5.0
(8)
443
riders
24
rides
Road cycling routes around Islip are characterized by the region's location on the South Shore of Long Island, offering views of the Great South Bay and Fire Island. The terrain is generally flat to gently rolling, providing accessible conditions for various cycling abilities. The area features a mix of coastal environments, salt marshes, and woodlands, with numerous parks and nature preserves. These landscapes contribute to a diverse range of road cycling experiences.
Last updated: June 28, 2026
4
riders
79.6km
03:06
200m
200m
This moderate 49.5-mile road cycling loop offers scenic views and a good workout, taking about 3 hours and 5 minutes to complete.
5.0
(1)
17
riders
48.4km
02:14
80m
80m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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17
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
10
riders
66.2km
02:50
100m
100m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(2)
9
riders
8.19km
00:30
10m
10m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Islip
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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This beach is open from Memorial Day to Labor Day, but only to Town of Babylon residents. You need a yearly Town of Babylon recreation permit in order to get in.
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Spanning 1,600 acres on Long Island's south shore, Heckscher State Park is an outdoor haven. Shady picnic groves host family gatherings, while open fields beckon sports enthusiasts for soccer, cricket, and lacrosse. Nature lovers explore 4 miles of trails, spotting deer and birds against the backdrop of the Great South Bay and Fire Island. The bay lures visitors for swimming, boating, and water sports. Newly built waterfront cottages offer cozy accommodations with spectacular views, complete with living areas, kitchens, and screened porches.
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Connetquot River State Park Preserve is a 3,473-acre refuge of sandy pine barrens, wetlands, ponds, and woodlands. Visitors can find over 200 bird species and 300 plant species, along with other mammals, reptiles, amphibians, butterflies, and moths that once lived all over Long Island. This area was created as New York's first "State Park Preserve," and remains a protected area open to the public today.
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This nearly 3,500-acre refuge of sandy pine barrens, wetlands, ponds and woodlands is nestled in central Long Island along the pristine, spring-fed Connetquot River. A wilderness surrounded by suburbs, the preserve provides excellent opportunities to see more than 200 bird and 300 plant species, as well as several mammal, reptile, amphibian, butterfly and moth species that once flourished throughout Long Island.
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Heckscher offers a beach, picnic tables with pavilions, a playground, playing fields and a disc golf course, recreation programs, hiking and biking, fishing, cross-country skiing, a boat launch, and a food concession. It includes the Heckscher Forest, a dedicated disc golf course established in the summer of 2014. The park formerly offered a campground with tent and trailer sites, as well as an Olympic-sized swimming pool, which were closed due to budget cuts.
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This lake was formed by retreating glaciers. It is the largest freshwater lake on Long Island.
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Islip offers a diverse selection of road cycling routes, with over 25 options available. These routes cater to various skill levels, including 10 easy routes and 17 moderate routes, ensuring there's something for every cyclist.
The terrain in Islip is generally flat to gently rolling, characteristic of Long Island's South Shore. This makes it ideal for road cycling, offering accessible conditions for various abilities. Routes often feature well-paved surfaces, though some longer or more challenging segments might include unpaved sections.
Road cycling in Islip provides scenic views of the Great South Bay and Fire Island, particularly along coastal paths and through parklands. You can also expect to see diverse landscapes including salt marshes, woodlands, and wetlands, especially within the numerous parks and nature preserves in the area.
Yes, Islip has several routes suitable for beginners. For example, the Heckscher State Park – Heckscher State Park Beach loop from Heckscher State Park is a moderate 7.9-mile (12.8 km) trail that offers a relatively flat ride within the park, perfect for those new to road cycling or looking for a leisurely experience.
For more dedicated road cyclists, Islip offers moderate routes with longer distances. The South Country Road Loop is a 49.5-mile (79.6 km) ride with about 200m of elevation gain, offering scenic views and taking approximately three hours to complete. Another option is the Nathaniel Hawkins Cemetery – Shore Road - Ocean View loop from Great River, which covers 60.8 km with 157m of ascent.
Many road cycling routes in Islip pass by significant natural features and landmarks. You might encounter the Heckscher State Park Beach, offering coastal views, or the historic Fire Island Lighthouse in the distance. Some routes also go near Southards Pond or offer views of the waterfall at the Belmont Lake outlet.
Heckscher State Park is a significant draw for road cyclists in Islip. It features twenty miles of trails, including a 3.3-mile paved bike/hike loop, with opportunities to extend rides and enjoy views of the Great South Bay. Other parks like Connetquot State Park and Gardiner County Park also offer trails suitable for cycling.
The best time for road cycling in Islip is generally during the spring, summer, and fall months when the weather is mild and pleasant. The flat to gently rolling terrain makes it enjoyable for most of the year, but coastal winds can be a factor, especially in cooler months.
Yes, parking is generally available at or near many road cycling routes, especially those that start or pass through state and county parks like Heckscher State Park. These parks often have designated parking areas for visitors.
Many of the easier and shorter routes, particularly those within parks like Heckscher State Park, are considered family-friendly due to their paved surfaces and relatively flat terrain. These routes offer a safe and enjoyable experience for families cycling together.
The road cycling experience in Islip is highly rated by the komoot community, with an average score of 4.8 stars from over 8 reviews. Cyclists often praise the scenic views of the Great South Bay and Fire Island, the well-maintained paved routes, and the diverse landscapes that include coastal areas, wetlands, and woodlands.
Yes, many of the road cycling routes in Islip are designed as loops, allowing you to start and end at the same point. Examples include the Overlook Beach – Heckscher State Park loop from Brentwood and the Heckscher State Park Beach – Heckscher State Park loop from Islip, providing convenient options for circular rides.


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