At Overland, we spend all year planning for, talking about, and supporting incredible trips across the US and around the world. So, it’s only natural that we want to get outside during our free time for some of our own adventures! Here in the Williamstown office, we have access to some amazing spots to recreate in the Berkshires and beyond. Today, I am going to share with you all a few of my favorite local spots inspired by Overland adventures.
Pine Cobble
3.2 miles, moderately challenging
A beloved Mountains & Sea Adventure day hike, Pine Cobble is the quintessential Williamstown outing. You’ll find everyone here from local dogs to Williams College students. The hike gets steep at the end but has great views. You’ll have a gorgeous view of Williamstown, Greylock and Stone Hill from the top! It is well worth pushing to the summit.
I first came down Pine Cobble in 2019 as I was completing my thru-hike of Vermont’s Long Trail. I crossed the border and went straight to Spring Street to enjoy some Lickety Split ice cream. These days, Pine Cobble is one of my go-to spots to catch the sunrise before work. Some highlights include the fairy pool embedded within the tree and the numerous options to extend the loop by way of the Class of ‘98 Trail, the Chestnut Trail, the Long Trail, or the Appalachian Trail towards Route 2.
Harmon Hill
4 miles, moderately challenging
Having lived in Vermont for ten years before moving to Williamstown, I always love to get back to the Green Mountains. Just a 20 minute drive away, this New England Adventure favorite, gives you a lot of bang for your buck. For this hike, I typically start at the Long Trail parking lot on Route 9 and cross the street to hike south. Watch out for cars as they drive fast here! This section of trail is always well-maintained as it overlaps with the southern Vermont section of the Appalachian Trail and the Long Trail. It also means there are opportunities to just keep going if you’re enjoying it out there!
Harmon Hill is locally known as The Staircase so follows that there is some steep incline for the first three quarters of a mile as you leave the parking lot and tackle the rock steps. Then the trail evens out and you cross through some rolling hills before coming upon a wide meadow that opens up to a beautiful Bennington overlook and the Taconic Mountain Range to the west. One of my friends loves The Staircase so much he hiked it every day during the month of May, and if that isn’t a glowing review I don’t know what is!
Snow Hole
5.7 miles, moderate
The Taconic Crest Trail is a scenic 40 mile ridge trail where MA, NY, and VT come together. At this point, I have now hiked the entire length of the ridge but there are some favorite spots I return to often including Snow Hole, the first hike for our Berkshire Adventure students.
From the top of Petersburg Pass on Route 2, you park and then cross the street to follow the Taconic Crest Trail north to Snow Hole. This is a relatively flat hike with some gradual incline after the initial short but steep climb. You will have nice views of New York to the west throughout the hike. After about 2 miles you’ll come to a sign indicating a brief departure from the Taconic Crest Trail. A short side trail will lead you to the rare geophysical feature, a 40 foot deep cavern. You will know you’ve arrived at Snow Hole when you see a large bedrock chasm that goes into the mountain. Despite the name, it’s possible that there won’t be any snow in the cavern if it’s been a warm spring. However, it’s a fun place to explore and a good snack spot even if there’s no snow!
Stony Ledge
3.9 miles, moderate
Beginning at the Mount Hope Trailhead, you’ll say goodbye to the cows next to the parking lot and head out to the grassy meadow on the right. The Stony Ledge trail ascends with an option for a more gradual or a steeper route. The summit offers different views of the valley and a phenomenal picnic spot at the top. There’s even a shelter and a picnic table to spread out.
Looking to extend the hike? Affectionately dubbed the “Hometown Loop”, you can link together Mount Prospect, Fitch, Williams, and Greylock ending on Stony Ledge looking back out over the valley you just traversed.
After a hot summer day on Stony Ledge, stop by Mount Hope Park to check out the water hole. There is a large grassy area, picnic tables, grills, and a place to splash around in the water.
Jiminy Peak
3 miles, moderately challenging
The Overland office crew has a longstanding tradition of a weekly morning uphill ski at Jiminy Peak on Fridays during the winter and a number of ambitious Environmental Stewardship New England trips have elected to stop here for a fun afternoon outing.
Jiminy is a ski resort in the winter but has various activities in the summer. Grab a summer trail map at the base lodge and hike up either access road or head up a ski trail that looks fun! Depending on the trail, it can be a pretty steep hike up. Going up the access road on the Left Bank will be one of the more mellow routes up. Make sure to avoid mountain bikers! There is a great view from the summit.
Whether your adventures are close to home or far away I hope you have a great time outside today!
