The Berkshires, Massachusetts

Best Places to Retire in Massachusetts

Profile of The Berkshires

Berkshire County, Massachusetts, with a population of about 131,500, is wondrously rural yet within a convenient traveling distance (150 miles) from Boston or New York. It lies in the western-most part of the state in an area of rivers, lakes and hills known as the Berkshires. Its appeal to metropolitan residents seeking a restful, idyllic getaway is legendary. Many visitors have purchased second homes here and countless others have relocated to the county. Cultural and recreational pastimes abound, giving residents and visitors alike a vast choice of activities. You will find innovative programs and events for families and individuals; historical sites; exhilarating sports and recreation opportunities; and world-class festivals alive with music, theatre and dance. The history of the area boasts a tradition of arts and letters from the 19th century, with famous American authors such as Herman Melville and Nathaniel Hawthorne, who resided in the area, and Henry David Thoreau, whose visits to the Berkshires are well-documented. In the early 20th century, this was home to Edith Wharton, who built a summer estate called, simply, The Mount. This was also the summer getaway for the rich and powerful during the Gilded Age, when many of the luxurious Berkshire “Cottages” were built. These summer homes were, in fact, grand homes for residents of metropolitan New York who summered here at the turn of the 20th century. For theologian Jonathan Edwards and Mother Lee’s Shakers, this region served as part of their separate journeys to find and serve God.

Strung along north-south U.S. Route 7, the major towns of the Berkshires offer a long procession of events, theater, dance, music, museums and historical sites. Recreational opportunities for downhill and cross-country skiing, bicycling, canoeing, fishing, and hiking are abundant.

Map of Berkshire County

Adams, with a population of over 8,800, is an inspiring place to visit. A history rich with religious and patriotic significance has produced this thriving community that sustains its industrial roots. Adams maintains a small town charm and friendliness, attracting visitors again and again. It began as a tiny farm village that became an industrial small town. Farmers and their sons tapped the energy of the nearby Hoosic River to provide power to textile and papermaking machinery. The result is today’s pleasant town surrounded by the lush landscape of the river valley and the Berkshire Hills. Mount Greylock State Reservation, which adjoins Adams, is the highest peak in Massachusetts and can be seen from five states. The reservation is a rich source of outdoor recreation in all seasons.

Great Barrington
Southern Berkshire’s largest town (population 7,600) 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. Its vibrant downtown invites a stroll along its charming tree-lined avenues. Main Street was the first in the United States to have electric lights. Railroad Street is one of the oldest streets in the country, and it offers a bit of “SoHo” in the Berkshires. The town has a monument commemorating the site of the first armed resistance against the British, two years before the Revolutionary War. This was also the site of the first slave being freed.

Named after prominent revolutionary patriot and commander, General Charles Lee, the town of Lee has been in existence since the 1760s. Several historic buildings are worthy of attention, including the Congregational Church – a Romanesque-design building with a 150-foot steeple and a Seth Thomas clock (one of only two of its kind ever made). The Lee Library and the Civil War Memorial Hall were both made from local marble, and Victorian homes with architectural and historical significance abound. Although Lee (with nearly 6,000 residents) continues its hard-working traditions, it has also turned its attention to revitalization projects. Besides its charming downtown area that’s listed in the National Register of Historic Places, Lee now has an outlet shopping center and a business park plus a fine assortment of restaurants, shops and other service businesses.

Tucked in a scenic corner of the lush Southern Berkshires, the charming hamlet of Lenox (population just over 5,000 permanent residents and second-home owners) is perhaps best known for being the former residence of literary legend Edith Wharton. Today, the downtown area is vibrant with unique shops, galleries and restaurants housed in renovated buildings along tree-lined avenues. Visitors enjoy touring the town’s many historical and architectural landmarks, including the Berkshire Cottages, the Cloyd House & Blacksmith Shop, the Church on the Hill and more. For the last six decades, Lenox has been famous around the world as the site of Tanglewood, summer home of the Boston Symphony Orchestra.

North Adams
North Adams is known as “The Town of Steeples and Peaks,” for the spires of its many churches – a lovely sight as you descend into the city from the west on Route 2. This tiny yet significant region has much to offer, from historical sites and cultural attractions to forests and parks with scenic vistas and outdoor recreation. Visitors can learn about the town’s history and the challenging construction of the Hoosac Tunnel at the Western Gateway Heritage State Park. Located in the restored freight yard district, the park houses restored 19th century structures, railroad exhibits, industrial histories, a gallery and a graphics studio. The town is also home to the Massachusetts Museum of Contemporary Art (MASS MoCA), the largest contemporary art museum in the country. It presents innovative exhibitions and performances in the visual, performing and media arts.

