Need a scenic escape filled with art, culture, and nature? Head to the Berkshires! In this post, I’ll share the winding backroads, cultural gems, and mountain vistas I discovered in the Berkshires—where art, nature, and New England charm come beautifully together. Nestled in western Massachusetts, this picturesque region offers mountain views, historic towns, and year-round attractions—from hiking and skiing to world-class museums and music festivals.
When I like to visit
The best time to visit the Berkshires is late spring through fall (May to October). Enjoy lush hiking trails, vibrant fall foliage, and outdoor concerts. Winter is great too for skiing and cozy fireside retreats.
Tips for getting There
- By Car: The Berkshires are accessible via the Massachusetts Turnpike (I-90), about 2.5 hours from Boston and 3 hours from NYC.
- By Bus: Peter Pan and Greyhound buses serve major towns like Pittsfield, Great Barrington, and Lenox.
- By Train: Amtrak’s Lake Shore Limited stops in Pittsfield, offering service between Boston, Albany, and beyond.
Where I like to stay
- Red Lion Inn – Historic inn in Stockbridge with charming rooms and classic New England hospitality.
Top Attractions
1. Monument Mountain Reservation
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Location:
Monument Mountain Reservation, Route 7, Great Barrington, MA (in the southern Berkshires)Highlights:
Looking for a rewarding hike with breathtaking views? Monument Mountain offers short but steep trails to Squaw Peak, where panoramic vistas of the Housatonic River Valley await.Recommended For:
Day hikers, nature lovers, families, and travelers exploring the scenic Berkshires who want a memorable outdoor challenge without an all-day trek.What I Love: ♥
The summit view from Squaw Peak, literary history with ties to Nathaniel Hawthorne and Herman Melville, and well-marked loop trails that vary in difficulty and length.- Reach the 1,642-foot summit of Squaw Peak via loop trails that never exceed three miles but rise over 720 feet in elevation.
- Try the 1.5-mile Indian Mountain Trail for a scenic and beginner-friendly route that still delivers big views.
- Challenge yourself on the 0.8-mile Hickey Trail, the steepest and most direct ascent, ideal for experienced hikers.
- Enjoy a relatively short outing—perfect for a half-day excursion or a stop while road-tripping through the Berkshires.
- Support conservation by visiting a Trustees of Reservations property that helps protect local landscapes and history.
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
2. Hancock Shaker Village
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Location:
Hancock Shaker Village, 34 Lebanon Mountain Rd, Hancock, MA (just west of Pittsfield in the Berkshires)Highlights:
Step into a preserved slice of 18th-century life at Hancock Shaker Village, where history, innovation, and simplicity come together in one of New England’s most immersive living museums.Recommended For:
History enthusiasts, families, architecture lovers, and anyone curious about early American craftsmanship and communal living.What I Love: ♥
The iconic Round Stone Barn, peaceful gardens, hands-on exhibits, and the farm-to-table café that connects visitors to the land just like the Shakers did.- Experience up to fifty historic room exhibits filled with handmade Shaker furniture, textiles, and tools.
- Explore the Round Stone Barn, an architectural marvel and the centerpiece of this unique agricultural community.
- Stroll through the farm and gardens and learn about the Shakers' innovations in sustainability and agriculture.
- Start your visit with an orientation video and Walking Tour Guide to move through the village at your own pace.
- Eat and shop at the farm-to-table restaurant and village store, both offering local and handmade goods.
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
3. Berkshire Botanical Garden
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Location:
Berkshire Botanical Garden, 5 West Stockbridge Rd, Stockbridge, MA (in the heart of the Berkshires)Highlights:
Looking for a peaceful, colorful stroll through curated natural beauty? The Berkshire Botanical Garden is a 15-acre floral wonderland with seasonal charm, educational exhibits, and family-friendly spaces tucked into scenic Stockbridge.Recommended For:
Garden lovers, photographers, families, educators, and anyone seeking serenity and inspiration in the outdoors.What I Love: ♥
The variety of themed gardens, hands-on discovery areas, and thoughtful design that changes beautifully with the seasons.- Explore over 15 acres of garden displays, each designed with a different seasonal palette.
- Stroll through visitor favorites like the Pond Garden, Daylily Walk, historic Herb Garden, and the Children’s Discovery Garden.
- Visit three glass houses, indoor education centers, and galleries featuring horticultural exhibits and local art.
- Join a free guided tour at 11 AM daily from June through September for added insight and behind-the-scenes stories.
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
4. Berkshire Museum
© Berkshire Museum
Location:
Berkshire Museum, 39 South Street (Route 7), Pittsfield, MA (in the heart of the Berkshires)Highlights:
Want a place where science, art, and history come together under one roof? The Berkshire Museum offers an engaging, hands-on experience that blends culture and curiosity for visitors of all ages.Recommended For:
Families, museum lovers, curious kids, and anyone seeking an enriching indoor activity in the Berkshires.What I Love: ♥
The mix of aquariums, natural history, and interactive exhibits that make learning fun and immersive—especially for kids!- Discover over 100 years of regional heritage through exhibits that connect science, art, and history.
