The Revised Toughest Ten

I drafted my inaugural Toughest Ten in December 2009 and after running the Wapack and Back back in the spring and then witnessing the Peak Ultra 500 this summer, I determined that it was due for an update and have worked this post on and off for a few months. I figured I would finish it, publish it, and use it as inspiration during my post-crash comeback.

Through today, these are the toughest races that I have ever done:

1) Jay Challenge, Jay, Vermont, 29-31 July 2005, 20:09:11

Hands down, this is the grandaddy of my palmares. Just finishing the Jay Challenge was an accomplishment.  It is a bit different from others on this list because it was a three-day stage race with the overall winner achieving the lowest cumulative time. Each of the three stages would make this list on their own. I was 10th overall and know I would have done better with a faster kayak, but that doesn’t matter. Finishing was the real accomplishment. The first day was a 27 mile kayak paddle across Lake Mephramagog from Quebec to Vermont. The second day was the classic Jay Mountain Marathon, but it wasn’t 26.2 miles, it was 33. The third day was a 65 mile mountain bike ride on hilly terrain. You summited Jay Peak in both the run and bike. There was so much climbing in this race (except the paddle) that it made you silly. The race was in late July and at the time, I had never been more fit. We completed our End-to-End hike of the Long Trail three weeks before Jay, so I had a pain threshold like never before…and never since. I could go all day long, get up and do it again. The LT was 13 days and 285 miles of supreme effort, so three days at Jay was simple, yet still very hard. Pain Index: 10

2) Ironman Brasil, Florianopolis, Brasil, 30 May 2010, 9:58:53

I’ve never gone deeper. As one day races go, Ironman Brasil  will be hard to top. I earned a Kona slot and had a sub-10 on the line with 10K to go and I buried myself to reach the goals. I was delirious at the finish and it was surreal. It was an epic trip with the family, which made the race that much sweeter. Check out the report and the coda report for the blow-by-blow. Pain Index: 10

3) Sea to Summit Triathlon, Jackson, New Hampshire, 22 July 2006, 9:29:21

It was difficult to rank the Sea to Summit Triathlon third ahead of races four and five because they were all wicked hard. However, given the fitness I had at the time, this one beats out the others. The Sea to Summit Triathlon was an 112 mile jaunt from Portsmouth, New Hampshire to Jackson, New Hampshire. The race consisted of a 12 mile kayak up the Piscataquis River to Berwick, Maine. Then, after a transition, you rode 90 miles to Jackson, New Hampshire. From there, you ran four miles uphill on Rt. 16 to Pinkham Notch. Then, you ran/hiked five and a half miles up the Tuckerman Ravine Trail to the summit of Mt. Washington. Only 40 people were allowed into the race. It was a special day, though I suffered dearly. I started the morning at sunrise in the pea soup fog at sea level near the mouth of the river. I finished wearing a skinsuit and a windbreaker on the top of the mountain in gale force winds blowing cold rain and sleet at 6322 feet, the highest point in New England. If it wasn’t for my awesome crew (Debbie, Art, Mel, and Bill), I might still be out on the course. It was shorter than an Ironman, but the weather conditions, lack of organized support/aid stations, and terrain, made it tougher than any other triathlon. Bad decisions by some of the racers resulted in a challenging day for the race directors and the race hasn’t been held since. Pain Index: 10

4) Ironman World Championship, Kona, Hawaii, 09, October 2010, 10:27:31

Despite the five months in between Ironman races, I still wasn’t on top form for the Big Dance on the Big Island, but I still survived the Ironman World Championship and lived to tell about it. The race report and highlights tell the story. The no-wetsuit swim was painful and I suffered dearly on the bike from the heat. The sun and its burn (mostly during the bike leg) sucked the life out of me and made for a very miserable marathon, but I never walked. I sorted of slogged my way through it. I feel like I honored my slot, though I missed my time goal. It doesn’t matter because I got to the race and got through the race. 2010 was a pressure packed year and I really haven’t been the same since then. Yeah, it’s four years on, but I left something on the course back in Brasil. I went so deep in that race that everything since then has sort of felt different. Pain Index: 10

5) American Zofingen Ultra-Distance Duathlon, New Paltz, New York, 12 October 2008, 8:28:02

The American Zofingen was also run at a time when I wasn’t quite at my top fitness, but it helped me get back to a high level after my first real long layoff. That means it hurt a heck of a lot. After I finished it, I knew that if I could learn to swim, then I could finish an Ironman. Zofingen is the toughest duathlon in the country, and maybe the toughest in the world. The first leg was a 5 mile trail run in the Mohonk Preserve. The second leg was an 84 mile bike ride around the Shawangunk Mountains. The third leg was 15 mile trail run on the same course as the first leg. Again, at 104 miles, it was shorter than an Ironman, and there was no swimming. Still, due to the terrain (major hills) and my lack of fitness, it was harder, but not by much. Pain Index: 10

