STAY at the RANCH

Jacquelyn
STAY at the RANCH

Culture & Arts

Tanglewood is one of the world's most beloved music festivals with an annual series showcasing classical, pop & contemporary artists & New England's premier concert with a picnic destination. Pack your favorite wine & beer, charcuterie snacks, chairs & blankets to enjoy the gorgeous estate views, renowned artists & your favorite company.
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Tanglewood
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Tanglewood is one of the world's most beloved music festivals with an annual series showcasing classical, pop & contemporary artists & New England's premier concert with a picnic destination. Pack your favorite wine & beer, charcuterie snacks, chairs & blankets to enjoy the gorgeous estate views, renowned artists & your favorite company.
The Massachusetts Museum of Contemporary Art in North Adams is internationally renowned for experiencing today's most evocative art from music to sculpture, dance, film, painting, photography, theater & works that altogether defy classification. Exhibits are everchanging to showcase from of world's most brilliant & innovative artists. On campus you'll find cafes, ice cream, local coffee & a microbrewery to satisfy any & all of your needs while touring the facilities.
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MASS MoCA
1040 Mass MoCA Way
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The Massachusetts Museum of Contemporary Art in North Adams is internationally renowned for experiencing today's most evocative art from music to sculpture, dance, film, painting, photography, theater & works that altogether defy classification. Exhibits are everchanging to showcase from of world's most brilliant & innovative artists. On campus you'll find cafes, ice cream, local coffee & a microbrewery to satisfy any & all of your needs while touring the facilities.
The Norman Rockwell Museum is dedicated to education & art appreciation inspired by the legacy of Norman Rockwell. The museum preserves, studies & communicates with a worldwide audience the life, art & spirit of Norman Rockwell & the field of illustration.
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Norman Rockwell Museum
9 Glendale Rd
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The Norman Rockwell Museum is dedicated to education & art appreciation inspired by the legacy of Norman Rockwell. The museum preserves, studies & communicates with a worldwide audience the life, art & spirit of Norman Rockwell & the field of illustration.
Shakespeare & Company aspires to create a theatre of unprecedented excellence rooted in the classical ideals of inquiry, balance, and harmony; a company that performs as the Elizabethans did. With a core of over 150 artists, the company performs Shakespeare, generating opportunities for collaboration between actors, directors, and designers of all races, nationalities, and backgrounds. Shakespeare & Company provides original, in-depth, classical training and performance methods. The company also develops and produces new plays of social and political significance.
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Shakespeare & Company
70 Kemble St
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Shakespeare & Company aspires to create a theatre of unprecedented excellence rooted in the classical ideals of inquiry, balance, and harmony; a company that performs as the Elizabethans did. With a core of over 150 artists, the company performs Shakespeare, generating opportunities for collaboration between actors, directors, and designers of all races, nationalities, and backgrounds. Shakespeare & Company provides original, in-depth, classical training and performance methods. The company also develops and produces new plays of social and political significance.
An independent movie theater with stadium heated reclining seating screening first-run films & offering beer & wine.
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Phoenix Theatres Beacon Cinema
57 North St
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An independent movie theater with stadium heated reclining seating screening first-run films & offering beer & wine.
A historic center for creative work that enriches, invigorates & transforms artists & audiences. Berkshire Theatre Group brings world-class theatre, legendary musicians, new works, famed artists & fun community events to the Berkshires year-round.
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Colonial Theatre
111 South St
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A historic center for creative work that enriches, invigorates & transforms artists & audiences. Berkshire Theatre Group brings world-class theatre, legendary musicians, new works, famed artists & fun community events to the Berkshires year-round.
The Sterling & Francine Clark Art Institute is one of the most beloved & respected art museums in the world, known for its intimate galleries & stunning natural environment. Continued additions to the collection & the institute's long history of collaborating with living artists & contemporary art historians ensures vibrancy & relevance in an ever-changing world.
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The Clark Art Institute
225 South St
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The Sterling & Francine Clark Art Institute is one of the most beloved & respected art museums in the world, known for its intimate galleries & stunning natural environment. Continued additions to the collection & the institute's long history of collaborating with living artists & contemporary art historians ensures vibrancy & relevance in an ever-changing world.

