A Leaf Peeper’s Guide to the Berkshires: 20 Things to Do This Fall

When to Go, What to Do, & Where to See Peak Color

There’s a certain point every September when the Berkshires starts to feel different.

The mornings get a little cooler. The first leaves begin to turn bright hues along the mountain roads. Apples are ready for picking, local menus start making room for heartier fall dishes, and weekends fill up with harvest festivals, outdoor adventures, and the last of the season’s warm-weather events. Then, almost imperceptibly, the green gives way to red, orange, and gold.

If you’re planning a fall trip to the Berkshires, you may be wondering when to come, where to find the best foliage, and how to make the most of your time here. The short answer is: there isn’t one perfect weekend. Fall arrives gradually, moving through the region from the higher elevations and northern Berkshires toward the south. That means there’s plenty to do before the leaves reach their peak, and plenty of reasons to come back once they do.

Here are 20 ways to experience fall in the Berkshires, from classic foliage drives and mountain hikes to apple picking, seasonal dining, small-town wandering, and a few places you might not have heard of yet.

1. Take in the View from Atop Mount Greylock

At 3,491 feet, Mount Greylock is the highest point in Massachusetts, and the view from the top is worth the trip any time of year. In autumn, it’s something else entirely.

The seasonal road to the summit winds through Mount Greylock State Reservation, with plenty of opportunities to stop and take in the changing landscape. At the top, the Veterans War Memorial Tower offers sweeping views across the surrounding mountains and valleys.

If you’d rather earn the view, there are miles of hiking trails throughout the reservation.

2. Ride the Ashuwillticook Rail Trail

For a more active way to see the fall scenery, hop on the Ashuwillticook Rail Trail.

The 12-mile paved trail runs through Cheshire and alongside Cheshire Reservoir, with views of mountains, forests, water, and wildlife along the way. It’s an easy option for cyclists and walkers, and a particularly good choice for families who want to spend some time outside without tackling a strenuous mountain trail.

3. Go Apple Picking

Fall and apple picking go hand in hand, and the Berkshires has plenty of opportunities to enjoy the harvest.

Bartlett’s Orchard and Hilltop Orchards & Furnace Brook Winery are two local favorites for spending an afternoon among the apple trees. Pick your own apples, grab some cider, and, if you’re lucky, bring home a cider donut or two.

You don’t need peak foliage to make an orchard visit feel like fall. In fact, September is often the perfect time.

4. Head to the Lenox Apple Squeeze

The Lenox Apple Squeeze is a Berkshire fall tradition and a great excuse to make Lenox part of your September itinerary.

The annual celebration brings the community together for a weekend of food, entertainment, and plenty of autumn spirit. It’s the kind of event that makes you feel like fall has officially arrived.

5. Spend a Day Enjoying the Lee Founders Weekend

Lee Founders Weekend offers a chance to experience one of the Berkshires’ smaller communities through its history, local businesses, and community events.

Make a day of it. Wander through town, grab something to eat, browse the shops, and take your time. The Berkshires is made up of 32 towns, and some of the best experiences happen when you step away from the major attractions.

6. Join the Adams Ramble

Adams Ramble Weekend celebrates the outdoors and the community surrounding Mount Greylock. Attend RambleFest on Sunday, October 11, for music, local bites, and craft brews only found at this fall festival. Then on Monday, October 12, hike your way to the top of Mount Greylock along with thousands of other foliage admirers!

It’s a particularly good time to visit if you like to stay active while you travel. Spend the weekend hiking, biking, exploring the town, or simply enjoying the scenery before the leaves reach their peak.

7. Dive into Autumn Colors at the Berkshire Botanical Garden Harvest Fest

Celebrate fall at one of the Berkshires’ most beloved traditions! Every October, the Garden’s 24-acre grounds are transformed into a lively celebration of community, culture, the natural world, and the region’s agricultural heritage.

On the schedule: pony rides, hay maze and hay jump, hayrides, face painting, haunted house, petting zoo, square dancing, live music, food, shopping, and more!

8. Step Back in Time at Hancock Shaker Village

Autumn suits Hancock Shaker Village. The historic buildings, fields, gardens, and surrounding landscape take on a distinctly New England feel as the season changes. Walk through the village, learn about Shaker history and daily life, and take some time to simply enjoy the setting.

It’s a particularly good stop for families, especially when you want an experience that gets everyone outside while also offering plenty to explore. Stop in for a farm to table dining event or bring the family for the Country Fair on September 26-27! The 28th Annual Country Fair includes an antique car show, fine artisanship, live music, workshops, and more. Or don’t miss Pumpkin Extravaganza on October 17!

9. Spend an Afternoon at Naumkeag

Naumkeag is one of those places where it’s easy to lose track of time.

The historic property in Stockbridge is known for its gardens and distinctive landscape, and fall brings a completely different character to the grounds.

Visit in the afternoon, wander through the gardens, and then continue into Stockbridge for dinner or a walk through the village. During the fall season, the annual Incredible Pumpkin Show adds even more color to the experience.

10. Take a Ride on the Hoosac Valley Train

There’s something wonderfully old-fashioned about seeing the Berkshires from a train.

Hoosac Valley Train Rides in Adams offers seasonal rides through the northern Berkshires, giving you a chance to sit back and enjoy the landscape without worrying about the road.

It’s a fun option for families, but there’s plenty of appeal for adults who simply like a slower way of traveling.

11. Get Out on the Water

Foliage isn’t just something to see from the road.

Grab a kayak or canoe and experience it from the water. Stockbridge Bowl, Laurel Lake, Onota Lake, Pontoosuc Lake, Richmond Pond, Goose Pond, and Lake Buel all offer opportunities to enjoy the Berkshire landscape from a different perspective.