6) Ironman Lake Placid, Lake Placid, New York, 26 July 2009, 10:44:48

Ironman USA in Lake Placid was an amazing race. I did it in August 2010 and it was my longest ever one day race at the time. 2.4 mile swim/112 mile bike/26.2 run. That should be enough to put it on the top of this list. However, I managed to get into top form, so it hurt, but not as bad as some of the other races on this list. I had my rough moments, and the swim was terrifying, but I managed to race within my limits and finish strong. The support was phenomenal (great volunteers) and the conditions were good. I’m sure that most people would put Ironman at the top of their list. For various reasons, it isn’t quite there for me. Thinking back, Zofingen and Sea to Summit were just plain harder, but mostly because I fell apart in both of those races. I was strong to the end during Lake Placid. I’m still proud of my first ever Ironman finish. Pain Index: 9

7) Wilderness 101, Coburn, Pennsylvania, 28 July 2012, 8:30:55

The 101 was ridiculously hard. It is my longest ever mountain bike race. I did it with teammate Arthur Roti. We were rookies at the 100 mile distance. This course is as rugged as it gets. The 30 miles of singletrack were hard, but the washboard/washed out dirt roads were even harder. I did the race on my Seven Sola SL singlespeed with a rigid fork, which was nuts. That is a brutal way to ride a race like this, but I wouldn’t do it any other way. The race organization was awesome. It was so hard that so far, I’ve had no desire to go back. Pain Index: 9

8) Wapack and Back 50, Ashburnham, Massachusetts, 10 May 2014, 11:53:20

I first ran a 50 mile trail race at the Lookout Mountain 50 Miler, but Wapack made Lookout look like a cakewalk. In hindsight, Wapack is what led to this year’s left foot stress fracture that has been a real drag on my year. I haven’t run in 13 weeks. The Wapack Trail just pummeled me. I pushed as hard as ever in an effort to stay in front of Debbie. See, were aren’t that competitive! I finished and said I would never run another 50 and certainly never run a 100, but time heals and you never know. Pain Index: 9

9) Survival of the Shawangunks Triathlon, New Paltz, New York, 13 September 2013 and 09 September 2012

I always knew that S.O.S. was hard from hearing the war stories of other athletes. I always wanted to do it and finally committed in 2012. I’m a weak swimmer, but the beautiful course really appealed to me and I wanted to test myself. This race is the real deal. I cramped horribly in 2012 and it slowed me a great deal. I figured I would return in 2013 and improve my time, but the cramping and suffering were even worse. After last year’s debacle, I had no interest in returning for 2014. I’m glad I didn’t because I’m injured now and the race is coming up soon. Maybe it will be a comeback race for 2015 when it celebrates its 30th year. I don’t know. It just doesn’t suit my strengths, but it is brutally hard and a finish is something to cherish. Pain Index: 9

10) Mt. Washington Auto Road Bicycle Hill Climb, Gorham, New Hampshire, 23 August 1997; 1:14:54, 21 August 1999; 1:10:37, 19 August 2000; 1:08:04, 25 August, 2001; 1:11:04, 16 August 2014, 1:17:33

I’ve done the Mt. Washington Auto Road Bicycle Hill Climb five times, including this year after a 13 year layoff. Incidentally, I’ve run it once, but it is the bike race that destroys the legs and puts your heart rate into a new category. Each time, I  pushed so hard that it made me dizzy. The last 22% grade is nothing like anything you have ridden before. As far as I’m concerned, it is the hardest section of road on Earth.  It comes after 7.6 miles of constant uphill at an average grade of 12%. For a hill, on a bike, this is as hard as it gets. My best finish was in 2000 when I rode a 38 x 25 low gear, which was way too hard. This year, I rode a 39 x 27, which isn’t much better. My knees are still hating me for that decision. Back in 2009, I said, “I haven’t done the race since 2001 when the entry fee rose to $300 (though it is for charity) and the event got too popular. I’ll do it again someday.” This year was the year to do it again and I was slower, but so happy to finish. This is the shortest race on the list, but there is no resting, and it is one of the most intense. The weather at the top is the most inhospitable in the world, with constant wind and cold temperatures, even in August. It is no surprise that two of my top ten toughest races have finished on the Washington summit cone. Pain Index: 8

Former Top Ten Toughest races that dropped off the list since 2009:

Ultimate XC (Jay Mountain Marathon), Jay, Vermont, 28 July 2007, 6:51:37

The Jay Challenge has not been held in the past few years, but the race morphed into an ultra-distance trail running race, when it was reduced to one day from three. Now known as the Ultimate XC, the Jay Mountain Marathon started as a run years ago, became part of the three stage Jay Challenge, returned to a run, and eventually migrated from Vermont to Quebec. A version of the race has also been held in Moab, Utah the past two years. All of the variations and names are hard to keep track of, but the one constant is the difficulty of the courses. This run took us up Jay Peak to an elevation of nearly 4000 feet. Then, it plunged us down the backside, through deep mud, into a bushwhacking section, then into a series of streams, then to a river crossing, then through a swamp, and eventually back to town. It was 33 miles of agony. Debbie caught me at mile 16 and I hung with her for 15 miles, before she dropped me like a wet sandbag. I finished, and that is what counts. Pain Index: 9