Outdoor Recreation

Pontoosuc lake is a lovely spot to picnic & swim with your family at one of the public beaches featuring sprawling views of the water. If you'd rather get out on the water, Berkshire U-Drive Boat rentals provides Pontoon boats for a day spent cruising & relaxing in the sun!
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Pontoosuc Lake
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Pontoosuc lake is a lovely spot to picnic & swim with your family at one of the public beaches featuring sprawling views of the water. If you'd rather get out on the water, Berkshire U-Drive Boat rentals provides Pontoon boats for a day spent cruising & relaxing in the sun!
Onota Lake is another beautiful recreational lake nestled in Pittsfield. Visit the public beach for swimming & picnicking with your family or get out on the water via Pontoon boat rental through Berkshire U-Drive Boat Rentals.
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Onota Lake
Lakeway Drive
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Onota Lake is another beautiful recreational lake nestled in Pittsfield. Visit the public beach for swimming & picnicking with your family or get out on the water via Pontoon boat rental through Berkshire U-Drive Boat Rentals.
Take in the panoramic views of the Housatonic River Valley from the 1,642 ft summit of Monument Mountain. The peak once drew the gaze of 19th century literary giants Nathaniel Hawthorne & Herman Melville spurning powerful discussion inspiring ideas featured in the work of Moby-Dick. The giant boulders, sheer cliffs & hidden caves will delight the adventure-seeker, but can also be appreciated from safe standpoints for the more conservative hiker. There are various paths, the most strenuous an 0.83 mi ascent directly to the summit.
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Monument Mountain Reservation
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Take in the panoramic views of the Housatonic River Valley from the 1,642 ft summit of Monument Mountain. The peak once drew the gaze of 19th century literary giants Nathaniel Hawthorne & Herman Melville spurning powerful discussion inspiring ideas featured in the work of Moby-Dick. The giant boulders, sheer cliffs & hidden caves will delight the adventure-seeker, but can also be appreciated from safe standpoints for the more conservative hiker. There are various paths, the most strenuous an 0.83 mi ascent directly to the summit.
Ramblewild's Tree-to-Tree adventure park is set on 10+ acres of pristine New England forest. The park is divided by a ravine that connects via a 200' high suspension bridge above the stream below. The obstacle course includes elements like high wires, zip lines, balancing logs, rope ladders, cargo nets, suspended bridges & more for those in search of a safe adrenaline rush.
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Ramblewild Adventure Park
110 Brodie Mountain Rd
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Ramblewild's Tree-to-Tree adventure park is set on 10+ acres of pristine New England forest. The park is divided by a ravine that connects via a 200' high suspension bridge above the stream below. The obstacle course includes elements like high wires, zip lines, balancing logs, rope ladders, cargo nets, suspended bridges & more for those in search of a safe adrenaline rush.
Bash Bish Falls is a great short hiking trail to the highest waterfall in MA dropping 80' into an emerald plunge pool. Visit to picnic, wade in the river, swim & camp.
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Bash Bish Falls State Park
Falls Road
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Bash Bish Falls is a great short hiking trail to the highest waterfall in MA dropping 80' into an emerald plunge pool. Visit to picnic, wade in the river, swim & camp.
This sprawling, 11,000-acre forest includes Berry Pond and 30 miles of trails. Whether hiking, mountain biking, horseback riding, or exploring the mountain range to Berry Pond, you're sure to find the perfect outdoor adventure.
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Pittsfield State Forest
1041 Cascade St
