Massachusetts' 'Big Cheese' Town Is Known For Its Iconic Trails, Outdoor Recreation, And Quirky History

There is a famous hiking trail that spans 2,100 miles from Maine all the way to Georgia. This is the Appalachian Trail, and 90 miles' worth of it go through the state of Massachusetts, resulting in some hiking-friendly small towns. One such town is Cheshire, tucked away in the Berkshire Mountains, andwith an interesting history related to mammoth-sized cheese and ample access to Massachusetts' highest point with panoramic views. Located an hour's drive east of Albany, New York, the town of Cheshire sits at the foot of Mount Greylock, and offers plenty of hiking trails, reservoir kayaking, as well as reservations and wildlife areas.

Now, about that cheese: Cheshire prides itself on being the town where a 14-foot diameter block of cheese weighing between 1,200 and 1,400 pounds was produced, the brainchild of the town's Baptist Preacher John Leland. In July 1801, Leland and many other Cheshire residents worked together to make a massive glob of cheese in support of recently elected president Thomas Jefferson; Cheshire, as it happens, was the only town in Berkshire County to support Jefferson's candidacy. Leland personally delivered the cheese to President Jefferson in time for New Years, and the commander-in-chief had to dedicate an entire room in the White House to storing what was by then referred to as "the Mammoth Cheese" — and he never did get the chance to finish it before it had to get tossed out over a year later. These days, Cheshire has a granite monument downtown to honor John Leland and his mammoth cheese.

After learning some of the town's cheesy history, make sure to set aside some time for some outdoor recreation and trail exploration. Outside of town is the Cheshire Reservoir, a 418-acre lake that is also referred to as the Hoosac Reservoir. To get a boat in the water, head to the North Basin and find the paved boat ramp. Just east of the boat ramp is a kayak/canoe boat launch. If you like fishing, you'll want to bring your gear, because there are plentiful fish populations such as bass, bluegill, yellow perch, crappie, bullheads, and more. And while you're on the water, you can enjoy a view of the Berkshire Mountains — one of New England's most iconic fall destinations.

From the reservoir parking lot, visitors can also access the Ashuwillticook Rail Trail. As implied by its name, the trail used to be a railroad before being converted into a paved path. Heading south, it winds along the reservoir through the wetlands, ultimately ending up in Pittsfield, MA. Heading north, the trail passes through Cheshire and across the Appalachian Trail, ending in the town of North Adams. Overall, this path is 14 miles long and is an easy, flat area for biking and skating.

Should you choose to hop off the Ashuwillticook Rail Trail onto the Appalachian Trail heading east, the trail will take you up to some nearby mountains called "The Cobbles." From here, hikers can access the Cheshire Cobble Trailhead to the top of the peaks, where there's a scenic vista of the town, the reservoir, and Mount Greylock, so make sure to bring a camera. The Cheshire Cobble Trailhead and the mountains are located within the Chalet Wildlife Management Area, which is the perfect nature-viewing spot. The park spans 7,406-acres with local wildlife such as bears, wild turkeys, deer, and even moose.

The most popular of all the trails around the Berkshires is the Appalachian Trail heading up Mount Greylock from Cheshire. It connects to several of Mount Greylock's various hiking paths, such as the Round Rocks Trail if you backtrack a bit toward the mountain base and Jones Nose Trail closer to the summit. The Round Rocks Trail is a very easy one-mile hike that travels gently up the mountain and through a dense hardwood forest. Eventually, the path leads to some rocky outcroppings with a scenic overlook and huckleberry bushes. Head farther up the mountain where the path merges with the Jones Nose Trail, which leads to a meadow at the top of Mount Greylock.

Mount Greylock is 3,491 feet tall and is part of the Mount Greylock State Reservation. It's popular for its many hiking trails and the massive Veterans War Memorial Tower. There are campsites available for tent camping with nightly rates of $8 for residents and $20 for non-residents. Group camping costs more, so check the rates beforehand for group camping. The Appalachian Trail continues down the north side of the mountain and continues north from there. To experience more scenic trails, check out the idyllic trails to Tannery Falls hidden in the Berkshire Mountains.