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Jump in your car and head out on a roadtrip to take a tour of some of Long Island’s quirkiest roadside attractions. Many have unusual stories and legends associated with them. Be sure to #discoverlongisland across your roadtrip.
Take the scenic route! Take Route 25A along the North Shore of Suffolk County for a beautiful scenic drive along the way.
Take a stroll around the largest freshwater lake in Nassau county. Then check out the hand-carved Hecksher Carousel built around 1914.
Peter’s Clam bar in Island Park is the oldest clam bar on Long Island, built in 1940.
Everything is made from scratch using only the finest ingredients and freshest seafood available.
Take a scenic drive down to Ocean Parkway to Jones Beach State Park. The 188-foot water tower was build in 1930. Take a break and stretch your legs along the two-mile boardwalk. (Seasonal fees may apply)
Head over toward Zach’s Bay and check out what Long Islander’s call “the best place to see a concert” Originally built in 1952 and then expanded 40 years later, this venue holds 15,000 seats.
The Inn At Fox Hollow is a Luxurious Boutique Hotel located in Woodbury (10 minutes from Melville), Long Island featuring 145 suites and has been voted Best Hotel on Long Island.n season, The Inn features an outdoor heated salt water pool, hot tub & cabanas in their private courtyard. Have dinner and drinks at Volpe restaurant
This 14-foot statue of Whisper the Bull was erected to honor the bull-riding founder of Smithtown. Displayed at the convergence of Route 25 and 25A, residents say that the boundaries of Smithtown were set when Richard (Bull) Smith rode his bull to form the perimeter.
Overlooking Stony Brook Harbor, the Hercules Pavilion on Main Street, Stony Brook, houses the figurehead and anchor from the prestigious U.S.S. Ohio, the first ship launched from the Brooklyn Navy Yard in 1820. Toward the end of the century, the U.S.S. Ohio was decommissioned, destroyed and sunk in Greenport, Long Island; however, the figurehead was saved. Part of Hercules pavilion is Polaris Whaleboat, thought to be the only surviving artifact from the Charles Hall expedition to the Arctic in 1870.
A true American Family Restaurant with outdoor patio dining. Sweet Mamas serves up breakfast, brunch and lunch paired with homemade ice cream and crafty milkshakes.
The Stony Brook Post Office is also home to the Mechanical Eagle that resides on its pediment, where it flaps its wings every hour, on the hour (from 8am – 8pm) – as it has done so since 1941, welcoming thousands of visitors to the village’s specialty shops and restaurants. The eagle was hand carved and its wings span 20 feet. The post office, a traditional hub of community activity, was the core of Mr. Melville’s original vision and project – his “living Williamsburg.”
Avalon Park and Preserve was created by the Paul Simons Foundation with the goal of reflecting Paul’s love of nature and the outdoors. Avalon is a re-creation of the natural environment that greeted the first indigenous people to settle New York State. Its five distinct natural habitats populated entirely by native flora hold the story of our past, and quite possibly, the seeds of our future.
The Big Chair is perfect for your next insta worthy photo. Come down for sunset to catch the colorful sky and waterfront in the background. Walk the pier and in the winter ice skate at the rinks.
Located in historic Port Jefferson, the boutique features breathtaking harbor views, a spectacular marina, and cozy and luxurious guest rooms. The brand new “mega deck” one of several outdoor entertaining spaces, provides the ideal location for sunset cocktails, outdoor dinner receptions and more served up directly from the property’s newly renovated restaurant, WAVE Seafood and Steaks.
A landmark when arriving to The Hamptons, the 70 foot steel sculpture of a red deer gazing up at the sky with an antler in its mouth was created by East End artist, Linda Scott. The Stargazer is the connection of the above to the below. This is definitely a roadside site to see; recommended at sunset.
If there is one roadside attraction on Long Island that you don’t want to miss, it’s the Big Duck. This great example of roadside novelty architecture on Long Island was built in 1931 by a Riverhead duck farmer named Martin Maurer. Standing 20 feet tall and 30 feet long with red glowing eyes made from a Model T Ford. Today, The Big Duck is a national historic site and is used as a souvenir spot and tourism information center where rubber ducks and duck shaped candies can be purchased.
If you’re here on a Saturday summer night, catch a race and greet the 12-foot tall Riverhead Raceway Indian who has been standing watch over the quarter-mile oval race track for more than 30 years. Some may recognize him from an episode of the Sopranos.
Long Island’s largest outlet center featuring over 165 manufacturer designer outlet stores. The 80 acre complex is easy and fun to shop and open 364 days a year. The center features a wide variety of famous brand designer and manufacturer outlet stores.
This 1905 historical home once owned by Henry H. Preston, the first salaried sheriff of Suffolk County, boasts original floors, beams, fireplace, stonework, barn doors, and hardware, restored to its original elegance, with modern refinements. Indulge in fresh seasonal fare at The Preston House, offering an impeccable menu of New American cuisine, with scenic outdoor seating and an inviting porch.
Explore world-renowned beaches, historical lighthouses, culinary delights, premiere golf courses, Gatsby-era Gold Coast mansions, and award-winning vineyards on Long Island – New York City’s Beachfront Backyard. Download a copy of the Travel Guide for inspiration and more information to plan your perfect getaway.
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