In addition to its historic harbor, Greenport has lovely, walkable beaches.

Long Island’s Greenport Village dates to the mid-1600s, when colonists from New Haven crossed the Long Island Sound and settled in Southold township. Thanks to its deep, well-protected harbor, the village has been an integral part of the North Fork’s economy and maritime tradition ever since, driving local whaling, fishing and oystering in the 19th and 20th centuries, then becoming a tourism hub in modern times.

Today, the village offers bountiful options for beachfront relaxation and activities, as well as a lengthy list of historical attractions spotlighting Greenport’s rich heritage.

Whaling became a massive industry in Greenport between 1795 and 1859, helping to also drive a shipbuilding boom. The mid-1800s also saw the zenith for menhaden fishing, and later in the first half of the 20th century, oyster harvesting hit its peak. Perhaps the most pivotal development in Greenport’s early years, however, was its selection as the first-ever LI destination on the embryonic Long Island Rail Road, which connected Greenport to Brooklyn in 1844. The new railroad line provided a turbo boost for North Fork growth, allowing local farmers to ship their products with unparalleled convenience and speed, while bringing city dwellers east for sun and respite.

Today, Greenport celebrates its history by making museums, galleries and landmarks foremost among its cultural offerings, providing an intellectually stimulating alternative to beachgoers seeking vacation variety. Wineries, brewpubs and fine dining also take center stage here. So, when you’re not lounging by the waterfront, be sure to sample the area’s top-flight cuisine and award-winning libations, while checking out Greenport’s many historical gems. 

The East End Seaport Museum is a must-see on any visit to Greenport.

The Museum Scene

To experience an intriguing component of Greenport’s long maritime tradition, spend some time at the Fireboat Firefighter Museum (Wiggins Street, Greenport Commercial Pier, 631-333-2230, americasfireboat.org), featuring the nearly 80-year-old Fire Fighter, the world’s most award-decorated fireboat. Designed by renowned naval architect William Francis Gibbs in 1938, Fire Fighter fought over 50 major fires during her career, including blazes aboard the SS Normandie, El Estero, Esso Brussels and Sea Witch, as well as several dozen major pier fires throughout New York Harbor.

Fire Fighter also led the FDNY Marine Unit response to the Sept. 11, 2001 attacks, supplying water for three weeks to emergency crews fighting fires at Ground Zero. A National Historic Landmark listed on the National Register of Historic Places, Fire Fighter is now a memorial and teaching museum, while still a fully operational vessel. She’s open for guided and self-led tours from April to October, on weekends from 11 a.m. to 5 p.m.

Another Greenport hotspot for oceangoing history is the East End Seaport Museum (3rd Street, 631-477-2100, eastendseaport.org), honoring the area’s longstanding relationship with the sea. Attractions include a 750-gallon saltwater aquarium featuring flora and fauna from Peconic Bay, a display of two Fresnel lenses, and exhibits devoted to subjects like LI’s

Baymen, oyster harvesting, devastating storms and artifacts salvaged from the wreck of the steamer Rye Cliff, as well as a sampling of the museum’s collection of miniature ships. Call or check the website for the latest open hours; admission with or without voluntary donation.

Fans of more terrestrial transportation aren’t left out when visiting Greenport, either. For all things pertaining to riding the rails, there’s the Railroad Museum of Long Island (440 4th St., at the LIRR Tracks, 631-477-0439, rmli.org), famous for its intricate model train layouts, restored vintage train cars and rides on its World’s Fair miniature train. Your admission ($10 for adults 13+, $5 for children 5-12, kids under 5 free) is good for guided tours of both the Greenport museum and its Riverhead sister site, as well as a miniature train ride.

Sometimes, transportation just means going in a circle. In that spirit, old meets modern to the delight of children and parents alike at Greenport’s 100-year-old antique carousel in the Jess Owen Carousel House (Front Street, Mitchell Park, 631-477-2200, villageofgreenport.org), named for Jesse Owen, the first operator of the ride.

Housed within a striking contemporary glass, steel and wood house, the 1920s Herschell Spillman portable carousel – a gift from former owners Northrup-Grumman – features 36 horses (all jumpers) plus two sleighs, including 18 hand-carved Herschell steeds, four turn-of-the-century carved Dare horses and 12 cast-aluminum horses dating to the 1930s. The carousel is open daily in-season (end of school through Labor Day) and on weekends the rest of the year, and costs just $2 for each magical spin back in time. Unless of course you catch a brass ring, which wins you one free ride. 

The Jess Owen Carousel House is home to a 1920s Herschell Spillman carousel.

