Henry'S Hollow Pine Barrens State Forest
Henry'S Hollow Pine Barrens State Forest
4.3
(13)
287
riders
13
rides
Road cycling in Henry'S Hollow Pine Barrens State Forest is characterized by its unique pine barrens habitat, featuring pitch pine woodlands and pitch pine-oak forests. The area is primarily undeveloped, offering a wilderness immersion experience. While the forest itself contains unmanicured footpaths more suited for hiking, the broader region provides road cycling opportunities on paved surfaces. The terrain generally features modest elevation changes, with some routes extending towards coastal areas.
Last updated: May 16, 2026
4.0
(1)
56
riders
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
20
riders
49.2km
02:04
170m
170m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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11
riders
30.3km
01:17
140m
140m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4
riders
76.3km
03:03
370m
370m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
15
riders
81.5km
03:24
410m
410m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Henry'S Hollow Pine Barrens State Forest
Just across the street, less than half a mile off of Paumanok Path, is Stony Brook's Southampton Campus. It has a little windmill on its 84-acre campus and might be worth a detour!
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A save beach, and one of a lot one Long Island
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The Old Montauk Highway leads to a trail through the woods with a gate that says closed to traffic. We took it and it’s fine. There’s a nice parking area with a cliff view at the end just before you get to the lighthouse, check it out.
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This is really a stunning area. Beaches as long your look is reaching. And please do a stop
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Just across the street, a short detour, less than half a mile, off of Paumanok Path to the south, is Stony Brook Southampton Campus. This campus has a little windmill on its 84-acre campus and might be worth a detour for windmill enthusiasts.
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The Shinnecock Canal was the first saltwater canal in New York State, built between 1884 and 1892. Once a site used by Native Americans to carry canoes over land, the Canal today connects two of the most stunning bays on Long Island's eastern side, Shinnecock Bay and Great Peconic Bay, which had become landlocked over time. Though the Hamptons officially begin 10 miles (16.09 km) west of the Canal, it is known as the starting point of this exclusive summer resort, as every modern bridge leading to the Hamptons crosses the Canal.
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Otter Pond is part of the Long Pond Greenbelt, known as the "string of pearls" due to its chain of 13 rare coastal plain ponds. These fragile ecosystems are crucial habitats for diverse plant and animal life, making them a significant conservation area.
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Napeague State Park, in Long Island, offers a pristine coastal respite. Its unspoiled beaches stretch for miles, providing a perfect setting for sunbathing, beach going and hiking. The park's natural beauty, encompassing dunes and diverse wildlife, inviting you to enjoy its natural beauty in this largely undeveloped and unspoiled park.
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While Henry'S Hollow Pine Barrens State Forest itself features unmanicured footpaths more suited for hiking, the broader surrounding region offers excellent road cycling opportunities on paved surfaces. These routes allow you to experience the unique pine barrens habitat and extend towards coastal areas.
Road cycling routes in the Henry'S Hollow Pine Barrens area primarily feature paved surfaces. You'll find a mix of pine barrens ecosystems, tree-lined roads, and coastal dune routes. The terrain generally has modest elevation changes, making it accessible for various skill levels.
There are 13 road cycling routes available in the Henry'S Hollow Pine Barrens region, offering a variety of distances and difficulties for cyclists.
Yes, for experienced riders seeking a challenge, the Montauk Point State Parkway – Montauk Point Lighthouse loop from Hampton Bays is a difficult 89.2-mile (143.5 km) route with significant elevation gain, leading to a notable coastal landmark.
Yes, there are several easy routes suitable for families or beginners. For instance, the Ponquogue Bridge View – Dune Road loop from Hampton Bays is an easy 16.9-mile (27.2 km) trail that takes about 1 hour 5 minutes, leading through coastal dune roads. Another easy option is the Dune Road – Dune Road loop from Village of Quogue, which is 23.2 miles (37.3 km) long.
The Henry'S Hollow Pine Barrens region is an excellent example of pine barrens habitat, characterized by pitch pine woodlands and pitch pine-oak forests. This unique ecosystem supports diverse wildlife, including white-tailed deer, red fox, opossums, and various birds like red-tailed hawks and ospreys. You might also spot Eastern box turtles or Eastern hognose snakes. The natural setting provides opportunities for birdwatching and wildlife viewing, especially along quieter sections of the routes.
Yes, many of the road cycling routes in the area are designed as loops. Examples include the Agawam Lake – Beautiful tree-lined lane loop from Hampton Bays and the Montauk Point State Parkway – Montauk Point Lighthouse loop from Hampton Bays.
The road cycling routes in the Henry'S Hollow Pine Barrens region are highly rated by the komoot community, with an average score of 4.4 stars from over 11 reviews. Cyclists often praise the varied terrain, from pine barrens ecosystems to coastal dune roads, and the options available for different ability levels.
While Henry'S Hollow Pine Barrens State Forest itself is a natural area where dogs might be permitted on hiking trails, specific regulations for dogs on road cycling routes can vary. Generally, dogs on leashes are often allowed on public roads and paved paths. However, it's always best to check local signage or specific route details for any restrictions before heading out with your pet.
Yes, some routes offer notable landmarks and scenic views. For example, the Montauk Point State Parkway – Montauk Point Lighthouse loop from Hampton Bays extends to the iconic Montauk Point Lighthouse. Other routes, like the Ponquogue Bridge View – Dune Road loop from Hampton Bays, offer coastal dune roads and views of the Ponquogue Bridge.
The Henry'S Hollow Pine Barrens area can be enjoyed for road cycling during much of the year. Spring and fall offer pleasant temperatures and beautiful scenery, with less humidity than summer. Summer can be warm, but coastal routes may offer refreshing breezes. Winters are generally milder than inland areas, but conditions can vary, so checking local weather is always recommended.
Many of the road cycling routes in the Henry'S Hollow Pine Barrens area start from towns like Hampton Bays or Village of Quogue, where public parking is typically available. Specific starting points and parking information are usually detailed within each route's description on komoot.


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