Berkshire County: Welcome

The Berkshires have been a much loved getaway for Bostonians and New Yorkers for over a century. The colonial aesthetic takes you back to the 1700s when towns across the Northeast were first being built. The windy gravel roads are surrounded by forest opening occasionally into idyllic farm scenes with old red barns, hay stacks, and windmills.

In the fall, the entire landscape transforms into a magical palette of red, gold, and orange.

Painter Norman Rockwell created an image of the picture perfect American town while living and working in the county. He painted happy scenes of quaint communities; beautiful, brightly-lit homes, families spending time together, children playing, and couples falling in love.

Norman Rockwell's painting of the Berkshire town "Stockbridge" in wintertime

Years later, Folk Singer James Taylor was equally inspired by this charming place describing it in his famous song "Sweet Baby James" as "dream-like."

Samuel Herrup Antiques in Sheffield, Massachusetts

In addition to the beauty, The Berkshires boasts first-rate dining, museums, theatre, an annual film festival, a small ski slope, hiking, world-class antiquing, art studios and galleries, and a thriving local food scene with boutique grocers and farmers markets.

The Old Inn on the Green in New Marlborough

This week Backpacktress will explore all it has to offer and show you why it's worth a road trip next time you're on the East Coast.