- Explore the interactive Curiosity Incubator and Lab 102 for hands-on learning and STEM engagement.
- Visit the Window on the World gallery, the Aquarium, and Berkshire Backyard, which features local wildlife and ecosystems.
- Enjoy year-round educational programs and activities for children, perfect for families and school groups.
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
5. Bousquet Ski Area
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Location:
Bousquet Ski Area, 101 Dan Fox Drive, Pittsfield, MA (centrally located in the Berkshires)Highlights:
Ready to hit the slopes without the big-mountain hassle? Bousquet Ski Area is a family-friendly ski resort with trails for every level, on-site rentals, and a snow tubing hill that’s just as fun as the skiing itself.Recommended For:
Families, beginner and intermediate skiers, snow tubing fans, and anyone looking for a relaxed yet exciting winter escape in western Massachusetts.What I Love: ♥
Affordable access to well-groomed trails, the ease of on-site rentals, and the 450-foot tubing hill that keeps the fun going even for non-skiers.- Ski on a variety of trails from beginner slopes to expert-only runs, ideal for all skill levels.
- Rent all your gear on-site—ski and snowboard equipment is available by the day, multi-day, or full season.
- Tube down the exciting 450-foot snow tubing hill with multiple lanes and a magic carpet lift to bring you back up with no effort.
- Relax between runs in the cozy lodge or grab a warm drink and meal at the on-site café.
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
6. Catamount Aerial Adventure Park
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Location:
Catamount Aerial Adventure Park, State Highway 23, South Egremont, MA (near the MA/NY border in the southern Berkshires)Highlights:
Looking to add a little adrenaline to your Berkshires escape? Catamount Aerial Adventure Park offers high-flying fun in the treetops, with ropes, platforms, and ziplines for all ages and skill levels.Recommended For:
Families with kids (7+), thrill-seekers, group outings, and outdoor enthusiasts who want an unforgettable canopy-level challenge.What I Love: ♥
The variety of 12 different aerial courses, the immersive forest setting, and the all-ages appeal that makes it a hit for both beginners and seasoned adventurers.- Climb through 12 unique aerial courses built into the forest canopy with 170 platforms linked by ropes, bridges, and ziplines.
- Challenge yourself with graded difficulty levels—perfect for kids, first-timers, and advanced climbers alike.
- Qualify with a minimum age of 7 years and height of 48 inches—great for families with adventurous children.
- Zip across select sections of the course for a high-speed, high-altitude thrill in a safe, guided environment.
Cost:
$$ – Rates vary by age and time on the course; group and family packages are available.Best time to visit:
- Late spring through early fall – For optimal weather and forest views. Weekdays offer fewer crowds.
Local tips:
Wear active clothing and closed-toe shoes. Book in advance during summer weekends and holidays. Don’t forget your GoPro if you want a treetop selfie!How to Get to Catamount Aerial Adventure Park:
Located right off State Highway 23 in South Egremont, MA. On-site parking available and easy access from Great Barrington or the NY border.Map & More Info:
Catamount Aerial Adventure Park, South Egremont, MAPhone: 518-325-3200
7. Catamount Ski Area
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Location:
Catamount Ski Area, State Highway 23, South Egremont, MA (on the Massachusetts–New York border in the southern Berkshires)Highlights:
Searching for a ski destination that caters to all skill levels? Catamount Ski Area is a welcoming and well-rounded resort with wide beginner trails, family zones, and steep expert terrain for thrill-seekers—all in a beautiful mountain setting.Recommended For:
Families, beginners, intermediate and expert skiers and snowboarders, winter weekenders, and anyone seeking variety on the slopes without the big-mountain crowds.What I Love: ♥
From learning zones and gentle runs to double black diamonds and terrain parks, Catamount delivers a personalized ski day for every type of rider.- Start in the Snowsport Learning Area, a beginner-friendly space located conveniently near the Base Lodge—ideal for kids and first-timers.
- Progress to the Meadows Complex for open, rolling slopes that help build confidence and control.
- Shred the Upper and Lower Sidewinder Trails for intermediate fun, or challenge yourself on double-diamond Lynx and Catapult for a high-speed, advanced ride.
- Improve your skills with group or private lessons offered daily for both skiing and snowboarding.
Cost:
$$ – 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
8. Chesterwood Museum
© Chesterwood Museum
Location:
Chesterwood, 4 Williamsville Rd, Stockbridge, MA (in the scenic southern Berkshires)Highlights:
Love art, sculpture, and historic homes? Chesterwood, once the summer home of Lincoln Memorial sculptor Daniel Chester French, offers an inspiring blend of history, creativity, and outdoor beauty.Recommended For:
Art lovers, families, history buffs, garden enthusiasts, and anyone looking for a peaceful cultural escape in the Berkshires.What I Love: ♥
The combination of sculpture-filled gardens, the artist’s original studio, and modern exhibitions that keep French’s legacy alive for new generations.- Tour the historic house and studio of Daniel Chester French, creator of the Lincoln Memorial sculpture.
