"To those who opened up and developed the wonderful resources of
Middlebury, the present and coming generations will owe eternal gratitude."
Chapman's History of Elkhart County, 1881
The first settlers arrived in 1832. One can only try to imagine their delight as these adventurous people discovered the hilliest section of the country, resembling their native Vermont. Enoch Woodbridge is said to be the first settler, and he came from Middlebury, Vermont. He was followed closely by a few more families.
It was in 1835 or 1836 that John Holmes sold his farm to Mssrs. Brown, Winslow, and Warren, of Niles, Michigan. It was either they or a Mr. Crocker who laid out the town around a central square. Many fifty-foot lots were sold for $100 each.
The first school was said to have been held in the Solomon Hixon home before a little red frame schoolhouse was built in the northwest part of town.
Dr. Cornell was the first justice of the peace; later W.T. Hunter, who put up the first frame building, Hunter's Inn, was also a justice of the peace. George S. Sayer was the first merchant; other merchants of the pioneer village were John C. Case, Swan & Earl, who are said to have had the first store, and Charles A. and James S. Dole, who had for a short time a distillery near the Northup mill. Others were Chauncey Hascall and David Mather.
The first marriage was performed by the Rev. Ira Woodworth, the first preacher in the area, in 1835 or 1836. The first children born in Middlebury, were in 1835.
Other early settlers were Thomas Evans, Dr. Cephas Dunning, the first physician, Orange Walker, Stephen Durgin, China B. Smith, Samuel Reynolds, John Degarmo, and Albert Meade, and Squier Lee, a carpenter who came in 1839 and lived to be 100 years old.
By 1835, there was a desire for a railroad connection. One didn't reach Middlebury until 1888. After that, the town changed its completely agricultural identity to include industry. Krider's Nurseries and the Eclipse Tank Co., later to become Pioneer Mfg. Co., were founded.
By 1839, there were only twelve families living at the settlement. It is also said that Stephen W. Remele, who also came from Middlebury, Vermont, gave Middlebury its name. John C. Holmes and George A. Buffman, also from Middlebury, Vermont, were sons-in-law of Mr. Woodbridge and they erected log cabins on the site of the town. Cornelius Northup erected a sawmill near the present-day Middlebury-Shipshewana Road, which soon was converted to a flouring mill. This building is still standing in 2014, making it the oldest existing structure in the town.
Middlebury was incorporated as a town in June 1868 and the first town officers were: Watson Hutchinson, chairman; Thomas Naylor, Thomas Elliott, Christian Stutz, W.F. Hani.
The turn of the century was an exciting time for Middlebury, and there was an energy and excitement about the community which has prevailed to the present day. The population of Middlebury had grown to 572 by 1900. As of the 2020 Census, the population has grown to 3,466.