UPDATED May 30, 2020
As far back as 1891 there was the idea of a town in the region of Asheville. Former Pennsylvania State Senator Jos. M Gazzam petitioned the North Carolina State Legislature to establish the town of Kenilworth by act of the legislature and an idea was born.
James Madison “Jake” Chiles, was a wealthy furniture merchant who moved to Asheville in 1908. He became inspired to rebuild the Kenilworth Inn when it burned down in 1909. He and some other partners, including EG Hester and Roland Wilson founded the Kenilworth Development Corp with Hester as president. Chiles and his company bought the old Patton Farm and began to build his dream. Inspired by a novel “Kenilworth” by Sir Walter Scott, Chiles named the streets accordingly. He fought to have a lake created on the 112-acre property (his partners wanted a golf course), but Chiles won out building the 50 foot dam to create the lake with a partner, Dr. H.H. Briggs at a cost of $108,000. However, he was dissuaded from placing a replica of Excalibur in a stone by the lakeside.
When the developers and the engineers disagreed on the plans to lay out the streets of Kenilworth, Chiles took his horse, Frank up the hill and let the horse pick its own path. Wherever the horse chose as the easiest path is where Chiles determined the streets should run stating “build the roads where the horse hoofs are” explaining the unique winding nature of the streets today.

Chiles was also determined to make his town a place where a young man getting his start in the world could afford to buy a home, perhaps even financing some of those homes himself.
Kenilworth, touted as Asheville’s “Pioneer Suburb”, wasn’t actually founded until 1913 when three local developers – James Madison Chiles, E. G. Hester, and Roland Wilson established the Kenilworth Development Corporation and the town itself. James “Jake” Chiles became the town’s first mayor in May 1915.
Per the Asheville Weekly Citizen 5/5/15 “Jake Chiles, candidate for mayor of Kenllworth, N. C, made an excellent campaign for the position and received six votes at the election yesterday. Largely through his personal strength with the voters of all classes he swung his whole ticket into office and obtained the election of three commissioners, E. G. Hester, Morris Meyers and Roland A. Wilson, all of whom received six votes. There are seven voters In Kenilworth, but one of them was out to lunch or ill in bed and did not vote.” The town was set up with a Board of Commissioners form of government. An article printed the day after the election noted the seventh voter was out of town and had wired not to hold open the polls for him. The same article noted the election cost the town “35 cents.” Until about three years ago every one In Kenilworth lived in the same house which proved no especial strain on the structure.”
The Greenville News in a May 14, 1915 article claimed that Kenilworth was then “the smallest municipality in North Carolina if not in the entire South.” and with “no city hall, no jail and not even a justice of the peace… officials must import a justice of the peace before they can be sworn in.”
In May of 1917, Chiles was re-elected without opposition and the town elected E.G. Hester, Roland A. Wilson, and Roscoe A. Marvel as town commissioners.
Jake served as mayor until the Spring of 1923 when he resigned but was then elected as a town commissioner in the next election in May 1923 receiving 18 votes. Mac Zindel served as the interim mayor until the election where he was re-elected a town commissioner with 23 votes along with E.G. Hester who received 15 votes. Edward Holland “millionaire cotton farmer” and Chile’s next door neighbor stated he was making the proper political connections to “land in the mayor’s chair of Kenilworth next year.”
Chiles then immediately appointed Laurence Creaseman as chief of the Kenilworth Fire Department as part of a “pre-election pledge.” The mayor turned over $1000 worth of firefighting equipment and cautioned Creaseman “about not getting it wet.” The news article of May 9, 1917 noted the town population had reached “219 residents.”
In 1925, after the death of Chiles, Mayor James Caine, pictured below, announced the purchase of a building to be used as a town hall and the news headline September, 20, 1925 noted “Structure a Unique One.” The building still stands and is back in use as a private home as the original town hall once was.
In 1927, a group of unhappy citizens of Kenilworth, mostly Chiles Ave residents, filed a lawsuit to force Mayor Caine, re-elected in 1923, to hold a new election. The suit was filed by M.K. Zindel (11 Chiles), Ronald Green (26 Chiles), A.H. Adams (36 Chiles), Roscoe Marvel (Unknown), Mills T. Holman (41 Chiles) and Rev. W.F. Sandford (8 Chiles) insisting an election was due. The town council claimed that as Kenilworth was likely to soon be annexed by Asheville an election was an unnecessary waste of taxpayer funds. A judge agreed with Zindel and the challengers and an election was called for February 17, 1928. Sometime in 1927 or prior Leah Chiles was appointed or elected a town commissioner as an August 21, 1927 article notes she is the town commissioner for parks.
