Upton State Forest

Upton, Massachusetts 01568

Upton State Forest

Upton State Forest Professional Guide

Detailed Trail Description from our Guidebook

"Well-marked dirt trails lead you past lady’s slipper flowers and lichen-crusted boulders to Dean Pond, a great place to stop for lunch. Return to your car on the Mammoth Rock Trail, scrambling between more boulders as you pass through the flat, thickly wooded forest. Hunting is permitted here in season, so take care if you’re hiking here in the fall."

More Upton State Forest Professional Guides

Detailed Trail Descriptions from Our Guidebooks

60 Hikes within 60 Miles: Boston - 2nd Edition (Menasha Ridge Press)
Lafe Low and Helen Weatherall
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"The 2,600-acre Upton State Forest takes you deep into the woods and to the shores of the swampy but scenic Dean Pond. Like many Massachusetts Department of Conservation and Resources properties, Upton State Forest is a varied mix of wider, firm, flat trails resembling an old fire road and narrow, winding true hiking trails. You can mix it up as you see fit. Start off from the parking area, which has room for 15–20 cars. You will hike through a closed metal gate (intended to keep out ATVs and other motorized vehicles). You start off on the wide, firmly packed Civilian Conservation Corps (CCC) road."
Snowshoe Routes: New England (The Mountaineers Books)
Diane Bair & Pamela Wright
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"The first time we ever hiked here, in springtime, we were greeted by an unusual sight; a parade of people dressed in Renaissance garb spilled out of the woods—a role-playing group, the Society of Creative Anachronism, all done up in brocades and velvets, not the typical shorts-and-wicking-tee-shirts crowd. And we thought we were the ones who’d discovered this pine-scented, boulder-studded 2660-acre forest! So it isn’t completely unknown, but Upton State Forest is still quite pristine-and pretty much overlooked in winter. This thickly forested paradise of white pine and maples is circled with a pretty 3-mile loop trail that can be shortened if you choose to follow the unpaved Park Road to Dean Pond and circle back on Loop Road. It’s easy for beginners and kids, with just a slight climb up the Hawk Trail."

Upton State Forest Trip Reports

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What a treat well groomed and wide enough for Cross Country and Snoe Shoes. We were snow shoeing and were pretty much bye our selves all morning. Enough room for the dog to romp and we went on a Sunday and were all alone on Whispering Cave Trail which was a wonderful trek. We went reverse of how the map depicts so we were at the Pond end to start which was completly froze and started up from that side. Saw a few fresh deer tracks but did not see a one.
It was a Heart pumper and rather steep but it is a place I will return to in the summer. I strongly reccomend it and the trails are easy to follow but only names at the junctions and no arrows or distances so depending on your sence of direction be carefull on the side trails which are narrow, and paint marked which is fadeing.
You can get turned around easy but this is a nice place.
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It's easy trail. My wife said, "It is great trail to me".

But some single track is nice and exciting.

I will enjoy this trail, because it is close to my home.
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My wife & I were on vacation in the Cape Cod area and finished with a visit to her sister, who lives only 2 miles from the trailhead. I had an opportunity to borrow my brother-in-law's Trek (thanks Doug!) and get a quick pump in. This trail has riding similar to some areas near my home in SC. The directions in the guide book were very accurate. All in all, this is a great ride if you are wanting to get a great workout in without having to spend tons of time on the trail. Most of the trail is single track. There are a couple of muddy stream crossings and some great technical downhills. I did not find any of the climbing to be difficult at all, with the exception of the steep, technical climb at the end. This required some pushing but it seems rideable if you are familiar with the trail and know it's coming. I wish I had more time to explore this very nice state forest. I feel like there is much more riding available here than what I experienced. Also, at the time this guide was written, it notes that the trail needed to be broken in due to its being new. I did not find this to be a problem at all. Great trail!
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Upton State Forest Photos

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Trail Information

Nearby City
Trail Type
Skill Level
2 hours
Best in Summer
Additional Use
Upton State Forest Headquarters, Upton
Local Contacts
USGS Milford, MA
Local Maps

Trail Log