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This sprawling, 11,000-acre forest includes Berry Pond and 30 miles of trails. Whether hiking, mountain biking, horseback riding, or exploring the mountain range to Berry Pond, you're sure to find the perfect outdoor adventure.
A 15-acre botanical garden in Stockbridge, MA containing over 3,000 species with an emphasis on plants that thrive in the Berkshires. On-campus classes, workshops, lectures, exhibits & special events are offered year-round.
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Berkshire Botanical Garden
5 W Stockbridge Rd
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A 15-acre botanical garden in Stockbridge, MA containing over 3,000 species with an emphasis on plants that thrive in the Berkshires. On-campus classes, workshops, lectures, exhibits & special events are offered year-round.
Harry Desmond, owner, head guide & founder of Berkshire Rivers Fly Fishing. His & his guides' mission is to share their enthusiasm for the outdoors & fly fishing by guiding tours for locals & travelers. Fly fishing is an immersive, calming & fun activity for kids & adults alike!
Berkshire Rivers Fly Fishing
Harry Desmond, owner, head guide & founder of Berkshire Rivers Fly Fishing. His & his guides' mission is to share their enthusiasm for the outdoors & fly fishing by guiding tours for locals & travelers. Fly fishing is an immersive, calming & fun activity for kids & adults alike!
At 3,491 feet, Mount Greylock is the highest point in Massachusetts. From its peak on a clear day, you can see as far as 90 miles away. No matter when you visit, there's plenty to do & see. Drive up, hike around, picnic with panoramic mountain views around you.
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Mount Greylock State Reservation Visitor Center
30 Rockwell Rd
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At 3,491 feet, Mount Greylock is the highest point in Massachusetts. From its peak on a clear day, you can see as far as 90 miles away. No matter when you visit, there's plenty to do & see. Drive up, hike around, picnic with panoramic mountain views around you.
Enjoy a day out on Pontoosuc lake with friends & family renting a Pontoon through Berkshire U-Drive!
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Berkshire U-Drive Boat Rental
1651 North St
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Enjoy a day out on Pontoosuc lake with friends & family renting a Pontoon through Berkshire U-Drive!
Explore Onota lake by boat through Onota Boat Livery offering pontoon boats, small speed boat, fishing boats, canoes, kayaks, pedal boats & rowboats.
Onota Boat Livery
463 Pecks Rd
Explore Onota lake by boat through Onota Boat Livery offering pontoon boats, small speed boat, fishing boats, canoes, kayaks, pedal boats & rowboats.
Cinch 'em Up Stables offers guided single or group horseback trail rides & pony rides. Family owned & operated, the stable sits on 430 acres of open fields & wooded mountain trails with stunning views.
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Cinch 'em Up Stables Horseback Riding
365 NY-43
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Cinch 'em Up Stables offers guided single or group horseback trail rides & pony rides. Family owned & operated, the stable sits on 430 acres of open fields & wooded mountain trails with stunning views.
For over 15 yrs Worthington Ballooning has specialized in hot air balloon rides over the beautiful Berkshire Mountains of Western MA. Experience a fight over some of the most beautiful scenery in the country.
Worthington Ballooning
159 Buffington Hill Road
For over 15 yrs Worthington Ballooning has specialized in hot air balloon rides over the beautiful Berkshire Mountains of Western MA. Experience a fight over some of the most beautiful scenery in the country.
Shortest route to the top of Mt. Greylock, the state's highest peak. Whether you're looking for a steep meadow hike or black-diamond level back country skiing, it is not for the faint-hearted. You'll get a workout in rewarded with spectacular views at the summit ridge.
Thunderbolt Ski Trail
Thunderbolt Ski Trail
Shortest route to the top of Mt. Greylock, the state's highest peak. Whether you're looking for a steep meadow hike or black-diamond level back country skiing, it is not for the faint-hearted. You'll get a workout in rewarded with spectacular views at the summit ridge.

