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  • 36 acres of land with 2 hiking trails and an outdoor fire pit
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Stunning red and green foliage covers a hill with a pond in the foreground

Best Ways to See Fall Foliage in The Berkshires

The end of summer signals it’s time to find the best ways to see fall foliage in the Berkshires. We look forward to a new season filled with new adventures. While you may need to add a layer or two, autumn is meant to be celebrated outdoors. Pack your sweaters and boots and head to the rolling hills of the Berkshires for some fun fall adventures outdoors!

Summer’s brilliant greenery turns varying shades of crimson and gold, and the beautiful Berkshire countryside becomes Mother Nature’s artwork. The sublime natural beauty of the region draws visitors back year after year. What better way to experience the changing fall colors than with an autumn getaway?

Join us at the Devonfield Inn for some fun fall festivals and spend quality time with friends or family. Reconnect with nature and make lasting memories exploring this special corner of the country during one of the most beautiful times of the year. There’s an outdoor experience waiting for all types of leaf-peeping adventurers. So, let’s take a look at some of our favorite ways to take it all in.

Couple on a hike taking in the autumn views

On Foot

Hiking is a favorite amongst our guests. With endless trails in the area, ranging in length and difficulty, there’s one for every level of experience, guaranteeing a stunning view. Do you want something short and sweet with sweeping vistas? Head 20 minutes north to Lenox Mountain and the Mahanna Cobble summit. For something a bit more challenging, head south to Monument Mountain, a popular hiking spot in the area, and for good reason! With a 360-degree view at its peak, it’s the perfect place to get a bird’s-eye view of the fall foliage. Nearby Kennedy Park in Lenox is also a wonderful place to spend a few hours exploring the 15 miles of well-maintained tree-lined trails.

Cyclists biking through a forest in the fall

On a Mountain Bike

If exploring on two wheels is more your style, there are many options for mountain biking too. The trails at Kennedy Park welcome bikes, as does Pittsfield State Forest, with 11,000 acres of forested land and 30 miles of trails. With so many challenging routes for experienced bikers, it’s just a matter of choosing the one that speaks to you. They all offer stunning scenery and local attractions perfect for pit stops along the way.

Three girls horseback riding in the fall

On Horseback

For our equestrian enthusiasts, there are plenty of beautiful ways to see the leaves from the saddle. Discover Kennedy Park and Lenox Mountain on horseback with Berkshire Horseback Adventures. Or, book our By Land or Sea Outdoor Adventure Package and saddle up for a ride through lush forests.

Car on a scenic drive through fall foliage

On 4-Wheels

Perhaps the easiest way to get the best views and cover the most ground is with a scenic drive through the backroads of the Berkshires. With so many roads to choose from, you’ll find routes through small towns and villages, past cultural attractions like Jacob’s Pillow and Tanglewood, and near open fields and wetlands. Of course, a trip up Mount Greylock reveals a stunning view of our neighboring states, as well as the well-loved Mohawk Trail, are among our guests’ favorite drives.

While these are some of the best ways to see fall foliage in the Berkshires, be sure to ask us for more recommendations when you check into our charming bed and breakfast. A fall foliage trip should be on everyone’s bucket list, and the Berkshires delivers the ultimate in scenery. Combine your adventure with a luxurious stay at one of the top-rated inns in the region for an unforgettable experience.

Updated September 2023

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