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Routes
Hiking trails & Routes
United States
Massachusetts
Berkshire County

Hickey and Peeskawso Peak Loop

Easy

5.0

(8733)

18,300

hikers

Hickey and Peeskawso Peak Loop

01:17

3.92km

170m

Hiking

Embark on the Hickey and Peeskawso Peak Loop, an easy hiking route that takes you through a shady forest. You'll climb steadily, gaining 557 feet (170 metres) in elevation over its 2.4 miles (3.9 km) distance. Along the way, look out for striking rock formations and pretty cascades, with 'peek-a-boo'…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

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1.11 km

Waterfall

Waterfall

2

1.77 km

Peeskawso Peak

Highlight • Summit

3

2.54 km

Monument Mountain (nature reserve)

Highlight • Natural Monument

Monument Mountain is a nature reserve in Great Barrington, Massachusetts, is a geological home for different rocks and minerals that are natural to the area. There are a number of …

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B

3.92 km

End point

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Way Types & Surfaces

Way Types

3.88 km

< 100 m

Surfaces

3.87 km

< 100 m

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Elevation

Elevation

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Weather

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Today

Wednesday 6 May

19°C

8°C

95 %

Additional weather tips

Max wind speed: 17.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Where is the trailhead for the Hickey and Peeskawso Peak Loop, and is there parking?

The trailhead for the Hickey and Peeskawso Peak Loop is located within the Monument Mountain Reservation near Stockbridge, Massachusetts. There is a parking lot available at the reservation entrance.

Are there any fees or permits required to hike this trail?

Yes, there is a parking fee to enter the Monument Mountain Reservation, which grants you access to the trail. No additional hiking permits are required.

Is the Hickey and Peeskawso Peak Loop dog-friendly?

Yes, dogs are welcome on the trail, but they must be kept on a leash at all times.

What is the best time of year to hike the Hickey and Peeskawso Peak Loop?

The trail is open year-round, but dry weather is recommended for the best experience. Fall is particularly popular due to the vibrant foliage and stunning panoramic views. Spring and summer also offer refreshing atmospheres.

What is the terrain like on the Hickey and Peeskawso Peak Loop?

The terrain is generally rocky, especially on the ascent to Peeskawso Peak and the subsequent descent. Hikers should be prepared for steady climbs through shady forests and narrower, more eroded sections. Shoes with good grip are highly recommended.

Is the Hickey and Peeskawso Peak Loop suitable for beginners?

While rated as easy, the trail involves a steady climb and rocky sections, particularly towards Peeskawso Peak. Beginners with good stamina should be able to manage it, but those new to hiking might find the rocky descent challenging. It's a rewarding hike for those looking for a moderate challenge.

How long does it typically take to complete the Hickey and Peeskawso Peak Loop?

The loop is approximately 3.9 kilometers (2.4 miles) long. Most hikers can expect to complete it in about 1 hour and 15 minutes, though this can vary depending on pace and time spent enjoying the views.

What kind of views can I expect on the trail?

The trail is renowned for its panoramic views. As you ascend, you'll catch 'peek-a-boo' glimpses of the surrounding countryside. From Peeskawso Peak, you'll be treated to incredible, sweeping vistas that stretch for miles, especially during the fall foliage season.

Are there any specific landmarks or points of interest along the trail?

Absolutely! The main highlight is the panoramic view from Peeskawso Peak. You'll also encounter striking rock formations and pretty cascades. A short side loop leads to an overlook with an excellent view of the Devil's Pulpit, a unique freestanding rock column.

Does the Hickey and Peeskawso Peak Loop intersect with other trails?

Yes, the route primarily follows the Hickey and Peeskawso Loop. However, it also passes through sections of the Hickey trail (yellow), the Mohican Monument Trail (blue), and the Peeskawso Peak Trail (red).

Is there a recommended direction to hike the loop for an easier experience?

Some hikers find it beneficial to ascend via the Hickey Trail and descend from Peeskawso Peak. The descent from Peeskawso Peak can be steep and rocky, so tackling it downhill might be more challenging for some. Consider your comfort level with steep, rocky descents when choosing your direction.

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Hickey and Peeskawso Peak Loop

01:17h

3.92km

170m

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