The first Hilly Hundred was held on June 15th and 16th, 1968, conducted by the Southern Indiana Bicycle Touring Association (SIBTA). Hartley Alley, with help from Bernard Clayton and Tom Prebys, started the ride in Bloomington, Indiana. 54 riders rode the first Hilly which was headquartered at the Poplars Hotel. THE INDIANAPOLIS NEWS covered the first event in its June 17th, 1968 edition:

About 60 Midwestern Cyclists are kneading sore backs and legs with liniment today after the first Hilly Hundred sponsored by the Southern Indiana Bicycle Touring Association over the weekend.

Fifty miles, including a 17 mile rally, were wheeled off Saturday west of Bloomington and an eastern route was run yesterday. It looked like nothing less than the Tour de France as the bicyclists left the Poplars Motor Hotel Saturday behind a Bloomington police car. Such an array of thin-tired, multi-geared equipment, you’ve never seen.

And there was one single sprocket, balloon-tired bike just like the machines used in the “Little 500.”

Dallas Shuck of Marion said “Wheezing up these hills isn’t worth it until you get at the top and see the beautiful country – then you don’t feel quite so much like a nut.”

The first Hilly Patch 1969

 CIBA and SIBTA jointly sponsored the Hilly Hundred with Charlie
Sanford as general chairman in 1971. This ride was again
covered by the press (source unknown):

The fourth annual Hilly Hundred Weekend for bicycle enthusiasts will be held Saturday and Sunday. Sponsored by the Southern Indiana Bicycle Touring Association, Inc. and the Central Indiana Bicycling Association, Inc., the tour will start and finish at the Poplars Midtown Motor Hotel in Bloomington.

The ride will include an European rally which is not a race, but a test of skill in riding an exact rate of speed. Riders may use a watch, cyclometer, or “use their instinct” in efforts to ride at an exact speed. Trophies will also be awarded to the oldest participant to finish the first loop, and to the participant cycling the farthest distance to this event.

CIBA took over full sponsorship in 1972.  Charlie was the chairman of the event until 1975 when he retired and moved to Florida.  Ross Faris took over as chairman, a role which he would hold into the nineties.  By 1976, the ride had grown to 1, 221 riders.

 In 1979 Ross Faris was transferred to England, leaving the “Hilly” in the capable hands of Tom & Nancy Revard.  The Hilly had a record-breaking crowd of over 1,900 registered riders from at least 15 states.

The traditional ride from Indianapolis to Bloomington also began in 1979. Eight riders met at Shapiro’s on Friday, October 5th, and rode to the Hilly. On the way to Bloomington, they picked up four addition cyclists.  Riders included  Charles Beard,  Marti Daily, Larry Downing, Jerry Driver,  Fred Evans,   Steve Leonard, Max Magnabosco, John Parli,  Ronald Ricketts,  Roger Schumacher, Robin Shields,and Richard Weiner.

In 1982, because of the large number of participants and in the interest of safety, the Hilly Hundred adopted a staggered start.  The traditional Friday night party at the Hilly was begun.  2,811 riders participated.

Ross Faris returned as ride chairman in 1983 and led the ride through 1995. To honor the 20th Hilly in 1987, an extensive history and fact sheet was researched.  During that time, the ride grew and a limit of 5,000 riders was adopted. 
As the ride moved into the nineties, added emphasis was placed on safety.  Participants were required to see a short safety presentation at registration. When Ross retired in 1995, he left an experienced group of directors and volunteers to continue the fine traditions of the Hilly Hundred.

 The November, 1995 Edition of the CIBANEWS acknowledged Ross’ contributions:

To Ross Faris – Thanks for the Memories

The Hilly Hundred was eight years old when Ross took charge in 1975.  (The ride started in 1968, chaired by Hartley Alley of the Southern Indiana Bicycle Touring Association; CIBA took over the Hilly in 1972 under the leadership of Charlie Sanford.)

From about 60 riders in 1968, the Tenth Annual Hilly had grown to 1400 riders (and 200 pounds of hot dogs, according to the October 1977 CIBANEWS.)  From 1979-82, Ross took a “leaf” from his Hilly duties, when Eli Lilly & Co. sent him to England. Tom and Nancy Revard filled in.

Celebrating the 20th Anniversary in 1987, it was noted that Ross had overseen 12 of the 20 Hillys and registration had to be limited to 5000 riders.

 The ride was chaired by Gary Robinson in 1996 and 1997.  Ron Jackson became chairman in 1998.  The 1999 Hilly won several national awards from BICYCLING MAGAZINE:  Best Overall Event, Longest Running Event, Largest Event, Best Map, and Best Entertainment.

Skip Higgins became the new Hilly Managing Director in 2001.  Over the first 35 years of the event, the routes saw little change, with occasional improvements provided by newly paved roads, or safer roads.  The original routes, with only small changes, proved challenging and entertaining year after year.  The Hilly took a major turn in 2003 as the headquarters site moved to Ellettsville, IN. New headquarters facilties, in four school buildings, and major expansion of parking and camping space provided a much-needed breather for the ever-expanding Hilly Hundred Weekend.   Newly plotted routes on both Saturday and Sunday were a big hit with riders who were treated once again to the beautiful autumn colors of Southern Indiana.

Mark Bettinger took over the helm in 2016 and is assisted by 30 directors and approximately 400 volunteers. 
These people are the heart and soul of the Hilly Hundred.