A Walking Tour of Stockbridge, Massachusetts

There is no better way to see America than on foot. And there is no better way to appreciate what you are looking at than with a walking tour. Whether you are preparing for a road trip or just out to look at your own town in a new way, a downloadable walking tour is ready to explore when you are.

Each walking tour describes historical and architectural landmarks and provides pictures to help out when those pesky street addresses are missing. Every tour also includes a quick primer on identifying architectural styles seen on American streets.

Stockbridge is the second oldest town in the Berkshires, after Sheffield, established in 1834 as a mission for the Mahican Indian tribe. Their missionary was a Yale reverend named John Sergeant and under his guidance "Indian Town" was a great success and Stockbridge, named for the town in Hampshire, England from which the mission hoped to elicit funds, was incorporated as a town in 1739. Unfortunately Sergeant would live only a decade longer and relations with the Stockbridge Indians deteriorated rapidly. By 1785 their land was sold and the impoverished tribe was led out of the Berkshires - by a son of John Sergeant - to Oneida County, New York where they would gain some notoriety through the writings of James Fenimore Cooper.

The town was little noticed for its first 100 years until the railroad arrived in 1850. But unlike other towns where the Iron Horse brought industry and commerce, to Stockbridge it brought wealthy New Yorkers looking to escape the stale summer air. They built impressive "Berkshire cottages" around town and in America's Gilded Age the town gained a reputation as the "inland Newport." In 1853 America's first village beautification organization, the Laurel Hill Association was formed and continues to this day.

The town gained a reputation as a mecca for writers and artists and it turned out that it would be a magazine illustrator would ingrain Stockbridge into the national psyche. Norman Rockwell spent the final 25 years of his life in Stockbridge, using the downtown scenes for his cover paintings in the Saturday Evening Post and others. And ever since the town has taken pains to insure that those indelible images are not going to go away anytime soon.

Our walking tour will begin off Stockbridge's busy Main Street and down by the meandering Housatonic River where there is a small park and space for cars and we'll head up into the town to see why Rockwell once declared, "Stockbridge is the best of America, the best of New England"...