4 of the Best Things to Do in the Upper Housatonic Valley

Housatonic Valley The Housatonic Valley in the Berkshires is a truly enchanting region overflowing with rich culture, history, and natural beauty. If your travels bring you to the Berkshires, you won’t want to miss an opportunity to explore the Upper Housatonic Valley National Heritage Area. This organization is comprised of 20 Massachusetts towns, including our beloved Lenox, and introduces visitors to the land that made significant national contributions to this nation in terms of literacy, art, music, and architecture. Whether you’re a history buff or avid explorer, you’ll find plenty of things to do in Housatonic Valley!

Planning a visit to Housatonic Valley? Be sure to download your free copy of our Berkshires Vacation Guide for even more local activities and attractions you won’t want to miss!

Upper Housatonic Valley National Heritage Area’s Mission

The organization exists solely to illuminate the diverse identity of the Upper Housatonic River Valley region. With so much history, culture, and resources to preserve, they use the support of visitors like you to stimulate the region’s economic vitality and overall quality of life. It is their hope that the National Heritage Area will serve as a working catalyst for regional thinking by revealing the fascinating stories that this land has to tell.

4 Things To Do in the Upper Housatonic Valley

The valley is renowned for its scenic beauty and history in nature conservation following the era of industrialization and deforestation. As a result, there are plenty of ways to enjoy the great outdoors and delve into the region’s history! Here are just some visitor favorites that we’re sure you’ll love to try!

Paddling on the Housatonic River

From Pittsfield, MA all the way to Kent, CT, the Housatonic River majestically carves its way through the valley. This popular waterway also appeals to a wide variety of visitors with its gentle flat waters and the heady rush of world-class rapids. With the Berkshires Paddling Guide, you’ll successfully voyage down the river and discover quaint New England towns along the way.

If you’re in need of canoe or kayak rentals, you’ll find just what you need at the Arcadian Shop in Lenox. They’ll even deliver your boat to the Lenox boat ramp for you!

Hiking and Biking

The Housatonic Valley is ideal for bicycle riding and hiking, especially in the Berkshire County area. You’ll find the East Mountain State Forest in Great Barrington, MA in which you’ll find an abundance of scenic hiking trails. The Pittsfield State Forest is also close by, providing its visitors with over 30 miles of trails through quiet forest and azalea fields. If you’re more of a biker than a hiker, there are still plenty of opportunities for you! In fact, you’ll find 5 scenic bike routes in Berkshire county, including our favorite Lenox Bike Trail!

Bike rentals of all shapes and sizes are available at the Village Pike Shop in Adams! You’ll find it along the paved Ashuwilliticook Rail Trail that runs 10 miles north towards Lanesboro.

Experience the Arts Heritage Trail

If you’re interested in the cultural aspects of the Housatonic Valley, the Performing Arts Heritage Trail is worth the journey! This trail was created to for both visitors and locals alike to explore the cultural offerings of the region. Several of the country’s oldest and most highly-esteemed stages are included on the trail, many of which are also on the National Register of Historic Places. Begin your journey down the trail and prepare to be enthralled by some of the nation’s best entertainers.

Discover Fascinating Historic Sites

Touring the Housatonic Valley is a history lesson you won’t receive in a normal classroom. Many of these sites can be found right here in the momentous town of Lenox. Here are the museums and historic sites that we insist you see during your visit!

Experience Everything Housatonic Valley Has to Offer During Your Stay With Gateways Inn

Located in the heart of Lenox, MA, our elegant and timeless bed & breakfast is the perfect accommodation for all your Berkshires adventures. Unlike typical hotels, the inn surrounds our guests with historic ambiance infused with charm and hospitality. The 11 guestrooms exude the ultimate luxury and comfort with all the modern amenities you desire. You will also be just steps away from our award-winning restaurant and one of the most popular nighttime lounges in Lenox! Ready to experience the Housatonic Valley the best way? Book your favorite room with us today and we look forward to welcoming you to Lenox soon!

If you haven’t already, don’t forget to download your free copy of our Berkshires Vacation Guide! It’s filled with great recommendations for local dining, shopping, activities, and more!