Need some inspiration on where to go? Check out BerkshiresOutside.org for ways to get outside and where to visit when you’re here!

12. Get Your Adrenaline Going

If your idea of a fall getaway involves more than a leisurely drive and a cup of cider, the Berkshires has you covered.

Jiminy Peak Mountain Resort, Catamount Mountain Resort, Berkshire East Mountain Resort, and Bousquet Mountain each offer ways to experience the mountains beyond hiking.

Depending on the resort and time of year, that might mean a scenic ride, ziplining, an aerial adventure, or another way to get above the trees and look out across the landscape.

13. See Something Completely Different at Natural Bridge State Park

Natural Bridge State Park in North Adams is one of the Berkshires’ more unusual landscapes.

The park is home to the remains of a natural marble bridge and an abandoned marble quarry, creating dramatic geological features you won’t find anywhere else in the region.

It’s a good choice when you’re looking for something a little off the beaten path.

14. Celebrate the Season at the Fall Foliage Parade

If you’re visiting on October 4, don’t miss the 70th Annual Fall Foliage Parade in North Adams! This time-honored tradition brings the community together for an unforgettable celebration featuring creative floats, imaginative costumes, marching bands, and memorable displays.

This year’s theme, 70 Years in Motion: Time-Traveling Through Northern Berkshire, celebrates the region’s rich past, vibrant present, and exciting future. Join the celebration and experience one of Northern Berkshire’s most beloved fall traditions!

15. Walk the Trails at Notchview

If you want to experience fall without a major attraction attached to it, head to Notchview in Windsor.

The property offers miles of trails through forests and open landscapes, making it a wonderful place for a quiet walk surrounded by changing leaves.

It’s also a good reminder that you don’t always need a famous viewpoint to find beautiful foliage in the Berkshires.

16. Eat Your Way Through Fall

Fall in the Berkshires isn’t just a visual experience. It’s a delicious one.

This is the time of year when local menus start leaning into apples, squash, mushrooms, root vegetables, maple, cider, and other seasonal ingredients.

For a meal in the northern Berkshires, try Casita, The Barn Kitchen and Bar, or Freight Yard Pub. In Pittsfield, Otto’s Kitchen & Comfort and Mazzeo’s are worth a look.

Further south, Mint Indian, Old Inn on the Green and Dream Away Lodge offer their own take on Berkshire dining.

For picnic supplies or local products to take along on a road trip, stop at Guido’s Fresh Marketplace or the Berkshire Food Co-op.

And if you see cider donuts, don’t overthink it. Get the cider donut! Hilltop Orchards, Whitney’s, and Bartlett’s are a few of our favorite spots.

17. Stay Somewhere With a View

One of the best parts of a fall trip is waking up and realizing the scenery is still right outside your door.

In the northern Berkshires, The Porches Inn at MASS MoCA, Blue Vista Motor Lodge, Hotel Downstreet, Hotel on North, and The Guest House at Field Farm offer a range of ways to stay in the area.

Further south, look to The Inn at Stockbridge, The Red Lion Inn, or Little Lion.

And for something truly memorable, check out the campgrounds in the Berkshires to sleep under the stars surrounded by foliage.

18. Take Your Time Strolling Downtown

It’s easy to spend an entire weekend rushing from attraction to attraction and miss one of the things that makes the Berkshires special.

Pick a town and wander.

Spend an afternoon in Williamstown or North Adams. Browse the shops in Lenox or Stockbridge. Explore Adams, Lee, Great Barrington, Sheffield, or West Stockbridge.

Stop for coffee. Find a bookstore. Browse a gallery. Sit down for lunch. Enjoy some unplanned time and wander!

19. Take the Long Way

The fastest route isn’t necessarily the best route in the Berkshires.

Try Route 2. The historic Mohawk Trail winds through the mountains between North Adams and Williamstown, with the famous Hairpin Turn providing one of the region’s most recognizable views. Stop there, take in the Hoosac Valley below, and then keep going. You’ll find plenty of reasons to pull over along the way.

Build in time to stop. The best foliage drives are often the ones where you don’t know exactly what you’ll find around the next corner.

20. Leave Some Room to Wander

Here’s our best advice for a Berkshire fall trip: don’t plan every minute.

Some of the best moments happen when you pull over because you see a view you weren’t expecting. Or when you find a farm stand, take a wrong turn, discover a trail, or decide to stay in town for another hour.

The Berkshires rewards curiosity. Come with a list, by all means. Just leave enough room to explore.

When Is Peak Fall Foliage in the Berkshires?

There isn’t a single day when the entire Berkshires turns peak color.

The region stretches from north to south and includes everything from river valleys to some of the highest elevations in Massachusetts, so foliage changes gradually throughout the season.

As a general guide, look for the first significant color in the northern Berkshires and higher elevations in late September. Early October is often a beautiful time to explore the northern and central Berkshires, while the southern Berkshires can continue showing strong color into mid- and late October.

Weather can shift the timing from year to year, so flexibility is important.

If your schedule allows, give yourself a few days rather than trying to hit one exact weekend. That way, you can follow the color.

Plan Your Fall Trip to the Berkshires

You don’t have to wait for peak foliage to experience fall in the Berkshires.

Come in September for apples, festivals, hiking, biking, and warm afternoons. Visit in early October as the northern and central Berkshires begin filling with color. Come later in the month to explore the southern Berkshires and enjoy the season at a slower pace.

Take a scenic drive. Find a trail. Order something with apples or cider. Spend an afternoon in a small town. Stay somewhere with a view.

And when you see a road that looks like it might lead somewhere beautiful, take it. That’s how you find fall in the Berkshires.