Another catalyst is the presence of the Massachusetts College of Liberal Arts, which adds educational opportunities and a vibrant campus atmosphere. Because of the city’s topography, many streets are steep, offering vistas of the neighboring mountains for many of its 14,681 residents. In addition to breathtaking views of the Berkshire hills and Mount Greylock (the state’s tallest summit), North Adams is also home to Natural Bridge State Park, located just north of downtown. Visitors marvel at the natural marble arch, a geological wonder 500 million years in the making, formed from glaciers and meltwaters. (No official Web site at this time; see

This largely unspoiled, rural area is the site of the Otis Reservoir, the largest recreational body of water in Massachusetts. You can rent a canoe to tour the shoreline, or rent a boat and motor for fishing. For the avid trout fisherman, the nearby Farmington River is famous for its stock. There is a state forest which offers camping opportunities, or trailer camps for your RV, or a variety of bed and breakfast establishments. Otis, with a population of 1,365, is home to both permanent and part-time residents. The town, which is mostly forested, attracts vacation- and second-home owners to its outdoor recreational opportunities. Otis has a small commercial center that serves both residents’ and visitors’ basic needs; however, the town’s major draw is an abundance of public lands which provide a variety of activities in all seasons.

Despite its delightfully preserved “backwoods” character, Otis has several good restaurants and fascinating shops that have retained their historic flavor. You can even find a post office that still uses the original bronze post boxes of its 19th century origins. Otis’ most wonderful treasure, however, is the friendliness and warmth of her people. (No official Web site at this time; see

Pittsfield enjoys the distinction of being the “City of Festivals.” Perfectly placed in the heart of the Berkshires, this surprising haven bustles with cultural and recreational amenities. The first county agricultural fair in America was held here in 1810, perhaps portending its current-day reputation for celebrations. The city offers a varied concert series, art, culture, nightlife, fine and fun dining, charming lodgings, a professional baseball team, a multitude of parks and plenty of hometown celebrations and parades.

Pittsfield’s 45,793 residents enjoy local features that give the city a distinctive quality: a variety of neighborhoods, dozens of parks, two lakes, golf courses, a ski area, wildlife sanctuaries, historical sites and an abundance of open space. The city embraces summer with an exciting Summerfest which includes countless arts and crafts, and other festivals, highlighted by Festival Americana Weekend in early July. Among other venues of Summerfest are top-quality exhibitions at the Berkshire Museum, which houses American landscape paintings and an inspiring collection of Americana. There is also historical and cultural programming at Arrowhead, headquarters of the Berkshire County Historical Society and former home of author Herman Melville.

Stockbridge, home to 2,276 permanent and summer residents, also offers a unique combination of shops, restaurants, galleries, theaters and museums. Outdoor enthusiasts will find that they are close to skiing, hiking and other recreational pursuits. Stockbridge was Norman Rockwell’s long-time residence and the home of what he called his “best studio yet.” The Norman Rockwell Museum in town has preserved his memory and his work with the world’s largest collection of his original art. Rockwell immortalized Stockbridge’s picturesque Main Street in his famous painting, Stockbridge Main Street at Christmas. Each year in early December Main Street traffic is detoured and the town is transformed into a magical New England village, decorated with holiday wreaths and sparkling lights. Antique cars are parked as they were in Rockwell’s painting. Other historic highlights of the town include Chesterwood, home of Daniel Chester French, sculptor of the Lincoln Memorial, and Linwood House, an early Berkshire cottage on the grounds of the Norman Rockwell Museum.

West Stockbridge
The historic village of West Stockbridge with a population of 1,416 people, is a tiny, eclectic arts community set along-side the peaceful Williams River. It is an easy, pleasant stroll around the square block town, and it is filled with treasures. This charming New England hamlet is easily reached and once you arrive, you’ll want to stroll the town, a quaint square block filled with small shops, unique craft galleries and a number of excellent restaurants. You will also find the Berkshire Center of Contemporary Glass. It offers tours, demonstrations of live glass blowing, and the Glass Café. In addition there is the Berkshire Hills Candle Company, which manufactures original candles and features Berkshire crafts.

