October 2024
Hiking the Hickey and Peeskawso Peak Trail at Monument Mountain Reservation – The Berkshires, Massachusetts
One of the best activities to add to your Berkshires itinerary is exploring the many hiking trails along western Massachusetts, some of which overlap with the famous Appalachian Trail. Completing these trails in the fall optimizes the opportunity to enjoy gorgeous fall foliage the New England area is known for.
The Hickey and Peeskawso Peak Trail at Monument Mountain Reservation (Alltrails link) is a moderate 2.5 mile loop trail with almost a 700 ft elevation gain that takes hikers up to several view points that span miles with thousands of trees decorated in the fall best. Also, do not miss the Devil’s Pulpit extension once you make it to the top!
There is a decently sized parking lot at the start of the trail head. We arrived at 9AM on a Thursday to plenty of spots but when we were done closer to lunchtime, the lot was full and I can imagine this lot fills up quicker on weekends. There is a $6 fee for parking that is paid at a kiosk that accepts credit cards.
You can complete the loop in either direction and we selected starting with the Hickey Trail as it is more steep and we typically prefer to climb than descend steep passes. The trail goes up through the forest at a moderate incline that we did not find difficult. The trail markers for the Hickey Trail are yellow. We also passed no one so we had the entire place to ourselves. The Hickey Trail potion is just under a mile and this section took us about forty minutes to complete.
We reached the point in the trail where we picked up the Peeskawso Peak Trail and we were happy to learn that the climbing was basically all done on the Hickey Trail. The trail markers for the Peeskawso Peak Trail are red. At this point, the trail takes you along the rock cliffs where we were able to get sweeping views. Unfortunately, the cloud coverage did not make the fall colors pop as much but I can imagine how spectacular they were be on a clear sunny day.
The trail then gives an optional side request to go to the Devil’s Pulpit Overlook which did not seem to add a measurable amount to the trail duration so we turned left and took the rock staircase up to the overlook. The view from here is stunning and definitely the best of the trail so do not “overlook” this overlook – it is definitely the views you want to see!
Counting on the Peeskawso Peak Trail started the descent back to the parking lot. This gradual decline was quite relaxing as we navigated through the forest. After a short time, the trail connects with the Mohican Monument Trail and you turn left to follow the blue trail markers to the parking lot. The rest of the trail was very easy and we made it back to the car at 11AM so it took us a total of two hours to complete with plenty of time relaxing and enjoying the view.
This trail is definitely a must when visiting the Berkshires. It is fairly easy to complete with some elevation gain and amazing sweeping views at the top. Definitely add the Devil’s Pulpit Overlook and I would recommend starting with the Hickey Trail to get the climbing out of the way over a shorter distance. I hope you enjoy this trail as much as we did!
Continue reading about our weekend in the Berkshires here!
Read all blog posts for the Berkshires here!
See our complete itinerary here!
Planning your trip? Check out the Perfect Fall Itinerary to the Berkshires here!
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