These Small Towns in the Berkshires have Big-City Amenities

It wasn’t just the patrons of the bar in the TV show “Cheers” that wanted to go where “everybody knows your name.” And of course, John Cougar Mellencamp has not been the only musician or artist to celebrate the appeal of living in a small town. For those in the know, the benefits of living in a small town are numerous.

 

To name a few, small towns are known for having a lower cost of living, less traffic, independent mom and pop-style stores and restaurants, less crime and a slower, more relaxed lifestyle. What many expect when relocating to a small town, however, is that accessing these advantages requires sacrificing many of the amenities that people love about big cities.

 

But that is not always the case, as illustrated in the examples of Lenox, Massachusetts, Great Barrington, Massachusetts, Hudson, New York, and Chatham, New York. All of these areas have a relatively small population size and a relaxed small-town atmosphere, combined with vibrant downtown areas, many local restaurants, thriving arts/cultural opportunities and robust government services.

 

 

Nestled in the Berkshires in western Massachusetts, Lenox is home to the theatre group Shakespeare and Company, as well as Tanglewood, summer home of the Boston Symphony Orchestra. As of 2020, the population size was just over 5,000. The small size may be surprising given that Lenox became a popular spot for the wealthy elite as early as 1821, when Catharine Sedgwick, an acclaimed writer at the time, moved there.

 

By 1850, Lenox was home to Nathaniel Hawthorne and, by 1880, Lenox had become a Gilded Age resort town as a result of many wealthy families creating large summer estates. At one point, Andrew Carnegie made his home there and Edith Wharton famously designed a home, The Mount, which is now a historic site and museum.

 

The appeal now is similar, in that Lenox has pristine natural beauty, shown by the 1000-acre Pleasant Valley Wildlife Sanctuary and Lenox Town Beach, along with many cultural attractions. To learn more about what Lenox has to offer, including information about public schools and the average sale price of Lenox area real estate, click here. To search for Lenox area homes, click here.

 

 

Located in the southern Berkshires and home to the Butternut Ski Resort, Great Barrington has a main street restaurant area that has earned it a reputation as the tastiest small town in New England. Similar to Lenox, Great Barrington’s scenic natural beauty made it a preferred destination for wealthy families during the Gilded Age, when large estates such as Searles Castle and Brookside were built.

 

Great Barrington’s arts and cultural scene, combined with its many nature preserves, have ensured that it has remained popular. Home to the Mahaiwe Performing Arts Center and the Berkshire International Film Festival, Great Barrington is also near the Barrington Stage Company.

 

With many other amenities on offer, Great Barrington real estate is highly sought-after. To learn more about the area, click here; to search Great Barrington home listings, click here.

 

 

With a population of less than 6,000, a trail system and many historic sites, including Hudson Hall, a theater/venue for the arts, Olana State Historic Site, the Hudson Lighthouse and the Hudson Area Library, a former armory, Hudson sees large numbers of tourists, especially in the summer. Set at the head of the Hudson River, the town was established in 1785.

 

Originally a port city due to its strategic location, Hudson has been transformed into a destination for the arts, as it has many art galleries and entertainment venues. The revitalization was initially led by a group of antiques dealers, who began opening shops there in the 1980s. Now, Hudson is host to over 70 antiques dealers, Hudson Farmer’s Market and Olde York Farm, a distillery and walnut tree grove that is located on a historic site.

 

To learn about Hudson and its many cultural attractions, click here. To search for a Hudson area home, click here.

 

 

Chatham is the smallest of the four towns profiled in this article, with a population size of just over 4,000 residents. Significantly, it also has the lowest average sales price for real estate out of the four communities, viewable here, along with extensive information about the many cultural attractions and natural areas that are present.

 

As it was established in 1795, Chatham offers a storied history with many historic sites. A few of these include the Melius-Bentley House, the Peck House, Riders Mill Historic District, and Spengler Bridge. The town is home to the Crandell Theatre, a movie theater that has been in continuous operations since 1926 and hosts the Film Columbia film festival.

 

Other main cultural offerings in Chatham include the Chatham Public Library, built in 1905, the Mac-Haydn Theatre, and PS21, a black-box theater for up to 99 in the winter and an open-air pavilion with seats for up to 300 in the warmer months. Notably, the Columbia Land Conservancy has set aside more than 30,000 acres in Chatham and the surrounding areas, including Hand Hollow and Ooms Conservation Area, which is adjacent to Sutherland Pond.

 

There are many other things to see and do in Chatham, including Borden’s Pond Conservation Area, Columbia County Fairgrounds, Chatham Skate Park, Stonykill Disc Golf, and the Chatham Farmer’s Market. If that were not enough, there are many art galleries, restaurants and shops. Also, the town hosts three annual festivals that are popular for residents and visitors alike, including SummerFest, Oktoberfest, and Winterfest.

 

With a convenient location that allows for relatively easy access to New York City via the Taconic State Parkway, an approximately two and a half hour drive, Chatham real estate is a valuable long-term investment for those who want to live there year-round or purchase a vacation home. For more information on available properties in Chatham, Chatham Village, North Chatham, Malden Bridge, East Chatham, or Old Chatham, click here .

 

For additional guidance on homes for sale in the Berkshires, click here and talk to a local agent today.

 

To connect with one of our agents and learn more about how to prepare your home for sale on the open market, click here today.