With its artistic offerings and scenic countryside, it’s no wonder Williamstown is known as “The Village Beautiful.” Surrounded by mountains, farmlands and hiking trails, picturesque Williamstown is a quintessential Berkshire village. Here you’ll find a wonderful blend of natural beauty, small town charm and heightened cultural awareness. Home of the venerable Williams College, one of the top liberal arts colleges in the country, this community offers much to refresh the mind, renew the soul and stir the imagination.

Among its wealth of natural treasures is the Hopkins Memorial Forest, the Taconic Trail State Park, Field Farm, and Bullock Forest. Williamstown flourishes with art and culture, despite its diminutive size. The Sterling and Francine Clark Art Institute is a fine arts museum particularly well-known for its many French impressionist paintings as well as other significant works. The Williams College Museum of Art has changing exhibitions and a diverse permanent art collection with works ranging from 9th century B.C. Summer nights in Williamstown light up with Broadway and Hollywood luminaries performing live at the Williamstown Theatre Festival. From mid-June through August, over 240 dazzling performances take place in the region’s most sophisticated summer theatre.

Other towns in Berkshire County

(Click for brief description)
Alford —
Becket —
Cheshire —
Clarksburg —
Dalton —
Egremont —
Florida —
Hancock —
Hinsdale —
Monterey —
Mount Washington —

New Ashford —
New Marlborough —

Peru —
Richmond —
Sandisfield —
Savoy —
Sheffield —
Tyringham —
Washington —
Windsor —

Arts & Culture

Becket Arts Center of the Hilltowns, located in Becket, offers artist exhibits, free lectures, art, crafts, writing, drama, and music. Workshops are available for adults, children and teens.

Eclipse Mill Artist Lofts is located in the historic mill building known as the Eclipse Mill. It has over 125,000 square feet of floor space that has been converted into 40 artist live/work studio loft condominiums. The founding purpose for the creation of the artists’ lofts is to provide affordable live/work spaces for the serious pursuit of creative/artistic endeavors. As such, all residents whether owners or tenants, are either practicing artists, or have some connection with the arts. Galleries are open to the public but call for the schedule.

Lichtenstein Center for the Arts is a lively visual and performing arts center in downtown Pittsfield featuring changing art shows, open studios, classes and special events. It is open Wednesday through Saturday from noon to 5 p.m.

Jacob’s Pillow Dance Festival in Becket is a National Historic Landmark for dance and features hundreds of performances and free events.

Berkshire Theatre Festival in Stockbridge has the unique distinction of being the longest running cultural organization in Berkshire County and one of the first established regional theatres in the United States. Consistently high quality productions can be enjoyed on both the Main Stage and in the Unicorn Theatre

Williams College Museum of Art in Williamstown houses 12,000 works that span the history of art. Within the broad range of periods and cultures represented, the collection emphasizes contemporary and modern art, American art from the late eighteenth century to the present, and the art of world cultures. Programming in the 14 galleries is enhanced by outreach activities involving faculty, students, community members, and school children.

The Williamstown Film Festival, usually held in mid-October, honors past achievements in cinema and showcases the best new films on the Amercan indie scene.

Chesterwood was the home of Daniel Chester French, sculptor of the Lincoln Memorial. Open from May through October, visitors can view the studio and museum shop as well as the garden and woodland walk.

Hancock Shaker Village is a 200-year old original Shaker Village that showcases 21 historic buildings, Shaker furniture, crafts, and a heritage farm and garden. There are galleries, a gift shop and café on the grounds.

The Williamstown Theatre Festival is a summer-long celebration of theater that brings together a vast and impressive array of artists and offers audiences varied cultural experiences. Every summer, WTF presents approximately two hundred performances of classic and new plays on its Main and Nikos stages, free theater, cabaret, countless readings, workshops, and other special events including a program for youngsters in North Adams called the Greylock Theatre Project.

The Berkshire Museum in Pittsfield was founded in 1903 by Zenas Crane, the grandson of the founder of Crane & Company. When he built the museum, his vision was to create an inviting environment for everyone, not just the elite. He sought to use the museum’s varied collection to enrich, educate and delight the county’s citizens of all ages. Today its mission is to enrich, inspire and educate through interactions with the arts, history and the natural world. The museum has 14 galleries, an aquarium, a 291-seat air-conditioned theater, classrooms, and a museum store.

Jacob’s Pillow in Becket has as its mission the support of dance creation, presentation and education, and to engage and deepen public appreciation and support for dance. A dance festival is held each summer with performances in the Ted Shawn Theatre and the Doris Duke Studio Theater.

