7 Things to Do in the Berkshires This Fall 🍂

Fall in the Berkshires is pretty hard to beat.

We're talking colorful mountain views, winding back roads, cozy little towns, apple cider donuts, and plenty of excuses to throw on a flannel and spend the day outside.

Whether you're planning a weekend getaway or just passing through western Massachusetts, here are seven ways to make the most of fall in the Berkshires.

1. Take in the Views at Mount Greylock 🌲

If you're looking for incredible fall foliage, Mount Greylock is a must-see. As the highest point in Massachusetts, it offers beautiful mountain views and plenty of hiking trails for anyone looking to get outside.

Not feeling an uphill adventure? You can also drive toward the summit when the seasonal roads are open.

2. Wander Through Stockbridge

Stockbridge is one of those classic New England towns that feels especially charming in the fall.

Spend the afternoon wandering around, browsing local shops, grabbing a coffee, or visiting the Norman Rockwell Museum. No big itinerary necessary.

3. Take a Scenic Drive Along the Mohawk Trail 🚗

Sometimes the best fall activity is simply getting in the car and seeing where the road takes you.

The Mohawk Trail is known for its winding roads, mountain scenery, and beautiful foliage. Bring a coffee, put on a good playlist, and don't forget to stop for the views.

4. Get Outside on the Ashuwillticook Rail Trail

If you're looking for something a little more relaxed than a mountain hike, the Ashuwillticook Rail Trail is a great option.

This paved trail winds through beautiful Berkshire scenery, making it perfect for a fall walk or bike ride.

Bonus points if you bring a warm drink.

5. Find an Apple Cider Donut (Or Three) 🍎

Is it really a New England fall weekend without apple cider donuts?

Stop by a local orchard or farm stand for fresh apples, cider, pumpkins, and whatever baked goods happen to catch your eye.

We're firm believers that snacks are an essential part of any outdoor adventure.

6. Explore Shops in Lee

After a morning of hiking or leaf peeping, head to Lee for a little shopping.

Grab a bite to eat, and check out the Lee Premium Outlets.

And while you're there, stop by Rise & Pine Candles & Gifts! We're a small, independently owned shop filled with hand-poured candles, outdoorsy gifts, apparel, and plenty of things you probably didn't know you needed.

Our candles are inspired by everything we love about the outdoors, from hiking through the woods to getting cozy around a bonfire.

Find us at Lee Premium Outlets, 17 Premium Outlets Boulevard, Lee, MA.

7. Spend a Rainy Afternoon Exploring Art

Not every fall day is sunny, and that's okay.

The Berkshires have some incredible museums, including MASS MoCA in North Adams and the Norman Rockwell Museum in Stockbridge.

They're perfect for slowing down and exploring something new when the weather isn't cooperating.

Make a Weekend of It 🍁

The best thing about fall in the Berkshires? You don't need an elaborate plan to enjoy it.

Take a hike, find a scenic road, explore a little town, eat something delicious, and enjoy being outside before winter rolls around.

And if you want to bring a little of that Berkshire fall feeling home, we'd love to see you at Rise & Pine.

Find us at Lee Premium Outlets, 17 Premium Outlets Boulevard, Lee, MA.