My First Hike Up Monument Mountain In Great Barrington, Massachusetts

For those who know me, I am a Northern Berkshire resident, but I am always up for an adventure, especially when it involves outdoor activities. You might be saying, it's cold for any activities this time of year, but you'd be surprised how many people in the Berkshires enjoy the outdoors even in winter.

Sometimes, I drive from Northern Berkshire to Southern Berkshire for work errands. Since I have some free time today, I thought, why not get in a few extra steps? The only place to do that is Monument Mountain.

The Ascent to the Peak of Monument Mountain

I parked the car just off Route 7 and started up the Hickey Trail, known for its steep, direct climb, scenic views of waterfalls and rock formations, and its connection to other trails for a longer loop.

 Hickey Trail Details

The Hickey is about 0.8 miles long, marked with yellow blazes, and provides a strenuous climb through forests and along a gorge before reaching Inscription Rock, where it connects to the Peeskawso Peak Trail for panoramic summit views. It's also important to note that proper footwear is recommended in winter since trails can be slippery from ice.

Peeskawso Peak Trail

Hickey Trail connects to the Peekawso Peak Trail, which climbs to the mountain's summit, also known as "The Devil's Pulpit." This is where the hike becomes challenging: the trail turns rocky, with drop-offs that can be deadly if you're not careful.

Monument Mountain Peak

Once you reach the top of Monument Mountain, the views are absolutely breathtaking at an elevation of 1,642 feet! Many of the sights include Mount Greylock State Reservation, the highest peak in Massachusetts, which has an elevation of 3,491 feet, the Housatonic River Valley, the Berkshires, the Taconic Mountains, and the Catskill Mountains of New York.

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The Descent Down Monument Mountain

It's best to start early because I have to descend before it gets too dark to see. Monument Mountain is open year-round and is owned and maintained by The Trustees. If you're looking for an outdoor activity with about 2 1/2 hours to spare, Monument Mountain might be the perfect choice. Trust me, the workout felt amazing afterwards!