Eye Candy

For a trip back into photographic history, be sure to check out Long Island’s surviving Camera Obscura (Front Street, Mitchell Park, 631-477-0248, villageofgreenport.org), housed in its own dedicated building in Mitchell Park. The view outside is reflected by a mirror through a lens, which projects the image onto a viewing table inside. The mirror can be rotated, to see in all directions. Today there are approximately 50 public camera obscuras in the world, five of which are in the United States. (Available by appointment only, and weather permitting. Admission is just $1.)

Your eyes will be equally dazzled when gazing upon the stunning creations of contemporary realist painter Isabelle Haran-Leonardi, whose work is showcased at the Nova Constellatio Gallery (419 Main St., 516-443-0242, novaconstellatiogallery.com). Haran-Leonardi specializes in large scale landscapes of Eastern Long Island’s vineyards and waters, winning multiple awards for her works in recent years. The gallery also serves as her working studio, so when you visit you may get the opportunity to witness a true artisan in action. 

Greenport Harbor Brewing Company’s two owners became buddies in college.

Drink Me

Wineries are a massive draw for the Greenport area (and Long Island’s East End, in general). The 62-acre, award-winning Kontokosta Winery (825 North Rd., 631-477-6977, kontokostawinery.com) is one of Greenport’s top spots for vino enthusiasts, and is the North Fork’s only waterfront winery and tasting room. Stop in to sample the latest favorites, and/or take a winery tour, which are offered every Saturday and Sunday from 11 a.m. to 3 p.m. The tour lasts roughly 45 minutes and includes a tasting of four wines, a cellar tour and a barrel sample. Tours cost $35 per person; reservations are highly recommended. You can also enjoy their wines while sitting at one of the many picnic tables available along the winery’s quarter-mile of oceanfront.

Or, if you prefer your libations to originate from hops instead of grapes, hunker down at Greenport Harbor Brewing Co. (234 Carpenter St., 631-477-1100, greenportharborbrewing.com), popular for its “flight” of five different beers, served on a Long Island/whale-shaped board. The brewery stays open an extra hour until 9 p.m. on the first Friday of every month, to coincide with the Greenport Gallery Walks event. 

The world-famous Claudio’s Restaurant.

Historic EatsIn Greenport, even the restaurants are historic. None more so than Claudio’s Restaurant (111 Main St., 631-477-0627, claudios.com), housed in a National Historic Registered Building circa 1845. Serving up fine seafood since 1870, Claudio’s is the nation’s oldest same-family-run restaurant, founded by descendant Manuel Claudio, a Greenport whaler from Portugal, who first opened the business as Claudio’s Tavern. When not gorging on shrimp and lobster, take a moment to peruse the restaurant’s Victorian bar dating to 1886, as well as its many local artifacts. 

Greenport’s downtown has been lively since the LIRR first stopped there in the 19th century. (photo credit: Joe Shlabotnik/Flickr)

Other recommended spots include:

1943 Pizza Bar
Stirling Square, 631-477-6984, rollingindoughpizza.com

Agave Grill & Cantina
110 South St., 631-333-2323, agavegrillandcantina.net

American Beech
300 Main St., 631-477-5939, americanbeech.com

Bruce & Son
208 Main St., 631-477-0023, bruceandsongreenport.com

First and South
100 South St., 631-333-2200, firstandsouth.com

The Frisky Oyster
27 Front St., 631-477-4265, thefriskyoyster.com

Little Creek Oyster Farm & Market
37 Front St., 631-477-6992, northforkoysters.com

Lucharito’s
119 Main St., 631-477-6666, lucharitos.com

Noah’s
136 Front St., 631-477-6720, chefnoahs.com

Salamander’s On Front
38 Front St., 631-477-3711, salamandersonfront.com

Sterlington Deli
3 Sterlington Commons, 631-477-8547, www.sterlingtondeli.net 

NY Auto Giant
Experience all that is historic, breathtaking and fun-filled in Greenport

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Brendan Manley is an award-winning journalist, screenwriter and content development/marketing professional. He has extensive experience in newspaper and magazine publishing, as well as digital media, covering topics including arts and entertainment, sports, lifestyle, news, technology, travel and history. He is an ongoing contributor to Military History, Hotel News Now.com and HOTELS magazine, as well as the Long Island Press, where he formerly served as Managing Editor and Lifestyle section head. He is currently developing several of his original scripts for Hollywood, and consults on various film and scripted TV projects for studios, producers and financiers. Brendan is based in upstate New York's southern Adirondacks region.