One of Webster's earliest residents was Nathan D. Allen. He bought his first properties in Webster before 1862. He was instrumental in developing the first buildings in Old Webster.

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Born May 15, 1819 at Watkins Glen, New York, he came to St. Louis in 1837 in company with 250 Indians, who were being removed from the Western Reserve to Indian Territory. There being no Western railroads at the time, the trip was taken down the Maumee River and Lake Erie to Cleveland, then to Portsmouth on the Ohio and Mississippi- a twenty day trip of 1,500 miles.

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He married Caroline Adams in 1841 and moved his wife and their family of 5 children to their new residence on 23 West Lockwood Avenue in Webster Groves on October 18, 1866. Nathan Allen helped found the public schools in Webster Groves as well as the Congregational Church.

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In 1879 he became one of the owners of The Oak Hill Cemetery in Kirkwood which had gone into bankruptcy and was listed as it's secretary until his death.

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In an 1884 article in the St. Louis Post Dispatch Mr. Allen was described as a frequent buyer of tax lien properties in the city of St. Louis. He also had invested in a quarry that went bust.

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In 1888 he built the house next door to his family residence at 17 West Lockwood Avenue and sold it to Charles W. Ferguson.

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In the early years in Webster he built a large building at the SW corner of Gore and the Pacific RR Tracks. It was a three-story brick building and covered the entire block. In a February 10, 1899 newspaper story, it was described as the largest building in Webster. It was called the Allen Building and housed a drug store, a grocery, hardware store, barber shop, a notions store and a bakery run by his son, Harry Allen. Nathan was fond of music (two of his daughters taught music lessons as well) so he incorporated a music hall on the third floor to present music programs. The building burned on Friday February 10th 1899 in a horrific fire that threatened to burn all of Old Webster. The bucket brigade was augmented by a horse-drawn water wagon from the City of St. Louis which saved the day.

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His personal diary describes a meeting with President-elect Lincoln on a train in 1860 and how he looked quite different in person. Ragged and rough. He also traveled quite a bit, was interested in the weather and several times mentioned how he was in despair over the amount of his personal debt. He was a risk taker and successful entrepreneur.

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Mr. and Mrs. Allen celebrated their 60th wedding anniversary in 1902 with a big party hosted by their children. The newspaper story in the St. Louis Republic described the couple as "still active."

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Nathan D. Allen passed away on May 9th, 1903 at the age of 85.