Long Island summers are unparalleled, and while Labor Day may mark the unofficial end of the treasured season, beach weather temps and outdoor entertainment often stick around through late September. So we put together a list of the best ways to experience an endless summer (or early fall!) right off the Long Island Rail Road. Get inspired and enjoy the last days of summer in the sun!
STEP INTO A SEA OF SUNFLOWERS
Soak up the glow of the Sunflower Fields at Waterdrinker Farms throughout September! Beyond the flower fields you’ll find barnyard animals, mini golf, tractor pedal cars, obstacle courses, a wooden playland and more. Harbes Family Farm in Jamesport has fun-filled weekend Sunflower festivals throughout September with a breathtaking sunflower maze.
Take the LIRR from Penn Station or Grand Central Madison to Riverhead for either location.
HIT THE BEACH
Lifeguards stay on duty at many of Long Island’s famed white-sand beaches past Labor Day weekend. So, take advantage of the thinner crowds and milder temperatures that September offers and hit the beach. Jones Beach in Wantagh, Robert Moses in Babylon, and Hither Hills in Montauk all have lifeguards on duty daily until September 17th. Main Beach in East Hampton will have lifeguards on duty on weekends through Columbus Day, October 9th.
Take the LIRR from Penn Station or Grand Central Madison to Freeport station and take the NICE bus N88 through October 1st to Jones Beach. Or take the LIRR to Montauk Station and take a rideshare to your favorite beach!
SOAR TO NEW HEIGHTS AT AN ADVENTURE COURSE
Jones Beach, New York state’s most popular beach is one of the closest to NYC and offers a wild array of amenities and attractions, like the WildPlay Adventure Course. The park is Long Island’s ultimate outdoor adventure, featuring several ropes course options from high elevated platforms, a 700ft zipline stretching along the beautiful Jones Beach coastline, a 40ft platform plunge jump, and much more. Enjoy a perfectly sunny September day while taking in sweeping views of the Atlantic Ocean from high above; it'll be the ideal weather to get active!
Take the LIRR from Penn Station or Grand Central Madison to Freeport station and take the NICE bus N88 through October 1st to Jones Beach
SAIL INTO THE SUNSET OR CATCH SOME WAVES
Some may be surprised to learn that Long Island waters are often the warmest at the tail end of the summer season. That’s why September is an ideal time for watersports! Whether you’re looking to wakeboard, surf, paddle board, kayak, or jet ski, every area of Long Island provides the gear, services, and lessons for your ideal watersports experience.
For something adventurous, look no further than jet skiing with Island Jet Ski, or Over the Top Watersports for wakeboarding and much more. Fall is also a great time of year to take advantage of the many boating opportunities across the island. You can also sail into the sunset with Long Island Boat Rentals, operating out of Port Washington on the North Shore — they offer everything from private yacht rentals to party boat charters, and more.
Take the LIRR from Penn Station or Grand Central Madison to Freeport, Northport, or Port Washington.
EXPLORE A LEGENDARY LIGHTHOUSE
Many of our region’s landmark lighthouses allow visitors to climb to the very top to take in sweeping ocean views and capture magnificent photos. Fire Island Lighthouse, Montauk Lighthouse, and Horton Point Lighthouse are all open for tours through November! So, climb the 182-step tower in Fire Island, or explore the Montauk Lighthouse, where you can learn about Long Island’s cherished maritime history at the oldest lighthouse in New York State, commissioned by President George Washington himself in 1792! Whether you’re a history buff or just looking for a memorable adventure, visiting one of Long Island’s legendary lighthouses is a fantastic opportunity to keep the nautical adventures going post-Labor Day.
Take the LIRR from Penn Station or Grand Central Madison to Bayshore and board the Fire Island Ferry to Kismet (Fire Island Lighthouse), or take the train to Southold (Horton Point Lighthouse), or Montauk (Montauk Lighthouse)
EXPERIENCE LI'S CHARMING NAUTICAL VILLAGES
As the sun sets on summer you can still experience the nautical charm of the many historic, waterfront, restaurant-laden bustling downtown villages across Long Island’s suburban landscape. The region's Main Streets come alive with festivals and entertainment throughout the year and are home to an array of locally owned shops, pubs, and museums. From Long Beach on the South Shore to Greenport and Port Jefferson on the North Shore, each village has a distinct personality of its own and many hidden gems to discover.
Take the LIRR from Penn Station or Grand Central Madison to Long Beach, Port Jefferson, or Greenport.
DISCOVER FIRE ISLAND'S SUNKEN FOREST
While Fire Island might be known across the globe, it’s home to a hidden treasure – a rare natural wonder missed by many. When you traverse the Sunken Forest and its meandering boardwalks, you’ll feel like you’re below sea level. This unique 40-acre nature oasis is home to a globally rare collection of plants which can be seen with a walk along the Sunken Forest Nature Trail, a thin strip of forest about a ¼ mile wide and 1.5 miles long. On the trail, you’ll likely encounter deer, foxes, and other wildlife, then complete your walk by strolling along the coast of Sailors Haven beach.
Take the LIRR from Penn Station or Grand Central Madison to Sayville and board the Sayville Ferry to Sailor’s Haven/Sunken Forest.
ENJOY A LEGENDARY LOBSTER ROLL
Lobster rolls are synonymous with a trip to Long Island, and it goes without saying no trip is complete without one (or maybe a dozen). There are several famed spots across Long Island like Claudio’s in Greenport, Duryea’s in Montauk, and The Restaurant at Baron’s Cove in Sag Harbor. Take your pick and savor this Long Island staple.
Take the LIRR from Penn Station or Grand Central Madison to either Greenport, Montauk or Bridgehampton
CELEBRATE LONG ISLAND'S WINE COUNTRY
2023 marks 50 years since the founding of the area's wine region in 1973 when Louisa and Alex Hargrave first planted the first wine grapes in the area. Rated by Wine Enthusiast as one of the ‘Top 10 Wine Regions’ in the world, Long Island Wine Country is home to over 60 vineyards and world-class tasting rooms. From rich Cab Francs to versatile roses and legendary bubbly, regional-inspired brews, and top-shelf liquor, Long Island has grown award-winning, high-quality ingredients for wines and spirits in unmatched settings with winding farmlands and waterfront vineyards that are just two-hours away from Midtown by train.
Among the many options throughout the area, Paumanok Vineyards in Aquebogue is a great choice as it was named 2023 Winery of the Year and won the Governor’s Cup for NY State.
Take the LIRR from Penn Station or Grand Central Madison to one of multiple stops throughout Long Island’s North Fork
For more ways to soak up the season, check out Discover Long Island’s guide to Long Island watersports activities too.