City/town information

Lenox is a cultural gem in the heart of the Berkshires. The small town is home to Tanglewood, Shakespeare & Company, Kripalu Center for Yoga & Health, Canyon Ranch Health & Wellness resort & Miraval Resort & Spa. Downtown is easy to walk with many boutiques & eateries. Visit one of the many historic estates such as Edith Warton's home- the Mount or Venfort Hall Mansion & Gilded Age Museum.
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Lenox
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Lenox is a cultural gem in the heart of the Berkshires. The small town is home to Tanglewood, Shakespeare & Company, Kripalu Center for Yoga & Health, Canyon Ranch Health & Wellness resort & Miraval Resort & Spa. Downtown is easy to walk with many boutiques & eateries. Visit one of the many historic estates such as Edith Warton's home- the Mount or Venfort Hall Mansion & Gilded Age Museum.
Surrounded by mountains, farmland & forest, picturesque Williamstown is known as "The Village Beautiful." Along with enjoying the area's natural beauty, check out fine art & performances at the town's esteemed institutions and festivals.
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Williamstown
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Surrounded by mountains, farmland & forest, picturesque Williamstown is known as "The Village Beautiful." Along with enjoying the area's natural beauty, check out fine art & performances at the town's esteemed institutions and festivals.
Southern Berkshire's largest town is one of natural beauty, cultural wealth and historical "firsts." Combined with its convenient location, fashionable shopping district, fine restaurants and recreational opportunities, Great Barrington is and has been a favorite holiday haven for more than 100 years. Great Barrington's vibrant downtown invites a stroll along its charming tree-lined avenues.
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Great Barrington
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Southern Berkshire's largest town is one of natural beauty, cultural wealth and historical "firsts." Combined with its convenient location, fashionable shopping district, fine restaurants and recreational opportunities, Great Barrington is and has been a favorite holiday haven for more than 100 years. Great Barrington's vibrant downtown invites a stroll along its charming tree-lined avenues.
Attend a new musical at Barrington Stage Company, enjoy national acts at the Colonial Theatre, discover new artists in downtown galleries & studios, celebrate at a summer festival, & explore the rich array of collections at the Berkshire Museum. Pittsfield is blessed with two beautiful lakes perfect for swimming & boating, the Pittsfield State Forest, the National Audubon Society's serene & accessible Canoe Meadows Wildlife Sanctuary, dozens of local parks, & a historic ski resort, all within city limits.
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Pittsfield
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Attend a new musical at Barrington Stage Company, enjoy national acts at the Colonial Theatre, discover new artists in downtown galleries & studios, celebrate at a summer festival, & explore the rich array of collections at the Berkshire Museum. Pittsfield is blessed with two beautiful lakes perfect for swimming & boating, the Pittsfield State Forest, the National Audubon Society's serene & accessible Canoe Meadows Wildlife Sanctuary, dozens of local parks, & a historic ski resort, all within city limits.
Steeped in art, culture, and community – what's happening in Massachusetts' smallest city may surprise you. North Adams is the Berkshire hub from which to delve into contemporary art, indie music, outdoor recreation, fine dining, independent retail, and antiques. It's a great place to live, work, and play!
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North Adams
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Steeped in art, culture, and community – what's happening in Massachusetts' smallest city may surprise you. North Adams is the Berkshire hub from which to delve into contemporary art, indie music, outdoor recreation, fine dining, independent retail, and antiques. It's a great place to live, work, and play!

