When my mother-in-law died, my father-in-law “gifted” us the timeshare they had purchased in the Poconos. Honestly, I didn’t spend a lot of time researching lodging options. It’s hard to believe that these mountains which, for the most part, are little more than rolling hills today were once almost as high as the Himalayas! Culturally, the Berkshires have been a haven for progressive thought the first successful lawsuit brought by a slave for her (!) freedom took place in Sheffield, MA in 1781 and the founders of the Women’s Rights movement and the NAACP were born in Adams and Great Barrington, MA respectively – all in the Berkshires. Geographically and geologically speaking, the Berkshires are a continuation in western Massachusetts and Connecticut of the Green Mountains of Vermont. If you would like to write about your recent travel experiences on The Flight Deal, submit your pitch here. Jim “The Travel Organizer,” who last wrote about Portland, Oregon, The Road to Hana, Maui’s “upcountry“, Hong Kong, Austin, San Antonio, Valley of Moon, California, Dubrovnik, Croatia, Split, Croatia, Krk, Croatia, Koper, Slovenia, Mendocino County, California, Auckland, Oslo, the small German town of Speyer and Deidesheim, Oahu, Napa Valley, Venice, Singapore, Bangkok, Sonoma County and Myrtle Beach, and here are his tips should you decide to visit The Berkshires. On a typical Summer weekend, the chances of you running into a New Yorker in the Berkshires for the weekend is pretty high. This site does not include all financial companies or all available financial offers. This compensation may impact how and where links appear on this site. This site is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as.