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Routes
Hiking trails & Routes
United States
Massachusetts
Berkshire County

Perry's Peak Loop

Easy

2.9

(4)

23

hikers

Perry's Peak Loop

01:47

5.84km

210m

Hiking

Embark on the Perry's Peak Loop, an easy hike that guides you through a delightful transition from sun-drenched open fields into a rich, mixed forest. You will encounter diverse ecosystems, featuring stands of oak, beech, and red pine, alongside ferns and old apple trees. The route covers 3.6 miles (5.8…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

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1

2.38 km

View of Pittsfield Valley from Hollow Fields Reserve

Highlight • Viewpoint

Hollow Fields Reserve encompasses over 660 acres and features some of the best views of the entire Pittsfield valley. There are numerous viewpoints along the trails that pass through the …

Tip by

2

3.02 km

Perry Peak

Highlight • Summit

B

5.84 km

End point

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Way Types & Surfaces

Way Types

5.83 km

< 100 m

Surfaces

5.29 km

475 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (620 m)

Lowest point (410 m)

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Weather

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Today

Friday 8 May

12°C

3°C

37 %

Additional weather tips

Max wind speed: 18.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the difficulty level of the Perry's Peak Loop?

The Perry's Peak Loop is generally considered a moderate or intermediate hike. While some sections involve gradual ascents and easy descents on wider woods roads, you will encounter moderate inclines, uneven terrain, and elevation changes, including a steep climb through the forest. It's a rewarding challenge for most hikers.

What kind of terrain can I expect on this route?

The trail offers diverse terrain. It typically begins by traversing open fields, which can be sun-splashed and windswept. After the fields, the path leads into a mixed forest with oak, beech, and red pine. You'll experience a steep climb along woods roads, and the footing can be uneven in places. Ridge tops are dotted with ferns, old apple trees, and wild berries.

Are there any notable viewpoints or landmarks along the way?

Absolutely! The trail offers several picturesque landscapes. From the open fields, you can enjoy views of Yokun Ridge and the crenellated hills of South Berkshire. As you ascend, clearings provide vistas towards Maple Hill and West Stockbridge Mountain. A significant highlight is the View of Pittsfield Valley from Hollow Fields Reserve, also known as Richmond Overlook or Scotty's Lookout, which provides expansive views. You'll also pass by Perry Peak itself.

Is the Perry's Peak Loop dog-friendly?

Yes, the Perry's Peak Loop is generally dog-friendly. However, it's always best to keep your dog on a leash to protect wildlife and ensure a pleasant experience for all trail users. Please remember to pack out any waste.

What is the best time of year to hike this trail?

The trail is beautiful in all seasons. Spring brings wildflowers, summer offers lush greenery and berries, and fall is spectacular for foliage. Even winter, with snow, provides unique beauty. However, be aware that during the spring thaw, the access road to the trailhead may experience poor conditions like deep mud or ruts.

Where can I park for the Perry's Peak Loop trailhead?

Parking is available at the trailhead, which is located within the Hollow Fields Reserve in Richmond, Massachusetts. It's advisable to check local conditions, especially during spring thaw, as the access road can be muddy or rutted.

Do I need a permit or pay an entrance fee to access the Hollow Fields Reserve?

No, there are no permits required or entrance fees to access the Hollow Fields Reserve or hike the Perry's Peak Loop. The reserve is managed by the Berkshire Natural Resources Council (BNRC) and is open to the public for recreation.

What kind of wildlife or plants might I see?

The diverse habitats of the Hollow Fields Reserve support various flora and fauna. You might spot plants like Chestnut, Indian Cucumber, Partridgeberry, and Sheep Sorrel. It's also a great spot for birdwatching, with species like the Black-Cap Chickadee common in the area. Keep an eye out for wild berries in season!

Is the trail suitable for families with children?

Given its moderate difficulty, uneven terrain, and elevation changes, the trail might be challenging for very young children or those not accustomed to hiking. However, active families with older children who enjoy a good climb and diverse scenery will likely find it rewarding.

Are there any temporary closures or important notices about the trail?

Yes, it's important to note that a section of the Perry's Peak Loop Trail has been temporarily closed due to private property concerns. Efforts are currently underway to relocate this section and restore full public access. It's always a good idea to check the Berkshire Natural Resources Council (BNRC) website for the most up-to-date trail status before your visit.

Are there any cafes or amenities nearby after the hike?

While the Hollow Fields Reserve itself is a natural area, the trail is located in Richmond, Massachusetts, which is close to larger towns in the Berkshires. You can find cafes, restaurants, and other amenities in nearby communities like Pittsfield or West Stockbridge, typically a short drive away.

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