4.6
(11)
247
riders
31
rides
Gravel biking around Sleepy Hollow, New York, offers diverse terrain within the Hudson River Valley. The region features a mix of historic trails, expansive park preserves, and quiet country roads. Riders can expect varied surfaces including pavement, hard-pack dirt, and double-track paths. The landscape is characterized by rolling hills, river valleys, and forested areas.
Last updated: May 20, 2026
4.0
(2)
35
riders
65.9km
04:42
1,010m
1,010m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.0
(1)
9
riders
38.6km
03:35
950m
940m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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9
riders
52.5km
05:00
1,510m
1,500m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
14
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
15.9km
01:33
490m
500m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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An absolute must-see for cycling enthusiasts! This museum in Fairfax tells the story of nearly 200 years of cycling history, from 19th-century velocipedes to modern racing bikes. It's also home to the Mountain Bike Hall of Fame, featuring unique specimens and stories about the pioneers of mountain biking. The collection is impressive and authentic—no replicas, but real bicycles that showcase the evolution of technology and design. An inspiring place where you can truly feel the passion for cycling.
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Constructed in 1917 this dam forms Alpine Lake, which sites between Kent and Bon Tempe Lakes. The road across the top of the dam make it a great place to ride on a loop around the lake.
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This lake was formed by the building of Alpine Dam in 1917. It sits between Kent Lake and Bon Tempe Lake, and is popular for a variety of outdoor activities.
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At the junction of Chicken Shack Fire Road and Ponti Ridge Trail. There are benches, a great view, and trail markers.
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The park pays homage to a 19th-century fishing village of Chinese immigrants who harvested shrimp from the bay. Much of the village has been preserved, and for a couple bucks you can pay to enter and explore the old town and pier.
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At this point on Sky Oaks Road, there is a junction with Shaver Grade Road, which connects with a dense network of trails and dirt roads near Bald Hill in the Mount Tamalpais State Park. From here, you can continue on the paved Sky Oaks Road or go arond the gate on to the gravel Shaver Grade Road.
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Steep heading West can have traffic on SFD
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There are over 35 gravel bike trails around Sleepy Hollow, offering a wide range of options for different skill levels. The komoot community has explored more than 250 of these routes.
Gravel biking in Sleepy Hollow offers diverse terrain, including pavement, hard-pack dirt, and double-track paths. You'll encounter rolling hills, river valleys, and forested areas, with some routes featuring more challenging climbs and even some chunky, washed-out sections. The region is known for its historic aqueduct trails and scenic carriage roads.
The spring and fall seasons generally offer the most pleasant conditions for gravel biking in Sleepy Hollow, with mild temperatures and beautiful foliage. Summer can be warm, while winter rides are possible but may involve colder temperatures and potential for snow or ice on trails, especially on less maintained sections.
Yes, Sleepy Hollow offers several challenging gravel routes. For instance, the Alpine Dam – Alpine Lake loop from Sleepy Hollow is a difficult 65.2 km route with significant elevation gain, taking about 5 hours 34 minutes to complete. Another difficult option is the Fish Gulch trail junction – Hoo-Koo-E-Koo Fire Road Trail loop from Fairfax, a 39.6 km trail with substantial climbs and descents.
Yes, there are easier options available. The region features trails like the Old Croton Aqueduct Trail, which is known for being relatively flat and accessible. A good moderate option is the Phoenix Lake – Fish Gulch trail junction loop from Fairfax, a 27.2 km path that offers a balanced ride through scenic landscapes in about 2 hours 26 minutes.
Many of the gravel routes in Sleepy Hollow are designed as loops, allowing you to start and end at the same point. Examples include the Alpine Dam – Alpine Lake loop and the Fairfax – Alpine Lake - Bon Tempe Dam loop, providing convenient options for exploring the area.
The gravel trails in Sleepy Hollow offer numerous scenic viewpoints and natural features. You can enjoy stunning views of the Hudson River Valley, especially along sections of the Old Croton Aqueduct Trail. The Rockefeller State Park Preserve features carriage trails winding through natural beauty along the Pocantico River. You might also encounter highlights like Mount Tamalpais Summits or the tranquil Pygmy (dwarf) sargent cypress forest.
Absolutely. Sleepy Hollow is rich in history. Many routes pass by or near sites like the Old Dutch Church and Philipsburg Manor, which are central to 'The Legend of Sleepy Hollow'. The Sleepy Hollow Cemetery also offers a unique natural setting with views of the Hudson River. The Old Croton Aqueduct Trail itself is a historic landmark, providing a blend of outdoor activity and cultural immersion.
The komoot community highly rates gravel biking in Sleepy Hollow, with an average score of 4.8 stars from over 9 reviews. Riders often praise the diverse terrain, the blend of historic trails and scenic natural beauty, and the variety of routes suitable for different ability levels. The quiet countryside roads and hidden local gems are frequently highlighted.
Yes, the Old Croton Aqueduct Trail is particularly well-suited for families due to its relatively flat and accessible nature. Rockefeller State Park Preserve also offers many miles of scenic carriage trails that can be enjoyed by families looking for a less strenuous ride through beautiful landscapes.
Parking is available at various access points for popular trails. For instance, the Old Croton Aqueduct Trail has several parking areas along its length. Rockefeller State Park Preserve also provides designated parking for trail access. It's advisable to check specific trailheads for detailed parking information before your ride.
Yes, Sleepy Hollow and Tarrytown are accessible by public transport, primarily via Metro-North Railroad from Grand Central Terminal in NYC. The train stations in these towns are often within cycling distance of trailheads, including the Old Croton Aqueduct Trail and access points to Rockefeller State Park Preserve, making it convenient for riders without a car.
Many trails in the Sleepy Hollow area, including sections of the Old Croton Aqueduct Trail and Rockefeller State Park Preserve, are dog-friendly. However, regulations can vary, so it's always best to check specific park or trail rules regarding dogs, especially leash requirements, before heading out.
Sleepy Hollow and neighboring Tarrytown offer a variety of cafes, restaurants, and pubs where you can refuel after your ride. Many establishments are conveniently located near the main trail access points, providing options for coffee, a meal, or a refreshing drink.


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