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Massachusetts Retirement - Massachusetts, USA

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Discover The Berkshires
Retirement Living With An Accent On Culture And The Arts

With its reputation as an expensive place to live, Massachusetts does not rank at the top of the list for many people when they start searching for their retirement destination. However, here is a suggestion… look closely at Berkshire County, a wondrously rural collection of small, picturesque towns and villages nestled among the beautiful Berkshire Mountains in the western part of the State. In this idyllic, restful setting, conveniently located within reasonable driving distance from Boston and New York, retirees will find themselves surrounded by a seemingly endless array of music festivals, art museums, performance venues alive with music, theatre and dance.

This compact region is a vibrant and internationally recognized hub for the arts with a year-round offering of events and attractions that annually attracts more than three million visitors. Combine this atmosphere with a wide selection of award-winning restaurants, a bountiful supply of antique galleries and other specialty shops, and there are more than enough sensory pleasures for even the most demanding patron of the arts.

Adding to the allure of The Berkshires as a retirement choice is the fact that, surprisingly, many of the housing options found here are priced significantly below real estate prices in other parts of Massachusetts. For example, in Pittsfield, a small town of about 41, 000 located right in the heart of the region, the average price of a home is less than $150,000. And in Williamstown, home prices are higher, but with a median price of $275,000, they are still substantially below those found in the metropolitan Boston area and along the Atlantic Coastal areas of the State.

In addition to being among the more affordable places to live in Massachusetts, Pittsfield is also somewhat unique in that, despite being a relatively small town, within its city government, there is an Office of Cultural Development, which spearheads an aggressive effort to develop and promote its cultural resources. Known as the "City of Festivals," this culturally-rich village bustles with musical and theatrical events throughout the year and features a historically renovated theater, several performing arts groups and rich collections of art, natural history and science.

Downtown Pittsfield is a thriving creative community with more than fifty artists having studios there.

One of the more desirable retirement choices among the small towns of the Berkshires may well be Williamstown, especially for active retirees who love the outdoors. With miles of cross-country skiing and hiking trails winding through the 2,400 acres of the near-by Hopkins Forest, outdoor lovers have the perfect setting to experience the serene beauty and tranquility of rural New England.

Home to Williams College, and the College's impressive Museum of Art, itself one of New England's cultural jewels, Williamstown has, for more than 220 years operated on the principles of an old New England town meeting, where every citizen has a right to attend and voice his or her opinions and concerns on matters of local government.

Retirees who love music will find the Berkshires especially appealing, with literally scores of summer musical festivals and year-round performances. Perhaps the best known of these is at Tanglewood in Lenox, which serves as the summer home for the Boston Symphony Orchestra. Here, in a variety of venues including a spectacular outdoor setting on the lawn, the open-air Koussevitzky Shed or within a smaller indoor hall, audiences are treated to a wide range of music and performers, from jazz to classical. Throughout the region, a seemingly never-ending calendar of musical events provides an assortment of concerts and performances. Regardless of whether you favor jazz, opera, classical or bluegrass, the Berkshires truly are alive with music throughout the year.

In exploring the possibility of retirement in Berkshire County, there are a number of other small towns that merit consideration, in addition to Pittsfield and Williamstown. Great Barrington, the largest community in the southern part of the County, boasts a vibrant downtown with a fashionable shopping district and fine restaurants. With its charming tree-lined streets, natural beauty and abundant cultural activities, this small town has much to offer for affordable retirement living.

Known as "The Town of Steeples and Peaks" for its many churches, the lovely village of North Adams is home to the Massachusetts Museum of Contemporary Art, the largest contemporary art museum in the country, with a wealth of innovative exhibits and performances in the visual, performing and media arts. Its residents also have access to a number of historical sites, other cultural attractions, parks and forests.

Yet another tiny village known for its cultural and artistic reputation is Shelburne Falls, which has been included among "the 100 best small art towns in America" in a recent publication. And in Stockbridge, where, on Sunday afternoon, Main Street is closed to vehicular traffic, life remains remarkably similar to the time it was painted by Norman Rockwell. In this nostalgic setting, there is a unique sense of history, imbued with small town warmth and hospitality. Visitors can still find lodging at the venerable 200 year-old Red Lion Inn, a Berkshire icon and stroll the charming streets that evoke memories of Rockwell's famous Christmas street scene.

But the rich cultural scene is just one reason to consider retirement in the Berkshires. For, in addition, it is a true outdoor playground with an abundance of natural scenery and green, wooded spaces, where those who so desire can experience a rich and rewarding outdoor lifestyle, with activities such as hiking, skiing, biking and even rafting virtually at their front door. In essence, if a sense of discovery and desire for a rewarding and adventurous lifestyle are of more importance in the way you plan to spend your retirement than a concern about the weather and budgetary issues, we highly recommend taking time to explore the small towns and charming villages of rural Berkshire County.

For more information on the best places to retire, visit

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The best place to find your retirement, vacation or second home

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