Best Things To Do on Long Island by Road Trip

By | Digital Editor
Last Updated: February 18, 2023
Long Island Road Trip Itinerary: Top Things To Do & See • Winetraveler

Long Island is the perfect destination for New Yorkers: it’s due east, it’s easily accessible, and it holds over 100 miles of goodies to discover. Long Island is entirely doable as a day trip, a weekend trip, or even longer. Here, we’ll explore an itinerary that covers a day (or two) of things to do out on Long Island via road trip.

Best Things To Do on Long Island via Road Trip

For clarity’s sake, we’ll be starting from New York heading east along the north side of Long Island, connecting with the South Fork via Shelter Island, and heading back west along the south side.

Nassau County Museum of Art

The North Shore of Nassau County saw a boom of luxury mansions built in the late 1800s and early 1900s, so much so that it became known as the Gold Coast and served as inspiration for “The Great Gatsby.” The Nassau County Museum of Art is housed in an example from this era. Take time to admire the architecture, indulge in the art collection, or explore the sculpture gardens.

Planting Fields Arboretum

Another example of the Gold Coast days, the Coe mansion is stunning but the real show-stopper is the gardens. Whether you explore the Italian Garden, the Camellia House, or the Main Greenhouse (or, all three), your wish for a green thumb will kick into overdrive. It’s flora heaven.

Garvies Point Museum & Preserve

Ever wonder where all those -ogue town names come from on Long Island? The once-thriving indigenous communities often named areas after proximity to water. Garvies Point Museum is dedicated to the history of Long Island’s native communities, some of which still exist today.

Joseph Lloyd Manor House

Considered the father of African American literature, Jupiter Hammon lived and wrote his poetry at the Lloyd Manor House. Although enslaved, Hammon learned to read and write and went on to be the first published black poet in what would become the United States. Such a formidable accomplishment in 1761 is now commemorated at the House, which is dedicated to the history of Black literature.

Heckscher Museum of Art

Located in picturesque Huntington, the Heckscher Museum of Art has an impressive collection of mostly European paintings and sculptures, with a heavy emphasis on new exhibits featuring Long Island artists. It’s an interesting mix and provides a glimpse at the up-and-coming talent in the region. Give yourself time to explore Huntington as well, which is home to an eclectic mix of boutiques and restaurants.

Staller Center for the Arts

Although Stony Brook University is one of the best in the State University system, its campus lacks a bit of charm and is very much a reflection of more functional architecture. That said, Staller Center for the Arts is an absolute jewel and holds perfectly executed performances, from ballet to jazz to literature talks. And thankfully, some beautiful little villages surround the otherwise lackluster campus.

Lewin Farm

Ok, enough art – let’s get to the good stuff: fresh produce! Many people don’t realize how many working farms still exist on Long Island and Lewin Farm is the perfect place to bring the kids – or heck, leave them home and go by yourself – to purchase the best produce or to pick your own. Lewin has pick-your-own strawberries, raspberries, apples, pumpkins and more.

Hallockville Museum Farm

Take a step back in time to explore how European settlers lived and adapted to Long Island through the 1700s and 1800s. The many branches of the Hallock family spread throughout the North Fork, and Hallockville was later established in some of their preserved homes. Events include basket weaving workshops, historical talks, and more.


Wineries exist along Routes 25 and 58 (which more or less run parallel) beginning around Aquebogue all the way to Greenport.

Long Island wineries have gotten much-deserved accolades in recent years and there are too many wineries to mention here. If you’re interested in exploring Long Island Wineries and/or hotels, please see our top recommendations here.

Shelter Island Ferry

Instead of driving all the way back around to Riverhead and heading south, take a break from driving by hopping on the ferry! From Greenport, follow the signs to Route 114 to get to the ferry landing. Once you’re on Shelter Island, you can either explore the island (it’s tiny so it won’t take long!) or stick to Route 114 to get to the south side, where you’ll exit into the hopelessly quaint town of Sag Harbor.

Elizabeth A. Morton Wildlife Refuge

Known locally as Jessup’s Neck, the Morton Wildlife Refuge is a sweet little spot of peace. A flat and easy trail empties out to a beach, where you can just hang out and relax. Bring plenty of birdseed with you because the chickadees will eat right out of your hand if you stand still enough!

Quogue Wildlife Refuge

Anyone can send you to the Hamptons, but we’re taking a different route: let’s explore wildlife. Quogue is a refuge where many of the animals are injured and would not otherwise survive. The dedicated caretakers ensure everyone stays healthy and safe. Take your time checking out the beautiful owls who live there.

Smith Point County Park

Even if you’re not road-tripping during the summer, Smith Point beach is always beautiful and worth checking out. In fact, having it to yourself in the winter might even be better! There’s also a memorial to TWA Flight 800, which went down about a few miles offshore in 1996.

Cherry Grove & the Pines

A small community on Fire Island, Cherry Grove and the Pines have long been an LGBTQ haven, particularly in the summer. To get there, take a short ferry trip from the adorable hamlet of Sayville. Plan your weekend well in advance because both can get packed out on summer weekends.

Bayard Cutting Arboretum

While the mansion might be magnificent, it’s the grounds here that will grab your attention. You can spend hours – or even an entire day – here checking out the variety of gardens. Arrange for a guided tour in advance.

Amityville Horror House

Even if you’re not a native Long Islander, you’ve probably make the holy trek like every teenaged-chucklehead to see the Amityville Horror House. We won’t put the actual address in here but it’s very google-able for those who want to see a ghoulish piece of Long Island history. 

Long Beach Boardwalk

Long Island is an island after all, so we may as well finish out this road trip by the water! Take a stroll down the Long Beach Boardwalk, where the people-watching can be pretty fabulous. Grab a drink in time for sunset or have fresh seafood dinner right by the water.

Travel Tips & Practicalities

Located east of Manhattan, Long Island juts out into the Atlantic Ocean for about 120 miles. Brooklyn and Queens, two of New York City’s boroughs, are actually on Long Island but most people would consider Nassau and Suffolk to be the counties that make up ‘the Island.’ Suffolk is the largest of the two and the otherwise densely packed population decreases the further east you go.

By car, Long Island is easily accessed from Manhattan via the many bridges and tunnels. The Long Island Expressway is the main highway that runs the length of the island and it connects up to bridges leading up to Westchester and down to Staten Island and New Jersey. The Long Island Rail Road runs constantly from Penn Station but public transportation is a bit more sparse once you arrive at your destination so a car really is better for exploring. You can take a look at flights into nearby airports here as well as some of our recommended hotels here.

Despite getting somewhat of a bad rap in the media – and, not without reason at times – Long Island has so much to offer. From mansions and museums to losing yourself at a park, there are endless possibilities. And as a native, I say that with pure “Lawn Gisland” pride! Enjoy!

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