The Toughest Ten

I started working on this post months ago. It took a very snowy day for me to find the time to finish the list. I have shaped it and updated it as I have reflected on the meaning of endurance sports in my life. The physical suffering associated with the training and competition is something that I thrive on. Athletics is a big part of who I am and I have gotten great pleasure from the activities that I have done during two decades of endurance sports. I played hockey as a youth, ran cross-country in middle school and high school, and remained active at the start of my college career in Army R.O.T.C.

However, it wasn’t until I took up road cycling in college, that I started on the current path. A while back, I started thinking about the most challenging races that I have done. I referred to them as the toughest. Not counting the cross-country and track meets that I finished in middle school and high school, I have done more than 700 endurance events. I’ve gone through different phases. After high school, I continued to run, andthen I did mountain bike racing, then road racing, then cyclocross, then trail running, then adventure racing, and now triathlon.  There have been other interesting variations in between (e.g. snowshoe racing) and all of these sports have overlapped at one point. There have been years, especially recently, when I’ve done all of these different sports in a twelve month period. I like mixing it up and I like the benefits of cross training. The variety helps minimize the risk of injuries.

I’ve never been great at any one of these sports. Body type/size and training time are two big limitations, but that hasn’t stopped me from competing and having fun. So, which ones have been the toughest to date? I’ve ranked them here with a brief description. A common thread is the length of these races and their multi-sport component. I have migrated more towards these types of races. Until now, these are the toughest races that I have 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 at Jay was simple, yet still very hard. Pain Index: 10

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

It was difficult to rank the Sea to Summit Triathlon second ahead of races three and four 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. Pain Index: 10

3) 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

4) 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 this past August and it was my longest ever one day race. 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

5) 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

6) 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: 9

7) 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

I’ve done the Mt. Washington Auto Road Bicycle Hill Climb four times. 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. My knees are still hating me for that decision. 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 is the second shortest race (time) on the list, but there is no resting. 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

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

9) 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

10) 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 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

7 Responses to “The Toughest Ten”


  1. 1 air9r 20 December 2009 at 7:44 pm

    I’m 2 for 10 (Mt.Washington Hillclimb – 1984 and Hampshire 100k – 2009) . How’s that for a range of 25 years?

    The Landmine50 was pretty tough last year. Its two 25 mile laps but the course just beats the tar out of you when you try and do it fast. VT50 was tough in the granny gear after I snapped my chain.

    Boston Marathon 1999 – 2:52:23 405th place. Best running day of my life, but very hard at the end.

    FIRM MAN Naragansett 1/2 Ironman – 2002? Tough because I’m not a swimmer, didn’t train and running 13 miles can be hard even if you did train.

    Housatonic Hills Road Race – or several other hilly road races but Housy Hills in particular. I can finish just about any event but I never suffer more in my life when I’m trying to hang with the front pack or off in a break. More often than not, the worst suffering is on a climb somewhere on the edge of detonation. I don’t have a very good record for Housy Hills out of three or four tries, and even when you don’t get dropped, there is still the finishing climb to contend with. There is some suffering when you hit the Mt. Wachusett Park entrance after a long hot day in July, trying to make Brandon Gap with the leaders of the KSR or just trying to bridge the gap coming over the top of Jiminey Peak.

    I can’t touch any of Scotty’s other races because I just won’t put myself through some of those things. I considered an Ironman but the training I would need to do has been displaced by other endeavors.


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