The Massachusetts Museum of Contemporary Art in North Adams is housed on a 13-acre campus of restored 19th century factory buildings. Exhibits include some of the liveliest, most evocative and provocative art being made today. It is open from September through June from 11 a.m. to 5 p.m.

The Norman Rockwell Museum in Stockbridge holds the largest collection in the world of original art by America’s favorite illustrator. It is open daily from May through October.

The Sterling and Francine Clark Art Institute, located in Williamstown, has a collection 19th century paintings by Renoir, Degas, Cassett, Monet, Toulouse-Lautrec, Winslow Homer. In addition it has old master paintings, prints and drawings, along with English and American silver.

Tanglewood is the summer home of the Boston Symphony Orchestra and home of the Tanglewood Music Center. It is located on a 550-acre estate where recitals, student concerts, chamber music and larger works which are presented in the Koussevitzky Music Shed and Seiji Ozawa Hall. It is open from late June to early September.

For information on other art and cultural activities, visit


Recreational activities abound in the Berkshires, regardless of the season. You will find cross-country and downhill skiing and snowboarding, snowmobiling, fishing, boating, golf, hiking, horseback riding, rafting, tennis, and swimming. A few of the locations and their Web sites follow:

Berkshire Scenic Treks & Canoe Tours –
Canterbury Farm Cross Country Skiing –
Cranwell Resort, Spa and Golf Club –
Bousquet Ski Resort and Summer Family Fun Center –
Catamount Ski Area — http://www/
Jiminy Peak Mountain Resort –
Butternut Ski Area –
Berkshire Fishing Club (private) – http://www/
Fishing (county-wide locations) –
Housatonic Anglers –
Egremont Country Club (golf) –
Forest Park Country Club (golf) – Adams – no Web site.
Onota Boat Livery (fishing) – Pittsfield – no Web site
Greenock Country Club (golf and tennis) –
Pontoosuc Lake Country Club (golf) –
Skyline Country Club (golf) –
Waubeeka Golf Links –
Bartholomew’s Cobble (hiking) –
Becket Land Trust (hiking) –
Pleasant Valley Wildlife Sanctuary (hiking) –
Berkshire Horseback Adventures –
October Mountain State Forest –
Pittsfield State Forest –
Tolland State Forest –
Wahconah State Forest –
Mount. Greylock State Reservation –
Beartown State Forest –


Berkshire Community College offers more than 40 credit programs with courses ranging from Anatomy to Zoology and everything in between, as well as non-credit career training programs and enrichment courses for people of all ages. Its main campus is in Pittsfield but also has a campus in Great Barrington. In addition, the college has an office of Life Long Learning that develops, coordinates, and implements noncredit initiatives. The division serves people of all ages whose educational and training needs cannot be met through traditional college-credit programs.

Massachusetts College of Liberal Arts is a fully-accredited public four-year liberal arts college in North Adams. It offers courses in computer science and information systems, business administration and education, and abundant research opportunities in subjects such as biology, physics and psychology. Its educational philosophy is that students learn best by actively participating in their own education, and the curriculum provides opportunities for independent study, service learning, and study abroad. Day, evening and summer programs are available.

Williams College in Williamstown is a liberal arts institution with graduate programs in the history of art and in development economics. The undergraduate enrollment is approximately 2,000. There are three academic divisions (humanities, sciences, social sciences), 24 departments, 33 majors, plus concentrations and special programs.

Senior Programs

Berkshire Institute of Lifetime Learning, based in Pittsfield, is a membership-run, non-profit educational organization offering non-credit courses created and developed by and for the institute. Members are encouraged to serve on committees, be planners, course coordinators, facilitators and lecturers. Programs include special events, travel and other activities to promote peer interaction. Courses are held at different institutions in the county.

Elderhostel programs for lifelong learning, hosted by Berkshire Community College (BCC), are part of the internationally renowned Elderhostel program. About 15 programs a year are sponsored by BCC and are held at the Crowne Plaza Hotel in Pittsfield. More than 400 people from around the country, and even around the world, enjoy several days of college-level courses with top-notch faculty, field trips to Berkshire sites, lively discussions, and stimulating company.

RSVP, the Retired and Senior Volunteer Program provides recruitment, training and placement of persons 55 years of age and over as volunteers. The program enables senior volunteers to use their time and lifetime experience to: meet new people, help others, be productive and creative, grow personally, explore new careers and make a difference in their community through volunteer service. The Berkshire County chapter is sponsored by the city of Pittsfield.