The 1928 election was a bitter one with charges of corruption made by a “Taxpayer’s Ticket” comprised of R.M. Romefelt (for mayor) and M. Zindel, A.H. Adams, and T.C. Farrell for town commissioners. One of their charges was that the private owners of Lake Kenilworth were going to “dump” it onto the Town of Kenilworth leaving them with the costs of maintenance. They ran against the “Citizen’s Ticket” representing the faction in power comprised of Dr. C.P. Edwards (for mayor) and G.O. Shepherd, Roscoe Marvel and Jack Faulkner for town commissioners. (Leah Chiles had resigned as town commissioner prior to this election). The Taxpayer ticket also charged the Citizen’s Ticket with attempting to rig the election by registering “Negro voters” especially from a recently annexed “Negro” area called Brackettville.
The Citizen’s Ticket handily won with their town commissioners receiving 184-200 votes each compared to the Taxpayer’s Ticket which won 75-83 votes each.
Another regularly scheduled election was held in November that same year. The Citizen’s Committee put forth another ticket with Leah Chiles as the candidate for mayor and Roscoe Marvel, T.G. Williamson and G.V. Varner for town commissioners. They were challenged by a “Progressives Ticket” consisting of J.W. Test (18 Chiles Ave), M.T. Holman (41 Chiles) and W.V. Greene for town commissioners. Leah handily won the election 161 to 51.
Her election generated news stories across the nation as the first woman elected mayor of a town in North Carolina. (A fact under dispute. There may have been an earlier uncredited first woman mayor). Some wondered if they should refer to her as “Mayoress.” She jumped into her role fully and was praised as being the first person to operate in a full-time capacity as mayor. She received praise on her election from the World League of Cities which formally invited her to the 300th anniversary of the founding of the Massachusetts Bay Colony to be held in 1930 in Boston which was extended to “our sister city Kenilworth.”
Boston noted “The local press here tells vividly here of your good stewardship in the creation of a city-human-beautiful-cooperative…. And we rejoice with the good people of Kenilworth who have made such a wise selection…” By January 30, 1929 there were 208 registered voters in Kenilworth according to the Asheville Citizen Times. But her term in office was short-lived.
Due to the collapse of the banks and the onset of the Great Depression, Asheville sought to annex the smaller nearby communities such as Kenilworth and Biltmore Forest.
In a bold move for the times, Leah Chiles blocked annexation until Kenilworth residents had the opportunity to vote on the matter. She was very vocal and many articles and statements were printed in the media with her reasons for standing up to Asheville. She ultimately prevailed and the issue was put to a vote of the citizens of Kenilworth who strongly approved the annexation. The town voted to dissolve itself in a document that stated the town was “condemned to die on June 30, 1929 to the bigger, better and wealthier City of Asheville” and Leah Chiles turned over the town records and decreed she would cooperate fully. The keys were handed over to Asheville in Leah Chiles dining room at her home at Bowling Park according to the April 2020 resident who said John Chiles visited her not long after she moved in and told her the story.
However, she also insisted on a better deal for the Kenilworth on many issues such as the town fire truck. Asheville offered her $500 and she wanted $3000 and challenged Asheville to a water duel in Pack Square and won. She sold the fire truck (perhaps the one below?) to another buyer. (Asheville Citizen Times article April 26, 1994)
The Town of Kenilworth ceased to exist but the sense of community continues through the Kenilworth Residents Association, which continues to continue the vision laid out by Jake and Leah Chiles creating a community embracing all that live here.

More images of historic Kenilworth

SOURCES:
fight-on-negro-votes-annexation-3-feb-1928
jake-chiles-elected-mayor may_5__1915_
kenilworth-election-1928-asheville_citizen_times_tue__feb_7__1928_
kenilworth-election-asheville_citizen_times_sat__apr_16__1927_
kenilworth-election-results-1928-asheville_citizen_times_wed__feb_8__1928_
lawsuit-to-compel-election-may-4-1927-deadwyler-listed
leah-appointed-commissioner-asheville_citizen_times_sun__aug_21__1927_
mayor-chiles-turns-over-town-records
mayor-leah-chiles-plea-let-town-vote-asheville_citizen_times_tue__jan_22__1929_
new-kenilworth-cop-leah-commissioner-of-parks-aug-21-1927
progressives-ticket-election-oct-31-1928
taxpayers-vs-citizens-ticket-part-1-asheville_citizen_times_sun__feb_5__1928_
candidates-forum-about-town-funny-business-involving-lake-kenilworth
citizen committee chooses commissioner candidates-including-leah-28-oct-1928