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Occupying a prominent corner on Main Street, Stockbridge’s Red Lion Inn features a wide front porch that is a favorite spot to see and be seen.

Red Lion Inn

The founding date of the venerable inn in Stockbridge, Massachusetts is likely 1773, when Silas Pepoon established a small tavern here, under the sign of the Red Lion. A welcome stop on the long, dusty road from Albany to Boston, Mr. Pepoon’s establishment was also an attractive gathering place for angry citizens protesting England’s oppressive Acts of Intolerance. They pledged to boycott British goods and added to the Revolutionary fervor spreading through the Massachusetts Bay Colony. From day one, the Red Lion Inn played a primary role in the life of the surrounding community.

The Inn’s fortunes rose and fell throughout the 19thcentury. The nadir was an 1896 fire that destroyed the entire building. Rebuilt the following year on the same footprint, it was again furnished with a vast collection of antiques that had been saved from the fire by helpful townspeople. Those antiques still grace the inn today.

In 1969, Jane and Jack Fitzpatrick, owners of Country Curtains, bought the Red Lion Inn and moved their business there. The Fitzpatricks saved the inn from demolition, preserving a historic building while providing Country Curtains with more space.

While Country Curtains closed in 2017, the Red Lion Inn has flourished. Descendants of the Fitzpatricks today own the last of the 19thcentury hotels that once dotted the Berkshires; this is one of the few American inns that have operated continuously since before 1800. Today, the Red Lion Inn not only includes the rambling wood frame hotel overlooking Main Street, but a number of additional buildings containing guest rooms.

The inn has hosted five presidents and a long list of celebrities including Bob Dylan and John Wayne. James Taylor sang about it and Stockbridge resident Norman Rockwell painted it in 1967. The Red Lion Inn continues to be a favorite lodging site for visitors to Tanglewood, the summer home of the Boston Symphony Orchestra, as well as to the many Berkshires-area cultural and historic attractions, including the Norman Rockwell Museum. 

This year, the Red Lion Inn commemorates the 50 years since its purchase, rehabilitation and reopening as an historic hotel by Jane and Jack Fitzpatrick. A series of celebrations, special events, and packages for guests will be offered for the occasion.

“The Red Lion Inn has been operating for more than 240 years, but this last chapter has been our family’s contribution to its ongoing stewardship,” said Sarah Eustis, third-generation owner and operator as CEO of Main Street Hospitality. “This is a celebration of the vision of Stockbridge as a vibrant, vital and creative community for residents and visitors that Jack and Jane Fitzpatrick had when they bought the hotel and reopened it 50 years ago this May.”