4.6
(17)
434
riders
47
rides
Road cycling routes around Middle Island, New York, are characterized by a diverse landscape on Long Island, offering both challenging and leisurely rides. The region features extensive woodlands, natural preserves like Glacier Ridge Preserve and Cathedral Pines County Park, and coastal influences from areas such as Mount Sinai Harbor. The terrain is generally varied, with some flat stretches and gentle rolling hills, providing options for different fitness levels.
Last updated: October 19, 2026
8
riders
80.3km
03:14
280m
270m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
54.7km
02:21
170m
170m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

8
riders
40.8km
02:04
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(1)
8
riders
61.9km
02:37
220m
220m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
74.4km
03:10
280m
280m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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This is a historical little cemetery, with graves dating back to the early 1800s. If it looks a little overgrown and unkempt it's because the locals decided to leave it that way after a streak of vandalism in the 1980s, hoping that if it didn't attract notice it wouldn't attract vandals, either.
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Long Island is known as the cradle of aviation and is the scene of many aviation premieres. Many aircraft manufacturers such as Grumman, Republic and Brewster had their headquarters on the island.
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The Vietnam Veterans Memorial Recreational Trail is a 9.5-mile trail that is mostly paved and, in some places, hard-packed dirt. It is mostly flat and takes bikers on long stretches around the Calverton Executive Airpark.
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This 191-acre undeveloped area is highly popular for hunting, hiking, skiing, snowshoeing, and biking. It features a nice single-track 8.5-mile loop bike trail that's great for beginners and intermediate riders, along with 1.5 miles of more advanced hill climbs.
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Spring Lake is on the eastern edge of the Spring Lake Golf Course, and this area is open weekdays from 6:30 a.m.– 6 p.m. and weekends from 5:30 a.m.– 6 p.m. Just north of Spring Lake is the public Bartlett Pond Park, another enjoyable part of this green space.
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This fast and good quality road travels through the Robert Cushman Murphy Country Park forest, with a tall canopy of trees enveloping the road. Keep an eye out for the trains passing on the adjacent line.
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The Wardenclyffe Tower, also known as the Tesla Tower, was an early experimental wireless transmission station designed and built by Nikola Tesla from 1901 to 1902.
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Grumman Memorial Park is right next to the Vietnam Veterans Memorial Recreational Trail. The park is open every day from 9 a.m.–5 p.m., and features two retired military planes. There are benches and informational plaques to read. It was a cool opportunity to see these aircraft up close and personal in this intimate park.
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There are nearly 50 road cycling routes around Middle Island, offering a diverse range of options for cyclists. These routes have been explored by over 350 road cyclists using komoot.
Middle Island offers a good mix of routes for various skill levels. You'll find 12 easy routes, perfect for beginners or a relaxed ride, and 34 moderate routes for those seeking a bit more challenge. There are no difficult routes listed in the area.
Yes, Middle Island has several easy road cycling routes suitable for families. One popular option is the Roadbike loop from Rocky Point, which is 19.1 miles long and features mostly well-paved surfaces. The Setauket-Port Jefferson Station Greenway Trail also offers a 3-mile paved path through varied landscapes, though be aware of road crossings.
The terrain around Middle Island is quite varied. You'll encounter extensive woodlands, natural preserves like Glacier Ridge Preserve and Cathedral Pines County Park, and coastal influences near areas such as Mount Sinai Harbor. The routes generally feature a mix of flat stretches and gentle rolling hills, with mostly well-paved surfaces.
Road cycling around Middle Island offers views of diverse natural landscapes. You can ride through significant woodland areas in Glacier Ridge Preserve and Cathedral Pines County Park. The Mount Sinai Harbor – Mount Misery loop provides coastal influences and views of the harbor. Additionally, the Setauket-Port Jefferson Station Greenway Trail connects old-growth forests, farmland, and meadows.
For experienced riders looking for a longer, moderate challenge, the Peconic River – Rocky Point Parking loop from Rocky Point is a great option. This route spans 49.9 miles (80.3 km) and takes approximately 3 hours 14 minutes to complete, offering extensive riding through natural settings. Another moderate option is the Peconic River loop from Yaphank, covering 62.1 miles.
The road cycling routes around Middle Island are highly rated by the komoot community, with an average score of 4.5 stars from more than 15 reviews. Cyclists often praise the diverse woodlands, natural preserves, and coastal areas that define the riding experience, as well as the variety of options for different ability levels.
Yes, many of the road cycling routes in Middle Island are designed as loops, providing a convenient way to start and end your ride in the same location. Examples include the Roadbike loop from Rocky Point, the Mount Sinai Harbor – Mount Misery loop, and the Peconic River loop from Yaphank.
The Middle Island region is rich in natural beauty. You can expect to see extensive woodlands, particularly within Glacier Ridge Preserve and Cathedral Pines County Park. The area also features the unique pine barrens habitat in East Bartlett Pine Barrens State Forest and coastal influences around Mount Sinai Harbor, a marine sanctuary.
Absolutely. The Mount Sinai Harbor – Mount Misery loop from Rocky Point is a 25.4-mile moderate route that leads through areas with both coastal influences from Mount Sinai Harbor and natural preserves, offering a varied and scenic ride.
For those seeking longer distances, the Peconic River loop from Yaphank covers 62.1 miles (100 km) and is a moderate route. Another substantial option is the Shore Road - Ocean View – Spring Lake loop from Terryville, which is 61.9 miles long and also rated moderate.


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