H. H. Bregstone was one of the most prolific photographers of the early twentieth century. He crisscrossed the American Midwest, capturing small-town scenes in thousands of places and putting those images on real photo postcards. He was a traveling man, but he didn’t start this chapter of his life until he was in his forties. Bregstone’s story is so much more. He was the immigrant from the old country who embraced his new country in baseball and politics. He was the attorney who didn’t practice law. He was the soldier who didn’t fight. He was the husband who didn’t stay married. He was the religious man who was not observant. Meanwhile, other branches of his family rose to fame and fortune. He lived his life on the frontier wherever he could find it. He was always moving toward a new place, or perhaps he was always running from a past that occasionally caught up with him. He lived his life on the edge, and his life ended there too. Told for the first time, here is his life story, as well as an inventory of his work and a gallery of his craft.