As someone who's spent 25 years writing about travel—and 10 of those living on the East Coast—I’ve wandered through the Berkshires more times than I can count. If you ever crave a place where rolling mountains meet art, culture, and incredible food, this is where I’d send you. You’ll get scenic views, charming historic towns, and a surprising number of things to do, no matter the season.
When I first discovered the Berkshires, I was living just a few hours away. You’ll find it tucked into the hills of Western Massachusetts, an easy getaway from New York City, Boston, or Albany. I always appreciated how close it was—and how quickly I could swap traffic for trees and galleries.
One of the things I love most? The variety. You might start your day exploring a museum, then head to a farm-to-table restaurant I still daydream about. If you're like me and need to stretch your legs, you’ll find trails, canopy tours, and biking routes that wind right into the hills. Come winter, I’ve skied here too—it’s a quiet gem for that.
Best Time to Visit
If you’re asking me, I’d say go between May and October. That’s when I find the region really shines. Fall foliage is something I’ve chased here more than once—absolutely worth it, but you’ll need to plan ahead. If you love winter, I’ve done romantic weekends here too, with snowy walks and cozy inns.
How to Get There
- By Car: I’ve always driven via the Massachusetts Turnpike (I-90). From Boston, it usually takes me 2.5 hours; from NYC, about 3.
- By Bus: If you’d rather not drive, you can take Peter Pan or Greyhound buses to towns like Pittsfield, Great Barrington, or Lenox. I’ve done it both ways, and each has its perks.
- By Train: You might like Amtrak’s Lake Shore Limited—it stops in Pittsfield and connects Boston and Albany. I’ve used it for relaxing, scenic trips.
Where to Stay
- Red Lion Inn in Stockbridge – I stayed here on my first trip, and I’ve returned more than once. You’ll love its old-world charm and the way it feels like stepping into a New England postcard.
Best Things to Do in the Berkshires
Monument Mountain Reservation
The remarkable view from the summit of Squaw Peak is what drew me to this area.
The reservation has several loop trails which will lead you to the 1,642-foot summit where you will be rewarded for your efforts by outstanding views of the Housatonic River Valley and the southern Berkshires.
None of the trails exceed three miles in length but all of them are quite steep and you need to be reasonably fit to cope with the 720-foot gain in elevation.
If this is your first time visiting, consider using the 1.5-mile Indian Mountain Trail (the least steep and most interesting trail). If you are very fit, the 0.8-mile Hickey Trail offers the most direct but steepest ascent. Monument Mountain is a Trustees of Reservations property.
Location:
Monument Mountain Reservation, Route 7, Great Barrington, MA (in the southern Berkshires)Cost:
$ – Free or low-cost with suggested donation or parking fee.Best time to visit:
- Spring and Fall – For cool temperatures and clear summit views, plus fall foliage in October.
- Summer – For shaded trails and a rewarding climb.
Local tips:
Wear sturdy footwear—the summit climb is steep and rocky. Arrive early on weekends to secure parking and beat the crowds to the peak.How to Get to Monument Mountain:
Located on Route 7 just north of Great Barrington. Parking is available at the base trailhead lot, and clear signage marks the trail options.Map & More Info:
Monument Mountain Reservation, Great Barrington, MAPhone: 413-298-3239
Hancock Shaker Village
The Hancock Shaker Village (established in 1783) gives you a rare glimpse into how the original Shaker immigrants went about their daily life.
Your day at the village will include visiting up to fifty room-setting exhibits which preserve and showcase much of the simple textiles, furniture and house-hold goods which were made by the early Shaker residents.
Your tour of the village will include a visit to the Round Stone Barn, the Farm and Gardens and talks about the innovation and simple Shaker life-style.
You can start your visit by viewing an orientation video and then explore at your own place using a Walking Tour Guide. Remember to pay a visit to their Farm-to-table restaurant and store before you leave.
Location:
Hancock Shaker Village, 34 Lebanon Mountain Rd, Hancock, MA (just west of Pittsfield in the Berkshires)Cost:
$$ – Museum admission includes access to all buildings and exhibits; additional cost for food and shop purchases.Best time to visit:
- Spring and summer – For full access to gardens, outdoor exhibits, and barnyard animals.
- Fall – For colorful foliage and seasonal programming.
Local tips:
Wear comfortable shoes—the grounds are large and mostly outdoors. Check the website for workshops and rotating exhibits for added value during your visit.How to Get to Hancock Shaker Village:
Located just off Route 20 and Route 41 outside Pittsfield. Free parking is available on-site, and signage directs visitors to the welcome center.Map & More Info:
Hancock Shaker Village, Hancock, MAPhone: 413-443-0188
Recommended Activities for Families
Berkshire Botanical Garden
The Berkshire Botanical Garden is one of my favorite trips, ideal for spending a few hours enjoying the year-round showcase of beautiful flowering plants and trees.
