Teach for America, Frontier Edition

What two young society women dared, and learned, out West in 1916.

Dorothy Wickenden

Say you find a trove of crumbling, very old letters in the back of a desk drawer. The letters are from your grandmother, telling the folks at home about the year she and her best friend spent teaching school in a remote corner of Colorado in 1916. If you are a normal person, you read the letters, probably marvel at them, wish you’d asked your grandmother more questions about her life, futilely try to interest your husband in reading them, and then file them away. If you are Dorothy Wickenden, executive editor of The New Yorker, you write and publish Nothing Daunted: The Unexpected Education of Two Society Girls in the West.

The book raises an interesting question: What makes a story history rather than family history? Why should we bother about someone else’s family, commonplace people who lived long ago? Wickenden’s book also answers that question, offering a nice primer on how to write the history of ordinary life. Though the origins of the book are homely, Nothing Daunted deserves an audience beyond the folks gathered around the potato salad at the author’s family reunion.

That’s because Wickenden tells a great story, with a richly appealing character at the center of it—her grandmother and namesake, Dorothy Woodruff. It’s also because Wickenden understands—as writers of family history so often don’t—that her grandmother is not inherently interesting qua her grandmother. Vivid characters have to face conflict, and Dorothy Woodruff’s conflict was internal yet also historically resonant. She was a society girl with the heart of an adventurer. Her audacious heart inspired her to set out on the quintessential American journey: into the West.

Dorothy was a Smithie from the moneyed and even-then liberal bastion of Auburn, N.Y. So was her lifelong best friend, Rosamond Underwood, known to all as Ros. Once the two returned home from Smith, they were restless in their luncheon-heavy role as society girls. First they staved off boredom with a grand tour of Europe. They saw Nijinsky dance, visited exhibitions by the Impressionists, and rode the funicular to the Matterhorn. It’s irresistible, here, to imagine an alternative history, one in which Dorothy and Ros take a more Jamesian route and become title-seeking heiresses at large in Europe. Instead, they came home and followed their more American destiny.

Back in Auburn, after a bit of casting about for something to do, they undertook the unthinkable: They got jobs. Paying jobs. Not just as school teachers, but as school teachers in Elkhead, Col. A friend from college arranged an introduction to a Wellesley grad, Ruth Carpenter Woodley, whose brother was a homesteader in Elkhead. Woodley wrote to Dorothy and Ros, encouraging them to apply for jobs as Colorado school teachers, saying that if the two young women “would like to catch a glimpse of one of the last of our fast disappearing frontiers, I’d urge you to try it.”

In these opening sections of the book, Wickenden contrasts Dorothy’s background with the story of Ruth’s brother, Farrington “Ferry” Carpenter, the young rancher and lawyer who helped start the Elkhead school. In alternating chapters, she toggles between the girls’ story and his, deftly playing out very gendered scripts without ever reducing her particular characters to roles. Carpenter was a fascinating character; as a kid, he was sent from Evanston, Ill., to Santa Fe to take the sun cure and fell in love with the West. After attending Princeton, and Harvard Law School, he went out to Colorado and was homesteading by the time he was 20. While he was planting out his claim, irrigating his land, and raising Herefords, the Auburn girls were attending meetings of the Young Ladies Benevolent Association, marveling at the new novelty food, grapefruit, and looking for meaningful volunteer work.

On the Elkhead end of things, the town was getting ready for its new teachers. The Elkhead school was expressly built to attract more homesteaders to the area. The teachers were part of the lure. “[Carpenter] realized that if Elkhead created its own district and school board, they could recruit new teachers every year or two—supplying the children with instruction, the residents with a community center, and the cowboys with a steady influx of prospective brides.” So important was this match-making element of the school that the cowboys actually surveyed photos of the prospective teachers, gatekeeping with their libidos. Once they got a load of the photos of Ros (who was “voted the best-looking girl in the junior class of Smith College”), the Auburn girls were a shoe-in, even though neither had ever taught school.

And so they headed west. On the eve of their departure, the Syracuse Daily Journal ran a headline: “SOCIETY GIRLS GO TO WILDS OF COLORADO.” After a long train trip, Dorothy and Ros landed in Elkhead, just west of Steamboat Springs, Col., a high desert place of “sage and badlands.” In this unforgiving country, the women found friendship, hard work, heartache, and even a little cowboy love. Wickenden has the sense to pull as much plot as possible out of this slender story and turns her book into a gentle romance as well as a tale of the triumph of determination over adversity.

The author calls her book an “alternative Western,” but the values on parade here are timeworn American verities: pluck, loyalty, courage, and indomitable optimism. Dorothy seemed to like just about everything she saw in Colorado. She wrote of her new neighbors, “It is an entirely new type to me, for we never see such keen, receptive wide-awake intelligent people living such hard lives.” Where others might have found desolation, she and Ros consistently found something to admire. Here is Ros on her new place of work: “The schoolhouse stands high on a mountain or hill between the two districts called ‘little Arkansas’ and ‘Calf Creek.’ It is the Parthenon of Elkhead!”

Dorothy and Ros boarded with the Harrisons, a homesteading family whose house was uninsulated and had no interior walls. Dorothy wrote with characteristic humor, “This lends intimacy to an unimagined degree and you know it—every time any one turns over in bed, and it is especially sociable when the wind blows.” Mrs. Harrison cheerfully made do with very little, and stretched what she had to accommodate the young teachers.

What is alternative about this history is its lens, which is trained on a strain of feminine resilience that doesn’t often come into focus in accounts of the frontier. Mrs. Harrison was but one of a seemingly unending parade of remarkable women. Wickenden writes, “The state seemed to be full of tiny invincible women who never complained—a source of inspiration particularly to Dorothy.” The young women made friends with a wealthy rancher named Bob Perry; Perry’s sister Marjorie was a daredevil and a famous horsewoman and hunter; Perry’s other sister, Charlotte, helped start a bohemian dance camp high in the Rockies—where Agnes de Mille, John Cage, and Merce Cunningham eventually all taught. Everywhere Dorothy and Ros went, they found yet another woman shaping an unusual and difficult life. It’s fascinating to see the very American quality of rugged individualism germinating and growing not just in the men but in the women of the West.

Dorothy’s enthusiasm was constant. Sometimes it even feels teeth-grittingly determined, but that doesn’t make it any less infectious. One sunny winter day, she scribbled a letter to her mother: “This immense expanse of snow reflects the color of the sky—until it is really bluer than any Impressionist pictures I have ever seen.” There’s something wonderfully American about this moment, about the way she rejects the Impressionist masters in favor of the real-life skies of the West. Dorothy turns her gaze away from culture, away from Europe, away from civilization, toward the new country opening up before her. Here is the society girl, free at last of society.