4.6
(14)
568
riders
61
rides
Road cycling routes around Water Mill offer a diverse terrain that includes coastal views, agricultural fields, and woodlands. The region is characterized by well-paved surfaces suitable for road bikes, with elevations catering to various experiences. Cyclists can explore routes that traverse pristine sandy beaches, historic farmlands, and areas with cultural points of interest. This blend of natural features and maintained roads makes Water Mill a destination for road cycling.
Last updated: July 2, 2026
4.0
(2)
100
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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27
riders
30.7km
01:11
60m
60m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
18
riders
56.5km
02:20
230m
230m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
21
riders
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Popular around Water Mill
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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Grace Estate Preserve offers over 500 acres of water and woods for exploring. It has miles of trails and nice views of Northwest Harbor, and it's ideal for bird watching, hiking, running, and photography. The park is open year-round, from sunrise to sunset. Note that swimming is prohibited, and there is no lifeguard on duty. Dogs are welcome on the condition that owners pick up after them.
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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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Shinnecock Bay, bordering Southampton, New York, is a scenic coastal stretch offering breathtaking views from Meadow Lane. The bay showcases tranquil waters and salt marshes, while Meadow Lane provides a picturesque drive with glimpses of elegant waterfront estates. This idyllic landscape captivates with a harmonious blend of natural beauty and upscale architecture.
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Road cycling routes in Water Mill offer a diverse terrain, blending coastal views, agricultural fields, and woodlands. The area is characterized by well-paved surfaces, ideal for road bikes, with elevations suitable for various experiences. You'll find a mix of flat stretches along the coast and gentle inclines through farmlands.
There are over 60 road cycling routes around Water Mill, catering to different skill levels and preferences. These include easy, moderate, and more challenging excursions.
Yes, Water Mill offers several easy, shorter rides suitable for families. For instance, the Water Mill Windmill – Lake Agawam loop from Water Mill is a 30.7 km (19.1 miles) easy trail that leads through historic areas and past the Water Mill Windmill, often completed in about 1 hour 10 minutes.
Water Mill's routes offer stunning coastal beauty, including pristine white, sandy beaches like Flying Point Beach, where Mecox Bay meets the ocean. You can also enjoy views of private estates, ride past local farms such as the iconic Milk Pail Farmstand, and explore historic sites like the Water Mill Museum and the Corwith Windmill.
The region's diverse landscapes are enjoyable throughout much of the year. Spring and fall generally offer pleasant temperatures and beautiful scenery, while summer provides warm weather for coastal rides. Always check local weather forecasts for optimal riding conditions.
Yes, for more experienced cyclists, the Long Island Greenway—Phase II is a challenging 101.5 km (63.1 miles) route that gains 415 meters (1365 feet) in elevation through diverse East End scenery. Another moderate option is the 78.1 km (48.5 miles) Napeague State Park – Hither Hills State Park loop from Bridgehampton.
The road cycling routes in Water Mill are highly rated by the komoot community, with an average score of 4.2 stars from over 14 reviews. Cyclists often praise the well-paved surfaces, the diverse scenery ranging from coastal views to farmlands, and the blend of easy and moderate options available.
Many of the routes around Water Mill are designed as loops, allowing you to start and end in the same location. Examples include the Water Mill Windmill – Lake Agawam loop from Water Mill and the Foster Memorial Bathing Beach – Water Mill Windmill loop from Southampton.
Beyond the natural scenery, you can explore cultural and historical attractions. The Lake Agawam area is often part of routes. You might also pass through Sag Harbor, or visit the Water Mill Museum. The Parrish Art Museum and Duck Walk Vineyards are also nearby attractions that can complement your cycling trip.
Absolutely. Water Mill offers numerous easy, shorter rides. An example is the Sag Harbor – Water Mill Windmill loop from Southampton, an easy 45.9 km (28.5 miles) route that can be completed in about 1 hour 45 minutes, offering a pleasant ride through the area.


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