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Hikes
United States
Virginia
Shenandoah County

Woodstock

The best walks and hikes around Woodstock

3

hikers

5

hikes

Hiking around Woodstock offers diverse landscapes within the Catskill Mountains, characterized by bluestone cliffs, dense forests, and varied ecosystems. The region features significant natural elements such as the Ashokan Reservoir and historical bluestone quarries. Elevations provide views of the Hudson River Valley.

Best hiking trails around Woodstock

  • The most popular hiking route is Bass Bight, Pawpaw, and Stonecrop Ridge Trail, a 5.7 miles (9.2 km) moderate trail that takes 2 hours 47 minutes to complete. This route features varied…

Last updated: June 29, 2026

2

hikers

#1.

Bass Bight, Pawpaw, and Stonecrop Ridge Trail

9.24km

02:47

300m

300m

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Moderate

Moderate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.

Moderate
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2.00km

00:40

160m

0m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

1.95km

00:30

0m

0m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Moderate hike. Great for any fitness level. Mostly accessible paths. Sure-footedness required.

Moderate

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Popular around Woodstock

Road Cycling Routes around Woodstock

Tips from the Community

maniboyflex
April 13, 2025, Woodstock Lookout Tower

A short detour from the Massanutten Trail leads to Woodstock Tower, perched at 2,000 feet on Powell Mountain. This historic fire tower offers sweeping 360Β° views of the Shenandoah Valley, including the winding bends of the North Fork of the Shenandoah River to the west and the ridges of Massanutten Mountain to the east. For those hiking the Massanutten Trail, it’s an excellent spot for a break, enjoy the views and take your time to appreciate. Note that the area can be busy on weekends.

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Frequently Asked Questions

How many hiking trails are available around Woodstock?

Our collection features 5 diverse hiking trails around Woodstock, catering to various preferences. You'll find 2 easy routes perfect for a relaxed stroll and 3 moderate trails for those seeking a bit more challenge.

Are there any easy, family-friendly hiking trails in Woodstock?

Yes, Woodstock offers several easy trails suitable for families. The Copernicus Ridge Trail is a gentle 2 km path, and the Gokotta Trail is just under 2 km, both offering pleasant, accessible experiences. Additionally, the Comeau Property near the village provides an easy, mile-long circular trail through woodlands, and the Ashokan Rail Trail is a paved, multi-use path ideal for leisurely walks with scenic reservoir views.

What kind of natural features and landmarks can I expect to see on hikes around Woodstock?

Hiking around Woodstock immerses you in the stunning Catskill Mountains, featuring dramatic rocky gorges, bluestone cliffs, and dense forests. You can discover impressive waterfalls like Kaaterskill Falls, explore historical bluestone quarries, and enjoy tranquil lakes such as Onteora Lake. Iconic landmarks include the abandoned hotel ruins and fire tower at Overlook Mountain, offering spectacular panoramic views of the Hudson Valley and Ashokan Reservoir.

Are there any circular hiking routes in the Woodstock area?

Yes, for those who prefer loop hikes, the Woodstock Lookout Tower loop from Little Fort Recreation Area is a moderate 2.7 km option. The Comeau Property also offers an easy, mile-long circular trail conveniently located near the village.

What is the best time of year to go hiking in Woodstock, NY?

Woodstock offers unique hiking experiences throughout the year. Spring brings beautiful blooms, while summer provides lush green landscapes. Autumn is particularly spectacular with vibrant fall foliage, making it a popular time for hikers. Winter offers expansive, clear views, especially from higher elevations, though some trails may require appropriate gear for snow and ice.

Are there any trails with significant viewpoints or panoramic vistas?

Absolutely. Overlook Mountain is renowned for its spectacular panoramic views from its 3,150-foot summit and fire tower, encompassing the Hudson Valley and Ashokan Reservoir. The Catskill Mountains themselves offer numerous vantage points where, on clear days, you can see across the Hudson River Valley and even up to five states. The Thorn Preserve also provides beautiful views of Overlook Mountain from its grasslands.

Can I find trails that are dog-friendly in Woodstock?

Many trails in the Woodstock area are dog-friendly, but it's always best to check specific regulations for each preserve or park before you go. Generally, trails within the Catskill Park and many local preserves welcome leashed dogs, allowing your furry companion to enjoy the natural beauty alongside you.

Are there any trails that feature waterfalls?

Yes, the Woodstock region is home to impressive waterfalls. Kaaterskill Falls is one of the tallest in New York and offers various trails to experience its grandeur. Plattekill Falls also provides a refreshing journey through forests to cascading waters, making for a memorable hiking experience.

What are some moderate hiking options around Woodstock?

For a moderate challenge, consider the Bass Bight, Pawpaw, and Stonecrop Ridge Trail, which is over 9 km long with a good elevation gain. Another excellent choice is the Massanutten, Lupton, Peters Mill Run ATV, and Wagon Road Trail Loop, an 8.1 km route. The Woodstock Lookout Tower loop from Little Fort Recreation Area is also a moderate 2.7 km option.

Are there any unique geological features or historical sites to explore on hikes?

Absolutely. The region is rich in bluestone quarries, some dating back to the late 1800s, offering unique insights into the area's industrial past. Sloan Gorge Preserve features an impressive bluestone quarry that descends into a dramatic rocky gorge with imposing cliffs and a unique rock-passage known as "The Chimney." Snake Rocks Preserve also showcases a striking quarry pond and historical bluestone quarry remnants.

Most popular routes around Woodstock

Road Cycling Routes around Woodstock

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