And on Main Street of this small town of 2000 people, happens to be the Red Lion Inn, a 1773 two story tavern and stagecoach stop that has grown over the centuries, and in 1967 it became part of Norman Rockwell's 8 foot long painting, Stockbridge Main Street at Christmas
Which I only learned of last month,
http://justacarguy.blogspot.com/2020/03/wow-ive-never-seen-this-norman-rockwell.html but you can read all about it at
https://www.redlioninn.com/wp-content/uploads/2018/04/HuffPost-Norman-Rockwell-Holiday-at-The-Red-Lion-Inn.pdf
or any of the many prestigious magazines and newspapers that have featured it:
https://www.redlioninn.com/press/ including Conde Nast, Martha Stewart Weddings, Architectural Digest, Forbes, Boston Globe, and Wine Spectator.
The current owners have been running this hotel for the past 50 years, but it's one of the few American hotels to remain in constant operation since before 1800.
In 1775 Ethan Allen stopped in and bought a jackknife. Perhaps he was the first famous patron, but he was not the last. Longfellow was there on New Years Day 1857.
In the 20th century, they called the Red Lion the Inn of Presidents. Grover Cleveland, William McKinley, Theodore Roosevelt, William Howard Taft, Calvin Coolidge and Franklin Roosevelt stopped by, and signed the guest book. Maybe they spent the night, maybe they simply had a good meal at the inn.
Two of those presidents spent the night due to car troubles;
the night President William Howard Taft arrived at the inn “His Ford motor car broke down near Monument Mountain. He walked from that location to the inn.” - after the arduous walk, he stayed at the inn waiting until transportation was arranged.
President Theodore Roosevelt came to the inn during Sept 1902 when his carriage was hit on South Street. The president was not injured, but the first member of the Secret Service to guard a president was killed.
https://theberkshireedge.com/connections-the-red-lion-inn-guestbook-summons-history/
If you go through this little town, stop by the Norman Rockwell Museum, they have 998 of his original paintings