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5 Dazzling Outdoor Destinations in Western Mass

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Posted by Massachusetts Office of Travel and Tourism

Fresh air is the best kind of cure for too much time inside.

For hiking, biking and all other manner of outdoorsy pursuits, there are few better places to go in Massachusetts than the western part of the Commonwealth. There’s all kinds of room to get out and about, and the bucolic landscapes only make it more enjoyable while you do.

Whether it’s during spring, summer or fall, here are five of the best places to go when you go to western Mass.

Monument Mountain in Great Barrington, MA

The Berkshires are known for stunning scenery and climbing Monument Mountain is one of the absolute best ways to see it. The ascent takes a couple of hours, and is moderately strenuous. So long as the weather cooperates and there hasn’t been recent precipitation, though, the trip isn’t troublingly steep or dangerous.

Monument Mountain

What awaits at the top of Monument Mountain

At the summit, hikers are rewarded with a magnificent panorama of the Housatonic River Valley; Squaw Peak, Monument Mountain’s highest point and one that stands 1,600+ feet above sea level, provides views as far as Mount Greylock and, in the distance, New York’s Catskill Mountains. The route is open year round, and for those who’d like to stay nearby, the Monument Mountain Hotel is the place to go.

Gunn Brook Falls in Sunderland, MA

Sunderland Bridge, which connects the town of the same name to Deerfield, is one of the best foliage peeping spots in Massachusetts during autumn. A little bit off the beaten trail, visitors can also find a lesser-known hidden gem that’s native to the area: Gunn Brook Falls.

Gun Brook Falls

Gunn Brook Falls in spring by Evan Gregg

Located on the lower west side of Mount Toby, the waterfall cascades down 35 feet through a verdant, forested area. The site is accessible through a path that’s connected to a public road, giving guests the option to either mostly drive and walk a bit or walk the whole way. For directions, click here. For overnights in the area, the Red Roof Inn in South Deerfield is convenient.

Naumkeag in Stockbridge, MA

Vestiges of the Gilded Age can still be found in many corners of western Massachusetts, where the upper crust of centuries past constructed opulent mansions for their summer retreats. If your trip only allows enough time to see one of the sites, no one could fault you for choosing Naumkeag.

Naumkeag Gardens

Blue Steps at Naumkeag Gardens

Built for Ambassador Joseph Choate once upon a time, the property is nowadays administered by the Trustees of Reservations, who make it open for visitation from May through mid-October. The shingled house is majestic, and the grounds are maybe even more so, with the Blue Steps (pictured above) being especially gorgeous. To sleep over, the Red Lion Inn, which also caters Naumkeag’s Oak Café, is a great pick.

Bartholomew’s Cobble in Sheffield, MA

Naumkeag is to botanical wonder as Bartholomew’s Cobble is to geological wonder. The “cobble,” which consists of twin rocky knolls, has been around quite a bit longer than anything man-made in western Mass, as its shape began to form from coral, shells and sand more than 500 million years ago.

Bartholomew's Cobble

Hiking towards Hurlburt’s Hill at Bartholomew’s Cobble

If intellectual interest in geology isn’t quite enough to draw you to Bartholomew’s Cobble, there is some terrific hiking and wildlife, too. Five miles of trails offer ample space for leg stretching, with Hurlburt’s Hill, the high point, rising more than 1,000 feet to present a superb view of the surrounding Housatonic River Valley; the area is also home to hundreds of bird species. Those coming to Sheffield can put their feet up nearby at the Staveleigh House B&B.

Mount Tom State Reservation in Holyoke, MA

Rumor has it that Mount Tom was the inspiration for literary legend and Springfield native Dr. Seuss’s Mount Crumpit. The reservation is not, it must be said, home to any grinches. It is home to more than 2,100 acres of natural beauty, however, which is better for everyone anyway.

Mount Tom

Looking out from the top of Mount Tom during autumn by Lynne Graves

How can you make the most of that natural beauty? Well, for starters, there’s a whole lot of room for walking and hiking, with 22 miles of trails. Lake Bray has fishing, while the children’s play area is suitable for young ones. Hawks and eagles also make it a habit to pass over the mountain, with countless birds passing through each year. Parking near Mount Tom runs $5 or $6, and D. Hotel & Suites in town is just a few minutes’ drive away.

With all the green space there is in western Mass, these five places offer only a sampling of the great outdoors. You can find much more here. And for a look at outside activities throughout all of Massachusetts, just click here.

Do you have a favorite scenic spot in western Massachusetts? Let us know below in the comments!

Photo at the top of Monument Mountain by Ogden Gigli

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  • John Rockwell

    My favorite is Chapel Ledge and Chapel Brook where you can hike or climb up to an amazing view, swim in a fresh spring creek, slide down one of a series of natural waterfalls and do some rock climbing! Beautiful place!

    • MassVacation

      Definitely, John. Thanks for adding that! Sorry for the delayed response.

    • Eric L’Esperance

      John, which areas can you slide down? This sounds really cool. Feel free to shoot me an email at ericccpaul@gmail.com

  • There are some
    beautiful places in Western Massachusetts to visit any time of year! They’re all
    a comfortable driving distance from Boston, too. Now that spring is here, it’s
    time to get out and enjoy the warm weather!

  • Great suggestions! Gunn Brook Falls is beautiful and seems like a nice visit for people looking for something a little off the beaten path. – Emme @ Green Global Travel

  • Alan George

    I highly recommend Williamstown and Mt. Greylock.

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