Eagle Archives, Aug. 8, 1963: Travel writer, courtesy Wilkie and Ike | History

How do travel writers get to be travel writers? One way is to work for unsuccessful presidential candidates.

That’s how Roland L. Hill, who’s been in the Berkshires the past couple of weeks while preparing the 10th edition of his travel guide, “Hillsway,” got started.

Mr. Hill, a professional eater and sleeper who has left a trail of used napkins and bedsheets throughout these 50 states as well as abroad, met his lifework whilst hitting the trial for Wendell Wilkie, the man who tried to unhorse F.D.R. in 1940.

Mr. Hill was a devout Democrat — still is, in fact — but he felt that eight years’ free rent in the White House was enough for any man, even Roosevelt. He had started in politics in his native Minnesota and had become national president of the Young Democrats clubs. As such, he was called to the White House to become a secretary, and served four years. When he bolted to Wilkie, he was sent around the country organizing Young Democrats for Wilkie clubs. He would send back postcards from all over to Roosevelt’s chief secretary, Louis Howe. Howe wrote him back, saying “You’re living the life of Rolly, putting Riley to shame.”

When Wilkie went the way of Floyd Patterson, Hill went back to Minnesota to rusticate, and while doing so wrote a book about his travels, using Howe’s quip as the title. It was called “Living the Life of Rolly.”

Then came the war, during which he was secretary to Gen. Eisenhower. After the war, he went back to travel writing, publishing the following travel books and guides:

“I Recommend,” “In Las Vegas I Recommend,” “In Long Beach I Recommend,” “In Minnesota I Recommend,” “Hillsway’s Guide to Las Vegas,” “The Best of Hillsway,” and “Hillsway.”

Incidentally, Hill swears that both Wilkie and Eisenhower were Democrats. “The Republicans,” he says, “take our best men from us when they want to win an election.”

The 10th edition of “Hillsway” will emphasize New England, which Hill says is “the top spot in the country for the summer.” Hill says he tries to get at least one place from every county in the U.S. into the book.

For Berkshire County, he has listed: Berkshire Inn and Golden Eagle Motel in Great Barrington; Curtis Hotel in Lenox; Brookbend Inn and Sun-Inside in Monterey; the Springs in New Ashford; the Wendell-Sherwood, Heart of the Berkshires Motel, Town & Country Motor Lodge, Yankee Motel, Ida & John’s, and the Yellow Aster in Pittsfield; Jug End Barn and Egremont Tavern in South Egremont; Oak n’ Spruce in South Lee; Red Lion Inn in Stockbridge; and Williams Inn and the 1896 House in Williamstown.

This Story in History is selected from the archives by Jeannie Maschino, The Berkshire Eagle.