5.0
(2)
28
riders
9
rides
Touring cycling routes around Village of Montgomery offer diverse landscapes for cyclists. The region features the flat, agricultural Black Dirt Region with its farm roads, alongside the scenic Wallkill River. Rolling meadows and forested areas contribute to the varied terrain, with views of the distant Shawangunk Mountains. Dedicated multi-use trails like the Orange County Heritage Trail and the Wallkill Valley Rail Trail provide accessible options for exploring the area.
Last updated: June 28, 2026
91.5km
05:41
580m
580m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
3
riders
16.6km
01:00
110m
110m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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3
riders
22.5km
01:58
210m
210m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
4
riders
20.5km
01:49
160m
160m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
17.1km
01:09
100m
100m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Whether you are looking for wide and smooth roads or tight singletrack trails, Stewart State Forest probably has it. This section of Drakes Trail is one of the most southern singletrack trails in the trail system. The paths cross over each other and over the service roads in the forest, so you can create an almost endless number of loops.
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Stewart State Forest, nestled in Orange County, New York, this expansive forest seamlessly blends wetlands, fields, and forest. With 22 miles of gravel roads and 18 miles of hiking trails, it's a haven for outdoor enthusiasts. Engage in hiking, biking, horseback riding, hunting, cross country skiing, snowmobiling, bird watching, and fishing. Encounter a diverse wildlife population, from white-tailed deer and coyotes to bobcats, wild turkeys, great blue herons, and majestic hawks.
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Capture the beauty of the pond with its diverse backdrop of trees, reeds, and occasional wildflowers. Keep an eye out for diverse birdlife, turtles, and other wildlife while exploring the pond and surrounding trails.
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The Rosendale Trestle Bridge is a famous bridge crossing along the Wallkill Valley Rail Trail between Joppenbergh Mountain Park and Hardenbergh Park. This wooden boards making the base of the bridge are a little weathered, so watch your footing as you cross.
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In this National Historic Landmark District, there are 7 historic stone-house museums, a reconstructed church from 1717, an old burying ground and a replica Esopus Munsee wigwam. This is a great outdoor museum to explore. Keep an eye out for the blue and yellow signs, which provide information on the different buildings.
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The Springtown Truss Bridge crosses the Wallkill River. It was once formed part of the Wallkill Valley Railroad, running between Ulster County and New York city. The bridge was originally built in 1870 and made of wood, but was rebuilt using iron in the early 1880s.
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The Stewart State Forest has several larger and smaller ponds that are popular for fishing. This is the largest in the pond and has eel, carp, crappie, and pickerel. The pristine waters next to the lush green trees make this a great spot to stop and enjoy the beauty.
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Stewart State Forest, nestled in Orange County, New York, this expansive forest seamlessly blends wetlands, fields, and forest. With 22 miles of gravel roads and 18 miles of hiking trails, it's a haven for outdoor enthusiasts. Engage in hiking, biking, horseback riding, hunting, cross country skiing, snowmobiling, bird watching, and fishing. Encounter a diverse wildlife population, from white-tailed deer and coyotes to bobcats, wild turkeys, great blue herons, and majestic hawks.
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There are over 10 touring cycling routes available around the Village of Montgomery, offering diverse landscapes for cyclists of all levels.
You'll encounter a variety of landscapes, including the flat, agricultural Black Dirt Region with its farm roads, scenic views along the Wallkill River, rolling meadows, and forested areas. Some routes also offer distant views of the majestic Shawangunk Mountains.
Yes, there are 3 easy touring cycling routes perfect for beginners. One such option is the Bike loop from Village of Walden, which leads through rolling meadows and countryside.
Yes, for those seeking a challenge, there is 1 difficult touring cycling route. The Wallkill Valley Rail Trail is a longer option, offering scenic vistas of mountains, water features, and prairies, including the historic Rosendale Trestle.
Many of the routes, especially those on dedicated rail trails, are suitable for families. The flat terrain of the Black Dirt Region and sections of the Wallkill Valley Rail Trail offer accessible and enjoyable rides for all ages.
Yes, several routes are designed as loops. For example, the Stewart State Forest – Stewart State Forest loop from Washingtonville Soccer Club Inc offers a moderate circular path through forested sections.
While cycling, you might encounter natural highlights like Maybrook Reservoir or Diamond Lake. The Stewart State Forest also provides extensive forested areas to explore. The Wallkill Valley Rail Trail itself passes over the historic Rosendale Trestle, offering impressive views.
Absolutely! The region is home to significant rail trails. The Wallkill Valley Rail Trail is a major draw, and the Orange County Heritage Trail is another excellent multi-use option, winding through a bird/wildlife sanctuary and past historic landmarks.
Parking is available at various access points for the major rail trails. For instance, the Orange County Heritage Trail has access points in towns like Monroe, Chester, and Goshen. For routes within Stewart State Forest, parking can often be found near trailheads or designated areas like the Washingtonville Soccer Club Inc.
Spring, summer, and fall generally offer the best conditions for touring cycling in the Village of Montgomery. The mild temperatures and vibrant foliage, especially in autumn, make for particularly enjoyable rides. Always check local weather conditions before heading out.
Many multi-use trails, including sections of the rail trails, are generally dog-friendly, provided dogs are kept on a leash. It's always best to check specific trail regulations before you go, but the natural settings often welcome well-behaved, leashed dogs.
The routes in the Village of Montgomery are highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the diverse terrain, from the flat Black Dirt Region to the scenic rail trails, and the opportunities to explore both agricultural landscapes and forested areas.


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