About Connections: Love it or hate it, history is a map. Those who hate history think it irrelevant; many who love history think it escapism. In truth, history is the clearest road map to how we got here: America in the twenty-first century.
Some visits hardly made a blip on the media radar and other visits left a lasting impression when First Ladies came to the Berkshires.

In 1886, President Cleveland married his ward, Frances Folsom. She and Flora Paine Whitney were great friends. In the summer of 1888, while Secretary of the Navy, William Collins Whitney suffered the heat of Washington D.C., Flora moved with the children to Lenox. She rented Ventfort and presided over one of the most important social events of the season, a lawn and archery party for two hundred women.
“The piazzas were laid with Turkish carpets and the music was supplied by a mandolin band from New York.” There was food and flowers spread over the lawn.
Flora’s intent was to invite the First Lady to the festivities and then to stay, but Whitney wrote to Flora warning her not to invite Mrs. Cleveland to Lenox that season. The President was suffering bad press, and Cleveland was afraid that the sumptuous entertaining of the Whitney’s, prominent members of “the 400,” would further alienate some voters.
Cleveland’s concerns were valid. Cleveland lost the election, and Frances was free to visit Flora. She was an annual guest of Flora’s in Lenox from 1889 until Cleveland was again elected President in 1892. After that, President and Mrs. Cleveland were guests in Tyringham both because Flora died in the winter of 1893 and because Tyringham was not considered as fancy and therefore not as potentially off-putting to voters as Lenox was.

Throughout his Presidency (1897 – 1901) President William and Mrs. Ida Saxton McKinley visited Berkshire County. They were guests of the Plunkett family and dined with Joseph Choate at Naumkeag and the Sloane family at Wyndhurst.
At Wyndhurst, an overzealous hostess fashioned a centerpiece rigged to explode into red white and blue roman candles. Intended to trigger oohs and ahhs, it triggered a petit mal. Mrs. McKinley was an epileptic.
Grace Goodhue Coolidge visited Pittsfield in the 1940s to shop – what an impressive picture that paints of shopping on North Street — and attended performances at Tanglewood.
In 1950, Eleanor Roosevelt attended a concert at Tanglewood to narrate Peter and the Wolf under Maestro Serge Koussevitzky’s direction. She stayed at the Curtis Hotel, and Carl Grosser, chef at the Curtis, had the honor of preparing her dinner.
Fans and press were in the lobby at the foot of the grand staircase waiting her decent from her room to the dining room. There was no sign of her.
Climbing the back stairs on her rounds, a hotel housekeeper was stopped in her tracks. There was Eleanor Roosevelt descending the servant’s staircase.

“Can I get quietly to the dining room from here?” The former First Lady asked.
In an expression of the correctness of things, the housekeeper replied, “Oh Madam, you can’t be using the back stairs. It won’t do for you to come this way.”
The women looked at each other, then Eleanor Roosevelt went back up the servant’s stair, and down the grand staircase into the midst of adoring citizens and press.
Earlier that day, the former first lady rehearsed with the orchestra. As Roosevelt read in her cut-glass accent and high, fluting voice, Koussevitzky, of all people, turned to the concertmaster Richard Burgin and whispered in Russian, “Doesn’t she speak English?”
The Berkshires was, all in all, a unique experience for the great lady.
The Curtis was a successful business on Main Street Lenox from its days as a stage- coach inn. It took clever management and moving with the times to remain in business from stagecoaches to trains to automobiles. As Tanglewood and the Berkshire Music Center became a permanent part of the Berkshire landscape, the Curtis devised a way of extending its reach. Using a school bus, idle in the summer months, the Curtis packed the bus with food and drink, hung a sign on it that read “Food Bus,” and drove to Tanglewood. The grounds crew at Tanglewood built a u-shaped ramp. The bus backed into the ramp and opened all the windows. Students and staff would circle around the bus on the ramp and buy lunch passing food and money through the windows. Among those in line for a sandwich and a cold drink was Eleanor Roosevelt.

That was lunch with Eleanor. At the other end of the financial continuum, in 2012, there was dinner with Michele. During President Obama’s bid for re-election, Michele Obama made a campaign stop in the Berkshires. There were grumbles and groans about the price of admission to meet the First Lady at the Colonial Theatre. Tickets started at $125. That may have been too rich for some folks in Berkshire County, but it was bargain basement compared to what came next. That night, at Governor Deval Patrick’s Richmond home, a place at the dinner table cost $20,000.
Bess Truman was at least in Union Station Pittsfield during Harry Truman’s “Whistle Stop” campaign. Laura Bush, a librarian, arrived to celebrate acquisition of the 2,600 volumes in the Edith Wharton library.
Possibly the most impactful visit to Berkshire by a First Lady happened in 1998. She was hours late as people stood in front of Miller’s store (soon to be the Colonial Theatre) awaiting the arrival of First Lady Hillary Clinton. Her visit was so important because of her commitment to “America’s Treasures” – saving the country’s historic architecture. There was a $400,000 grant to help restore the Colonial Theatre to its former splendor. Then Clinton was on to The Mount to present a $2.9 million challenge grant to assist in that restoration. Her visit bolstered restoration of two iconic structures in the Berkshires.