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Orange County

Village of Montgomery

The best gravel rides around Village of Montgomery

By Fede from komoot

·

Updated May 29, 2026

If you've ever tried to plan gravel biking around Village of Montgomery, you know how quickly the options can become overwhelming. With so many trails and roads, it's tough to tell which routes are genuinely worth your time and effort, and which are just filler. That's where we come in. Our komoot community has mapped, ridden, and reviewed these routes, and we've curated this guide to save you the guesswork, pointing you straight to the rides that truly deliver.

Gravel biking around Village of Montgomery feels like a true Hudson Valley adventure, blending extensive forest areas with former rail lines. You'll find yourself on everything from the hard-packed surfaces of rail trails to the more varied, sometimes chunky, gravel roads within Stewart State Forest. The terrain generally offers gentle gradients and rolling hills, making it accessible for many, and the Wallkill Valley Rail Trail's consistent surface means it's often rideable even after inclement weather.

If you only do one ride, we'd start with the Stewart State Forest – Stewart State Forest loop from Coldenham. At 16.9 miles (27.3 km), this moderate route gives you a fantastic taste of the varied paths and woodlands that make this area special. For something a bit easier, the Pond in Stewart State Forest – Whalenburgh Pond loop from Washingtonville Soccer Club Inc is a great choice, offering 10.8 miles (17.4 km) of easy riding with lovely views of Whalenburgh Pond. With more than 20 gravel bikers already exploring these paths with komoot, you're in good company.

If you only do 3 of these routes

  1. 1

    Pond in Stewart State Forest – Whalenburgh Pond loop from Washingtonville Soccer Club Inc
  2. 2

    Stewart State Forest loop from Berea
  3. 3

    Whalenburgh Pond – Pond in Stewart State Forest loop from Coldenham

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Pond in Stewart State Forest – Whalenburgh Pond loop from Washingtonville Soccer Club Inc

17.4 km

150 m

Easy

Stewart State Forest loop from Berea

18.4 km

100 m

Easy

Whalenburgh Pond – Pond in Stewart State Forest loop from Coldenham

15.9 km

140 m

Easy

Wilkens Pond – Stewart State Forest loop from Coldenham

41.3 km

370 m

Moderate

1.

Pond in Stewart State Forest – Whalenburgh Pond loop from Washingtonville Soccer Club Inc

17.4km

01:21

150m

140m

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

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2.

Stewart State Forest loop from Berea

18.4km

01:28

100m

100m

The Stewart State Forest loop from Berea offers a delightful gravel biking experience, winding through a tranquil landscape of wetlands, open fields, and deep oak and hickory forests. You'll navigate mostly dirt and gravel roads, with a notable 1.25-mile double track section on Krahn Lane and a small water crossing near Beaver Pond, adding a touch of variety to the journey. This easy 11.4-mile (18.4 km) route, with its gentle 335 feet (102 metres) of elevation gain, is a fantastic option for a relaxed ride, typically taking about 1 hour and 28 minutes.

Planning your visit is straightforward; the trail is accessible year-round, making it a reliable choice for a spontaneous outing. To ensure a comfortable ride on the mixed surfaces, it's advisable to use tires of at least 30mm. While the majority is off-road, be prepared for brief sections on paved roads (207/208) that link the gravel segments, ensuring a continuous loop.

Stewart State Forest is a vast 6,700-acre area known for its extensive network of multi-use trails, making it a popular destination for various outdoor activities beyond just biking. This particular loop provides a great introduction to the forest's diverse ecosystems, where you might spot white-tailed deer, wild turkeys, or even great blue herons amidst the picturesque ponds and streams. It's a prime example of the accessible gravel biking routes available in the Hudson Valley.

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4.

Wilkens Pond – Stewart State Forest loop from Coldenham

41.3km

03:21

370m

370m

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

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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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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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The trail system at Stewart has something for everybody. But keep in mind that at the end of the year (November/December) mountain bike trails are closed due to hunting season. Check this site for updates: https://business.facebook.com/pg/stewart.forest.MTB/posts/

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Cuse
December 13, 2021, Wishing Well Trail

There is a small well off the trail if you know where to look...