Food scene

The signature restaurant of The Williams Inn, the Barn serves New England classics with an open mind & a fresh vision. The restaurant has been thoughtfully designed for those who crave a dining experience with seasonal & locally sourced ingredients inspiring a deeper connection with the community.
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The Barn Kitchen & Bar
103 Spring St
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The signature restaurant of The Williams Inn, the Barn serves New England classics with an open mind & a fresh vision. The restaurant has been thoughtfully designed for those who crave a dining experience with seasonal & locally sourced ingredients inspiring a deeper connection with the community.
District serves contemporary American cuisine with gastropub influences. The surrounding region boasts a rich food and agricultural culture of which the restaurant takes full advantage by offering an ever-changing seasonal menu showcasing locally sourced ingredients.
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District Kitchen & Bar
40 West St
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District serves contemporary American cuisine with gastropub influences. The surrounding region boasts a rich food and agricultural culture of which the restaurant takes full advantage by offering an ever-changing seasonal menu showcasing locally sourced ingredients.
Family-owned, festive, go-to for homestyle Mexican eats & margaritas.
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Coyote Flaco
505 Cold Spring Rd
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Family-owned, festive, go-to for homestyle Mexican eats & margaritas.
A small plates dining experience featuring artisanal & season ingredients & live music, celebrating the bounty of the Berkshires. Live music schedule & menu available online.
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Mission
438 North St
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A small plates dining experience featuring artisanal & season ingredients & live music, celebrating the bounty of the Berkshires. Live music schedule & menu available online.
One of Lenox's hidden gems is Chocolate Springs Cafe where you'll find the most pleasant baristas, excellent coffee, hot chocolate, gourmet European desserts, homemade gelato & cozy nooks to enjoy your treats!
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Chocolate Springs Cafe
55 Pittsfield Rd
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One of Lenox's hidden gems is Chocolate Springs Cafe where you'll find the most pleasant baristas, excellent coffee, hot chocolate, gourmet European desserts, homemade gelato & cozy nooks to enjoy your treats!
Berkshire Mountain Bakery Pizza Cafe features some of the best bread you will ever experience. In addition to their signature sourdough pizza crusts, they also feature spelt & wheat & have sandwiches & pastries galore. A local favorite worth stopping in to eat, or grab a take-&-bake pizza for later!
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Berkshire Mountain Bakery Pizza Cafe
180 Elm St
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Berkshire Mountain Bakery Pizza Cafe features some of the best bread you will ever experience. In addition to their signature sourdough pizza crusts, they also feature spelt & wheat & have sandwiches & pastries galore. A local favorite worth stopping in to eat, or grab a take-&-bake pizza for later!

Wineries/Breweries/Bars

A boutique winery focused on producing wicked, ultra-premium wines from grapes grown by world-class CA vineyards. Bring your own food anytime & check out their website for live music & food truck appearances. There's a large yard to spread out, play games & picnic with your kids, while great wine & beautiful surroundings!
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Balderdash Cellars
81 State Rd
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A boutique winery focused on producing wicked, ultra-premium wines from grapes grown by world-class CA vineyards. Bring your own food anytime & check out their website for live music & food truck appearances. There's a large yard to spread out, play games & picnic with your kids, while great wine & beautiful surroundings!
Shire Breu-Hous is a 7-barrel craft brewery, restaurant & taproom in Dalton, MA. We specialize in brewing quality craft beer, & also offer a delicious, beer-centric restaurant menu of scratch made foods.
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Shire Breu-Hous
63 Flansburg Ave
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Shire Breu-Hous is a 7-barrel craft brewery, restaurant & taproom in Dalton, MA. We specialize in brewing quality craft beer, & also offer a delicious, beer-centric restaurant menu of scratch made foods.
Down-to-earth bar featuring a rotating selection of craft brews on tap, plus a long whiskey list. Voted best bar in the Berkshires.
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Moe's Tavern
10 Railroad St
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Down-to-earth bar featuring a rotating selection of craft brews on tap, plus a long whiskey list. Voted best bar in the Berkshires.
A local production brewery dedicated to making beer and smiles, cheers!
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Big Elm Brewing
65 Silver St
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A local production brewery dedicated to making beer and smiles, cheers!

Health & Wellness

For more than 50 years Kripalu has been a leader in yoga & mindfulness-based education. More than just poses on a mat, we believe yoga is an accessible practice that inspires connection, compassion & joy.
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Kripalu Center For Yoga & Health
57 Interlaken Rd
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For more than 50 years Kripalu has been a leader in yoga & mindfulness-based education. More than just poses on a mat, we believe yoga is an accessible practice that inspires connection, compassion & joy.