15 Perfect Things to Do in the Berkshires: Explore the Best of Massachusetts

543

The Berkshires are a slice of New England magic that somehow feels like a well-kept secret—until now. Picture rolling hills dotted with vibrant forests, tucked-away museums, and charming towns where local history mixes effortlessly with nature’s beauty. The region has a vibe that’s equal parts relaxing and adventurous, from hiking the stunning peaks of Mount Greylock to savoring farm-to-table dishes at a countryside inn. Whether you’re chasing waterfalls, exploring cultural hotspots, or simply soaking in the scenery, there’s something uniquely enchanting about the Berkshires. Let’s dive into 15 perfect experiences that will make you fall in love with the Berkshires, MA.

Best Sights and Attractions in the Berkshires: Your Ultimate Guide to Western Massachusetts

Ready to explore the best of the Berkshires? From historic estates and world-class museums to scenic hikes and stunning mountain views, this region is packed with unforgettable experiences. Here are 12 must-visit places in the Berkshires, Western MA.

1. Tour Norman Rockwell’s studio in Stockbridge

The Norman Rockwell Museum in Stockbridge is a must-visit for art and history lovers. Home to the world’s largest collection of Rockwell’s original works, the museum features over 570 paintings and drawings, including The Problem We All Live With and the Four Freedoms series. Visitors can explore Rockwell’s artistic process through sketches, drafts, and rare memorabilia that offer insight into his impact on American culture. Seasonal exhibitions also highlight the works of other illustrators who shaped visual storytelling.

One of my favorite parts was stepping inside Rockwell’s preserved studio, which was moved to the museum’s grounds. His brushes, books, and unfinished sketches remain as he left them, offering a glimpse into his world. Walking through the museum feels like flipping through a visual history book of America. If you appreciate storytelling through art, this museum is one of the best places to visit in the Berkshires.

2. Zipline through the Berkshires at 60 MPH

If you’re craving a serious adrenaline rush with killer valley views, the zipline courses at Berkshire East deliver. This isn’t some tame backyard setup. You’re talking dual racing lines, speeds hitting 60 mph, and cables stretching up to 2,600 feet over the Deerfield River Valley. The Valley Jump Tour is the showstopper, with six lines that’ll have you screaming in a good way as you fly nearly 200 feet in the air.

First-timers or groups with mixed skill levels should go for the Mountain Top Tour instead. It’s still thrilling but less intense, with seven shorter lines perfect for easing into the whole zipline thing. Both tours start with a scenic chairlift ride to the summit, and the fall foliage season makes those views absolutely ridiculous.

After you’re done, swing by Crazy Horse Bar & Grill at the resort for a well-earned burger and beer.

3. Picnic on the lawn for a concert at Tanglewood

For an unforgettable night of live music, Tanglewood in Lenox is the place to be. As the summer home of the Boston Symphony Orchestra, it hosts concerts at the Koussevitzky Music Shed, Seiji Ozawa Hall, and the expansive lawn seating area. The venue attracts top-tier performers, from world-renowned classical musicians to contemporary artists like James Taylor and Yo-Yo Ma.

I attended a John Williams Film Night, where the orchestra played scores from Star Wars, Harry Potter, and Jurassic Park while the sun dipped behind the mountains. Spreading out a picnic blanket with local cheeses from Berkshire Mountain Bakery and a bottle of wine made the evening even better. Whether you prefer a formal pavilion seat or a relaxed outdoor experience, Tanglewood delivers an unmatched mix of nature and music, making it a Berkshires tradition you shouldn’t miss.

4. Hike Sages Ravine on the Appalachian Trail

The Appalachian Trail runs through the Berkshires, offering hikes that range from easy forest walks to challenging mountain climbs. One of the best routes is the Mount Greylock Summit Trail, a 3-mile trek leading to Massachusetts Veterans War Memorial Tower, where you can see Vermont and New York on a clear day. Another great option is the Tyringham Cobble Loop, a 2-mile hike with rolling meadows and panoramic views.

I hiked the Sages Ravine section near Sheffield, where waterfalls, wooden footbridges, and moss-covered boulders created a peaceful, storybook-like setting. The shaded trail kept it cool even in summer, and the sounds of rushing water made it an unforgettable escape. Whether you’re a seasoned backpacker or just want a refreshing nature walk, the Berkshires’ stretch of the Appalachian Trail has a route for every type of adventurer.

5. Hike Mount Greylock with a guide during fall foliage season

Want to see the Berkshires at peak fall color without dealing with crowded scenic drives? Book a private hike with Jeff on Mount Greylock, the highest peak in Massachusetts. This isn’t a big group tour where you’re stuck at the back straining to hear. It’s just you, your friends, and a knowledgeable local guide who tailors the route to match your fitness level.

