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Coecles Harbor off Shelter Island is an excellent spot for paddleboarding into the fall season. (Photos by Hillary Gulley)

There are two types of people: those who think summer ends in August, and those who know the best of the season is yet to come. No matter which camp you’re in, you can still enjoy paddleboarding on the North Fork and Shelter Island well into fall — though you might spot a hardcore paddler on Peconic Bay as late as the winter winds will allow. The pleasures of summer on the water are obvious, but the advantages to paddling into the fall are undeniable: parking becomes less restricted, fewer boats make for lake-like water, and as the ospreys take off for warmer climes, fish like menhaden move closer to shore to feed, offering a view into their world for anyone on a board. While we often associate exploring with wide-open country lanes, the best of the East End can arguably be found at its dead ends. Here are a few of the top spots to check out as you paddle out this time of year.

Coecles Harbor, Shelter Island

For a challenging endurance workout that will reward you with unparalleled wildlife sightings, head to Coecles Harbor in the Peconic Estuary and follow as much of the Marine Water Trail as your arms (and core) will allow. Tick-free exploration of the Mashomack Preserve from the water comes at the price of a boat channel navigable with some common sense and awareness (no selfies here) and quick mud that can be avoided by not going too close to the marshes. The handy trail map onsite and online says to stay close to shore for the best sightings and to allow three to four hours to complete the whole trail… on a kayak.

Entry Point: 80 Burns Rd., Shelter Island

On-site boards available: Seasonally (Kayak Shelter Island, 631-749-1990)

Long Beach Bay at Orient Point

If you swoon at windswept pines and driftwood-strewn beaches, look no further than the Hallock Bay entry point at Orient State Park for sweeping views, protected paddling, year-round greenery and even resident osprey onlookers when the season is right. Drive slowly along the peninsula to absorb the otherworldly views and to look out for box turtles, a threatened species on the North Fork.

Entry Point: Hallock Bay, Orient Point State Park

On-site boards available: Seasonally (see Eagle’s Neck Paddling Co., State Pkwy, Orient, NY 11957; 631-765-3502)

Dickerson Creek, Shelter Island Heights

Restrooms and accessible parking make this beach ideal for families looking to spend time out together. The creek is protected enough to offer minimal currents and waves. Head out into the open water, more like a lake, or seek out the snug shoreline contours that will lure you into following their outline, where you can spot the resident fiddler crabs.

Entry Point: Wades Beach, S. Midway Rd., Shelter Island Heights  

On-site boards available: no

Rocky Point Cove, East Marion

Best for intermediate to advanced paddleboarders who are comfortable with currents and tidal charts, this spot on the Long Island Sound is reached by sixty-seven steps. However, it’s not to be confused with its eponymously named westward neighbor. It is, however, something to consider when deciding how much you want to sweat it out before and after your workout: there are no boards available onsite which means not only is it BYOB (bring your own board), but you get to haul yours up and down a cliff, too. The rewards for those who are game include crystalline water and the host of geological wonders that make up this former glacial shelf.

Entry Point: End of Rocky Point Rd.

On-site boards available: no

Pipe’s Cove, Greenport Town and Greenport Village

Picture this: you’ve decided to brave the nip in the air and paddleboard on a crisp fall evening. Out on the water, you catch a whiff of smoke from a wood stove warming a house overlooking the bay. Just ahead, hundreds of menhaden—a local bunker fish—are foraging closer to shore than they do in the summer, and from your board you can see their fin tips piercing the water’s serene surface. Back on shore, the sun is setting over the Silver Sands Motel. Two vacant osprey nests are becoming craggy shadows against the darkening sky. Maybe it’s time to go back in for a drink. Or then again, maybe not.

Entry Point: End of Silvermere Rd. or, for a challenge, the 6th Street Beach in Greenport Village

On-site boards available: Not yet (Silver Sands, we’re looking at you!)

Brick Cove Marina, Southold

Just around the bend from Pipe’s Cove lies Brick Cove Marina. This is private property, so access is exclusively by renting one of the boards on site through North Fork Paddle Co., which offers private lessons, group excursions, and a gorgeous moonlight paddle session. This spot is notable for its Sunday night beer and oyster parties, as well as its irresistibly Instagrammable beach entry path edged with lights strung up on weathered wood posts. Rumor has it there’s not only a rare blue heron that appears near the slips from time to time but an even rarer green one. The local ospreys aren’t fussed about the collapse of their nest, currently being restored—they’ve taken up residence atop the marina’s massive chimney, arguably preferable real estate if they don’t plan to stay too long past summer. 

Entry Point: Brick Cove Marina, Sage Boulevard, Southold

On-site boards available: Seasonally (North Fork Paddle Co., 631-965-8334)