Capote, Steinbeck, and Kurt Vonnegut, among others, used to frequent.”

Baron’s Cove will be holding its official anniversary celebration on Memorial Day, but the celebrating will be ongoing all year.

No trip to the East End should be considered complete unless it includes The End. Over the years, Montauk has gone from the kind of dreamy and unassuming beach town you’d find nestled quietly along California’s Pacific Coast Highway to one of the hottest spots on the island, and while that does mean higher prices and more crowds, it doesn’t mean all the charm is gone.

The entire town is bordered by beaches, and you’re pretty much always in walking distance of a ton of beachy shops like Montauk Surf & Sports (716 Main St., 631-668-9300, www.montauksurfandsports.com) and iconic eateries like John’s Drive-In (677 Montauk Hwy, 631-668-5515), along with various other great restaurants, gift shops, hotels, and more.

Related Story: The North Fork: The East End’s Road Less Traveled