Each Memorial Day, we pause to honor those who served and sacrificed so we might live in freedom. In our family, the Woolsey name carries with it a deep legacy of courage, duty, and devotion to both country and kin. This year, we reflect on the men in our Woolsey line who answered their nation’s call—not just in one generation, but across two defining wars in American history. Private Daniel Woolsey – Revolutionary War PatriotBorn in colonial New York, Daniel Woolsey served as a Private in the 3rd Regiment of the Ulster County Militia during the American Revolution, under Colonel John Cantine. He was the son of Henry Woolsey, who also served in the same regiment, making theirs a proud father-son legacy of service to the emerging nation. After the war, Daniel built a life with Ann Halstead, and together they helped settle new lands, moving westward to Ohio around 1829 or 1830. They made the journey in a wagon driven by a future in-law, with Daniel’s elderly mother and his invalid sister-in-law traveling alongside them—a reflection of the family’s enduring commitment to one another. It was a difficult journey, but one undertaken with grit and grace. The 1790 census shows Daniel living in Half Moon Town, New York, with his growing family. But it was not just land he helped build—he helped build a country, fighting for its independence and then carving out a new life in its frontier. He was not a famous general or a man of wealth, but he served. He showed up. He gave what he could for the cause of liberty, and for that, we remember him. Richard Woolsey – Grandson of a PatriotOne of Daniel’s grandsons, Richard Woolsey, is the central figure in my book His Greatest Regret. Born in 1826 in Ulster County, New York, Richard was just a toddler when his grandparents, Daniel and Ann, moved west to Ohio. He may have known his grandfather briefly as a young child—perhaps even shared his lap or listened to his stories—though it’s unlikely he remembered much after they parted. Travel across that kind of distance was no small thing in those days, and visits would have been rare. Still, the legacy of Daniel’s service likely shaped the Woolsey family values that Richard inherited—duty, perseverance, and deep ties to both land and family. In His Greatest Regret, Richard’s life becomes a story of chasing dreams, facing hard consequences, and wrestling with the question of what it means to be a father and a man of honor. These are the same questions his grandfather would have faced in very different times. Generations of Service and StrengthFrom Daniel and his father Henry, who stood at the cradle of American independence, to Richard, who lived in the shadow of their legacies while forging his own path—the Woolseys remind us that history is shaped not just by the battles won, but by the values passed from one generation to the next. This Memorial Day, we remember them not just as soldiers, but as real men with real stories—farmers, fathers, dreamers, and defenders of freedom. But always it is rooted in love—for God, Country, family, and for the hope of a better tomorrow. Let me know if you'd like this adapted for your newsletter or for Instagram/Facebook again! |
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