Hike Monument Mountain

Monument Mountain Trailhead

Distance

2 Miles

Elevation Gain

720 Feet

Activities

Photography, Hiking

Skill

Intermediate

Season

Spring, Summer, Autumn

Type

Loop

Added by

Shannon Kalahan

Dog Friendly
Easy Parking
Family Friendly
Forest
Scenic
Waterfall
Wildlife

Looking for the perfect local hike? Monument Mountain is definitely for you. As far as New England's smaller mountains go, has one of the best views of the southern Berkshires and the Housatonic River Valley. Add some interesting geology and history, opportunities to spot wildlife, a waterfall (with several other cascades along the route) and you have got yourself a wonderful day trip!

At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under 3 miles round trip.

Personally, I chose to take the Hickey Trail for the bulk of the elevation gain, before hitting Squaw Peak Trail to reach the summit. The Hickey Trail is notably harder than the Indian Monument Trail, but also much more direct. The Hickey Trail is characterized by stretches of deciduous forest, pine and an abundance of mountain laurel mixed with vertical rock stair cases. Once you reach Squaw Peak Trail, where you’ll find the summit and best views, you are out on open ledges. If you have a severe phobia of heights, you may want to avoid this portion of the trail….. though in my opinion, the view is the best part of the hike!

As a word of caution, New England weather is notoriously unpredictable and there was still snow along the upper reaches of the trail in April. Ice patches along the vertical sections of the route and open ledges can be very dangerous. Also, due to the rapid elevation gain, Hickey Trail is difficult on the knees. If you have knee problems, consider bringing poles or taking the Indian Monument Trail, which is very well maintained and not as steep.

Overall, Monument Mountain was satisfyingly difficult, but short enough to accomplish in a few hours. There are no facilities here, except some picnic benches at the parking lot so bring your own food and water. Dogs are allowed on the trail, but should be leashed. There is a parking fee, and in the winter, the parking lot for the trailhead is not plowed.

Always practice Leave No Trace ethics on your adventures and follow local regulations.

Nearby Lodging

From $150/night

Long Pond Ridge Top

Great Barrington, Massachusetts

From $100/night

Running Spring Farm

Sandisfield, Massachusetts

From $100/night

Hillsdale Hideaway

Hillsdale, New York

Reviews

Leave a Review

Overall rating: 

Great little hike

Went up the “strenuous “ and Dow the carriage road. Beautiful views, dog friendly, and overall enjoyable.

Distance

2 Miles

Elevation Gain

720 Feet

Activities

Photography, Hiking

Skill

Intermediate

Season

Spring, Summer, Autumn

Type

Loop

Added by

Shannon Kalahan

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Hike the Benedict Pond Loop Trail

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