- Wander through formal gardens and forested paths filled with marble and bronze works by French and contemporary artists.
- Engage with rotating art exhibitions that connect the past and present, highlighting new talent and historic creativity.
- Bring the family—there are hands-on art activities designed for children and creative young visitors.
- Shop and stroll—visit the museum store and enjoy a woodland walk through this peaceful artist’s retreat.
Cost:
$$ – Modest admission fee; discounts may be available for families, seniors, or students. Children’s programming often included.Best time to visit:
- May through October – Chesterwood is a seasonal attraction, open during warm weather months when gardens are in bloom.
Local tips:
Bring your camera—sunlight through the trees creates beautiful photo ops. Ask about artist talks or seasonal sculpture walks happening during your visit.How to Get to Chesterwood:
Located just a few minutes from downtown Stockbridge, off Route 102. Ample free parking is available on-site.Map & More Info:
Chesterwood, Stockbridge, MAPhone: 413-298-3579
9. The Clark Art Institute
© The Clark Art Institute
Location:
The Clark Art Institute, 225 South Street, Williamstown, MA (in the northern Berkshires)Highlights:
If you’re looking for world-class art in a peaceful New England setting, The Clark Art Institute blends fine art, stunning architecture, and natural beauty into a must-see cultural experience.Recommended For:
Art lovers, museumgoers, scholars, families, and anyone seeking inspiration among masterpieces by renowned European and American artists.What I Love: ♥
The incredible collection of French Impressionists, the rolling hills surrounding the campus, and the smart, accessible layout that makes the art feel personal and engaging.- Admire masterpieces by Monet, Degas, Renoir, John Singer Sargent, Winslow Homer, and other celebrated artists in the permanent collection.
- Explore art history from the Renaissance to the early 20th century through thoughtful exhibitions and installations.
- Enhance your visit with a free multi-media guide to learn more about the works at your own pace.
- Engage with workshops, lectures, family programs, and rotating special exhibitions offered year-round.
- Experience art inside and out—picnic on the pastoral grounds or enjoy a stroll along trails connected to the museum campus.
Cost:
$$ – General admission is reasonably priced; children and students may qualify for free entry. Outdoor grounds are often open to the public at no charge.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
Attractions for First Time Visitors
- Tanglewood – Summer home of the Boston Symphony Orchestra, hosting world-class concerts in an idyllic outdoor setting.
- The Mount – Edith Wharton’s estate and gardens, offering tours and literary events.
- Mass MoCA – One of the largest centers for contemporary art in the U.S., located in a converted factory complex.
- Norman Rockwell Museum – Celebrates the iconic illustrator’s work with galleries and scenic grounds.
- Bash Bish Falls – A stunning waterfall hike located near the New York border.
Where I Like to Eat
- Nudel Restaurant – Creative farm-to-table fare in the heart of Lenox.
- Mezze Bistro + Bar – Upscale dining in Williamstown featuring local ingredients and seasonal menus.
- Six Depot Café – Coffeehouse and café in a restored train station in West Stockbridge, known for artisan drinks and fresh bites.
Local Events
- Tanglewood Music Festival (Summer) – A must for classical music fans, with performances under the stars.
- Berkshire International Film Festival (June) – Screenings and discussions with filmmakers in Great Barrington and Pittsfield.
- Fall Foliage Festival (October) – Parades, craft fairs, and leaf-peeping celebrations across the region.
Day Trips Within 30 Minutes of the Berkshires, Massachusetts
- Lenox (0–10 min) – Known for Tanglewood, upscale dining, and a refined small-town atmosphere.
- Stockbridge (5–15 min) – Classic New England charm with historic inns, shops, and the Norman Rockwell Museum.
- Great Barrington (10–15 min) – A vibrant artsy town with eclectic shops, eateries, and a walkable downtown.
- Lee (10–15 min) – Home to outlet shopping, quaint streets, and access to nearby trails and parks.
- Pittsfield (10–20 min) – The Berkshires' largest town with theaters, museums, and urban amenities.
- Becket (20–25 min) – A quiet rural escape with access to forest trails, lakes, and summer camps.
- West Stockbridge (10–15 min) – Small but artsy, with galleries, antique shops, and cozy cafés.
- Sheffield (20–25 min) – A peaceful farming town with antique barns, museums, and countryside charm.
- Richmond (10–15 min) – A quiet town nestled in hills, perfect for scenic drives and backroad exploring.
- Tyringham (15–20 min) – A hidden gem with pastoral beauty and the Appalachian Trail winding through.
- Housatonic (10–15 min) – A small mill village within Great Barrington known for its local art scene.
- Monterey (20–25 min) – Serene lakes, forest trails, and charming rural roads perfect for a quiet getaway.
- North Adams (25–30 min) – Home to MASS MoCA and a growing creative community in an old mill town setting.
Plan Your Trip