“The present and future generations will forever be indebted to those visionary individuals who ventured into the beautiful landscapes of Middlebury, unearthing its abundant resources and unlocking its true potential.” – Chapman’s History of Elkhart County, 1881

In the year 1832, the first pioneers arrived in Middlebury, their hearts brimming with anticipation. The undulating terrain of this region, reminiscent of their beloved Vermont, brought them immense joy. Enoch Woodbridge, hailing from Middlebury, Vermont, is attributed as the initial settler, followed closely by several other families.

Around 1835 or 1836, John Holmes sold his farm to Mssrs. Brown, Winslow, and Warren from Niles, Michigan, or possibly Mr. Crocker. It was they who, along with Mr. Crocker, laid out the town, creating a central square. Numerous fifty-foot lots were sold for $100 each.

Before a small red frame schoolhouse was erected in the northwest part of town, the first school was said to have been conducted in the Solomon Hixon home.

Dr. Cornell served as the first justice of the peace, succeeded by W.T. Hunter, who constructed the town’s inaugural frame building, known as Hunter’s Inn, and also held the title of justice of the peace. George S. Sayer established himself as the pioneer merchant, joined by other enterprising merchants like John C. Case and Swan & Earl, who are reputed to have operated the first store. Charles A. and James S. Dole briefly ran a distillery near the Northup mill. Additional merchants included Chauncey Hascall and David Mather.

The first marriage ceremony, conducted by the Rev. Ira Woodworth, Middlebury’s inaugural preacher, took place in 1835 or 1836. The first children born in Middlebury arrived in 1835.

Among the early settlers were Thomas Evans, Dr. Cephas Dunning, the first physician, Orange Walker, Stephen Durgin, China B. Smith, Samuel Reynolds, John Degarmo, Albert Meade, and Squier Lee, a skilled carpenter who arrived in 1839 and lived to be a centenarian.

By 1835, there arose a yearning for a railway connection, which would not reach Middlebury until 1888. With the advent of the railway, the town underwent a transformative shift from its predominantly agricultural identity to embrace industry. Krider’s Nurseries and the Eclipse Tank Co., which later became Pioneer Mfg. Co., were established.

In 1839, merely twelve families resided in the settlement. It is also believed that Middlebury acquired its name from Stephen W. Remele, another settler from Middlebury, Vermont. John C. Holmes and George A. Buffman, both hailing from Middlebury, Vermont, were sons-in-law of Mr. Woodbridge, and they constructed log cabins on the town site. Cornelius Northup erected a sawmill near the present-day Middlebury-Shipshewana Road, which was later converted into a flouring mill. Remarkably, this structure still stands today, making it the oldest extant building in the town as of 2014.

Middlebury was officially incorporated as a town in June 1868, with the following individuals serving as the first town officers: Watson Hutchinson, chairman; Thomas Naylor, Thomas Elliott, Christian Stutz, and W.F. Hani.

The turn of the century brought an exhilarating period for Middlebury, brimming with energy and enthusiasm that persists to this day. By 1900, the population of Middlebury had grown to 572.

2020 Census

As per the 2020 Census, the population has further expanded to 3,466, symbolizing the continued growth and prosperity of the community.