Hamptons Bicycle Adventures: Pedal Your Way Through Fall

Fall bicycle ride in woods
Photo: Алексей Резин/123RF

According to David Streever, author of Best Bike Rides Long Island, “the historic communities of the Hamptons are full of family-friendly attractions, cute town centers and picturesque beaches, all best reached by bicycle.” Autumn is the best time to bike these areas and see what nature has to offer on the East End, as summer days give way to crisper conditions more suitable for biking adventures.

Before you embark on your biking journey, make sure you have the proper equipment.

Looking to pedal through town?
A road bike or hybrid is your best bet. These bikes have thinner tires, enabling you to go faster on hard surfaces. If you’re a serious biker who enjoys rides that exceed 10 miles on the roads, hop on a thin-tired road bike for optimal performance. Hybrid bikes combine the functionality of a road bike with the durability of a mountain bike. The tires are wider than those of a road bike, but thinner than those of a mountain bike. Hybrids are best for the average biker who wants to go on a quick adventure. Using these bikes on the South Fork will enable you to explore the lovely towns and beaches.

So, where should you go?
“Everybody stays south of the highway because the roads north don’t have shoulders,” says James McNamara of Rotations Bicycle Center in Southampton. It’s best to avoid main roads, including Route 27, if you can. Even though bikers would be riding on hard surfaces, McNamara still says wider tires are preferable. If you plan to go near any of the beautiful beaches, thicker tires with puncture resistance are necessary to deal with some of the sharp crushed seashells near the shore. “You could buy a brand new bike,” McNamara says, “and ruin the tires the first day because you ran over a seashell.”

Sweet fat bike on the beach
Fat bikes are ideal for the beach, Photo: Michal Adamczyk/123RF

The skinny on fat bikes.
The fat bike is a new and popular option on the East End. These wide-tired bicycles have lower tire pressure than other bikes, allowing them to handle the sandy terrain near beaches and on certain trails. “Most trails out here are sand, not dirt,” McNamara says, meaning the trails have less traction, making fat bikes a more favorable option. “They can be used on the beaches and the bay. A lot of people ride them up and down Long Beach Road in Sag Harbor,” he says. Long Beach Road and Ferry Road in Sag Harbor have a clear bike lane and less traffic. Add that to the panoramic water views and you’ve got yourself quite the serene ride.

If you choose to ride a fat bike, “Bring a pump with you to let air out and put it back in when you want to ride home,” McNamara suggests. “You lower the tire pressure down to 10 psi so you get a wider base when you’re going in sand and then bring it back up to 15 or 20 [psi] when you get back on the road.”

Jason Lucas, owner of Sag Harbor Cycle Company, says that he also recommends Shelter Island for relaxing rides with breathtaking views. “Shelter Island is a great area to ride because there’s much less traffic,” Lucas says. “From our store [on Bay Street], you can take a bike lane all the way to the ferry. Once you’re on the island, there are a lot of great places to ride. My favorite is Ram Island Drive.”

Streever, the author, suggests North Sea and Big Fresh Pond for a slow-paced ride along backroads that can take you to quaint local markets for lunch.

Take advantage of the beaches while they’re still wonderful, but as the leaves start to change color, consider local biking trails in woodsy areas. For these trails, you should opt for a mountain bike. The thicker, specially designed tires counter unsteady and potentially hilly terrain.

The premier spot for mountain biking on the East End is undoubtedly Hither Hills in Montauk, which boasts miles of trails that take you through the woods and along the shore. “The state parks have plenty of land to explore, the trail system is pretty big, there’s a lot of good riding,” Lucas says.

The Hither Woods Preserve on the north side of Route 27 expands from Napeague State Park past the eastern side of Napeague Harbor. The trails go through the woods and run along the coast of Napeague Bay. The less-manicured trails by the southern tip of Montauk Point will bring you near the landing spot of the Amistad, a slave ship that landed in Montauk after an uprising onboard, which inspired Hamptonite Steven Spielberg’s film of the same name.

“There are several entry points,” to Hither Hills, Lucas says. “Some people start by the overlook or down Navy Road. The trail system there has a lot of good riding. It’s a little bit more aggressive in terms of hills than Northwest Woods.”

Northwest Woods in East Hampton, on the eastern side of Route 114, is where many of Lucas’s patrons choose to ride. Many begin at the parking lot on 114 just before Edwards Hole Road, where there’s a trail map that can serve as a guide. Lucas says, “A lot of people will cut in there and do a loop that goes out toward Scoy Pond and you can pick up the orange trail and it will circle back to 114.” Scoy Pond is near Cedar Point County Park, another park that one can pedal through and explore wooded areas that give way to rocky beaches on Gardiners Bay. On the western side of 114, there is a trail along Merchants Path and you can also go near the East Hampton Airport.

The trails through Northwest Woods aren’t as hilly as those in Montauk, so they are more suitable for beginners, and since there is some riding along low-volume roads, you can use a hybrid bike. The cooler weather and the absence of those pesky ticks make fall the best time to bike these trails.

Finally, make sure you keep safety in mind. Lucas suggests, “As you get into the tail end of the fall, daylight becomes limited, so have your bike equipped with lights to make sure you’re visible to vehicles. Road conditions can change, I find that shoulders are swept a lot less during fall and winter, so there’s more debris and sand on the road. Lowering the pressure in your tires is a good idea to get more grip on the road.”