Cross-Country Skiing, Hiking in Berkshire Mountains

With an abundance of hills, forest and meadows, our Berkshire Mountains area offers numerous possibilities for winter fun. Depending on the amount of snow, you can cross country ski, snowshoe, or hike. Start you day with a hearty breakfast at the B&B, then head out to one of these great locations for a little fresh air and exercise.x-country-skiing

Bartholomew’s Cobble, a designated National Natural Landmark that is located close to Sheffield, has 329 acres with two rocky knolls that give the area its name (cobble is German for rocks). There are five miles of trails here; all are fairly moderate, which make it great for cross-country skiing as well as hiking. This is an area that has a lot of wildlife, so keep a watch out for hawks and bald eagles. The Visitor’s Center is open year-round, but hours vary, so it’s best to call ahead.
105 Weatogue Rd, Sheffield, MA
413-298-3239, extension 3013
Parking, $5/car

Those who hike or snow shoe to the top of Monument Mountain will be rewarded with glorious views of the southern Berkshires and the valley below. Though the three trails are relatively short—all three miles or less, round-trip—they do have some elevation. Longest is the Indian Monument Trail at 1.51 miles, an interesting path that takes you past the remains of ancient Native American trails, old stone walls, and cart paths used for transporting hemlock bark to tanneries.
Route 7
Great Barrington, MA
413-298-3239
Open year-round, though the parking lot is not plowed in winter.

Located about one hour’s drive from our Inn, Mount Greylock, the highest point in Massachusetts, offers stunning vistas and more than 70 miles of trails, many good for winter outings. For easier skiing and hiking, check out the 1.8-mile Bradley Farm Trail or the March Cataract Trail at 1.6 miles round-trip. Many shorter trails can be combined into longer loops, such as Bellows Pipe and Ragged Mountain that combine for a five-mile hike. The Visitor’s Center is open year-round, but hours vary, so it’s best to call ahead.
30 Rockwell Road, Lanesborough, MA
413-499-4262
Parking: $5/MA residents, $6/non-MA residents

After a day outside, head back “home” to the B&B and warm up by our cozy fire with a hot cup of cocoa. Now that’s how to do winter!

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