Massachusetts

5 Favorite Outdoor Activities in the Berkshires

Blessed with an abundance of natural beauty, the Berkshires offer plenty of opportunities for outdoor adventure. Here are five favorites.

By Aimee Tucker|Aug 21 2017| Print icon

5 Favorite Outdoor Activities in the Berkshires

Stockbridge Bowl | 5 Favorite Outdoor Activities in the Berkshires

Credit: Aimee Tucker
Sponsored by The Red Lion Inn The cultural riches of Western Massachusetts’s Berkshire Hills region have long made it a favorite destination for visitors, but its scenic landscape provides ample opportunities for outdoor fun, too. Heading to the Berkshires for in search of fresh air and adventure? First, you’ll need a place to stay! There are many lodging options for visitors to the Berkshires, but the Red Lion Inn in Stockbridge is arguably the region’s oldest and most visited. Dating back to 1773, the sprawling Main Street staple is known for its historic character, on-site dining options, fitness room, year-round pool and hot tub, and seasonal charms such as the wicker-strewn front porch in the summer — the perfect place to relax after a long day of boating or hiking. For Berkshires-bound adventure seekers, here are five favorite outdoor activities to try.

5 FAVORITE OUTDOOR ACTIVITIES IN THE BERKSHIRES

STOCKBRIDGE BOWL

5 Favorite Outdoor Activities in the Berkshires

Stockbridge Bowl | 5 Favorite Outdoor Activities in the Berkshires

Credit: Aimee Tucker
Stockbridge Bowl | 5 Favorite Outdoor Activities in the Berkshires
Credit: Aimee Tucker Stockbridge Bowl (also known as Lake Mahkeenac) offers many kinds of aquatic fun in the Berkshires, including swimming, kayaking, paddleboarding, fishing, waterskiing, and canoeing. If you don’t have your own gear, the Arcadian Shop in Lenox offers kayak and paddleboard rentals, with convenient drop-offs and pick-ups daily from the boat launch in Stockbridge.

MONUMENT MOUNTAIN

5 Favorite Outdoor Activities in the Berkshires

Monument Mountain | 5 Favorite Outdoor Activities in the Berkshires

Credit: Aimee Tucker
Monument Mountain | 5 Favorite Outdoor Activities in the Berkshires
Credit: Aimee Tucker Located on Route 7 in Great Barrington, the 2.8-mile Monument Mountain hike is one of the most popular moderate hikes in the southern Berkshires. The rugged, steep trail rewards hikers with views of Beartown State Forest to the east and the Taconic Range to the west. Pay a nominal fee to park, then choose from two route options that traverse though lush forests and past rocky boulders to reach the top.
A #MyBerkshires backpack, courtesy of The Red Lion Inn, came stuffed with local goodies sustain us during our hike.

A #MyBerkshires backpack, courtesy of The Red Lion Inn, came stuffed with local goodies sustain us during our hike.

Credit: Aimee Tucker
A #MyBerkshires backpack, part of the The Red Lion Inn “Take a Hike” package, came stuffed with local goodies sustain us during our hike.
Credit: Aimee Tucker
5 Favorite Outdoor Activities in the Berkshires

All outdoor adventure requires a little planning, protection, and sustenance.

Credit: Aimee Tucker
All outdoor adventures require a little planning, protection, and sustenance. Inside our backpack were edible goodies and a signed copy of 50 Hikes in the Berkshire Hills by Lauren Stevens, which is also available in the Red Lion Inn gift shop.
Credit: Aimee Tucker Other favorite hikes and up-close nature experiences in the Berkshires include Mount Greylock in Lanesborough (you can even drive to the top, if you like), Bash Bish Falls and Mount Everett in Mount Washington, and foliage visits to October Mountain State Forest in Lee.

ASHUWILLTICOOK RAIL TRAIL

5 Favorite Outdoor Activities in the Berkshires

Ashuwillticook Rail Trail | 5 Favorite Outdoor Activities in the Berkshires

Credit: Wikimedia Commons
Ashuwillticook Rail Trail | 5 Favorite Outdoor Activities in the Berkshires
Credit: Wikimedia Commons
In the northern corner of the Berkshires, a former stretch of railroad track from Lanesborough to Adams is now the 11.2-mile Ashuwillticook Rail Trail, with views of the Hoosic River Valley, Cheshire Reservoir, and assorted wildlife. Open from dawn to dusk, the trail is great for walking, roller blading, cycling, and (in the winter) cross-country skiing and snowshoeing. Leashed pets welcome.

KRIPALU YOGA

5 Favorite Outdoor Activities in the Berkshires

Kripalu | 5 Favorite Outdoor Activities in the Berkshires

Credit: Aimee Tucker
Kripalu | 5 Favorite Outdoor Activities in the Berkshires
Credit: Aimee Tucker
Like your outdoors with a side of om? The Kripalu Center for Yoga & Health in Stockbridge is one of the largest residential facilities for holistic health and education in the country. While long-term guests attend programs and spiritual retreats, day passes are available for anyone who wants to take advantage of the center’s yoga, meditation, and mindful living and nutrition workshops. It also includes access to the center’s walking and hiking trails and beachfront. One of the most popular outdoor Kripalu events is the Saturday yoga class held in July and August on the lawn at Tanglewood during the Boston Symphony Orchestra’s morning rehearsal (grab a lawn pass at the Tanglewood main gate or join in for free if you have a rehearsal ticket). You’ve never experienced yoga like this before!

SERIOUS STROLLING

5 Favorite Outdoor Activities in the Berkshires

Berkshire Botanic Garden | 5 Favorite Outdoor Activities in the Berkshires

Credit: Aimee Tucker
Berkshire Botanical Garden | 5 Favorite Outdoor Activities in the Berkshires
Credit: Aimee Tucker
Prefer a gentler Berkshires outdoor adventure? You’re in luck. Along with the walking paths you’ll find in the region’s parks and natural areas, many of the wonderful museums and historic properties in the Berkshires include meandering routes and trails through landscaped gardens and past art installations. Some of my favorites include the Berkshire Botanical Garden, Edith Wharton’s The Mount, David Chester French’s Chesterwood, the country estate Naumkeag, and Hancock Shaker Village. These are just a few of the many wonderful outdoor adventures available in the beautiful Berkshires, and the perfect complement to a summer stay at the Red Lion Inn. What would you add to the list?

SEE MORE: 5 Reasons to Plan a Summer Weekend in the Berkshires

Aimee Tucker

Aimee Tucker is Yankee’s senior digital editor. A lifelong New Englander and Yankee contributor since 2010, Aimee has written columns devoted to history, foliage, retro food, and architecture, and regularly shares her experiences in New England travel, home, and gardening. Her most memorable Yankee experiences to date include meeting Stephen King, singing along to a James Taylor Fourth of July concert at Tanglewood, and taking to the skies in the Hood blimp for an open-air tour of the Massachusetts coastline.

More by Aimee Tucker

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  1. Great information. I have been to the berkshires many times and have not seen all of the recommended attractions. I plan on taking advantage of all that is available. Planning for this weekend.

    Reply

  2. This made me so home sick. I feel sorry for people who did not grow up in New England. Florida where I live is lovely and temperate but to walk in the Berkshires is worth the cooler fall(not sure about those winters though.

    Reply

    1. I am moving to the Berkshires from Florida in two weeks, can’t wait for the fresh cool mountain air 🙂 Autumn is definitely something I miss after living in the South for the past several years (and at least their winters aren’t as long and cold as where I grew up in Minnesota)!

      Reply

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