Uncovering the long history of the Lewis Flynn house

I should men­tion at the out­set that the Lewis Flynn House is no longer stand­ing, but may still be recalled by some of our old­er cit­i­zens. The unoc­cu­pied res­i­dence burned to the ground in the fall of 1976. This very ear­ly house has been includ­ed in this series due to its long and inter­est­ing his­to­ry. The last res­i­dent, Lewis Baldwin Flynn (1896−1970), acquired the house in 1947 from his moth­er, Ella Flynn, and lived there with his fam­i­ly until about 1963.

Architectural his­to­ri­ans report­ed that in the ear­ly 1900s Ella Flynn remod­eled the house in the bun­ga­low style, adding a mas­sive shed dormer and a wide porch with over­hang­ing eaves. The house had four rooms on the first floor with a kitchen wing behind, pre­sum­ably detached at one time. A res­i­dent in the 1870s or ’80s added a heavy brack­et­ed cor­nice to the front door, and pre­vi­ous own­ers had remod­eled the inte­ri­or, replac­ing the wood­work with Greek Revival trim. After the fire, the five stand­ing chim­neys gave a more accu­rate age of the house than the much-altered exterior.

Lewis B. Flynn had a long and var­ied career. He grew up on his father’s farm, attend­ed high school at Bingham Military Academy in Asheville, North Carolina, and grad­u­at­ed from the University of Virginia, Class of 1915. Back home, he became one of Winchester’s ear­ly auto deal­ers (1916−1920). As the local agent for Hupmobiles, he would trav­el to Detroit and bring cars back for buyers.

His car sales were inter­rupt­ed by ser­vice dur­ing World War I. He was draft­ed in May 1917. The war end­ed in November 1918 and Lewis received his dis­charge from the U.S. Navy in December. The fol­low­ing August, he mar­ried Mary Elizabeth Dooley.

In 1920 Lewis opened Cloverdale Dairy at the cor­ner of Euclid and Boone Avenue. The cows were raised on his own farm and he was list­ed in the city direc­to­ry as a dairy­man. Then in 1931 Lewis received a per­mit for a new build­ing at the cor­ner of Euclid and Boone and soon opened a con­fec­tionary shop/restaurant. Flynn’s became a pop­u­lar hang­out for high school kids known for its ham­burg­ers, milk­shakes, juke­box and dance floor. Flynn’s closed after an explo­sion dam­aged the build­ing in 1954.

By that time, Lewis had embarked on a new busi­ness ven­ture. In 1949 he opened a night­club at the cor­ner of Cherry and Sycamore streets called the Old Silo, near a silo on his farm. By the fol­low­ing year it was just “The Silo.” The enter­tain­ment des­ti­na­tion, styled as Flynn’s City Heights, offered a dri­ving range, fish­ing lake, restau­rant and danc­ing venue. They served “steak and chick­en din­ners and beer with atmos­phere.” Several nights a week The Silo held dances with live music by the Blue Grass Rhythmaires, Bob Eckler and the Mel-O-Tones, Tag Vail Trio and others.

In the 1950s and ’60s the club was leased out to a series of man­agers and became the scene of fre­quent dis­tur­bances and shoot­ings. The most seri­ous came in 1972. In February three men were wound­ed in a shootout, in April a for­mer deputy sher­iff was shot, then in September a patron was shot to death in the club. That December the club was gut­ted by fire and nev­er reopened.

Lewis was heav­i­ly involved in local real estate devel­op­ment over the years, espe­cial­ly in the North Park area where he owned numer­ous build­ing lots, which he offered for sale. Here he had the Silo club, rental prop­er­ty and a small trail­er park. North Park includ­ed the area rough­ly bound­ed by Maple, Holly, Oak and Sycamore streets. He also sold a num­ber of farms he had inher­it­ed from his parents.

After 25 years of mar­riage, Lewis divorced his wife Elizabeth and the fol­low­ing year (1946) mar­ried Eugenia Bishop. Shortly after this, the cou­ple took up res­i­dence in the Flynn House, the sub­ject of this arti­cle. In 1963 the cou­ple moved to Oakwood, the famed Alpheus Lewis estate at Wades Mill.

Lewis B. Flynn passed away in 1970 leav­ing two sons, Lewis Jr. and John.

I’d like to extend my thanks to Kyle Flynn for pro­vid­ing infor­ma­tion for this arti­cle. He is the son of Lewis Flynn Jr. and grand­son of Lewis Sr.

Note: The Hampton Bush House is locat­ed at 11 Boone Avenue. The loca­tion of today’s mys­tery house will be revealed in next week’s article.

More photos (click to enlarge)