Course Adjustments: Greg Gleason and the Tour Divide - Part Two

We continue our three part series; Course Adjustments: Greg Gleason and the Tour Divide

Click here to read Part One…

Part Two

With the rediscovery of his mountain bike, and “The Thing” to help him meet his fitness goals, Greg Gleason began his training for 2006’s Chequamegon 40 in May of that year. “I started riding with a race date of mid-September knowing I needed to get out enough to be able to complete 40 miles of rolling, nasty off-road hills.” He started riding two to three times a week with short rides at first, slowly increasing the distance and time. “It was painful. My lower back would start hurting 10 miles into the ride, every time. By mid-July, I could finally ride 23 miles non-stop. It was time to celebrate! I was pumped. Still a long way from 40 off-road miles, but I started to believe I was going to be able to finish.”

2008 and making a course adjustment…

Gleason finally reached his 40-mile goal a couple of weeks before the race was to begin. “I figured then was a good time to do a weigh-in to see if this silly goal of mine was working. 225 pounds. Success!” It was time to start planning the trip to the race. “I started asking others what they wore in a race like this to stay comfortable. Everyone told me that it depended on the weather. I thought to myself, ‘Oh yeah! The weather!’ Now I’m panicking. I forgot to check the weather. RAIN! And a starting race temperature of 34 degrees. WHAT AM I GOING TO DO?”

At that point, Gleason had never ridden in rain, mud, or the cold. He called a friend of his in Butte, Montana that was a year-round bike commuter for some advice on clothing and how to ride in those conditions. “He was awesome. He told me what to get and told me to never give up. It was all I needed to hear because I had worked way too hard to give up!”

The day of the race came, the rain cleared, and it warmed up to a steamy 37 degrees. Gleason was slightly less worried at the start line. “Gary (Crandall) the race director started the traditional countdown 10…9….8… I hear crack of the gun and I was off. I was racing again! It had been years and it felt great! I felt free and relaxed. This was the start of my adventure!”

“I was 39 weighing in at 225 pounds. My Chequamegon finishing time was 3 hours, 17 minutes, and 22 seconds. I finished 193rd out of 340 in the 35 to 39 age group, and 876th out of 1677 finishers. And when I finished I could hardly walk or talk. I had given that race every ounce of energy I had.”

For anyone who’s only known “Greg Gleason the Cyclist,” hearing the story of not only his 2006 Chequamegon, but the years prior probably seems hard to believe. Accomplishments from the last five years would lead one to think Gleason has been pedaling non-stop his whole life.

2011 at the Chequamegon Forty…

2012 climbing Nederland…

2013 Highlights:

Winter Ultra Cycling

  • Tuscobia 75 Mile Winter Ultra, 1st Overall
  • RiddleBox 100k, 1st Overall

2014 Highlights:

Winter Ultra Cycling

  • Triple D Winter Race, 2nd Overall

Gravel Road Racing

  • Trans Iowa v.10, 1st Overall
  • Dirty Kanza 200, 15th Overall/ 2nd age group
  • Filthy 50, 3rd Overall
  • Omaha Jackrabbit 125, 2nd Overall

2015 Highlights:

Winter Ultra Cycling

  • RiddleBox 100k, 1st GC
  • JayP’s Fat Pursuit 200k, Finished

Gravel Road Racing

  • Land Run 100, 3rd Overall
  • Trans Iowa v.11, 1st Overall – race stopped
  • Almanzo Royal, 3rd Overall
  • Gold Rush Mother Lode, 1st Overall
  • Odin’s Revenge, 1st Overall

2016 Highlights:

Gravel Road Racing

  • Trans Iowa v.12, 1st Overall – Tie
  • Gold Rush Mother Lode, 1st Overall
  • Omaha Jackrabbit 125, 1st Overall

Bikepacking Racing

· Black Hill Expedition, 1st Overall

2017 Highlight:

· Trans Iowa v.13, 2nd Overall, only 6 finished out of 78 starters, rode with a loaded bike to prep for TDR

· Almanzo Royal 162, 1st Overall - with a full Tour Divide load on my Salsa Cutthroat

Personal Milestone Accomplishments

· 2010 Triple Bypass 125-mile road ride - 1st major long ride

  • 2013 Blue Ox Trail Expedition Fat Bike, 217 miles, temperature range 46 to 36 degrees, 40% rain, 8 miles of route was under water sometimes waist deep. Time: 15 hours (Note: This is the ride that gave me the confidence to sign up for Trans Iowa v.10 and start the ball rolling to go all in on the Divide.)
  • Trans Iowa Masters – 380 Miles of gravel river to river across Iowa – 2014 Only ITT to finish, 2016 Training Ride that I learned what “sleep biking” was all about.

Mountain Biking Cross Country Accomplishments

  • Chequamegon 40 – 2006, 2007, 2008, 2009, 2011, 2012, 2013, 2014
  • Butte 100 – 2011
  • Barn Burner 100 – 2013
  • Leadville Silver Rush – 2012, 2013, 2014, 2015
  • Leadville Trail 100 – 2012, 2013, 2014, 2015, 2016

USA Cycling Road Accomplishments

  • Twin Bing Road Race – 2 Time, 1st Overall
  • SD State 40k Time Trial Championship, 1st GC, Cat 3
  • SD State 20k Time Trail Championship, 2nd Cat 3
  • Nebraska State Time Trial Championships, 3rd Cat 3
  • Chris Lillig Memorial Cup/Old Capitol Criterium-Time Trail, 3rd Cat3
  • Bicycle Blues and BBQ – 3rd Overall Omnium Cat 3

Will racing the Tour Divide be as challenging to a rider that’s achieved so much in such a short time? Gleason’s not taking any chances, although he admits, “When I declared I was going to do the Divide it was just to finish. Now I’m preparing my rig to go as fast as my 50-year-old body will allow! Just crazy what can happen over five years!”

When asked how he’s been preparing for TDR, Gleason shares the, “little tests or challenges I made for myself.”

  • Hard work, a strong mental attitude, and mileage in the range of 12–14k a year
  • Ride Leadville MTB 100
  • Ride Almanzo 100
  • Ride over 200 miles in the nasty fall time weather
  • Ride a century every weekend for a year
  • Ride seven centuries in row in a week after working all day
  • Ride Trans Iowa
  • Ride in early spring weather lasting over a 24+ hour’s period
  • Ride several 200-plus-mile events: Trans Iowa Masters 380 miles, Dirty Kanza, Gold Rush Motherlode, and Odin’s Revenge
  • Participate in bikepacking tours and races
  • Ride multiple trips around the area: Trans South Dakota 700 mile; Ponca, Minneapolis, and the Black Hills Expedition (BHX) practice multiple times
  • BHX practices with different setups each time

That’s a lot of crossed “t’s” and dotted “i’s” for a fast border to border run this June. Barring any unforeseen problems, Gleason looks set up to surprise again – maybe himself most of all.

Check back Friday for Part Three of Course Adjustments: Greg Gleason and the Tour Divide, to see how he’s feeling for this year’s TDR run…

This post filed under topics: Bikepacking Fatbike Gravel Greg Gleason Mark Sirek Mountain Biking Road Sponsored Riders Tour Divide Touring Trans Iowa Ultra Racing

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Mark Sirek

Mark Sirek

I had to live on both coasts a couple of times to realize that maybe being born in the Midwest wasn’t just arbitrary. I’m drawn to the terrain here, and if you catch me with one of this region’s supreme IPAs in hand, I’ll talk your ear off about my favorite spots. I’ll always take every opportunity though to explore every nook and cranny anywhere I can on a bike, because that’s what makes me feel most alive.


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