The garden was started back in 1934 and covers more than 15 acres you can walk through year-round. Some of the highlights your can explore include the Pond Garden, the Daylily Walk, the historic Herb Garden and the Children’s Discovery Garden.
There are three glass houses, an education center and several galleries. One of the best ways to explore the garden is to join a free guided tour at 11am daily from June to September.
Location:
Berkshire Botanical Garden, 5 West Stockbridge Rd, Stockbridge, MA (in the heart of the Berkshires)Cost:
$ – Modest entry fee, free for children under a certain age; guided tours included with admission.Best time to visit:
- Late spring through early fall – For full bloom displays and warm weather tours.
- Early summer – For peak color and guided tour availability.
Local tips:
Check the event calendar for seasonal festivals, plant sales, and workshops. Arrive early to enjoy cooler temperatures and fewer crowds.How to Get to Berkshire Botanical Garden:
Located just outside downtown Stockbridge on Route 102/West Stockbridge Road. Free parking is available on-site.Map & More Info:
Berkshire Botanical Garden, Stockbridge, MAPhone: 413-298-3926
Berkshire Museum
The Berkshire Museum has been stimulating the minds of thousands of adults and children for over 100 years and remains a fascinating attraction which I enjoyed exploring.
The main focus of the museum is to demonstrate the connections between science, history and the arts through its many permanent and temporary exhibitions.
Highlights of your visit to the museum will include the inter-active Curiosity Incubator and Lab 102, the Window on the World exhibition, the Aquarium and the Berkshire Backyard which features all the little critters to be found in the area.
The museum also hosts a full program of fun educational activities for children.
Location:
Berkshire Museum, 39 South Street (Route 7), Pittsfield, MA (in the heart of the Berkshires)Cost:
$ – Family-friendly admission rates; some special programs may require reservations or additional fees.Best time to visit:
- Year-round – The museum offers indoor exhibits and events ideal for all seasons, especially as a rainy day option.
Local tips:
Check the event calendar for themed weekends, rotating exhibits, and science demonstrations. Great stop before or after a visit to downtown Pittsfield restaurants or shops.How to Get to the Berkshire Museum:
Located directly on Route 7 in Pittsfield with on-site parking. Easy access from other Berkshire attractions like Tanglewood and Hancock Shaker Village.Map & More Info:
Berkshire Museum, Pittsfield, MAPhone: 413-443-7171
Attractions for Couples
Bousquet Ski Area
Bousquet Mountain Ski Area is a must-visit destination if you love winter.
The popular ski area includes a large variety of down-hill skiing or boarding slopes for all levels of expertise, including a couple of really tricky slopes for experts only.
Regardless of your skiing ability you will be able to find a ski program to suit you and the other members of your family.
Everything you need for some fun in the snow can be rented on site, either for a day or two or for the entire season.
If you enjoy snow tubing you can have hours of fun on the multi-lane 450 foot snow tubing hill which has a wonderful magic carpet which will effortlessly whisk you back up to the top for another ride.
Location:
Bousquet Ski Area, 101 Dan Fox Drive, Pittsfield, MA (centrally located in the Berkshires)Cost:
$$ – Lift tickets, rentals, and tubing are moderately priced; packages and seasonal passes are available for longer stays.Best time to visit:
- December through March – Prime ski and tubing season with full trail access and snowy fun.
Local tips:
Arrive early on weekends and holidays—tubing spots in particular can fill quickly. Check snow conditions online before heading out, and dress in warm layers for changing temps.How to Get to Bousquet Ski Area:
Just minutes from downtown Pittsfield and Route 7. Free on-site parking is available. Great stop on a winter Berkshires loop including nearby lodging and museums.Map & More Info:
Bousquet Ski Area, Pittsfield, MAPhone: 413-442-8316
Catamount Aerial Adventure Park
For a day of thrilling outdoor adventures you can make your way to the Catamount Aerial Adventure Park in South Egremont.
Provided you have a good head for heights you are in for an exhilarating aerial adventure which includes navigating the forest canopy on a series of 12 courses which have been set up between 170 aerial platforms, linked by a series of cables, ropes and zip-lines.
The course is suitable for the whole family (minimum age 7 years – 48 inches minimum height) and there are designated areas for beginners to find their feet.
As your confidence improves you can move to the more challenging courses which require greater balance and strength to navigate.
