King of Pain: Gary Kessler is Keeping Bicycle Racing Alive in Vermont

Kirk Kardashian
Posted March 30th, 2010

Riders on Route 100 in Granville during the 2009 Mad River Road Race. Photo by Ilke Van Genechten.
Everybody has an anxiety nightmare. You know, the one where you wake up in the middle of the night, sweating because you dreamed you’re playing the lead role in your high school play and have forgotten your lines. Gary Kessler’s goes something like that, but the stakes are higher in his dream. “I jolt awake, thinking the race is tomorrow and that I haven’t arranged for the police to be at a certain intersection, and I freak out,” he says. So go the unconscious torments of a bicycle race organizer.
It would be an exaggeration to say that Kessler, a wiry, kinetic 50-year-old who lives in Fayston, is single-handedly keeping road bike racing alive in Vermont. But not much of an exaggeration. After all, he pretty much runs the Green Mountain Stage Race, and this year is organizing the revival of the Killington Stage Race. Kessler is quick to point out that his longtime friends Sam Hoar and Tom Moody of the Green Mountain Bicycle Club are in charge of the Burlington Criterium, so he can’t take all the credit for GMSR, a four-day stage race that most New England-based riders put on their calendar.
Still, the fact remains that at least 75 percent of the details of the event, which drew 850 riders last year, fall on Kessler’s narrow shoulders. Then there are the emails from the inquisitive bikers; he gets hundreds of them in the weeks leading up to the start of the race. “I enjoy the interaction,” he admits. “But the problem is, the race is over and I’m still getting hundreds of emails, and usually by then I’m pretty smoked.” It’s a good thing that, at heart, he’s a bike-racing fanatic. Otherwise, he would have given up years ago.
Kessler, whose day job is as an attorney for the Vermont Agency of Natural Resources, moved to Vermont in 1987, after his illusions of living a glamorous LA Law lifestyle were dashed on the rocks of reality. He was hired by a big law firm in Los Angeles upon graduating from Boston University Law School, installed in a big office with a view of the ocean, and paid handsomely. In exchange, he was assigned to a senior partner who dealt with an obscure, dense federal statute. The assignment was supposed to be temporary, but after a few years had gone by, Kessler started longing for Vermont, where he had spent a lot of time skiing as a kid. So he packed his stuff and moved to the Mad River Valley.
Fast forward to 1994. Kessler had found a lively biking scene and made a lot of friends while racing in Stowe, Putney, and Killington. The GMBC had been organizing the Burlington Criterium, but a poor turnout in 1993 had caused them to get creative. “GMBC realized,” Kessler recalls, “that people didn’t want to drive all the way to northern Vermont for one race.” So the bike club asked Kessler to help organize the first Mad River Road Race, to be held the day before the criterium. It was, in the style of the time, low-budget. “We had no permits, no police, no nothing,” Kessler says.
But the race was a hit, and when the Killington Stage Race was discontinued in 2000, Kessler decided to make the leap from a road race/criterium weekend event to a full-blown stage race. The GMSR was born. The following year, Jason Bear, the captain of the cycling team at the University of Vermont, asked for Kessler’s help in designing the race courses for the collegiate national championships in May. “I learned an immense amount, putting that race on,” Kessler says, “because USA Cycling sent a technical director to provide guidance.” His main advice was to hire the state police to escort the races and block traffic at intersections. Was it good advice? “It totally went to a different level from where it had been before,” Kessler says. Today, he wouldn’t run a race without police help.
This year, the GMSR is celebrating its 10th year. And although it has endured floods in Granville Gulf and a complete washout of Middlebury gap, the event is as popular as ever. In fact, the race’s success—in terms of tourism and economic development—caused the Town of Killington to wonder why it ever killed the Killington Stage Race. Last winter, the town contacted Kessler to inquire if he would help bring the race back. The idea of racing in a different part of the state, though daunting, excited Kessler, and he agreed to do it.
So, after a nine-year hiatus, the Killington Stage Race is back. Scheduled for Memorial Day weekend, the race will have three stages: a flat individual time trial, a circuit race around the 18-mile loop of Routes 100A and 100 in Bridgewater and Plymouth, and a hilly road race through Killington, Bethel, Barnard, Woodstock, and Bridgewater.
The road race will travel from Route 107 to the center of Barnard via the picturesque and punishing North Road, which can be surprisingly steep. Kessler’s counsel? Pre-ride the course. “I’m not trying to kill anybody,” he asserts. Then he cracks a devilish grin. “But I want to make it fun.”
Kirk Kardashian lives and writes in Woodstock, VT. The only bike race he ever won was the criterium at the Green Mountain Stage Race, as a Cat 4. He’ll be watching the Killington Stage Race from the sidelines, imagining when he would have been dropped on the finishing climb to the base lodge.
May 29-31, 2010
Stage One, Saturday
A circuit race around the 18-mile course that, in the original Killington Stage Race, was known as the Sunrise Loop. It starts at the Skyeship base area and travels along Route 4 to Bridgewater and then gradually climbs to Plymouth Notch via Route 100A. A fast descent to Route 100 is followed by a more gradual descent along Route 100 back to Bridgewater. The finish is arrow-straight and slightly downhill, and will surely be very fast.
Stage Two, Sunday
An individual time trial along some of the flattest roads in this part of the state. The 11-mile course begins at the Skyeship base area and heads west on Route 4, then veers right on River Road, a smooth, scenic lane that passes the headwaters of the Ottauquechee River. Total elevation gain is a modest 300 feet.
Stage Three, Memorial Day
The queen-stage of the KSR is a 61.5-mile course with two leg-busting climbs. It starts at the Skyeship base area and goes west on Route 4, up the so-called Post Office Hill to Route 100 North, through Pittsfield and Stockbridge, then east on Route 107. As the riders enter Bethel, the first of the major climbs begins, with a sharp right onto North Road to Barnard. The course then follows Route 12 to Woodstock, goes west again on Route 4, and just before passing the start, turns left onto East Mountain Road in Killington, a nasty ascent that begs for a 25- or even a 27-tooth cog. The finish is another climb up the Killington access road to the K1 base lodge.
September 3-6, 2010
Stage One, Friday
Egan’s Big World Individual Time Trial
A 5.7-mile race against the clock that starts in Warren Village. It follows Flat Iron Road and then climbs for 2.3 miles to East Warren Road. There’s a short, tough climb a half-mile from the finish.
Stage Two, Saturday
The Bridges Resort Circuit Race
An interesting, varied course that starts at Harwood Union High School in Duxbury. There’s an immediate 2-mile climb up Route 100, followed by a descent into Waterbury, and then some flat roads along the Winooski River on Route 2 to Middlesex. For the final leg, the course turns right onto Route 100B to Moretown. A full lap is 19 miles, with a finishing lap of 13.6 miles.
Stage Three, Sunday
The Mad River Road Race
This is the race that makes GMSR famous and gives it the feel of a much bigger event. In 2009, it was 12 miles longer than usual, because Route 125 over Middlebury Gap was in poor condition from a flood. This year, the old course might be back, but at this time, race director Gary Kessler isn’t sure. Either way, there are two major climbs in the race: one over Brandon Gap (or Middlebury Gap, if it’s in good shape) and a finishing climb to the top of Appalachian Gap.
Stage Four, Labor Day
The Burlington Criterium
A technical, turny, hilly criterium in the heart of Vermont’s Queen City. To be a rider in this crit is to scream along the bricks of Church Street as spectators cheer and lounge in the sun. When your race is done, you’ll want to join them.

Kirk Kardashian

Kirk Kardashian is a writer based in Woodstock. You can see more of his work at