A trip back in time, trolley tracks from the now defunct Northport Traction Company serve as a reminder of yesteryear. Pictured are existing rail lines across from Cow Harbor Park along Main Street in Northport Village. Photo by Jennifer Uihlein

With the vast bustle of Huntington village to its west and the suburban sprawl of Smithtown to the east, the Village of Northport has long offered a lower-key, more insular vibe than some of its larger neighbors on the North Shore waterfront.

Even now, it’s easy to see why legendary beat poet Jack Kerouac made Northport his home from 1958 to 1964. It’s a timeless, understated place that’s somewhat difficult to get to, and even harder to leave.

English colonists acquired the land that is now Northport from the Matinecock Indians in 1656, essentially transforming the area into a massive cattle pasture, earning it the original name Great Cow Harbour. That all changed in the 1830s, when shipbuilding became its prime industry, and by 1837 the village was renamed Northport. The village’s shipbuilding boom lasted for roughly 50 years, until the end of the 19th century, when steel-hulled boats began replacing the wooden vessels produced in the village. But fortunately, some of the character of that era still endures.

“Northport has one of the finest harbors on Long Island and has been the port in the storm for sailors for many years,” said Northport Deputy Mayor Tom Kehoe. “Today we still have reasonably priced transit docking that attracts boaters from New York City, Connecticut and elsewhere. Our Village Board has also worked to remove impediments to our local businesses; we realized that a thriving local business district was an attraction to tourists and a positive anchor to our community. We now have 20-plus restaurants with permits for outdoor seating, and that has changed our village. Additionally, the opening of the Engeman Theater has also helped to make us a destination.”

Today, when you spend time walking the village streets, taking note of the old trolley rails on Main Street and perhaps grabbing a quiet drink at one of Northport’s unassuming pubs, you can almost hear the sounds of the shipwrights working, and of Kerouac’s typewriter. Soak it in. Some essential Northport diversions include:

THE SALT LIFE

Start your Northport excursion at the heart of the village: Northport Village Park (1 Bayview Ave.), a treasured stretch of green grass and shade trees running along the harborfront, occupying much of the area where the Victorian shipyards once stood. These days there are two playgrounds, a gazebo, basketball court and dock, as well as free parking, and in fair weather the park hosts events ranging from live concerts to farmer’s markets and craft fairs. This is where both residents and visitors alike come to relax and enjoy the village’s quaint charm.

While taking in all the seaside splendor, you may feel the spirits of Northport’s long-gone mariners, inspiring you to leave land behind entirely. Should that occur, nearby Kismet Cruising (Northport Harbor, 631-897-4517, kismetcruising.com) can scratch your oceanic itch, offering a range of cruise options — including afternoon, sunset, dinner and local history cruises — guided by veteran captain Brian Baldauf on his 42-foot sailboat. Baldauf is a fountain of local information, so count on a lively waterborne chat.

ARTISTIC LEANINGS

It doesn’t take long to see how Northport’s sweeping scenery and small-village allure make for the ideal artist’s hideaway, most famously for Kerouac, but also producing homegrown talents like Edie Falco, Patti LuPone, Chris Messina, rapper Aesop Rock and members of the band Wheatus. For anyone with literary longings, taking a deeper dive into that heritage requires a mandatory stop at Kerouac’s favorite Northport watering hole, Gunther’s Tap Room (84 Main St., 631-754-4156, guntherstaproom.com), newly reopened in 2018 after the historic pub was ravaged by a 2017 fire. It’s the quintessential Northport watering hole, steeped in lore right down to its men’s room, where Kerouac would infamously sneak off to sip whiskey he’d hidden in a valise. We recommend you purchase yours from the bartender, instead.

Also on Main Street is another vital strand of Northport’s creative DNA, The John W. Engeman Theater (250 Main St., 631-261-2900, engemantheater.com), occupying the old Northport Theater, first opened in 1932 and reopened in its current form in 2007. Today it is named in honor of Army Chief Warrant Officer Four John William Engeman, brother of co-owner Patti O’Neill, who was killed in Iraq on May 14, 2006. It’s now a year-round professional theater, casting actors from the Broadway talent pool, and features stadium seating, deluxe lighting and sound, The Green Room Piano Bar and Lounge, and even in-seat beverage service. Current and upcoming performances include The Buddy Holly Story, Seussical The Musical, A Gentleman’s Guide To Love and Murder and Madagascar – A Musical Adventure.

And for fans of the visual arts, be sure to also add a stop at LaMantia Gallery (127 Main St., 631-754-8414, lamantiagallery.com) to your Northport itinerary, even if you can’t really afford to take home one of the expertly curated works there on display. For some 30 years owner James LaMantia has been bringing a worldly, metropolitan aesthetic to Northport’s art marketplace through his esteemed gallery, which hosts more than 10 exhibitions annually, featuring the work of internationally known artists, masterworks and creations by promising new artists. A conversation with LaMantia or one of the gallery’s other art experts is sure to be enlightening.

EMBRACING THE PAST

Although Northport has retained a healthy dose of its bygone flavor, the village has also changed substantially over the centuries, which is why a visit to the Northport Historical Society (215 Main St., 631-757-9859, northporthistorical.org) is another highly recommended excursion. Housed in a former Carnegie Library chartered in 1914, the Society maintains a museum with various exhibits on Northport’s past, as well as a well-stocked shop offering eclectic oddities, silver, china, jewelry, linens, ephemera and books. There’s also a research library and a photo collection with more than 4,000 images, many of which have been digitized and catalogued.

AGRARIAN ROOTS

We know, it’s hard to drag oneself away from Northport’s picturesque Main Street and waterfront, but it’s worth it in order to devote a few hours to also exploring the village’s rich agricultural offerings. Ever since its early days when it was known as Cow Harbor, Northport has been fertile farm territory, still visible now at places like Richters Orchard (1318 Pulaski Rd., 631-261-1980, facebook.com/RichtersOrchard). Richters has been selling lovingly grown apples and fresh-pressed apple cider for the last century, along with pies, jams and jellies, and a host of other edible delights. Stock up and go home happy.

Finally, you might not want to exit “Great Cow Harbour” without seeing an actual cow, so if you’re so inclined, Lewis Oliver Farm Animal Sanctuary (Burt Ave., 631-261-6320, lewisoliverfarm.org) has you covered. A historic landmark dating to the mid-1800s, the farm comprises three acres that are home to numerous rescued farm animals, including Annabelle the cow, goats, sheep, alpacas, chickens, ducks, peafowl, and turkeys. There are also original barns, botanical and vegetable gardens, a collection of native wildlife, a country store, and an education center. Just like the village’s human residents, the livestock here are quite happy to call Northport home.

Where To Dine In Northport

Aunt Chilada’s Mexican Grill
729 Fort Salonga Rd., 631-757-8226, auntchiladasrestaurant.com

Bistro 44
44 Main St., 631-262-9744, bistro44.net

Main Street Cafe
47 Main St., 631-754-5533

Maroni’s
18 Woodbine Ave., 631-757-4500, maronicuisine.com

Nina’s Pizza
487 Main St., 631-261-6822, ninaspizzanorthport.com

Robke’s Country Inn
427 Fort Salonga Rd., 631-754-9663, robkescountryinn.com

Rockin’ Fish
155 Main St.., 631-651-5200, rockinfish.net

Seven Quarts Tavern
688 Fort Salonga Rd., 631-757-2000, sevenquartstavern.com

Shipwreck Diner
46 Main St., 631-754-1797, shipwreckdiner.com

Tokyo Japanese Restaurant
192 Laurel Rd., 631-754-8411, tokyoeastnorthport.com

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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.