Some time around 1773, Anna and Silas Bingham established a general store in Stockbridge on the road that connected Boston to Albany, which soon evolved as a stagecoach stop, tavern and Inn, under the sign of the red lion. Travel at the time was difficult and uncomfortable, and the Bingham's little tavern quickly became a popular and welcome rest stop for bruised and battered travelers.

The Red Lion Inn also became the center of village life, where people could gather, exchange pleasantries, discuss the issues of the day and relax at the end of the day. In the winter of 1786, Daniel Shays led a group of more than 100 local farmers and citizens in protest to British oppression and unfair taxation. Stockbridge was chosen as its headquarters for what became known as "Shays Rebellion," and sentinels stood on guard and patrolled the streets. The Red Lion Inn's participation in these early events in the birth of the United States has earned it a place in the history books.

In 1807, the now "widow" Bingham sold her Inn for the sum of $10,000 to Main Street store owner Silas Pepoon. Today, Mrs. Bingham's role at the Red Lion is commemorated in the popular Widow Binghams Tavern. In her day, the Inn was much smaller than it is today, consisting of only eight rooms, with low ceilings, massive beams and posts. On cool days, a fire always blazed in the hearth to welcome chilly travelers and townspeople alike. In a publication issued in 1903, Allen T. Treadway, then the owner of the Inn, had this to say: "The bar room was naturally the main feature of the Tavern. The original house consisted of the public rooms on the ground floor, perhaps eight bedrooms upon the first floor and a ballroom on the upper floor."

As time went on, the Inn changed hands many times. In 1862, Charles H. Plumb and his wife Mert (for whom the charming Plumb Room was named) bought the Inn and began a ninety-year family management dynasty. In 1893 the Inn's operation was taken over by Mr. Plumb's nephew Allen T. Treadway, aided by his assistant James H. Punderson, whose daughter Molly later became the third wife of famed illustrator Norman Rockwell.

Through the years, as so many changes were taking place at the Inn, the little town of Stockbridge changed, too. Early in the nineteenth century the area was mostly a farming community, with a few small factories in nearby towns. Patrons of the Inn and its Tavern in those days were hardy travelers of the stage coach era, local farmers and landowners.

By mid-century, Stockbridge had been "discovered" by wealthy families who came to escape the hustle-bustle and grit of city life. They built their "cottages," really very grand homes, and settled in to enjoy the "bucolic ambience" of the area. The arrival of the Housatonic Railroad in 1842, and its extension to Pittsfield in 1850, had made the town easier to get to, and Stockbridge was no longer isolated from the outside world.

The establishment of a literary colony in Lenox and Stockbridge brought further changes to the area and, in 1848, the Stockbridge House, as The Red Lion Inn was then known, expanded its facilities with an addition in order to accommodate the many new visitors. In 1884, the Inn was enlarged again and could now accommodate more than 100 guests. As the Inn grew, the quality of amenities and food it offered improved and the Inn was able to satisfy the more sophisticated tastes of its "city-folk" guests.

By this time, there was increased appreciation for the kinds of antique furniture, crockery and pewter that could be found at the Inn. To add to the collection, his wife, Mert, published a standing offer of "50 cents for a pitcher, $1.00 for an antique mirror." She was often seen scouring the countryside in search of fine antiques to furnish the Inn, which had been renamed Plumb's Hotel. Many of the teapots and fine antique furnishings seen in The Red Lion Inn today are from Mrs. Plumb's original collection.

After the last of Mr. Treadway's improvements were completed, on August 31, 1896, there was a fire that almost destroyed the hotel. As reported in the Pittsfield Sun, it originated in the pastry kitchen. When the fire could not be contained the fire department was called.

The Berkshire Courier in Great Barrington reported that "Mrs. Plumb's noted collection of colonial china, pictures, wearing apparel and furniture, the largest of its kind in the country, and the delight of everyone who went to Stockbridge, was saved. A few pieces were broken but in the main the collection was intact."

Mr. Treadway undertook the restoration of the inn and in early May 1897, The Valley Gleaner in the nearby town of Lee announced that "Red Lion Inn was opened to the public last Friday evening [April 30, 1897], when several out of town guests took tea and spent the night there. Red Lion Inn never looked so handsome as it did after the entire building had been lighted up and many people were out in the streets to see the pretty sight. Just eight months from the time the old inn went up in smoke and ashes the new one was opened."

In 1904, Mr. Treadway was elected to the Massachusetts House of Representatives, where he served for four years. He was elected to the state Senate in 1908, where he served as president of that body for three successive years, and in 1913 was elected congressman from the First Massachusetts District, serving until 1944.

From The Red Lion Inn's inception until it was leveled by fire, its crest was a red lion waving a green tail. It is believed that while the red lion was symbolic of the Crown, the green tail indicated sympathy for the colonists during the Revolutionary War. At its rebirth in 1897, Mr. Treadway unveiled a new crest in the form of a shield. At the top were a lion and the two dates, 1773 and 1897, indicating the birth and rebirth of the Inn. Within the body of the shield were a teapot, plate, Franklin stove, highboy, clock and two large keys, representing the Inn's fine collection of antiques. In the early 1920s the shield was replaced with the traditional lion that we see today, plump and well fed, to indicate the high quality of food served at the Red Lion, and now sporting the familiar red tail.

In November 1968, the Inn was slated for destruction to make room for a gas station. It was rescued by John and Jane Fitzpatrick, the founders of Country Curtains, a mail order business selling old-fashioned muslin curtains. They originally planned to use part of the main dining room and most of the kitchen for Country Curtains growing business. They became so taken with the Inn and its history that they decided to continue its operation as an Inn, rather than solely a home for Country Curtains.

The Fitzpatricks installed a large new kitchen and dining room. Part of a former lounge became the Widow Bingham's Tavern. All the public rooms were redecorated to better compliment the Inn's wonderful collection of antique furniture, china and pewter. Especially dear to Mrs. Fitzpatrick's heart is the charming collection of teapots on permanent display throughout the Inn. On May 29, 1969, The Red Lion Inn was opened for year-round business for the first time.

Beginning in 1974, several neighboring buildings were purchased and converted into guesthouses, including the former village Firehouse, which is the most popular of all the accommodations in the Inn. Mr. Fitzpatrick served four terms as Massachusetts State Senator, from 1972 to 1980, and once again The Red Lion Inn became the center of political activity in Berkshire County. The Inn is now owned and operated by their daughter, Nancy.