2
hikers
04:25
15.9km
290m
Hiking
Embark on the Beartown Mountain and Mount Wilcox Loop, a moderate hike that takes you through diverse terrain. You will experience evergreen forests and deciduous woods, vibrant with ferns and mountain laurels, as the trail winds through hilly, timbered mountains. This 9.9-mile (15.9 km) route involves a climb of 958 feet (292 metres) and typically takes around 4 hours and 25 minutes to complete, offering a rewarding day out.
Accessing the trailhead for this loop is straightforward, as parking is available on site. While the route is generally considered moderate, be ready for some rougher sections, especially on the Mount Wilcox Trail, which features rocks and roots. Always check local conditions before you head out, as weather can affect the trail's state and your overall experience.
Along the way, keep an eye out for the scenic Benedict Pond, a beautiful highlight that provides a peaceful stop. The loop also offers sweeping views of the South Taconic Mountains and the Catskills from various overlooks. This trail is a great option if you are looking for a solid day hike in the Massachusetts Berkshires, combining varied landscapes with rewarding vistas.
Last updated: April 23, 2026
Waypoints
Start point
5.41 km
Highlight • Forest
Tip by
15.4 km
Highlight • Lake
Tip by
15.9 km
End point
Parking
Way Types & Surfaces
Way Types
15.3 km
660 m
Surfaces
15.1 km
467 m
313 m
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Sign up for freeElevation
Highest point (620 m)
Lowest point (470 m)
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Saturday 10 October
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This route was planned by komoot.
Komoot rates this loop as moderate. While some sources describe the overall loop as easy for hiking, the Mount Wilcox Trail portion is considered moderately challenging due to its length, steep inclines, and rougher path with a significant amount of rocks and roots. Hikers should be prepared for varied terrain.
Yes, as the name suggests, this is a loop trail, meaning you will end up back at your starting point without needing to retrace your steps. The full loop is approximately 10.5 to 11 miles.
The loop is located within Beartown State Forest in Great Barrington, Massachusetts. Parking is typically available at designated areas within the state forest. Specific trailhead parking information can often be found on the mass.gov website or local park signage.
As of current information, there are generally no entrance fees or permits required for hiking in Beartown State Forest. However, it's always a good idea to check the official mass.gov website for the most up-to-date regulations before your visit.
The loop offers diverse terrain, moving through both evergreen forests with spruce and pine, and deciduous forests with oak, ash, and maple. You'll encounter hilly, timbered mountains, and the path can be rough with rocks and roots, especially on the Mount Wilcox section.
The Beartown State Forest is rich in wildlife, with possibilities of spotting bobcats, beavers, and even black bears. The underbrush is vibrant with ferns, mountain laurels, and hobblebush, and you might see colorful mushrooms and wildflowers. The forest is also known for impressive displays of azaleas and laurels.
The Beartown State Forest offers year-round recreational opportunities. Spring brings wildflowers and lush greenery, while autumn showcases spectacular fall foliage. Summer is popular, but be prepared for insects. Winter hiking is possible but requires appropriate gear for snow and ice conditions.
Yes, the loop features the scenic Benedict Pond. You'll also find scenic overlooks providing sweeping views of the South Taconic Mountains, the Catskills, and the Hudson Valley. Historical elements like old farmstead cellarholes and a small cemetery can also be discovered.
Yes, the route integrates with the extensive trail system of Beartown State Forest. A section of the Appalachian Trail skirts Mount Wilcox and intersects with other trails. The loop itself primarily uses the Beartown Mountain Trail and the Mount Wilcox Trail, and also touches sections of the Wildcat Trail and Mount Wilcox Road.
Generally, dogs are allowed on trails within Beartown State Forest, but they must be kept on a leash. Always practice Leave No Trace principles and clean up after your pet.
There are no guaranteed potable water sources directly on the trail. It is highly recommended to carry all the water you will need for the entire hike, especially given its length and moderate difficulty.
Given the trail's length and varied terrain, essential items include sturdy hiking boots, plenty of water, snacks, a map or GPS device, sun protection, insect repellent, and layers of clothing suitable for changing weather conditions. A first-aid kit is also advisable.
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