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United States
New York
Ulster County

Woodstock

The best cycling routes around Woodstock

4.6

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20

rides

Touring cycling around Woodstock offers routes through picturesque landscapes characterized by rolling hills and scenic dirt roads. The region features the Ottauquechee River and historic covered bridges, providing varied terrain for cyclists. These routes allow for exploration of the area's natural beauty and historical points of interest.

Best touring cycling routes around Woodstock

  • The most popular touring cycling route is Ashokan Rail Trail Loop, a 23.0 miles (37.0 km) trail that takes 2 hours 30 minutes to complete. This…

Last updated: May 21, 2026

5.0

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2

riders

#1.

Ashokan Rail Trail Loop

37.0km

02:31

470m

470m

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

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Hard

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

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

Hard

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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Tips from the Community

Janine & Marcel
July 30, 2025, Ashokan Rail Trail

Beautiful rail trail with parking at both ends.

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You cycle the entire route through the forest. The path is easy to cycle and, with its bridges, offers wonderful natural surroundings. There are parking spaces at both the beginning and the end.

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Good view. Don’t touch, has poison ivy

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Lisa
September 25, 2024, Ashokan Reservoir

This massive reservoir spans more than 8,000 acres and, depending on who you talk to, is somewhere around 180 to 190 feet deep. It makes for great scenery on your ride or, if you're really feeling ambitious, you could pack a travel fishing pole and try your hand for brown and rainbow trout. (Make sure you check local fishing regulations before getting your line wet!)

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Beautiful and peaceful. Very little shade so dress accordingly.

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Forest area between the Ashokan Reservoir and the Ashokan Rail Trail, south from Shokan. It is a true delight cycling through it, whether you're approximating the water or just cruising through the Rail Trail.

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Scenic road that runs right next to the Ashokan Reservoir. Great views of the Reservoir and the Catskill Mountains.

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The Ashokan Rail Trail is a great multi-use trail, that has a compact surface. This trail runs beside the Ashokan Reservoir. It is open during daylight hours. There are parking areas and restrooms at the trailheads.

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Frequently Asked Questions

How many touring cycling routes are available around Woodstock?

There are over 20 touring cycling routes around Woodstock, offering a variety of experiences. These include 5 easy routes, 11 moderate routes, and 6 difficult routes, catering to different skill levels and preferences.

What kind of terrain can I expect on touring cycling routes in Woodstock?

Woodstock's touring cycling routes feature picturesque landscapes with rolling hills and scenic dirt roads, making it a premier gravel road riding destination. You'll also find paved sections, especially on routes like the Taftsville Covered Bridge – Quechee Covered Bridge loop, providing diverse terrain for exploration.

Are there any family-friendly touring cycling routes in Woodstock?

Yes, Woodstock offers routes suitable for families. The region has 5 easy touring cycling routes. For a local attraction that families might enjoy, consider visiting the Billings Farm & Museum, which is accessible by bike and offers a chance to see farm animals up close.

What are some notable landmarks or scenic viewpoints I can discover while cycling?

Woodstock is rich in scenic beauty and historical landmarks. You can cycle past historic covered bridges, such as the Taftsville Covered Bridge, Middle Covered Bridge, and Lincoln Covered Bridge. The area also offers stunning natural features like Quechee Gorge, known as Vermont's 'Little Grand Canyon'. For panoramic views, consider routes that offer glimpses of Mt. Tom or the Ottauquechee River. You can also explore highlights like View of Ashokan Reservoir and Catskill Mountains or Overlook Mountain Fire Tower.

Are there any circular touring cycling routes around Woodstock?

Yes, many routes around Woodstock are designed as loops, allowing you to start and end in the same location. An example is the Ashokan Rail Trail Loop, which offers a challenging ride. Another option is the Ashokan Rail Trail – Frozen Ashokan Reservoir loop from West Hurley, providing scenic views around the reservoir.

What is the best time of year for touring cycling in Woodstock?

Woodstock is appealing year-round, but for touring cycling, spring, summer, and especially autumn are highly recommended. The region is known for its lush greenery in warmer months and vibrant fall foliage, making for picturesque rides. Some trails, like those at Quechee Gorge, open up fully in the summer.

Where can I find easy touring cycling routes for beginners?

For beginners or those seeking a more relaxed ride, Woodstock offers 5 easy touring cycling routes. A good option to consider is the Old stone wall – Ashokan Rail Trail loop from Lower Ashokan Reservoir, which is an easy path suitable for a leisurely tour.

Are there any routes that explore the Ashokan Reservoir area?

Absolutely. The Ashokan Reservoir is a prominent feature in the region, and several touring cycling routes explore its surroundings. You can try the Frozen Ashokan Reservoir loop from South Yankeetown Pond Unit, which leads through varied terrain. Another excellent choice is the Ashokan Reservoir – Ashokan Rail Trail loop from Shokan.

What do other touring cyclists say about the routes in Woodstock?

The touring cycling routes around Woodstock are highly regarded by the komoot community, with an average rating of 4.5 stars from 5 reviews. Over 90 touring cyclists have used komoot to explore the varied terrain, often praising the picturesque landscapes and the mix of rolling hills and scenic dirt roads.

Are there opportunities to combine cycling with other outdoor activities?

Yes, Woodstock offers a wealth of outdoor activities. Many cycling routes are near areas perfect for hiking, such as the Pogue Trail on Mt. Tom, which offers panoramic views. The Marsh-Billings-Rockefeller National Historical Park also features a 20-mile network of carriage roads and trails, ideal for combining cycling with a walk through historically managed forests.

Can I find less crowded touring cycling paths in Woodstock?

While popular routes like the Ashokan Rail Trail are well-loved, Woodstock's extensive network of scenic dirt roads and varied terrain allows for finding quieter paths. Exploring some of the longer or more challenging routes, or venturing onto the less-traveled gravel roads recommended by local associations, can lead to a more secluded experience.

What should I pack for a touring cycling trip in Woodstock?

Given the varied terrain and potential for longer rides, it's advisable to pack essentials like water, snacks, a repair kit, and appropriate layers for changing weather conditions. For gravel sections, tires suitable for mixed surfaces are recommended. Don't forget a camera to capture the stunning landscapes and historic covered bridges.

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