1.
Mill Pond – Lake Jefferson loop from Holy Cross Catholic Church
52.3km
02:27
610m
610m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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By Fede from komoot
·
Updated May 28, 2026
If you've ever tried to plan road cycling around Callicoon, you know how quickly the sheer number of routes can feel overwhelming. It's tough to tell which ones are genuinely worth your time and effort, and which are just filler. That's where we come in. Our komoot community has ridden, mapped, and reviewed countless routes here, so we've done the legwork to bring you a curated shortlist of the very best, saving you the guesswork.
Road cycling around Callicoon is all about embracing the rolling hills of the Sullivan Catskills and the picturesque Delaware River Valley. Expect a mix of terrain, from routes that hug the river and circle large reservoirs to more challenging ascents through dense old-growth forests. It's a region that offers everything from moderate climbs to truly demanding days in the saddle, with vibrant fall foliage making for particularly scenic rides.
If you only do one route, make it the Gossweyler Pond loop from Big Island. At 31.9 miles (51.4 km) with 1,871 feet (570 m) of elevation gain, it's a moderate ride that delivers fantastic views of the pond and woodlands without being overly punishing. For those seeking a bigger challenge, the Swinging Bridge Reservoir loop from Lake Huntington is a difficult 55.0 miles (88.5 km) with a significant 3,500 feet (1,067 m) of climbing, offering expansive views around the reservoir. With more than 20 road cyclists already exploring Callicoon's varied terrain on komoot, you're in good company.
Trail | Distance | Elevation | Difficulty |
|---|---|---|---|
| Mill Pond – Lake Jefferson loop from Holy Cross Catholic Church | 52.3 km | 610 m | Moderate |
| Swinging Bridge Reservoir loop from Lake Huntington | 88.5 km | 1,070 m | Hard |
| Lake Jefferson – Mill Pond loop from Kenoza Lake | 46.0 km | 500 m | Moderate |
| Lake Huntington loop from Pine Flat School | 44.6 km | 420 m | Moderate |
| Gossweyler Pond loop from Callicoon | 61.2 km | 870 m | Moderate |
| Montgomery Lake – Bodine Lake loop from Kenoza Lake | 68.8 km | 820 m | Moderate |
| Pine Lake – old growth loop from Villa Roma Gym | 62.1 km | 960 m | Hard |
| Gossweyler Pond loop from Villa Roma Gym | 51.0 km | 950 m | Hard |
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Sign up for free52.3km
02:27
610m
610m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
View route
88.5km
04:49
1,070m
1,070m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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46.0km
02:15
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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44.6km
03:02
420m
420m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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61.2km
02:57
870m
870m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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68.8km
03:31
820m
820m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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62.1km
03:14
960m
960m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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51.0km
02:59
950m
950m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
View route
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You won't catch continuous views of Swinging Bridge Reservoir as you cycle past it, but you will see glimpses of it through the trees and have several opportunities to get down closer to the water. Keep an eye out for people fishing (especially for trout, bass, and perch) and boaters too.
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Road cycling routes around Callicoon feature a diverse landscape of rolling hills, numerous ponds, and dense old-growth forests. You'll find routes that circle large reservoirs and lakes, with elevations ranging from moderate climbs to more challenging ascents.
The routes listed in this guide are primarily moderate to difficult. While there are no routes specifically graded as 'easy' in this selection, moderate routes like the Gossweyler Pond loop from Big Island offer a good introduction to the region's terrain without extreme challenges.
For experienced riders seeking a challenge, the Swinging Bridge Reservoir loop from Lake Huntington is a difficult 55.0-mile (88.5 km) path featuring significant elevation gain and expansive views. This route will test your endurance.
Yes, many of the road cycling routes in Callicoon are scenic loops. Examples include the Gossweyler Pond loop from Big Island, the Swinging Bridge Reservoir loop from Lake Huntington, and the Old growth loop from Kenoza Lake.
Route durations vary depending on distance and elevation. For instance, the Gossweyler Pond loop from Big Island, at 31.9 miles (51.4 km), typically takes about 2 hours 27 minutes. Longer, more difficult routes like the Swinging Bridge Reservoir loop from Lake Huntington can take over 4 hours.
The spring, summer, and fall months generally offer the most pleasant conditions for road cycling in Callicoon, with vibrant foliage in autumn. While winter cycling is possible, be prepared for colder temperatures and potential snow or ice, especially on less-trafficked roads.
Yes, the Old growth loop from Kenoza Lake is a notable route that leads directly through mature forests, offering a serene and shaded cycling experience.
Many routes offer picturesque views of the region's natural beauty. You can expect expansive vistas around reservoirs and lakes, such as on the Swinging Bridge Reservoir loop from Lake Huntington, and serene scenes of woodlands and ponds.
This guide features 6 distinct road cycling routes around Callicoon, offering a range of moderate to difficult options for exploring the region.
More than 20 road cyclists have used komoot to explore Callicoon's varied terrain. Users often highlight the scenic loops around lakes and reservoirs, the challenging climbs through rolling hills, and the routes passing through old-growth forests as defining characteristics of the area's cycling experience.
Absolutely. The Gossweyler Pond loop from Big Island and the Gossweyler Pond loop from Callicoon Center both offer circuits around Gossweyler Pond. Additionally, the Lake Huntington loop from Pine Flat School provides a route around Lake Huntington.


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