Happening in the Hills

The Towns

At a Glance and On Their Own


Known as much for its fall splendor than as a “destination to get away, go into hermit mode,” the towns that comprise the Northwest corner of Connecticut are anything but quiet. At least upon further inspection. While you’re welcome to take things easy, we hope to provide a bit of incentive for looking around a bit, peeking around the corner, so to speak, to find something unexpected. But we totally understand if you find yourself pacified by the clean air, blanket of stars, and absence of urban cacophony. For the rest of us, we’ve got this down to a science – a social science – where the latest opening is a celebration of family news mixed with a bit of friendly gossip and the annual rummage sale provides a good excuse to snag a friend’s sweater, all legal and ladylike, of course.




  • Also called Litchfield County
  • Known as The Hidden Corner or the Secret Corner
  • 1,000-square-mile enclave tucked into the foothills ofthe Berkshire Mountains
  • Situated in Southern New England
  • A collection of 26 small towns, and a few independent villages
  • Uncrowded, unspoiled
  • Second home for many New Yorkers
  • Home to 150,000 residents
  • Litchfield County has the lowest population density of any county in Connecticut and is geographically the state’s largest county.
  • Borders the states of New York and Massachusetts
  • Less than two hours’ drive northeast of New York City
  • 100 miles from New York city and 155 miles from Boston
  • Close to Metro-North’s Harlem-Valley train route to Grand Central Station in NYC
  • 25 miles from end to end
  • Eastern US Time Zone, 5 hours behind Greenwich Mean Time and 6 hours behind Western European time
  • Two area codes: 860 and 203
  • Tipping is customary in Connecticut; for very good service a 15% to 20% tip is appropriate.
  • Has 4 distinct seasons
  • Has more state parks and public lands than any other area in Southern New England
  • Mohawk Mountain is the site of Connecticut’s largest ski area


The NW corner offers plenty to do and see, but we also enjoy a pleasant Sunday ride or day-trip, especially when it entails literally driving a mile outside the county border. Here are a handful of of nearby villages and towns worth a detour.

  • Amenia, NY
  • Brimfield, MA
  • Great Barrington, MA
  • Lenox, MA
  • Middlebury, CT
  • Millerton, NY
  • New Britain, CT
  • North Adams, MA
  • Northampton, MA
  • Pine Plains, NY
  • Pittsfield, MA
  • Rhinebeck, NY
  • Sheffield, MA
  • Sherman, CT
  • Southbury, CT
  • Stockbridge, MA
  • Wassaic, NY

Check out our DAY TRIPS section for listings in these towns

  • Subscribe to our newsletter
  • Wright Electrical
    The Matthews Group HIH Ad
    Milton Market
    bantam frameworks
    Berkshire Place
    Wright Electrical
    Elyse Harney Real Estate
    Byrde + the b
    the smithy
    Karen Raines Davis
    salvatore anthony
    KMR Arts
    Haver & Skolnick
    George Home