How do you become a travel writer? One way is to work for unsuccessful presidential candidates.
So began Roland L. Hill, who has been in the Berkshires for the past two weeks as he prepared the 10th edition of his travel guide, “Hillsway.”
Mr. Hill, a professional eater and sleeper who has left a trail of used napkins and sheets in these 50 states as well as abroad, met his life’s work while on trial for Wendell Wilkie, the man he tried to take down FDR in 1940.
Mr. Hill was a devout Democrat — still is, in fact — but he thought eight years rent-free in the White House was enough for anyone, even Roosevelt. He had become involved in politics in his native Minnesota and had become the national president of the Young Democratic clubs. As such, he was called to the White House to become secretary and served four years. When he joined Wilkie, he was sent around the country organizing Young Democrats for Wilkie clubs. He would send postcards from all over to Roosevelt’s chief secretary, Louis Howe. Howe wrote back to him, saying: “You’re living Rolly’s life, embarrassing Riley.”
When Wilkie went the way of Floyd Patterson, Hill returned to Minnesota to talk country, and while doing so wrote a book about his travels, using Howe’s joke as the title. It was called Living the Life of Rolly.
Then came the war, during which he was secretary to General Eisenhower. After the war, he returned to travel writing, publishing the following books and travel guides:
I Recommend, Las Vegas Recommend, Long Beach Recommend, Minnesota Recommend, Hillsway Guide to Las Vegas, The Best of Hillsway, and Hillsway.
Incidentally, Hill swears that both Wilkie and Eisenhower were Democrats. “Republicans”, he says, “take our best people when they want to win elections”.
The 10th edition of Hillsway will highlight New England, which Hill says is “the best spot in the country for summer.” Hill says he tries to include at least one location from every U.S. county in the book.
For Berkshire County, he listed: Berkshire Inn and Golden Eagle Motel in Great Barrington; Hotel Curtis in Lenox; Brookbend Inn and Sun-Inside in Monterey; Springs in New Ashford; Wendell-Sherwood, Heart of the Berkshires Motel, Town & Country Motor Lodge, Yankee Motel, Ida & John’s and Yellow Aster in Pittsfield; South End Barn and Egremont Tavern in South Egremont; Oak n’ Spruce in South Lee; Red Lion Inn in Stockbridge; and the 1896 Williams Inn and House in Williamstown.
This story in the story is selected from the archives of Jeannie Maschino, The Berkshire Eagle.