Roadside Attractions

A Long Island Roadtrip

3 Days

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.

Insider Tip

Take the scenic route! Take Route 25A along the North Shore of Suffolk County for a beautiful scenic drive along the way.

Day 1

  • Hempstead Lake State Park,
  • (516) 766-1029

Hempstead Lake State Park is a multi use facility. Included are 20 tennis courts, children's playgrounds, bridle trails for horse back riding, biking and hiking trails, shaded picnic areas and a historic hand carved wooden carousel. There is a picnic pavilion available for large parties. For fresh…

  • Ocean Parkway
  • (516) 785-1600

Jones Beach State Park's top attraction has always been swimming. The park offers fine surf bathing along 6.5 miles of ocean beach, one-half mile of bay beach for stillwater bathing, and two swimming pools. The west end of the park provides wonderful surf fishing, a boat basin and undeveloped areas…

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.

  • 7755 Jericho Turnpike
  • (516) 224-8100

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. Complimentary amenities include: - Full American breakfast buffet daily - Dinner buffet Monday-Thursday - Hi-speed…

Day 2

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…

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…

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…

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.

  • 25 East Broadway
  • (631) 928-5200

Danfords is located in historic Port Jefferson, on the beautiful North Shore of Long Island and is easily accessible by car or train from New York City and all points in between and by ferry from Connecticut. Breathtaking harbor views. Cozy and luxurious guest rooms. Superb dining and entertainment…

Day 2

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…

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…

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.

  • 428 E Main St
  • (631) 775-1500

THE PRESTON HOUSE & HOTEL – A MODERN BOUTIQUE HOTEL AND NEW AMERICAN RESTAURANT IN THE HEART OF LONG ISLAND’S EAST END Located minutes from the famed Hamptons on the South Fork and historic Wine Country on the North Fork of Long Island, The Preston House & Hotel is a beautifully reimagined…

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