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Outdoor Activities 

Ioka Valley Farm

3475 Rt. 43
Hancock, MA 01237

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. 

Arcadian Shop

413.637.3010Yankee Inn Pool
91 Pittsfield Rd. (Rt. 7S)
Lenox, MA 01240

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. 

Berkshire Outfitters

413.743.5900Yankee Inn Pool
Rt. 8, Grove St.
Adams, MA 01220

Berkshire Outfitters has a great selection of bicycles, canoes, kayaks and SUP's for sale or rent. Located only 300 yards from the paved Ashwillticook Rail Trail for those looking to take a relaxed bike tour in northern Berkshire County. Shuttles are available to transport watercraft to nearby Cheshire Reservoir, a 1.5 mile long, pleasant recreational lake, for an additional fee. They also carry camping gear, hiking equipment and footwear for all your outdoor excursions. 

Cinch ‘em Up Stables

518.733.5949Yankee Inn Pool
365 Rt. 43 
Stephentown, NY 12168

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! Jiminy lodging guests can save 10%. Reservations are recommended. 

Donnybrook Country Club

413.499.7888Yankee Inn Pool
775 Williamstown Rd. (Rt. 7N)
Lanesborough, MA 01237

Donnybrook Country Club offers everything a golfer could ask for in a nine-hole layout. We’re talking country club-like conditioning, challenging holes on beautiful rolling terrain and scenic views to match any in the area. Multiple tee options allow play anywhere from a forgiving 2,426 yards to a testing 3,338. Play two different sets of tees for a memorable 18-hole round. 

Waubeeka Golf Links

137 New Ashford Rd. (Rt. 7N)
Williamstown, MA 01267

Waubeeka Golf Links is an 18-hole championship golf course, with driving range, putting green and restaurant, open to the public. Golfers will enjoy pristine course conditions as well as breathtaking views of the mountains, including Mount Greylock, the highest peak in Massachusetts. The large, undulating greens and many elevation changes ensure the course is a fun golf experience, while challenging for players of all ability levels.

Historical Points of Interest

Braveheart Books

874 State Rt. 43
Stephentown, NY 12169


Located 10 minutes west of Jiminy Peak on Route 43, just outside the village of Stephentown, is a cozy pre-civil war general store and post office that is now home to Braveheart Books. They offer bookworms thousands of gently used and rare books from classic and esoteric authors. Open seasonally 11 am - 6 pm, Friday - Sunday in the spring, and Friday - Monday in the summer. Closed on holidays. Stop in and ask Orson the Bookstore Cat to help you find your treasure!

Berkshire Museum

413.443.7171Yankee Inn Pool
39 South St., (Rt 7S) 
Pittsfield, MA 01201

Berkshire Museum founder Zenas Crane, inspired by such institutions as the American Museum for Natural Science, the Smithsonian, and the Metropolitan Museum of Art, decided to blend the best attributes of these establishments in a new museum for the people of Western Massachusetts. Thanks to Crane’s efforts, the broad and varied collections of Berkshire Museum include objects from virtually every continent, from important fine art and sculpture to natural science specimens and ancient artifacts.

Clark Art Institute

413.458.2303Yankee Inn Pool
225 South St.
Williamstown, MA 01267

The Clark Art Institute has become one of the most beloved and respected art museums in the world, known for its intimate galleries and stunning natural environment. One of the few institutions in the United States that combines a public art museum with research and academic programs, the Clark is now a leading international center for research and discussion on the nature of art and art history.

Hancock Shaker Village

413.443.0188Yankee Inn Pool
1843 W. Housatonic St (Rt 20)
Pittsield, MA, 01201

Hancock Shaker Village brings the Shaker story to life and preserves it for future generations.Go back in time, forward in thought. A living history museum, Hancock Shaker Village consists of 750 acres of farmland, woods and pasture, 20 historic buildings, and a premier collection of Shaker furniture and artifacts.

Mass MoCA

413.662.2111Yankee Inn Pool
87 Marshall St.
North Adams, MA, 01247

Massachusetts Museum of Contemporary Art (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. 

Norman Rockwell Museum

413.298.4100Yankee Inn Pool
9 Rt. 183
Stockbridge, MA 01262

Norman Rockwell Museum is dedicated to the enjoyment and study of Rockwell’s work and his contributions to society, popular culture, and social commentary. The Museum houses the world’s largest and most significant collection of Rockwell’s work, including 998 original paintings and drawings. The Museum also houses the Norman Rockwell Archives, a collection of more than 100,000 items, including working photographs, letters, personal calendars, fan mail, and business documents.

Cultural Attractions

Jacob’s Pillow Dance Festival

413.243.0745Yankee Inn Pool
358 George Carter Rd
Becket, MA, 01223

“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. Its mission is to support dance creation, presentation, education, and preservation; and to engage and deepen public appreciation and support for dance.

Mac Hayden Theatre

518.392.9292Yankee Inn Pool
1925 Rt. 203
Chatham, NY, 12037

A mutual love of musical theatre led co-founders Linda MacNish and Lynne Haydn to put on musicals in Chatham, NY, for one summer in 1969. The Mac-Haydn Theatre proves our area can and will support good theatre. After almost 50 years, the Mac-Hayden Theatre continues to bring quality Broadway musicals to our area!

Mahaiwe PAC

413.528.0100Yankee Inn Pool
14 Castle St.
Great Barrington, MA 01230

The mission of The Mahaiwe Performing Arts Center (pronounced muh-HAY-we) is to be the leading year-round presenter of performing arts, film, and educational programs for the Berkshires and neighboring communities. Through programs of the highest quality in dance, music, theatre and opera, we ensure a diversity of talent on the stage of our newly restored historic theater, at ticket prices affordable to our community. Our goal is to present available programs that appeal to all ages and interests.

Shakespeare & Company

413.637.3353Yankee Inn Pool
70 Kemble St.
Lenox, MA 01240

Shakespeare & Company was founded in 1978 to create a theatre of unprecedented excellence in Performance, Training, and Education.  We aspire to perform as the Elizabethans did—in love with poetic language, visceral experience, and the mysteries of the universe, while rooted in the classical ideals of inquiry, balance and harmony.


617.266.1492Yankee Inn Pool
297 West St.
Lenox, MA 01240

Tanglewood is a music venue in Lenox. It has been the summer home of the Boston Symphony Orchestra since 1937 and is home to three music schools. Besides classical music, Tanglewood hosts the Festival of Contemporary Music, jazz and popular artists, concerts, and frequent appearances by James Taylor, John Williams, and the Boston Pops. 

Williamstown Theatre Festival

413.597.3400Yankee Inn Pool
1000 Main St.
Williamstown, MA 01267

Since 1955, the Williamstown Theatre Festival has brought America’s finest actors, directors, designers, and playwrights to the Berkshires. Each season is designed to present unique opportunities for artists and audience alike, revisiting classic plays with innovative productions, developing and nurturing bold new plays and musicals, and offering an array of accompanying cultural events.