Location:
Catamount Aerial Adventure Park, State Highway 23, South Egremont, MA (near the MA/NY border in the southern Berkshires)Cost:
$$ – Rates vary by age and time on the course; group and family packages are available.Best time to visit:
- Late spring through early fall – For optimal weather and forest views. Weekdays offer fewer crowds.
Local tips:
Wear active clothing and closed-toe shoes. Book in advance during summer weekends and holidays. Don’t forget your GoPro if you want a treetop selfie!How to Get to Catamount Aerial Adventure Park:
Located right off State Highway 23 in South Egremont, MA. On-site parking available and easy access from Great Barrington or the NY border.Map & More Info:
Catamount Aerial Adventure Park, South Egremont, MAPhone: 518-325-3200
Catamount Ski Area
Perfect for families with differing levels of skiing prowess, Catamount Ski Area stands out as offering a very diverse network of skiing and boarding trails which vary from super easy to super steep and challenging.
Your kids can find their ski legs on the Snowsport Learning Area which is located close to the Base Lodge.
Your next stop will be the Meadows complex which offers a variety of relatively easy open slopes that will suit your kids. Experts and dare-devils can opt to take on the Upper and Lower Sidewinder Trails and the double-diamond Lynx and Catapult Trails.
Both private and group lessons are available to ensure you have the time of your life.
Location:
Catamount Ski Area, State Highway 23, South Egremont, MA (on the Massachusetts–New York border in the southern Berkshires)Cost:
$$ – Lift tickets and rentals are mid-range; season passes and lesson packages are available for frequent visitors.Best time to visit:
- December through March – Snow conditions are best during these core winter months.
Local tips:
Arrive early on weekends to avoid lift lines. The Base Lodge has a great view of beginner slopes—perfect for parents to watch while warming up with hot cocoa.How to Get to Catamount Ski Area:
Located directly on State Highway 23 in South Egremont, MA, just minutes from Great Barrington and the NY border. On-site parking is available and free.Map & More Info:
Catamount Ski Area, South Egremont, MAPhone: 518-325-3200
Must-see museums
Chesterwood Museum
Fabulous Chesterwood is a historic artist’s retreat which is essential viewing if you are an art lover.
Home to the famous American sculptor Daniel Chester French, whose imposing works are dotted all around the US and include the Abraham Lincoln sculpture at the Lincoln Memorial, the museum is still providing inspiration for modern-day artists.
You can tour the historic house, studio and gardens and admire hundreds of marble and bronze sculptures on display.
In addition, there are some hands-on activities for your kids, a museum shop and a beautiful woodland walk. The museum is open from May to October.
Location:
Chesterwood, 4 Williamsville Rd, Stockbridge, MA (in the scenic southern Berkshires)Cost:
$$ – Modest admission fee; discounts may be available for families, seniors, or students. Children’s programming often included.Best time to visit:
- May through October – Chesterwood is a seasonal attraction, open during warm weather months when gardens are in bloom.
Local tips:
Bring your camera—sunlight through the trees creates beautiful photo ops. Ask about artist talks or seasonal sculpture walks happening during your visit.How to Get to Chesterwood:
Located just a few minutes from downtown Stockbridge, off Route 102. Ample free parking is available on-site.Map & More Info:
Chesterwood, Stockbridge, MAPhone: 413-298-3579
The Clark Art Institute
Dedicated to furthering public understanding and appreciation of art, The Clark is a must-visit attraction to add to your Berkshire itinerary.
The Clark is the custodian of a very impressive permanent collection of European and American art which spans the period from the Renaissance to the early 20th century.
You will find a good representation of the works by the French Impressionists and several prominent American artists including John Singer Sergeant and Winslow Homer.
The best way to broaden your knowledge of the collection is to pick up a multi-media guide at reception and enjoy the experience at your own pace.
Check their website to see if your visit will coincide with one of their educational programs and workshops.
Cost:
$$ – General admission is reasonably priced; children and students may qualify for free entry. Outdoor grounds are often open to the public at no charge.Location:
The Clark Art Institute, 225 South Street, Williamstown, MA (in the northern Berkshires)Best time to visit:
- Year-round – Indoor galleries and events continue through all seasons, while spring through fall offer the best for enjoying the outdoor landscape and sculpture trail.
Local tips:
Visit midweek for a quieter experience. Check their calendar online for live music events, outdoor movie nights, or family programs during school breaks.How to Get to The Clark:
Located just south of downtown Williamstown, off Route 7. Free on-site parking and public transportation options available from regional hubs like Pittsfield and North Adams.Map & More Info:
The Clark Art Institute, Williamstown, MAPhone: 413-458-2303
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