The experience lasts one to two hours, and Jeff fills you in on everything from Greylock’s history to the abandoned ski area that used to operate here. He knows these trails inside out and makes the whole thing feel relaxed and conversational, not like a forced nature lecture.

Grab breakfast at Tunnel City Coffee in North Adams before heading to the trailhead. You’ll want fuel for those uphill stretches.

6. Walk the herb gardens at Berkshire Botanical Garden

Located in Stockbridge, the Berkshire Botanical Garden spans 15 acres and features over 3,000 species of plants across themed gardens. The Cottage Garden bursts with colorful perennials, while the Herb Garden showcases medicinal and culinary plants. Visitors can also explore the Woodland Garden, home to native ferns and wildflowers, and the Wetland Garden, which supports aquatic plants and wildlife. Seasonal events like the Harvest Festival and Plant Sale make each visit unique.

During my visit, I took part in a hands-on gardening workshop, where I learned about sustainable planting techniques and composting. Strolling through the gardens, I discovered plants I had never seen before and appreciated how thoughtfully each section was curated. This peaceful retreat offers a perfect blend of education and relaxation, making it a rewarding stop for plant enthusiasts and casual visitors alike.

7. Hike to Bash Bish Falls

The Bash Bish Falls Trail leads to Massachusetts’ tallest waterfall, a stunning 80-foot cascade that splits into twin streams before plunging into a rocky basin. The most popular way to reach the falls is via the 0.75-mile New York trailhead, a relatively easy path with scenic river views. For a more moderate challenge, the 1.5-mile Massachusetts trailhead offers a steeper ascent with rewarding overlooks.

When I hiked from the Taconic State Park entrance, the sound of rushing water grew louder with every step, building anticipation for the breathtaking view ahead. Arriving at the falls, I found a perfect rock to sit on and take in the refreshing mist. The sight of water tumbling down the rugged cliffs made it a spot I could’ve lingered at for hours. If you’re looking for a quick but scenic outdoor escape, Bash Bish Falls is a must-see in the Berkshires.

8. Pick dahlias and make a bouquet at a Great Barrington flower farm

I’ve done plenty of farm tours, but nothing quite like this dahlia harvesting experience at Pryjma Petals in Great Barrington. Luke and Britta start you off with homemade lemonade and local cheeses in their garden, then walk you through their growing process before turning you loose in the fields. You get to snip your own stems and build a custom bouquet with blooms in colors and sizes I’ve never seen at a regular florist.

The whole thing feels like visiting friends who happen to run an incredible flower farm. Their dog Walt made the rounds, and the hosts genuinely love talking about their work without making it feel like a lecture. It’s relaxed and perfect for groups or solo visitors.

Book early because this sells out during dahlia season. After, hit the art galleries along Railroad Street downtown.

9. See Sol LeWitt’s wall drawings at Mass MoCA

For contemporary art lovers, Mass MoCA (Massachusetts Museum of Contemporary Art) in North Adams is a must-visit. This massive museum, housed in a former factory complex, features large-scale installations, thought-provoking exhibits, and live performances. The museum’s Sol LeWitt retrospective, a collection of vibrant wall drawings spanning three floors, is a highlight, while rotating exhibits showcase works from cutting-edge artists worldwide.

I spent hours exploring immersive installations like James Turrell’s “Into the Light”, which plays with perception and color. The outdoor courtyard also hosts live concerts and art festivals, making each visit unique. After the museum, grabbing a bite at Bright Ideas Brewing, located on-site, is a great way to cap off the experience. With its mix of visual art, music, and community events, Mass MoCA is one of the most dynamic cultural spots in the Berkshires.

10. Climb Mount Greylock for views of three states

At 3,491 feet, Mount Greylock is the highest peak in Massachusetts and offers some of the best hiking in the Berkshires. The Cheshire Harbor Trail is a 6-mile round trip hike to the summit, while the Bellows Pipe Trail provides a shorter but steeper climb. For those who prefer a scenic drive, the Mount Greylock Auto Road leads to the top, where the Veterans War Memorial Tower stands as a tribute to fallen soldiers.

During my hike up the Hopper Trail, I encountered dense forests, babbling brooks, and occasional glimpses of the valley below. Reaching the summit, the Bascom Lodge offered a cozy spot to grab a snack and take in the 90-mile panoramic views. Whether you hike or drive, the top of Mount Greylock delivers an unforgettable vantage point of the Berkshires.

