Backyard Road Trips

Fall Foliage & Family Hikes: Discovering Autumn in the Berkshires

Get ready to experience the beauty of autumn in the Berkshires! This region is known for its stunning fall foliage and family-friendly hiking trails, making it the perfect destination for a seasonal getaway.

fall tree Berkshires, MA
Autumn awaits in the Berkshires.

Best Time to Visit

Autumn is spectacular in the Berkshires.

The peak fall foliage season in the Berkshires typically occurs in early to mid-October. However, it can vary depending on the weather conditions. Check local foliage reports for the most up-to-date information.

Family-Friendly Hikes

Here are some of the best family-friendly hikes in the Berkshires:

Natural Bridge State Park
Exploring the Natural Bridge State Park in North Adams
  • Monument Mountain-Great Barrington: This moderate hike offers panoramic views of the surrounding countryside. 
  • Pleasant Valley Wildlife Sanctuary- Lenox: Explore trails through forests, meadows, and wetlands.
  • Ashuwillticook Rail Trail- Pittsfield to Adams: A paved, flat trail perfect for walking, biking, or pushing strollers.
  • Natural Bridge State Park- North Adams: Check out the awesome rock formations, including the natural white marble bridge

What to Do

Norman Rockwell Museum
Autumn’s in full view on the grounds of the Rockwell Museum
  • Norman Rockwell Museum: Be inspired by the artists’ collection of work and take a look into his studio, all located in a picturesque setting in Stockbridge.
  • Berkshire Botanical Garden: A worthy visit anytime of year with acres of flora, but it also plays host to a Harvest Festival annually in mid-October with activities for all ages, plenty to eat, and live entertainment.
  • Explore: Touristy towns such as Lenox and Stockbridge, but also wander off the beaten path to lesser-known locales, including Dalton and Adams
Berkshire Botanical Gardens
Enjoying the Berkshire Botanical Gardens’ Harvest Festival

Where To Stay

There are plenty of lodging options in the Berkshires, from chain hotels and Airbnbs to quaint inns and luxurious spas. Let’s take a look at two of my favorite inns, both of which are in Lenox. 

The Dewey in Lenox
  • The Dewey: Perched on a hill within walking distance to downtown, the Dewey is a perfect Lenox getaway. With impressive rooms and welcoming common areas, cozy up by the fireplace on a cold autumn evening.
  • Brook Farm Inn: This Victorian bed and breakfast is known for its historic charm and wonderful hospitality. Don’t miss breakfast in the morning! 
Brook Farm Inn in Lenox

For more Berkshire-area fun, check out the High and Mighty Connecticut Berkshires, better known as the Litchfield Hills, in this series of hikes.

Even on a rainy day, autumn is stunning.

Enjoy your autumn adventure in the Berkshires!

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