Private Day Hike Menu For 2024
Northern Berkshires
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About this hike:
Hike this "bucket list" mountain, the highest peak in Massachusetts at 3,491 feet. The state reservation is owned and managed by the Department of Conservation and Recreation (DCR).
We follow the Cheshire Harbor trail approach to the Appalachian Trail, which is considered to be the “easiest and shortest ascent” to the summit. However, don't underestimate the rigor required for this moderate to challenging hike. We hike “Berkshire Camino style,” which is moderately paced and with lot of stops to let the heart rate equalize. We stop frequently to catch our breath, rest and hydrate.
The hike is an "out and back" format, meaning that we retrace the route to return to the parking lot after reaching the summit.
We'll have about 30 minutes at the summit to visit the War Memorial Tower and take in the view. Visit Bascom Lodge, constructed in the 1930's by the Civilian Conservation Corps where there are bathrooms and grab and go food and drink items available to purchase.
Duration: 5-6 hours depending on your pace
Distance: 6.5 miles
Level of challenge:
This is a moderate to challenging hike. Hike 6.5 miles in an out and back format that starts and ends at the Cheshire Harbor trailhead at the base of Mt. Greylock. During the hike we will gain nearly 2000 feet of elevation over 3.2 miles as we pass from a hardwood forest into a boreal forest at the summit. The elevation gain is slow and steady with just a few stepper sections. It is up the whole way!
A portion of the trail is on a gravel road. Much of the trail is a woodland trail requiring attention to footing as there are rocks, roots and depending on the season, some muddy sections depending on recent rainfall and season.
Well behaved dogs on leash are welcome on this route.
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About this hike:
A forested wonderland lies just minutes from the heart of downtown Williamstown, MA.
The hike starts at the Williams Inn in the heart of downtown Williamstown and is open to everyone. After a short stroll on a quiet residential street we enter the grounds of The Clark Art Institute and hike on a loop through the woods. We'll cover the uphill section during the first half of the hike, making the second half an easy and gentle descent back to the Williams Inn.
Some of the breathtaking moments of this hike are at the reflecting pond and the upper pasture where we peer down over the museum and all of downtown Williamstown.
You have the option to end the hike at The Clark should you wish to tour the museum, spend an extended period of time relaxing at the reflecting pond or to purchase grab-and-go food and beverages in the cafe.
Also, consider having breakfast, lunch or dinner at The Barn at the inn and shop along Spring St either before or after the hike.
Well behaved dogs on leash are welcome on the grounds of The Clark.
Duration: 2.5 Hours
Distance: 4.5 miles
Level of challenge:
This is a moderate hike that starts with a steady, but not overly steep, uphill trek with about 500 feet of elevation gain over the first 2 miles of the hike. The descent returning to the Williams Inn is gradual. There are no steep downhill sections.
Well behaved dogs on leash are welcome on this route.
Central Berkshires
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About this hike:
Start at the Mahanna Cobble trailhead at Bousquet Mountain Ski Area. Hike to two majestic scenic overlooks (Mahanna Cobble and Yokun Seat) on the iconic High Road, a trail network developed by the Berkshire Natural Resources Council. After reaching Yokun Seat, the second overlook, we will reverse the route back to Bousquet. This hike is a steady, but uphill for the first half.
Duration: Approx 4 Hours
Distance: 4 miles
Level of challenge:
Moderate with a steady incline of about 1000 feet to Yokun Seat. The trail contains many tree roots and rocks.
Sorry, dogs are not permitted on the trail that extends to Yokun Seat. If you wish to hike with you dog, please let us know and we will adjust the route..
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A forested wonderland just a few miles from the heart of downtown Pittsfield, MA
About this hike:
If you are looking for a solid 4 hour hike immersed in the woods, then this hike at the Department of Conservation and Recreation's (DCR) Pittsfield State Forest is a great option for you.
The pay-off at the summit, reached at the half way point in the hike, is an expansive view looking west toward New York State. Locals know that this is one of the best sunset viewing spots in the Berkshires.
Visit Berry Pond, the highest natural body of water in Massachusetts for a short snack and rest break, before descending back to the trailhead at the base of the forest.
Duration: 4 Hours
Distance: 6 miles
Level of challenge:
This is a moderate to strenuous hike that starts with a steady, but not overly steep, uphill trek with 1000 feet of elevation gain over 2.5 miles of woodland trails. The 3.5 mile descent is gradual, substantially on switch back trails. There are no steep downhill sections.
Well behaved dogs on leash are welcome on this route.
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About this hike:
If you are looking for a shorter yet satisfying woodland hike then the Tranquility Loop at Pittsfield State Forest is a great choice.
This hike starts and ends on a peaceful all persons accessible trail that runs along side a babbling brook. Never fear, we'll get the heart pumping just a bit on a section with a some up and down elevation change.
Duration: Approx 1.5 Hours
Distance: 2 miles
Level of challenge:
East to Moderate with a slow and steady incline of about 350 feet. The trail contains some tree roots and rocks.
Well behaved dogs on leash are welcome on this route.
Southern Berkshires
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About this hike:
Hike this trail that is very close to the historic downtown of Lenox, MA. Enjoy a coffee, meal and shopping in town before or after the hike.
Explore Lenox’s town owned, Kennedy Park a restored woodland trail system. Visit the ruins and scenic overlook at what was the elegant Gilded Age era Aspinwall Hotel that tragically burned to the ground in April 1931.
Duration: 2 - 2.5 Hours depending on pacing
Distance: 3 miles
Level of challenge:
Moderate with a slow and steady incline of about 400 feet. The trail contains some tree roots and rocks.
Well behaved dogs on leash are welcome on this route.
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About this hike:
Hike a portion of the High Road - Yokun Ridge from the trailhead at Kripalu Center for Yoga & Health. The loop route includes pauses at the serene Monks Pond and a stunning scenic overlook at Kennedy Cliffs that gives you a bird's eye perspective of the historic village of Lenox.
Please inquire about a shorter loop to Kennedy Cliffs if you are seeking less challenge or a shorter hike.
Duration: 3 Hours
Distance: Approx 5 miles
Level of challenge:
Moderate with a steady incline of about 600 feet from the start of the hike to Kennedy Cliffs. It is mostly downhill for the second half the hike. This is a loop format. The trail contains some tree roots, rocks and muddy at times in some sections.
Well behaved dogs on leash are welcome on this route.
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About this hike:
The trail to Flag Rock passes through beautiful, dense forest with views of substantial glacial boulders. Flag Rock is a scenic overlook that provides westward views of the hamlet of Housatonic, MA. This is on the lesser quieter and less busy "backside" of the popular Monument Mountain Reservation that is owned and maintained by The Trustees of Reservations.
Please inquire about a longer loop from the Flag Rock trailhead if you are seeking more challenge. We can add a section to Devil's Pulpit for an additional fee.
Duration: 2.5 Hours
Distance: 4 miles
Level of challenge:
Moderate with a steady incline of about 800 feet from the start of the hike to the midway point at the summit of Flag Rock. This is an out and back format. The return is a descent on the same trail. The trail contains some tree roots, rocks and muddy at times in some sections.
Well behaved dogs on leash are welcome at the Monument Mountain Reservation.