Berkshires Massachusetts

Posted on October 17th, 2023 by Dan McCarthy

Events and Things to do in the Berkshires this Fall

The Berkshires is easily one of the most popular areas of Massachusetts. However, if you’re looking for a real treat for the senses, spend some time in the area when autumn settles in. Quaint New England towns like Lenox, Lee, and Stockbridge come alive with seasonal festivals, apple picking, and charming farm stands.

The crisp, cool air carries the promise of cozy evenings and crackling fireplaces, as well as the ever-present scent of spiked or spiced cider and hearty farm-to-table food. All this happens against the backdrop of one of nature’s most spectacular shows of fall foliage: the seasonal metamorphosis of the trees that hug the highland regions of the Berkshires. Check out this collection of things to do in the Berkshires in the fall.

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Things to Do in the Berkshires in the Fall

1. Take a hike to get the best peek at the Berkshires fall foliage

When it comes to the best fall hikes, Berkshires treks never disappoint. When you hit these trails in the fall, you’re in for a wholly different experience. The areas around the Berkshires are filled with awesome hikes, whether you’re looking for an easy trail with amazing views or something more of a challenge. A few good picks include:

  • Basin Pond Trail – A moderate 2.1-mile trail with shallow brooks, a lot of foliage, and just the right level of solitude
  • Felton Lake from Gorge Trail at October Mountain – A 1.8-mile loop that takes you to Fenton Lake and to a summit with amazing views
  • Olivia’s Lookout – A quarter-mile hike that grants you two awesome east-to-west views of the surrounding foliage in Lenox, Stockbridge, and Richmond
  • The Lee Chamber of Commerce offers an excellent list of hikes in and around the area listed from easy to difficult, many of which are perfect for leaf-peeping in the fall.

Berkshire Mountains Massachusetts in the Fall

2. Check out Shakespeare and Co in Lenox

Shakespeare and Co in Lenox is situated in one of the most picturesque places in the Berkshires and boasts multiple theaters, including a 500-seat amphitheater outdoors. Through the fall, the setting takes on a new level of inviting charm as the surrounding foliage transforms from green to gold, blazing orange, and red. And you can always catch a good show, whether you’re into true Shakespearian works or other more contemporary plays.

3. Catch the Naumkeag Pumpkin Festival in Stockbridge

Also known as the Naumkeag Pumpkin Show, this autumn celebration is one the locals look forward to every year. Naumkeag is a gorgeous estate that holds all kinds of New England charm. However, every autumn as Halloween draws near, the estate is decorated with hundreds of pumpkins, gourds, and jack-o-lanterns carved by local talents. Hot apple cider flows during the visit, as well as fall treats to nibble as you explore the impressive display.

The Incredible Naumkeag Pumpkin Show

4. Visit the Berkshire Botanical Garden’s Harvest Festival in Stockbridge

The Berkshire Botanical Garden hosts an annual Harvest Festival that’s been happening every year since the Garden itself was founded nearly 90 years ago. This iconic event takes place every October and boasts activities and entertainment that are enjoyable to people of all ages. Often sponsored by one or more local breweries, the Berkshire Botanical Fest has a full beer garden. Plus, the 24-acre area is completely transformed into a lively scene with numerous musicians, food vendors, and artisans peddling their wares.

5. Head to Hilltop Orchards and the Furnace Brook Winery in Richmond

Hilltop Orchards is one of the true gems of The Berkshires when it comes to wineries. However, when the apples ripen and the leaves start to turn, this place takes on new life. You still have access to all the awesome wine and house-made hard cider, but you can also take a hike through the orchards for some amazing views of the Berkshires fall foliage. You can also pick your own apples to take home or get your hands on fresh-made cider donuts.

Visit Your Friendly Neighborhood Dispensary in the Berkshires

Whether you’re just traveling through to get a peak at the leaves or you’re looking for a fun festival, stop in and examine the full bloom of flowers we’ve got at Canna Provisions. Our recreational dispensary in Lee is full of the best cannabis and cannabis products in the state. Take a few to explore our menu online before you arrive, order ahead, and we’ll have your order ready to go when you stop in.

Shop the Top Cannabis in The Berkshires




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