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From Tip to Tip, These Are Long Island’s Best Hiking Trails

Outdoor National Parks Insider Guides Hiking Beaches and Islands
by Maggie Peikon Dec 20, 2018

From its beaches to its bagels, Long Island has quite a few things that warrant bragging rights. Among the island’s better-kept secrets, kept from outsiders at least, are the incredible hiking trails. Seasoned hikers and beginners alike will appreciate the variety of trails this island has to offer. From tip to tip, these are the six trails you need to get your boots on.

Bethpage Bikeway Trail
Length: 12 miles

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Starting from Bethpage State Park and ending at the Massapequa Preserve, the Bethpage Bikeway Trail is about 12 miles long. This paved, mostly flat, out-and-back trail sees some pretty heavy traffic through all seasons, save particularly fierce winter days. Head out early in the morning to avoid a crowd. Walkers, runners, bikers, and dog walkers alike share the trail, so be mindful of the ‘on your left’ call-outs when you hit the pavement.

Take a break or have a snack at one of the benches along the trail, and don’t overlook trail etiquette — as with any outdoors journey, leave no trace. Dogs are allowed but should be kept on a leash, and be sure to pick up whatever your four-legged friend might be puttin’ down. A fun local’s tip for those bringing a dog: There are a few streams that dogs often can play in along the trail, a nice relief in the heat of the summer.

Cold Spring Harbor
Length: Five miles

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Cold Spring Harbor packs a powerful punch into its nearly five-mile out-and-back trail. With stairs and some steep hills, this hike — which is manageable for most fitness levels — will certainly get your heart pumping along the way. While you won’t have to dodge any bikers here, there will undoubtedly be plenty of hikers and their four-legged friends to work your way around. While dogs are required to be leashed, you’ll likely notice that some dogs will not be.

This trail is heavily trafficked, especially in the morning to mid-afternoon, though less so in the winter months. The small parking lot next to the Cold Spring Harbor Library fills up fast. Hikers who want to avoid a big crowd, or at the very least find parking, should plan to arrive by 8:30 AM. The trail can also be picked up from Lawrence Hill Road, and though street parking at this point is an option, there’s minimal space available. Winter hiking on this trail is fun, but a little treacherous when the ground is covered in snow. If you want to brave the cold temps in favor of a nearly empty trail, pack crampons and bring a trekking pole for added safety and stability.

Nassau-Suffolk Greenbelt Trail
Length: 20 miles

A Weimaraner puppy hiking New York trails in autumn

Photo: James Parascandola/Shutterstock

This trail actually connects the Cold Spring Harbor State Park trail and the Bethpage Bikeway, making it a perfect stretch for those who really want to put some miles in. Altogether, the out-and-back Nassau-Suffolk Greenbelt Trail covers nearly 20 miles. As it encompasses two very popular trails along its path, it’s safe to say this is moderately to heavily trafficked, depending on your route. If you plan to bike your way down the trail, keep in mind that it’s not entirely paved. A mountain bike may be a better bet in some stretches than a road bike, particularly through Stillwell Woods.

Stony Brook
Length: Varies

Photo: Jay Gao/Shutterstock

Avalon Park and Preserve offers a collection of relatively short, sweet, and scenic trails and walkways throughout its eight acres. The variety of trail options include a handicap-accessible boardwalk trail, though it’s worth mentioning that the accessible area only runs for a short stretch. Summer and fall draw the biggest crowds, but the fall foliage over the park’s pond makes it well worth joining the masses.

While Avalon is accessible and free all year round, it’s only open during daylight hours. In winter, hikers should take note that dusk, and thus the park’s closing time, come early. To beat the crowds, head out in the morning hours. The old adage holds true: the early bird gets the worm, which in this case is a much quieter trail. Dogs are welcome throughout the park and preserve though, as elsewhere, they must be kept on a leash.

Stump Pond Loop Trail
Length: Six miles

Autumn in the park, beautiful landscape of fall trees in long island park

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Tucked within Blydenburgh Park, the Stump Pond Loop Trail might arguably be one of the best trails to enjoy fall foliage with water views. At a little over six miles, this trail is generally lightly trafficked through all seasons, making it a great spot to enjoy any time of day. Its terrain is mostly flat throughout, so it’s accessible for all skill and fitness levels. Smithtown is enjoyed by quite a few varieties of four-legged species. Dogs are welcome, and there’s even a large fenced-in dog park here. Horses also use the Stump Pond trail, further emphasizing the need to keep dogs on leashes for everyone’s safety.

Don’t be surprised if you spot deer along the way, too. Keep in mind that during the warmer months, it’s easy to pick up ticks on this trail, so be sure to check yourself and your pup. Also, be mindful and aware of trail markers on trees as this trail can get a bit confusing at some points. Use the pond as guidance on this loop trail if you’ve gotten off track.

Montauk Point and Camp Hero State Park
Length: Varies

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It doesn’t get much more Long Island than a summer day spent in Montauk. There’s no shortage of hikes to enjoy throughout Montauk Point and Camp Hero State Park, and surprisingly, they are generally only moderately trafficked. As is the case for many of these hikes, it’s best to head out in the morning to have the trail to yourself or to share the trail with just a handful of other hikers.

The out-and-back Oyster Pond Trail offers a nice walk on the beach, and, of course, great water views. At just over two miles, it’s not a strenuous hike either. To switch it up, head out to the end in the winter months to catch a glimpse of seals. The popular Seal Haul Out Trail is easy to navigate, and you can access it from the Oyster Pond Trail to add some mileage to the original hike. This short-and-sweet, out-and-back hike only adds a mile. Even if you don’t get to spot a seal, the views of the sound are reason enough to do it.

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