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Frequently Asked Questions

What kind of terrain can I expect on gravel bike trails around Village of Montgomery?

The terrain around Village of Montgomery primarily features gentle gradients and rolling hills, making it suitable for gravel cycling. You'll encounter extensive forest areas and former rail lines, such as the Wallkill Valley Rail Trail, which offer consistent surfaces for longer rides. Routes often explore varied paths within areas like Stewart State Forest.

Are there any family-friendly gravel bike trails in the Village of Montgomery area?

Yes, several routes are suitable for families. The area's trails, particularly those on former rail lines and around natural ponds, generally offer easy to moderate difficulty levels. For example, the Pond in Stewart State Forest – Whalenburgh Pond loop from Washingtonville Soccer Club Inc is an easy 10.8-mile path offering views of Whalenburgh Pond and surrounding woodlands, which can be a great option for a family outing.

What natural features or landmarks can I see along the gravel bike trails?

The gravel bike trails around Village of Montgomery offer views of several natural features. Within Stewart State Forest, you can find picturesque spots like Whalenburgh Pond and Wilkens Pond. The Stewart State Forest itself is a significant landmark. Additionally, the Shawangunk-Walden-Wallkill Rail Trail provides a scenic route through the landscape.

Are there any circular gravel bike routes available?

Yes, many of the gravel routes in the Village of Montgomery area are designed as loops. For instance, the Stewart State Forest – Stewart State Forest loop from Coldenham is a popular 17.3-mile circular trail that explores the diverse paths within the forest. Another option is the Stewart State Forest loop from Berea, an 11.4-mile loop through varied terrain.

What is the best time of year for gravel biking in Village of Montgomery?

The region is enjoyable for gravel biking across multiple seasons. Spring and fall offer pleasant temperatures and vibrant scenery, with autumn foliage being particularly beautiful. Summer provides longer daylight hours, while winter can be an option for those prepared for colder conditions, especially on well-maintained rail trails. Always check local weather conditions before heading out.

Where can I find parking for gravel bike trails near Village of Montgomery?

Parking is generally available at access points for popular trails and state forests. For routes within Stewart State Forest, you can often find parking near entry points like those used for the Whalenburgh Pond – Whalenburgh Pond loop from Coldenham or the Stewart State Forest – Stewart State Forest loop from Brittany Terrace Mobile Home Park. Specific parking details are usually provided on individual route pages.

Are there any long-distance gravel trails near Village of Montgomery?

While the immediate routes are typically shorter loops, the Wallkill Valley Rail Trail, which passes through areas like New Paltz, is a significant draw for longer rides. This multi-user path is approximately 22 miles in length and provides an excellent surface for extended gravel biking adventures, connecting various towns and natural areas.

What are the difficulty levels of gravel bike trails in this area?

The gravel biking network around Village of Montgomery offers options for both easy and moderate ability levels. Many routes feature gentle gradients, making them accessible. For example, the Pond in Stewart State Forest – Whalenburgh Pond loop from Washingtonville Soccer Club Inc is rated as easy, while the Stewart State Forest – Stewart State Forest loop from Coldenham is considered moderate.

Can I bring my dog on the gravel bike trails?

Many outdoor areas and trails in the region, including parts of Stewart State Forest and rail trails, are generally dog-friendly. However, it's always best to check specific regulations for each trail or park regarding leash requirements and waste disposal to ensure a pleasant experience for everyone.

Are there cafes or places to eat near the gravel biking routes?

The Village of Montgomery and surrounding towns offer various amenities, including cafes, pubs, and restaurants. While specific establishments directly on the trails might be limited, you'll find options in the nearby communities to refuel before or after your ride. Planning your route to pass through or end near these towns is recommended.

How many gravel bike trails are available around Village of Montgomery?

There are several gravel bike trails available around Village of Montgomery. This guide features 6 distinct routes, with options ranging from easy to moderate difficulty, primarily exploring Stewart State Forest and areas around natural ponds.

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