• Read Next: 8 Reasons to Visit the Berkshires in Fall

11. Ride the historic Hoosac Valley Train

Train enthusiasts and history buffs will love the Berkshire Scenic Railway Museum in Lenox, which offers a glimpse into the region’s rich railroad past. The museum, located at the historic Lenox Station, features vintage locomotives, restored passenger cars, and exhibits detailing the Berkshire Hills’ railway history. The main attraction, however, is the Hoosac Valley Train Ride, a scenic journey through the rolling countryside.

I hopped aboard the historic 1955 Budd RDC car for a leisurely ride along a picturesque route between Adams and North Adams. As the train chugged along, guides shared stories about the railroads’ role in shaping local industry and tourism. The experience transported me back in time, offering a nostalgic way to see the Berkshires. For a fun and educational outing, this museum is a must for visitors of all ages.

12. Kayak and fish on Pontoosuc Lake

For a peaceful retreat, Pontoosuc Lake in Pittsfield offers a mix of relaxation and outdoor adventure. The Pontoosuc Boat Ramp provides easy access for kayaking, paddleboarding, and motorboating, with rentals available at Onota Boat Livery. Fishing enthusiasts can cast a line for largemouth bass, northern pike, and rainbow trout, making it one of the best fishing spots in the Berkshires.

I spent an afternoon at Osceola Park, enjoying a lakeside picnic while watching sailboats drift by. Walking along the Causeway, I found a quiet bench perfect for soaking in the Berkshire Hills’ reflection on the water. The Proprietor’s Lodge, a lakeside restaurant, serves delicious seafood and cocktails with panoramic views of the lake. In winter, the frozen lake transforms into a hotspot for ice fishing and snowmobiling. No matter the season, Pontoosuc Lake is a perfect spot to unwind.

• Read Next: Ultimate New England Road Trip Itinerary

13. Catch a show at the Colonial Theatre

The Berkshire Theatre Group presents top-tier productions across two venues: the historic Colonial Theatre in Pittsfield and the intimate Unicorn Theatre in Stockbridge. The Colonial Theatre, a 1903 architectural gem, hosts Broadway-style productions, live concerts, and stand-up comedy, while the Unicorn Theatre features edgy plays and new works in a cozy setting.

During my visit, I saw “A Little Night Music” at The Colonial Theatre, where the gold-gilded ceiling, grand balconies, and vintage chandeliers made for an elegant experience. Before the show, I dined at District Kitchen & Bar, known for its grass-fed burgers and house-made pasta, then grabbed post-show cocktails at Methuselah Bar and Lounge. The theater group also offers behind-the-scenes tours, summer youth programs, and outdoor performances at The Fitzpatrick Main Stage. For theater lovers, the Berkshire Theatre Group delivers unforgettable live entertainment.

14. Walk the wetland trails at Canoe Meadows Wildlife Sanctuary

For a peaceful nature escape, Canoe Meadows Wildlife Sanctuary in Pittsfield offers three miles of scenic trails through forests, wetlands, and meadows along the Housatonic River. The Sacred Way Trail leads to a quiet marsh, where you can spot beavers, otters, and painted turtles. Birdwatchers will love the Canoe Meadows Overlook, a prime spot for observing blue herons, bald eagles, and red-tailed hawks.

I walked the Beaver Lodge Trail, which winds through woodlands and wildflower fields, making it a great spot for photography. Along the way, I saw monarch butterflies resting on milkweed and deer grazing near the pond. In winter, the trails transform into snowshoeing paths, offering a serene way to explore the sanctuary. Mass Audubon hosts guided bird walks and educational programs, making this a perfect stop for nature lovers seeking a quiet retreat in the Berkshires.

• Read Next: 15 Must-Visit Places in New England

15. View Renoir and Degas at The Clark Art Institute

The Clark Art Institute in Williamstown is a must-visit for art lovers, featuring European and American masterpieces alongside a 140-acre campus with scenic walking trails. The museum’s galleries house works by Renoir, Degas, Winslow Homer, and John Singer Sargent, while the Stone Hill Center offers rotating exhibitions with breathtaking views of the Berkshire countryside.

I spent time admiring Renoir’s “A Box at the Theater”, then took a stroll on the Fern Glen Trail, where sculptures blend seamlessly with nature. The Reflecting Pool area is a tranquil spot to unwind before grabbing a coffee at Cafe 7, the museum’s on-site café. Outdoor installations and summer concerts add to the experience, making The Clark more than just an art museum—it’s a cultural and natural retreat. For those who appreciate both art and the outdoors, this destination offers the perfect combination.