Berkshire Health Systems (BHS) is the region’s leading provider of comprehensive health care services. With award-winning programs, nationally recognized physicians, world-class technology and a sincere commitment to the community, BHS serves the region through a network of affiliates which include Berkshire Medical Center, the Fairview Hospital, BMC Hillcrest Campus, and Berkshire Visiting Nurse Association.

Berkshire Medical Center is the flagship hospital for BHS and is the region’s leader in neurosurgery, trauma, expert care for stroke patients, diagnostic imaging, endoscopy, general surgery and a full range of rehabilitation services. It has state-of-the-art surgical and emergency care facilities, with diagnostic tools and technology that are second to none anywhere in the region. With its high quality programs, excellent patient outcomes and broad range of health care services, BMC is a community hospital that functions at the level of a major medical center.

Fairview Hospital in Great Barrington is a community hospital, which has a federal designation as a critical access hospital, one of only three in Massachusetts. The 24-bed acute care facility provides 24-hour emergency care by a skilled medical team equipped with state-of-the-art technology. Medical services include cardiology, diagnostic laboratory and imaging (including CT-scan, mammography and ultrasound), surgical services, physical therapy, sports medicine, occupational therapy, pain management and The Family Birthplace.


Harriman- West Airport, North Adams – A general aviation airport located three miles west of the city. One 4,300-foot runway.

Pittsfield Municipal Airport, Pittsfield – A general aviation airport located two miles west of the city. Two runways, 5,000 feet and 3,500 feet.

Great Barrington Airport, Great Barrington – A general aviation airport located two miles west of Great Barrington with one 2,579-foot runway.


The average temperature in July for Berkshire County, as measured in centrally located Pittsfield is 79.7 degrees. The average low in January is 31.6 degrees. Pittsfield is 1,171 feet above sea level. The highest point in the county is Mount Greylock at 3,491feet. Rainfall averages 39.8 inches a year with the bulk of it falling in June, July and November.


Berkshire Eagle —

Chambers of Commerce

Berkshire Chamber of Commerce –
North Berkshire Chamber of Commerce –
Southern Berkshire Chamber of Commerce —
Lee Chamber of Commerce —
Lenox Chamber of Commerce —
Stockbridge Chamber of Commerce —
Williamstown Chamber of Commerce —

Property Taxes

Property in Berkshire County is tax by the local towns and cities. To view tax rates in the southern part of the county, visit Tax rates for some of the other cities and towns can be found on their municipal Web site. If they do not have one, then a phone call is in order.

The legislature has authorized local governments to administer the property tax under state supervision. Massachusetts municipalities are subject to a budgetary law known as “Proposition 2 ½.” This law limits the amount of money (the property tax levy) that can be raised by a municipality. There are two parts to the property tax limit calculation. First, the Levy Ceiling which says a community may not collect more than 2.5% of the total full and fair cash value of all taxable real and personal property in the community. Second is the Levy Limit which must be below the levy ceiling. The levy limit is calculated by adding 2.5% to the previous year’s levy limit and adding in a value to cover growth in the community.

State Taxes

State Aging Agency

Driving Distances (Mid-county)

Albany, NY – 36 miles
Boston, MA – 147 miles
Buffalo, NY – 338 miles
Burlington, VT – 208 miles
Cape Cod, MA – 220 miles
Hartford, CT – 90 miles
Manchester, NH – 169 miles
Montreal, Canada – 358 miles
Mystic, CT – 130 miles
New York City – 147 miles

« Back to the Massachusetts Index
« Back to the State Index

We believe everyone deserves to make thoughtful, informed purchase decisions. As a result, we provide our buyers guides and local guides free for consumers.

We may receive compensation from our partners. However, Retirement Living independently researches companies, and the compensation we receive does not affect the analysis of our staff or the opinions of our subject matter experts. The subject matter experts mentioned in our guides have specific knowledge or credentials in their field.

Retirement Living will not include companies on our guides that do not meet our quality standards. The compensation we receive from our partners may impact how and where companies appear on our site, including the order in which they appear.

Retirement Living independently researches companies, and we use editorial discretion to award companies with special recognition (i.e. Best Value) based on our staff's judgement or subject matter expert's judgement. We do this to help you identify companies that will meet your specific buying needs, and we do not receive compensation for these designations.

Additionally, Retirement Living is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to,, or