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Routes
Road cycling routes
United States
New York
Orange County

Village of Montgomery

The best road cycling routes around Village of Montgomery

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Road cycling around Village of Montgomery, located in New York's Hudson Valley, offers diverse terrain and scenic routes. The region is characterized by picturesque landscapes, including the Wallkill River and views of the Shawangunk Ridge. Cyclists can find accessible trail networks with options ranging from well-paved surfaces to routes with significant elevation gains. The area provides a variety of road cycling experiences suitable for different fitness levels.

Best road cycling routes around Village of Montgomery

  • The most popular road cycling route is View of the Shawangunk Kill – Amazing View Of The Shawgunks loop from Town of Montgomery, a 53.5 miles (86.1 km) trail that takes 3 hours 56 minutes to complete. This route offers vistas of the Shawangunk Kill and the Shawangunk Ridge.
  • Another top favourite among local road cyclists is Skydive the Ranch – View of the Shawangunk Kill loop from Town of Montgomery, a moderate 42.9 miles (69.1 km) path. This route provides views of the Shawangunk Kill within the picturesque Hudson Valley landscape.
  • Local road cyclists also love the Deli Breakfast & Lunch – Skydive the Ranch loop from Town of Montgomery, a 40.1 miles (64.5 km) trail leading through the scenic Hudson Valley, often completed in about 2 hours 50 minutes.
  • Road cycling around Village of Montgomery is defined by the Wallkill River, the Shawangunk Kill, and views of the Shawangunk Ridge. The network offers options for different ability levels, from moderate loops to more challenging rides.
  • The routes in Village of Montgomery are highly rated by the komoot community with an average score of 5.0 stars from a few reviews. More than 100 road cyclists have used komoot to explore Village of Montgomery's varied terrain.

Last updated: July 12, 2026

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riders

#1.

View of the Shawangunk Kill – Amazing View Of The Shawgunks loop from Montgomery

86.1km

03:58

550m

550m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Village of Montgomery

Hiking around Village of Montgomery

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Tips from the Community

David Burleson
August 18, 2024, Walden-Wallkill Rail Trail (paved section)

The windiest piece of rail trail I've ever seen

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This longer section of the Walden-Wallkill Rail Trail is completely paved and is pretty flat. Since it follows an old train line, it technically climbs slightly uphill in one direction and is completely downhill when traveling in the other direction.

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The Shawangunk Grasslands National Wildlife Refuge covers an area of 597 acres. It was initiated to support migratory birds and wintering raptors. It has great views of the stunning Shawangunk Ridge. It is a beautiful area to cycle around.

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Shawangunk Kill is a 47.2-mile-long stream that flows through several counties in New York. This point provides a nice view of the stream from a small bridge, making it an ideal spot for a quick break before you continue.

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The lake is somewhat concealed from the road, but it becomes visible from the bridge, offering a clear view of the lake and the Mara Kill branching from it. This spot is perfect for a quick view before continuing on your ride.

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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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Great view of the Minnewaska State Park Preserve and the Adirondack Mountains in the distance.

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The Huguenot Street Historic District is an outdoor musuem displaying the 300 year history of the area.

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Frequently Asked Questions

How many road cycling routes are available around Village of Montgomery?

There are over 20 road cycling routes available around the Village of Montgomery, offering a variety of experiences for different skill levels. You'll find options ranging from easy rides to more moderate challenges.

What is the typical difficulty level of road cycling routes in this area?

The road cycling routes around Village of Montgomery are predominantly moderate, with 16 routes falling into this category. There are also 6 easy routes available, making the area accessible for various fitness levels. Currently, there are no routes classified as difficult.

What kind of scenery can I expect on road cycling routes near Village of Montgomery?

Cyclists can enjoy picturesque landscapes, including stunning views of the Shawangunk Ridge and the Wallkill River. Many routes, such as the View of the Shawangunk Kill – Amazing View Of The Shawgunks loop from Town of Montgomery, offer vistas of the Shawangunk Kill, providing a beautiful backdrop for your ride.

Are there any family-friendly or beginner road cycling routes?

Yes, the Village of Montgomery area offers 6 easy road cycling routes, which are suitable for beginners or families looking for a more relaxed ride. While specific family-friendly routes are not detailed, the presence of easy options ensures a comfortable experience for those new to road cycling or riding with children.

What are some notable attractions or points of interest along the cycling routes?

As you cycle, you might encounter natural features like the Maybrook Reservoir, Diamond Lake, and the Streams of Highland Lakes State Park. The region also features the Shawangunk-Walden-Wallkill Rail Trail, which offers a different surface for cycling and connects to other paths.

Are there loop road cycling routes available?

Yes, many of the road cycling routes in the Village of Montgomery area are designed as loops. For example, the popular Skydive the Ranch – View of the Shawangunk Kill loop from Town of Montgomery is a moderate 42.9-mile loop, and the Deli Breakfast & Lunch – Skydive the Ranch loop from Town of Montgomery is another scenic loop option.

What do other cyclists say about road cycling in Village of Montgomery?

The road cycling routes around Village of Montgomery are highly rated by the komoot community, with an average score of 5.0 stars from several reviews. Over 100 road cyclists have used komoot to explore the varied terrain, often praising the scenic views and diverse route options.

What is the best time of year for road cycling in Village of Montgomery?

The Hudson Valley region generally offers excellent cycling conditions from spring through fall, when the weather is mild and the scenery is vibrant. While specific winter conditions are not detailed, it's advisable to check local weather forecasts for ice or snow before planning a winter ride.

Are there any long-distance road cycling routes?

Yes, there are several routes suitable for longer rides. The longest route, View of the Shawangunk Kill – Amazing View Of The Shawgunks loop from Town of Montgomery, spans 53.5 miles (86.1 km) and typically takes around 3 hours and 56 minutes to complete, offering significant distance and elevation.

Can I find places to eat or rest along the routes?

While specific cafes are not listed, the region's charming towns like New Paltz and Rosendale, which are accessible via trail networks like the Wallkill Valley Rail Trail, offer opportunities for pit stops to shop or eat. The Deli Breakfast & Lunch – Skydive the Ranch loop from Town of Montgomery route name suggests local eateries are part of the experience.

Are there any rail trails suitable for road cycling in the area?

Yes, the Wallkill Valley Rail Trail is a significant draw for cyclists in the broader region. While it features a stonedust surface in many sections, it's suitable for biking and offers magnificent views of the Shawangunk Ridge. It also connects to other paths like the River-to-Ridge Trail and is close to the Hudson Valley Rail Trail, expanding cycling opportunities.

Where can I find information about parking for road cycling trails?

While specific parking locations for individual routes are not detailed here, trailheads for major networks like the Wallkill Valley Rail Trail typically offer designated parking areas. It's recommended to check local resources or the specific route details on komoot for parking information before your ride.

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