Roughly 118 miles from end to end, and no more than 23 miles across at its widest point, Long Island reigns as the longest and largest island in the contiguous United States. It is, undoubtedly, among the most oddly shaped as well. Walt Whitman, an American poet and native of the area, most notably pointed this out in Leaves of Grass in 1860, referring to his home by its Native American name of Paumanok, or fish-shaped. Shane Herrick, Long Island resident, gives his take on what the best locations are and picks four favourite routes.
The ‘head’ – home to the boroughs of Brooklyn and Queens – lies to the west, with New York City reaching skyward just across the East River. The tail stretches off to the east, pointing two ragged tips out across the Atlantic Ocean. In between, over a hundred miles of pristine beaches and sprawling bays line its southern shore, while the calmer waters of the Long Island Sound lap its rocky northern coast.
Few places are so uniquely home to a rich history and the varied landscape of the city, the country and the sea, making Long Island ideal for a day trip on the fly or an extended run on two wheels.
The Rockaways – Fort Tilden – Breezy Point (Queens)
In keeping with the fish likeness, the Rockaway Peninsula looks like the lower jaw of the fish, hanging out under Brooklyn. And on this spit of land sit Breezy Point, Fort Tilden and The Rockaways.
Working your way south and away from the bustle of the city via Flatbush Avenue, the buildings, houses and towers disappear almost at once. The land abruptly gives way as the Marine Parkway Bridge yawns out ahead over the open waters of Jamaica Bay. About here you want to hang tight and keep things straight and true as you speed over the ever-unsettling surface of drawbridge grates. That loose and slippery feeling gives us all on two wheels pause and here it goes on for several football fields.
As you clear the bridge and get back on solid roadway, the dunes, low-lying maritime pines and sprawling natural beaches of the peninsula open out in front of you. Head west along Rockaway Point Boulevard and run the straight shot among the dunes, boatyards and marinas.
Fort Tilden looms large along the shore. Once a United States army coastal artillery installation from WWI through the Cold War, Fort Tilden has since been decommissioned. Though some structures have been renovated for the arts and educational purposes, many of the bunkers, batteries and other military structures remain abandoned in ominous, graffitied contrast to the often-packed beaches around them.
Further west, and at the very tip of the Rockaway Peninsula, sits the curious beachside neighbourhood of Breezy Point. It’s a beautiful place to take a load off, stretch your legs and get a truly remarkable view across the water of Brighton Beach, of Coney Island and of the towering skyline of New York City just beyond.
On the ride back east, cut south a few blocks on 108th Street until you’ve joined the unmistakable boardwalk party that is the Ramones’ old stomping grounds of Rockaway Beach.
Ocean Parkway and the Robert Moses Causeway
Ocean Parkway is among the most beautiful stretches of roadway on Long Island. It runs along the entirety of Jones Beach Island, one of Long Island’s largest barrier islands. These barrier islands are largely protected state parks and so have minimal development, minimal traffic, no work or transit trucks, and also no traffic lights. Just two lanes in each direction flanked by the Great South Bay, just off the side of the road to the north, and the Atlantic Ocean, just across the sand to the south.
Cedar Point County Park – Northwest Woods
If you’ve already had your fill of sun and sand and coastal straightaways, take refuge in the back roads of the Northwest Woods and Cedar Point Park in Sag Harbor and East Hampton. Nestled in the low hills of the northern region of Long Island’s South Fork, and north of the sprawling farm fields and famous mansions of the East End, these roads bob and weave in the shade of the trees. Blind corners, abrupt hills and steep sudden switchbacks abound in these woods, so a few passes to get familiar with some of the more drastic turns wouldn’t go amiss before you attempt to flex your cornering chops.
A couple of things to look out for as you weave your way through: mind cars cutting corners; keep an eye out for deer; and watch for sand, salt and loose material in some of the dips and corners.
At the northernmost end of the headland sits Cedar Point County Park. Here you can pitch a tent and camp for the night and have a go at catching some dinner in the waters of the Northwest Harbor or Gardiner’s Bay. Also worthwhile is the walk out to the point itself for a look at the original Cedar Point lighthouse, first built in 1860 to guide the fishermen and timber merchants heading in and out of Sag Harbor.
As you approach the easternmost tip of the South Fork, the land narrows and begins its run out to Montauk, or The End. The first leg is the Napeague Stretch; a beautiful woodland straightaway cutting through the coastal pine lands. As the pines again give way to low-lying brush and sand dunes, pull off at one of the two duelling lobster roll joints – Clam Bar or Lunch – and get yourself a towering roll of fresh local lobster: it’s a staple.
A few miles on, past Hither Hills State Park and its beachside campground, the highway splits into new and old. Take Old Montauk Highway to the south. It weaves somewhat recklessly over, down and around the houses and hotels that sit perched on the steep hillside and bluffs looking out over the Atlantic Ocean below.
Montauk’s main drag of surf shops, bait and tackle shops, small beachside hotels, restaurants and bars rolls out ahead along the beach.
The road bucks and weaves on for roughly 10 miles as you ride out of town to the east. The abrupt and sudden swooping hills of Montauk mark a drastic change in elevation and landscape to the rest of the island, as if the tail end of this odd fish-shaped island is giving one last kick and struggle before surrendering to the sea.
At its very end, past Deep Hollow Ranch, sits the Montauk Lighthouse and the Atlantic Ocean. Standing tall, the coastal sentinel guides ships in and around the ragged coastline where the Atlantic Ocean meets Gardiner’s Bay. Here at the end also sits the eerily abandoned Camp Hero. Steeped in history and conspiracy – most recently as a thematic basis for the show Stranger Things – it is certainly worth a creepy exploration.