STOP 01
16 Church St, Lenox, MA 01240
Dating to the 1770s, The Whitlock began as the farmhouse of early Lenox settler John Whitlock, who opened his home as an inn for travelers. But Whitlock adds an intriguing twist to the Revolutionary story—he remained loyal to the British Crown while rebellion spread throughout the colonies. He eventually sold his extensive Lenox holdings and left for Canada. Today, the property offers a fascinating connection to a time when the Revolution divided not only a nation, but neighbors and communities throughout New England.
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STOP 02
101 N Main St, Sandisfield, MA 01255
The New Boston Inn traces its tavern roots to the mid-1700s and the family of Captain Daniel Brown, an early Sandisfield settler and colonial militia officer who operated a tavern here. During the Revolutionary era, soldiers trained on the property, adding to the inn’s remarkable early-American history. The old tavern also carries one of the Berkshires’ best-known legends—the tale of Harriet, a young bride said to have been murdered here by a jealous former suitor. For generations, unexplained footsteps, voices, and music have been attributed to Harriet’s lingering spirit.
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STOP 03
134 Hartsville–New Marlborough Rd, New Marlborough, MA 01230
Built in 1760, the Old Inn on the Green was welcoming travelers sixteen years before the Declaration of Independence. The inn served as a tavern and stagecoach stop along an important inland route connecting Hartford and Albany, offering weary travelers food, drink, lodging, and news from beyond the Berkshire settlements. More than 260 years later, its candlelit rooms, fireplaces, wide-plank floors, and old tavern atmosphere offer a remarkably evocative glimpse into the experience of an early New England inn.
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STOP 04
854 S Undermountain Rd, Sheffield, MA 01257
Hidden beneath Mount Race in Sheffield, the Stagecoach Tavern at Race Brook Lodge preserves the character of the roadside inns and taverns that once welcomed travelers through the Berkshire countryside. Hand-hewn beams, wide-plank floors, fireplaces, and intimate tavern rooms recall an era when a journey through western Massachusetts meant long days on horseback or by coach. Here, the attraction isn’t a famous name or grand historical event—it is the feeling of an old Berkshire tavern, where travelers once gathered around the fire to eat, drink, and exchange stories from the road.
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STOP 05
30 Main St, Stockbridge, MA 01262
The Red Lion Inn’s tavern tradition reaches back to the eve of the American Revolution, when Stockbridge residents gathered in local taverns to debate the growing conflict with Great Britain. In July 1774, townspeople gathered at the tavern associated with today’s Red Lion Inn to condemn Parliament’s Intolerable Acts and pledge their support for a boycott of British goods. The gathering occurred nearly two years before independence was declared, making this more than simply an old inn—it was part of the community conversation that accompanied America’s march toward Revolution.
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FROM THE BERKSHIRES
A visual ledger of Berkshire taverns, country roads, and the places that carry the story forward.