Hampshire 100, Greenfield, New Hampshire, 17 August 2008, 7:41:57

Other than the third stage of the Jay Challenge, the Hampshire 100 is the hardest mountain bike race that I have done. It was 100 kilometers, but it felt like 100 miles. Thanks to a month’s worth of unseasonable rain, the course was a quagmire. It was one big loop, which added to its epic nature. There was a ton of climbing and there was the added benefit of racing against two teammates for the honors of fastest mate. I kept dropping off their little group, before getting shed for good. Then, I had a wild mechanical failure when a stick wedged into my lower derailleur pulley going downhill at 20mph. I came to an abrupt halt and my chain was jammed. With less than five miles to go, I was afraid that I was going to have to walk the rest of the way. I made a delicate repair, extricated my derailleur from my rear wheel, and rode it in. It was a long day! Pain Index: 8

Jay Mountain Bike, Jay, Vermont, 30 July 2006, 8:56:00 DNF

It is a testament to Jay Race Director, Dan DesRosiers, that his events show up on this list three separate times. They are unique, they are painful, and they are unmatched. He goes out of his way to make the races difficult. You feel like a champ just for finishing. Unfortunately, this one, I didn’t finish. I was a DNF at the Jay Mountain Bike, with only five miles to go in the 70 mile race. It was one of two DNF’s on this list. I stopped at nine hours and I was at least an hour from the finish. Debbie was eight months pregnant and crewing for me (no excuse). It was hot (no excuse). I did Sea to Summit  a week prior (see number two on this list, but no excuse). I just didn’t have the legs, and suffered terribly. I walked the five miles before I quit and was resigned to the fact that I just wasn’t going to make it, so I climbed off after hours of struggling on the bike. It was the brutal fresh-cut singletrack that was the last straw for me.  No regrets. Pain Index: 8

Borgt-Grimbergen Kermesse, Grimbergen, Belgium, 06 August 1994, 2:19:56

I spent the summer of 1994 racing kermesses all over Belgium. In 15+ races, this was the hardest one. There have been many longer bike races over the years and many that hurt a lot, but the Borgt-Grimbergen Kermesse had the romance of racing in Belgium. I made the front group for the first time all summer. There were 15 other riders in a breakaway and I had to give it everything I had just to stay with the group and take my pulls. My heart rate hit 200bpm in this race, which was typical at the time, but still very high. This was the race where I started to burn out on road cycling. The other riders in the break were downright violent. There is no question that performance enhancing drugs (amphetamines) were being used. I risked being crashed out of the race at the hands of these merciless riders. I was happy to be up there, but wasn’t going to make it to the finish with them anyway, so I dropped off the group and finished behind them. I’ve never had to ride harder to stick with a break. Pain Index: 8

Race for the Gate, Nashua, New Hampshire, 24 June 2000, 1:08:00, DNF

I did a lot of tough road cycling events over my career. I’ve wrecked in many, but that doesn’t mean they were hard. There have been long and hilly road races. There have been intense cyclocross races where I was in oxygen debt. But, the longest cross races were 65 minutes. I did the Race for the Gate criterium when it was held as a twilight/night-time race. That alone made it different and difficult. I recall that it was a crash fest. The race was delayed by a huge pileup and people were going down left and right. The shadows cast by the large spotlights that the organizers had on the course, were very deceiving. There were more than 100 riders in this Pro/1/2/3 race and I was hanging on for dear life. I wish I had made it to the finish, but I got popped off the back with only a couple of laps to go. I was completely anaerobic and I was in danger of losing control in a corner. I was ecstatic to have made it as far as I did. It was a long criterium and it was a hard one. Pain Index: 8

Honorable Mention’s in no particular order: Ironman Mont Tremblant, Lookout Mountain 50 Miler, Ironman 70.3 Rhode Island, NipMuck Trail Marathon, 7 Sisters Trail Race, The Bluff 50km, National Cyclocross Championships (Providence), Vermont 50 Mile Ride, Vermont 50km Run, Wapack Trail Race, Six Foot Track Marathon, Walt Disney World Marathon, Moby Dick, Mt. Washington Road Race, Tour of the Adirondacks Road Race, Stowe Road Race, Killington Stage Race, Josh Billings Runaground Triathlon, National Collegiate Cycling Championships Road Race

Most of these races can be easily searched on my blog. Some wintry day, I’ll add the links. I look forward to the day that I displace the next race on this list and get to update it again. I’m open to suggestions. Tell me how to top these. But for now, I’ll go for a little rest and recovery.

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