RoutesPlannerFeaturesUpdates
App
Login or Signup
Get the App
Login or Signup
Routes
Road cycling routes
United States
New York
Sullivan County

Callicoon

The best road cycling routes around Callicoon

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.

If you only do 3 of these routes

  1. 1

    Mill Pond – Lake Jefferson loop from Holy Cross Catholic Church
  2. 2

    Swinging Bridge Reservoir loop from Lake Huntington
  3. 3

    Lake Jefferson – Mill Pond loop from Kenoza Lake

Compare these routes at a glance

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

Sign up to see all 8 routes

Sign up for free

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.

View route

Save
Navigate with deviceSend to Phone
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.
Sign up for free
Sign up for free to see 3 more rides around Callicoon.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

See every route on the map

Tips from the Community

Lisa
February 20, 2024, Swinging Bridge Reservoir

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.

0

0

Frequently Asked Questions

What kind of terrain can I expect on road cycling routes around Callicoon?

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.

Are there road cycling routes suitable for beginners in Callicoon?

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.

What are some challenging road cycling routes for experienced riders?

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.

Are there any loop road cycling routes around Callicoon?

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.

How long do road cycling routes typically take to complete in this area?

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.

What are the best times of year for road biking in Callicoon?

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.

Are there any road cycling routes that pass through old-growth forests?

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.

What kind of views can I expect on the scenic road bike routes?

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.

How many road cycling routes are featured in this guide for Callicoon?

This guide features 6 distinct road cycling routes around Callicoon, offering a range of moderate to difficult options for exploring the region.

What do other komoot users say about road cycling in Callicoon?

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.

Are there any routes that circle specific lakes or reservoirs?

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.

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now
Store rating

Explore more

Browse the best Road cycling routes in other regions.

GrahamsvilleSouth FallsburgBridgevilleRock HillJeffersonvilleMongaup ValleyKauneonga LakeIroquois Hunting And Fishing ClubKiamesha LakeSmallwoodThe Hartwood Club IncWoodbourneWoodridgeFallsburgBarryvilleWolf Lake IncLake HuntingtonLoch SheldrakeHankinsWhite LakeRoscoeLivingston ManorHurleyvilleMountain DaleVillage of MonticelloLake Superior State ParkEldredHortonvilleLibertySwan LakeWurtsboro Ridge State ForestVillage of BloomingburgWurtsboro Hills
background

Get ready to conquer new peaks

Sign up for Free
Explore
RoutesRoute plannerFeaturesRedeem a voucherHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy