Cynthia's Guidebook
Outdoor Activities
The Ashuwillticook Rail Trail is an old railroad track converted into a 10-foot wide paved trail. The trail runs 12.7 miles through the towns of Cheshire, Lanesborough and Adams. Cheshire Reservoir, and the Hoosic River offer outstanding views of the scenery and wildlife. Parking lots and restrooms are available at selected locations along the way.
https://www.mass.gov/locations/ashuwillticook-rail-trail
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Ashuwillticook Rail Trail
Rail TrailThe Ashuwillticook Rail Trail is an old railroad track converted into a 10-foot wide paved trail. The trail runs 12.7 miles through the towns of Cheshire, Lanesborough and Adams. Cheshire Reservoir, and the Hoosic River offer outstanding views of the scenery and wildlife. Parking lots and restrooms are available at selected locations along the way.
https://www.mass.gov/locations/ashuwillticook-rail-trail
Four Generations of the Bartlett family have been growing, packing and shipping apples for 71 years. Their fine trees produce an average crop of 11,000 bushels of apples every year on 24 acres of choice apple growing land on Lenox Mountain in rural Massachusetts.
https://www.bartlettsorchard.com
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Bartlett's Orchard
575 Swamp RdFour Generations of the Bartlett family have been growing, packing and shipping apples for 71 years. Their fine trees produce an average crop of 11,000 bushels of apples every year on 24 acres of choice apple growing land on Lenox Mountain in rural Massachusetts.
https://www.bartlettsorchard.com
The Driving Range is a 300+ yard, uphill driving range. It is very spacious to challenge you with aiming your shots. They have five target greens and a target net and offer a sand trap and putting green.
They have an 18 hole Miniature Golf Course. The course opened in 1943, but has seen some changes over the years. It was rebuilt in 1968 and 1993.
http://www.bakersgolfcenter.com/
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Baker's Golf Center
633 S Main StThe Driving Range is a 300+ yard, uphill driving range. It is very spacious to challenge you with aiming your shots. They have five target greens and a target net and offer a sand trap and putting green.
They have an 18 hole Miniature Golf Course. The course opened in 1943, but has seen some changes over the years. It was rebuilt in 1968 and 1993.
http://www.bakersgolfcenter.com/
Bousquet Ski Area is a 200-acre ski area in Pittsfield, MA, nestled within the Berkshires cultural region. The resort features a vertical drop of 750 feet, twenty-four trails, two lifts, two magic carpets, one terrain park, and 85% snow-making coverage. Bousquet has a rich background of ski area history becoming one of the first ski areas in America to host snowmaking abilities as well as night time skiing with our early partnership with General Electric.
https://bousquetmountain.com
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Bousquet Ski Area
101 Dan Fox DrBousquet Ski Area is a 200-acre ski area in Pittsfield, MA, nestled within the Berkshires cultural region. The resort features a vertical drop of 750 feet, twenty-four trails, two lifts, two magic carpets, one terrain park, and 85% snow-making coverage. Bousquet has a rich background of ski area history becoming one of the first ski areas in America to host snowmaking abilities as well as night time skiing with our early partnership with General Electric.
https://bousquetmountain.com
http://www.cinchemupstables.com/
Enjoy some fun family time at Cinch ‘em Up Stables. They offer 1 hour and ½ hour horseback and pony trail rides. The stable sits on 430 acres of open fields and wooded mountain trails, with the Kinderhook Creek flowing through the entire property. Experience the beautiful scenery and native wildlife on horseback!
Reservations are recommended.
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Cinch 'em Up Stables Horseback Riding
365 NY-43http://www.cinchemupstables.com/
Enjoy some fun family time at Cinch ‘em Up Stables. They offer 1 hour and ½ hour horseback and pony trail rides. The stable sits on 430 acres of open fields and wooded mountain trails, with the Kinderhook Creek flowing through the entire property. Experience the beautiful scenery and native wildlife on horseback!
Reservations are recommended.
www.iokavalleyfarm.com
Ioka Valley Farm is home to natural, hormone free beef, perfect pumpkins & squash, fragrant, real Christmas trees, contented farm animals, pure maple syrup, and specialty maple products. Ioka Valley Farm is a diversified, family owned and operated working farm dedicated to providing high quality locally grown products as well as enjoyment for all ages. Open seasonally, so please call ahead for hours & activities.
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Ioka Valley Farm
3475 Hancock Roadwww.iokavalleyfarm.com
Ioka Valley Farm is home to natural, hormone free beef, perfect pumpkins & squash, fragrant, real Christmas trees, contented farm animals, pure maple syrup, and specialty maple products. Ioka Valley Farm is a diversified, family owned and operated working farm dedicated to providing high quality locally grown products as well as enjoyment for all ages. Open seasonally, so please call ahead for hours & activities.
Nestled at the foothills of the Berkshires and on the border of upstate New York, Hilltop Orchards is a 187-acre working farm with an orchard-to-can cidery, winery and tasting room. They’re proud to sustainably grow many apple varieties and other fruits at the orchard. Some of their apples are heirloom apples with century-old trees that date back to the start of the orchard. They turn them into amazing apple and fruit products with complete quality control on-site.
https://www.hilltoporchards.com
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Hilltop Orchards Home of Furnace Brook Winery
508 Canaan RdNestled at the foothills of the Berkshires and on the border of upstate New York, Hilltop Orchards is a 187-acre working farm with an orchard-to-can cidery, winery and tasting room. They’re proud to sustainably grow many apple varieties and other fruits at the orchard. Some of their apples are heirloom apples with century-old trees that date back to the start of the orchard. They turn them into amazing apple and fruit products with complete quality control on-site.
https://www.hilltoporchards.com
Jiminy Peak Mountain Resort is the largest ski and snowboard resort in southern New England, summer home to Mountain Adventure Park and the only mountain resort in North America to generate its own energy using alternative wind power.
https://www.jiminypeak.com
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Jiminy Peak
37 Corey RdJiminy Peak Mountain Resort is the largest ski and snowboard resort in southern New England, summer home to Mountain Adventure Park and the only mountain resort in North America to generate its own energy using alternative wind power.
https://www.jiminypeak.com
Town-owned & maintained hardwood forest with old carriage roads & nearly 15 miles of groomed trails. Ideal for hiking, picnics, & X-country skiing.
https://lenox.org/kennedy-park/
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Kennedy Park
275 Main StTown-owned & maintained hardwood forest with old carriage roads & nearly 15 miles of groomed trails. Ideal for hiking, picnics, & X-country skiing.
https://lenox.org/kennedy-park/
For almost two centuries, Monument Mountain has been a source of inspiration to poets, novelists, and painters. On August 5, 1850, Nathaniel Hawthorne and Herman Melville enjoyed a well-chronicled picnic hike up Monument Mountain. It was their first meeting, and, when a thunderstorm forced them to seek refuge in a cave, their lengthy and vigorous discussion inspired powerful ideas for Melville’s new book, Moby-Dick, which he dedicated to Hawthorne. Today, more than 20,000 hikers explore these pale boulders, cliffs, and ledges every year.
https://thetrustees.org/place/monument-mountain/
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Monument Mountain Reservation
For almost two centuries, Monument Mountain has been a source of inspiration to poets, novelists, and painters. On August 5, 1850, Nathaniel Hawthorne and Herman Melville enjoyed a well-chronicled picnic hike up Monument Mountain. It was their first meeting, and, when a thunderstorm forced them to seek refuge in a cave, their lengthy and vigorous discussion inspired powerful ideas for Melville’s new book, Moby-Dick, which he dedicated to Hawthorne. Today, more than 20,000 hikers explore these pale boulders, cliffs, and ledges every year.
https://thetrustees.org/place/monument-mountain/
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 and see.
Hiking: The trails at Mount Greylock Reservation vary in difficulty from casual to extremely difficult. Examine the trail map to see which is right for you.
Snowmobiling: During the winter months, ride snow-covered trails to the summit.
Restrooms Available (Visitor Center Restrooms OPEN 9am-4pm)
https://www.mass.gov/locations/mount-greylock-state-reservation
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Mount Greylock
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 and see.
Hiking: The trails at Mount Greylock Reservation vary in difficulty from casual to extremely difficult. Examine the trail map to see which is right for you.
Snowmobiling: During the winter months, ride snow-covered trails to the summit.
Restrooms Available (Visitor Center Restrooms OPEN 9am-4pm)
https://www.mass.gov/locations/mount-greylock-state-reservation
Ramblewild is Feronia Forests’ first tree-to-tree adventure destination.
I highly recommend this!
https://ramblewild.com/
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Ramblewild Adventure Park
110 Brodie Mountain RdRamblewild is Feronia Forests’ first tree-to-tree adventure destination.
I highly recommend this!
https://ramblewild.com/
Ski Butternut
380 State Rdhttps://skibutternut.com
City/town information
Designated one of the Cultural Districts in Massachusetts, Pittsfield’s downtown, known as the Upstreet Cultural District, boasts a lively roster of music, dance, theater, community festivals, and celebrations, including two highly acclaimed professional theaters—the Colonial Theatre, part of Berkshire Theatre Group, and Barrington Stage Company—presenting a wide array of performances. There’s a vibrant visual arts scene in Pittsfield, too, with public art (Artscape), thriving galleries, artist studios, cooperatives, and the monthly First Fridays Artswalk. Cultural festivals include 3rd Thursdays, the WordXWord Festival, Pittsfield CityJazz Festival, 10X10 Upstreet Festival, and more!
https://downtownpittsfield.com
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Pittsfield
Designated one of the Cultural Districts in Massachusetts, Pittsfield’s downtown, known as the Upstreet Cultural District, boasts a lively roster of music, dance, theater, community festivals, and celebrations, including two highly acclaimed professional theaters—the Colonial Theatre, part of Berkshire Theatre Group, and Barrington Stage Company—presenting a wide array of performances. There’s a vibrant visual arts scene in Pittsfield, too, with public art (Artscape), thriving galleries, artist studios, cooperatives, and the monthly First Fridays Artswalk. Cultural festivals include 3rd Thursdays, the WordXWord Festival, Pittsfield CityJazz Festival, 10X10 Upstreet Festival, and more!
https://downtownpittsfield.com
Museums
The Berkshire Museum is a museum of art, natural history and ancient civilization.
https://berkshiremuseum.org
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Berkshire Museum
39 South StThe Berkshire Museum is a museum of art, natural history and ancient civilization.
https://berkshiremuseum.org
The Clark is one of only a handful of institutions globally with a dual mission as an art museum and a distinguished center for research and higher education, dedicated to advancing and extending the public understanding of art.
In 1950 Sterling and Francine Clark chartered the Sterling and Francine Clark Art Institute as a home for their extensive art collection. Opened to the public in 1955, the Clark has built upon this extraordinary group of works to become one of the most beloved and respected art museums in the world, known for its intimate galleries and stunning natural environment.
https://www.clarkart.edu/
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The Clark Art Institute
225 South StThe Clark is one of only a handful of institutions globally with a dual mission as an art museum and a distinguished center for research and higher education, dedicated to advancing and extending the public understanding of art.
In 1950 Sterling and Francine Clark chartered the Sterling and Francine Clark Art Institute as a home for their extensive art collection. Opened to the public in 1955, the Clark has built upon this extraordinary group of works to become one of the most beloved and respected art museums in the world, known for its intimate galleries and stunning natural environment.
https://www.clarkart.edu/
Hancock Shaker Village is a landmark destination of 750 acres, 20 historic Shaker buildings, and over 22,000 Shaker artifacts. On the National Historic Register, it is the most comprehensively interpreted Shaker site in the world, and the oldest working farm in the Berkshires of Western Massachusetts.
https://hancockshakervillage.org
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Hancock Shaker Village
1843 W Housatonic StHancock Shaker Village is a landmark destination of 750 acres, 20 historic Shaker buildings, and over 22,000 Shaker artifacts. On the National Historic Register, it is the most comprehensively interpreted Shaker site in the world, and the oldest working farm in the Berkshires of Western Massachusetts.
https://hancockshakervillage.org
MASS MoCA is one of the world’s liveliest centers for making and enjoying today’s most evocative art. With vast galleries and a stunning collection of indoor and outdoor performing arts venues, MASS MoCA is able to embrace all forms of art: music, sculpture, dance, film, painting, photography, theater, and new, boundary-crossing works of art that defy easy classification. Much of the work we show in our light-filled spaces, on our technically sophisticated stages, and within our lovely network of late 19th-century courtyards is made here during extended fabrication and rehearsal residencies that bring hundreds of the world’s most brilliant and innovative artists to North Adams all year round.
https://massmoca.org/
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MASS MoCA
1040 Mass MoCA WayMASS MoCA is one of the world’s liveliest centers for making and enjoying today’s most evocative art. With vast galleries and a stunning collection of indoor and outdoor performing arts venues, MASS MoCA is able to embrace all forms of art: music, sculpture, dance, film, painting, photography, theater, and new, boundary-crossing works of art that defy easy classification. Much of the work we show in our light-filled spaces, on our technically sophisticated stages, and within our lovely network of late 19th-century courtyards is made here during extended fabrication and rehearsal residencies that bring hundreds of the world’s most brilliant and innovative artists to North Adams all year round.
https://massmoca.org/
The Mount is an historic house museum and vibrant cultural center with a variety of tours, programs, and events for you to enjoy. The grounds are open for public use unless otherwise posted on their calendar of events.
https://www.edithwharton.org
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The Mount, Edith Whartonova kuća
2 Plunkett StThe Mount is an historic house museum and vibrant cultural center with a variety of tours, programs, and events for you to enjoy. The grounds are open for public use unless otherwise posted on their calendar of events.
https://www.edithwharton.org
Norman Rockwell Museum presents the world's largest collection of original Norman Rockwell art as the best of American illustration.
https://www.nrm.org/
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Muzej Normana Rockwella
9 Glendale RdNorman Rockwell Museum presents the world's largest collection of original Norman Rockwell art as the best of American illustration.
https://www.nrm.org/
Theatre
Barrington Stage creates theatre experiences that engage and excite our audiences by entertaining as well as challenging them with the most dynamic and provocative productions possible. BSC creates a platform for new voices and diverse perspectives that drives all of our work.
https://barringtonstageco.org/
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Barrington Stage Company
30 Union StBarrington Stage creates theatre experiences that engage and excite our audiences by entertaining as well as challenging them with the most dynamic and provocative productions possible. BSC creates a platform for new voices and diverse perspectives that drives all of our work.
https://barringtonstageco.org/
Berkshire Theatre Group’s mission is to support wide-ranging artistic exploration and acclaimed performances in theatre, dance, music and entertainment. Berkshire Theatre Group’s celebrated four stages reflect the history of the American theatre; they represent a priceless cultural resource for the community.
The Colonial Theatre opened on September 28, 1903 with a production of the operetta Robin Hood by the Bostonians, a famed touring group. The house was sold out.
In subsequent years the Colonial has enhanced the learning experience for tens of thousands of area school children, has served hundreds of thousands of visitors, generated millions annually in community economic impact, and has fulfilled or surpassed the expectations most people in the Berkshires had when the struggle to restore The Colonial Theatre got underway.
berkshiretheatregroup.org
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Berkshire Theatre Group
6 East StBerkshire Theatre Group’s mission is to support wide-ranging artistic exploration and acclaimed performances in theatre, dance, music and entertainment. Berkshire Theatre Group’s celebrated four stages reflect the history of the American theatre; they represent a priceless cultural resource for the community.
The Colonial Theatre opened on September 28, 1903 with a production of the operetta Robin Hood by the Bostonians, a famed touring group. The house was sold out.
In subsequent years the Colonial has enhanced the learning experience for tens of thousands of area school children, has served hundreds of thousands of visitors, generated millions annually in community economic impact, and has fulfilled or surpassed the expectations most people in the Berkshires had when the struggle to restore The Colonial Theatre got underway.
berkshiretheatregroup.org
“The Pillow” is a treasured 220-acre National Historic Landmark, a recipient of the prestigious National Medal of Arts, and home to America’s longest-running international dance festival.
Each year thousands of people from across the U.S. and around the globe visit the Berkshires of Western Massachusetts to experience the Festival with more than 50 dance companies and 500 free performances, talks, and events; train at The School at Jacob’s Pillow, one of the most prestigious professional dance training centers in the U.S.; explore the Pillow’s rare and extensive dance Archives; and take part in numerous Community Programs designed to educate and engage dance audiences of all ages.
https://www.jacobspillow.org
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Jacob's Pillow
358 George Carter Rd“The Pillow” is a treasured 220-acre National Historic Landmark, a recipient of the prestigious National Medal of Arts, and home to America’s longest-running international dance festival.
Each year thousands of people from across the U.S. and around the globe visit the Berkshires of Western Massachusetts to experience the Festival with more than 50 dance companies and 500 free performances, talks, and events; train at The School at Jacob’s Pillow, one of the most prestigious professional dance training centers in the U.S.; explore the Pillow’s rare and extensive dance Archives; and take part in numerous Community Programs designed to educate and engage dance audiences of all ages.
https://www.jacobspillow.org
Shakespeare & Company strives to be a thriving center of creative and collaborative excellence in Performance, Training and Education, rooted in Shakespeare’s work and the Elizabethan ideals of inquiry, balance and harmony. They are committed to nurturing the creative impulse, exploring the universal themes of human experience, engaging with the widest possible audience, and influencing future generations.
https://www.shakespeare.org
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Shakespeare & Company
70 Kemble StShakespeare & Company strives to be a thriving center of creative and collaborative excellence in Performance, Training and Education, rooted in Shakespeare’s work and the Elizabethan ideals of inquiry, balance and harmony. They are committed to nurturing the creative impulse, exploring the universal themes of human experience, engaging with the widest possible audience, and influencing future generations.
https://www.shakespeare.org
Tanglewood annually draws over 350,000 visitors. Each season offers not only a vast quantity of music, but also a vast range of musical forms and styles, all of it presented with a regard for artistic excellence that makes the festival unique.
https://www.bso.org
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Tanglewood
Tanglewood annually draws over 350,000 visitors. Each season offers not only a vast quantity of music, but also a vast range of musical forms and styles, all of it presented with a regard for artistic excellence that makes the festival unique.
https://www.bso.org
Food scene
Baja Charlie's California Cuisine
62 W Center StDistrict Kitchen & Bar
40 West StMazzeo's Ristorante
1015 South StMission
438 North StNew Asian Garden
Newell StreetRoasted Garlic
483 W Housatonic StTito's
34 Depot StVong's Thai Cuisine
157 Seymour StZucchini's
1331 North StHealth & Wellness
For more than 49 years, Kripalu has been a leader in yoga- and mindfulness-based education. More than just poses on a mat, they believe yoga is an accessible practice that inspires connection, compassion, and joy.
https://kripalu.org
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Kripalu Center For Yoga & Health
57 Interlaken RdFor more than 49 years, Kripalu has been a leader in yoga- and mindfulness-based education. More than just poses on a mat, they believe yoga is an accessible practice that inspires connection, compassion, and joy.
https://kripalu.org
Shopping
https://arcadian.com/
The place to go in the Berkshires for outdoor clothing and equipment. They feature bicycles, kayaks, and stand-up paddleboards (SUP's) for sale or rent. Located next to Kennedy Park, providing hundreds of acres of public trails accessible from their parking lot, for biking and hiking. Watercraft delivery to the public boat launch at Stockbridge Bowl or the Housatonic River, in southern Berkshire County, is available for an additional fee.
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Arcadian Shop
91 Pittsfield Rdhttps://arcadian.com/
The place to go in the Berkshires for outdoor clothing and equipment. They feature bicycles, kayaks, and stand-up paddleboards (SUP's) for sale or rent. Located next to Kennedy Park, providing hundreds of acres of public trails accessible from their parking lot, for biking and hiking. Watercraft delivery to the public boat launch at Stockbridge Bowl or the Housatonic River, in southern Berkshire County, is available for an additional fee.
Guido's Fresh Marketplace
760 S Main StLee Premium Outlets include well known brands such as Kate Spade, Gap, Talbots, Michael Kors, Bath & Body Works, Coach, Ralph Lauren and many more! Check out their website to see all their offerings:
https://www.premiumoutlets.com/outlet/lee
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Lee Premium Outlets
17 Premium Outlet BoulevardLee Premium Outlets include well known brands such as Kate Spade, Gap, Talbots, Michael Kors, Bath & Body Works, Coach, Ralph Lauren and many more! Check out their website to see all their offerings:
https://www.premiumoutlets.com/outlet/lee
Market32
555 Hubbard AveTarget
655 Cheshire Rd