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New York
Orange County

Village of Montgomery

The best cycling routes around Village of Montgomery

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.

Best touring cycling routes around Village of Montgomery

  • The most popular…

Last updated: June 28, 2026

#1.

Wallkill Valley Rail Trail

91.5km

05:41

580m

580m

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

5.0

(1)

3

riders

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Popular around Village of Montgomery

Hiking around Village of Montgomery

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Road Cycling Routes around Village of Montgomery

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Tips from the Community

Matthew
May 31, 2024, Drakes Trail Singletrack, Stewart State Forest

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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Scott
January 15, 2024, Wilkens Pond

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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Matthew
January 15, 2024, Rosendale Trestle

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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Frequently Asked Questions

How many touring cycling routes are available around the Village of Montgomery?

There are over 10 touring cycling routes available around the Village of Montgomery, offering diverse landscapes for cyclists of all levels.

What kind of landscapes can I expect to see while cycling around the Village of Montgomery?

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.

Are there easy touring cycling routes suitable for beginners in the Village of Montgomery area?

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.

Can I find challenging touring cycling routes near the Village of Montgomery?

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.

Are there family-friendly touring cycling routes around the Village of Montgomery?

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.

Are there any circular touring cycling routes in the Village of Montgomery area?

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.

What are some scenic highlights or landmarks I can see while touring cycling near the Village of Montgomery?

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.

Are there any rail trails I can explore by bike in the Village of Montgomery area?

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.

Where can I find parking for touring cycling routes near the Village of Montgomery?

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.

What is the best season for touring cycling in the Village of Montgomery?

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.

Are touring cycling routes around the Village of Montgomery dog-friendly?

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.

What do other touring cyclists enjoy about the routes around the Village of Montgomery?

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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