4.2
(21)
858
riders
77
rides
Road cycling around Bridgehampton features a landscape characterized by coastal stretches, state parks, and rural roads. The region offers generally flat to gently rolling terrain, making it suitable for various road cycling experiences. Routes often traverse scenic areas, including natural preserves and agricultural land. The overall elevation gain across routes is moderate, reflecting the area's coastal geography.
Last updated: April 25, 2026
4.0
(2)
97
riders
101km
04:01
420m
420m
Embark on the Long Island Greenway—Phase II, a moderate road cycling route spanning 63.1 miles (101.5 km) with an elevation gain of 1365 feet (416 metres). You can expect to…
53
riders
78.1km
03:06
270m
270m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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9
riders
46.4km
01:48
160m
160m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
9
riders
41.6km
01:36
110m
110m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5
riders
32.6km
01:16
120m
120m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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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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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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Southampton is a beautiful quaint town with some fantastic architecture. With spots to have a refreshing drink, ice cream or coffee, it makes a great spot for a mid ride refuel.
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The Water Mill Windmill at 695 Montauk Highway in Water Mill, New York, holds historical significance as a tangible link to the area's past. Erected in the 18th century, it stands as an iconic reminder of early milling practices, showcasing traditional craftsmanship and serving as a testament to the region's agricultural and industrial history.
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Sag Harbor is a picturesque village on the East End of Long Island, New York. It boasts a rich maritime history dating back to the 18th and 19th centuries and served as a vital port for whaling and shipping industries. With historic landmarks like the Old Whaler's Church and the Sag Harbor Whaling and Historical Museum, the village preserves its seafaring heritage. The scenic waterfront is dotted with boats and surrounded by historic architecture, adding to the village's charm. Sag Harbor also has theaters, galleries, local shops, and great restaurants and coffee shops making it an awesome place to relax after a long ride.
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The community dedicated this bridge to honor a 19-year-old native of Sag Harbor who sacrificed his life while fighting in Iraq. Following his death, he received recognition for his "extraordinary heroism" as he opened fire on a suicide bomber, bravely sacrificing himself to save the lives of many others.
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There are over 85 road cycling routes around Bridgehampton, offering a wide range of options for different skill levels and preferences.
Yes, Bridgehampton offers many easy routes. More than 50 routes are classified as easy, featuring generally flat to gently rolling terrain. A great option is the Water Mill Windmill – Lake Agawam loop from Water Mill, which is 19.1 miles (30.7 km) and leads through rural landscapes.
For those seeking longer rides, options like the Long Island Greenway—Phase II offer a substantial challenge, covering 63.1 miles (101.5 km). Another excellent long-distance route is the Napeague State Park – Hither Hills State Park loop from Bridgehampton, which is 48.5 miles (78.1 km).
Road cycling around Bridgehampton is characterized by generally flat to gently rolling terrain. Routes often traverse coastal stretches, state parks, and rural roads, providing varied scenery without significant elevation gains.
While the region is mostly flat to gently rolling, there are a few routes with slightly more elevation. The komoot community has identified 2 routes as difficult, though the overall elevation gain across routes remains moderate.
The spring and fall seasons typically offer the most pleasant conditions for road cycling in Bridgehampton, with mild temperatures and beautiful scenery. Summer can be warm, while winter may bring colder weather, though many routes remain accessible.
Many routes offer scenic views, including coastal paths, natural preserves, and agricultural land. You can enjoy vistas of the Atlantic coastline, pass through state parks, and experience the quiet charm of rural landscapes.
Yes, several routes pass by notable attractions. You might encounter historical sites like the Gardiner Windmill and Rev. Thomas James Homesite, or natural features such as Lake Agawam. The Foster Memorial Bathing Beach – Water Mill Windmill loop from Village of Sag Harbor, for example, offers coastal views and passes by the Water Mill Windmill.
The road cycling routes in Bridgehampton are highly rated by the komoot community, with an average score of 4.2 stars from over 23 reviews. Cyclists often praise the varied terrain, from coastal paths to quiet rural roads, and the well-maintained routes.
Yes, many routes in Bridgehampton are designed as loops, allowing you to start and end at the same point. Examples include the Water Mill Windmill – Lake Agawam loop from Water Mill and the Northwest Woods Trails – Grace Estate Preserve loop from East Hampton Airport.
Bridgehampton offers numerous quiet rural roads and routes that traverse natural preserves, providing a peaceful cycling experience away from heavy traffic. Look for routes that pass through agricultural land or state parks for a more serene ride.


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