John Calabrese

TWOT 100

I contacted the creator of The Wild Oak Trail 100 (TWOT), Dennis Herr, to make sure he was okay with me talking about Wild Oak. He was very nice and agreed. I have never met Dennis in person, but I feel like we would be good friends.

Wild Oak 100 and Me

I found out about Wild Oak 100 from locals here in Virginia. When I first started running, I was obsessed with The Barkley Marathons and met a lot of others like me doing the Barkley Fall Classic.

The views from the ridges during TWOT in the winter are amazing

One runner in particular, VHTRC member Jeremy Lucier, who I knew from BFC and who is just an extremely talented trail runner, ran Wild Oak and volunteered at the event. From his involvement, I found out that many people who ran the Barkley Marathons had run The Wild Oak Trail. There are many parallels between the races, both are great races but distinctly different and have completely different vibes.

This is my fourth time running Wild Oak. The most loops I’ve done to this point is 2. I feel like I’ve been in shape to complete this race over the years, but I just didn’t like being out there alone with my demons. It’s hard to spend close to 48 hours out there. Also, if there’s bad weather it’s extremely difficult.

Don’t go to this race because you think it’s Barkley! Go to this race because it’s fun and the people who volunteer and run it are truly unique and care about the event almost to absurd levels! It’s a family like environment.

Guy Towler in the TWOT lot tending a very warming fire

Guy Towler is an amazing person who volunteers at many major VHTRC events; is the director for MMT Training Academy Run #2, and sometimes The Hill of Broken Dreams (please bring this one back!). I know he’s going to really keep the vibe of this race the way it was intended. Anyone who wants it bad enough can do TWOT, you don’t need a resume or sponsorship, just the desire to finish.

The Haunting of John Calabrese

It’s funny, every time I’ve signed up for TWOT 100, time immediately speeds up and before you know it, it’s time to go.

Also, it’s pretty incredible, but everything that could potentially go haywire in my personal life will go haywire the day before TWOT. I’ve just learned to plan for it over the years.

I have been removed from the race for 3 years. My mind was constantly thinking about all the mistakes I made in previous years. Physically I believe I’ve always been capable of finishing this race but mentally I just didn’t have the toughness. I missed my daughter and just couldn’t balance getting prepared during the week leading up to the race or just had extreme cases of regret and thought I was a bad dad for being gone. It’s been intense so I had to just step back for a bit.

So Many Bad Omens

I hit a skunk on way to the race while arguing about things on the phone and fighting off sleep as I headed to the trail to spend the night before the race. Everything stunk of skunk in the parking area thanks to me. I’m sorry, guys!!

Chillin’ like a villain in the car; John camping in the TWOT lot

Car Camping!!

My mobile aid station was pretty well organized, definitely better than in previous years. I put everything I needed in 4 bags, one for each loop. It was like 4 races worth. The only thing I really regret was not organizing food better. I knew I’d be hungry and frantic each loop and I did the best I could. I was well organized with electronics. I had 3 headlamp batteries, a portable charging station, and my watch.

All around, with the exception of the way I organized my food, I’m proud of my overall car setup.

Bathroom Situation

There are no restrooms at TWOT. As the name of The Wild Oak Trail race hints: you’ve got to get wild out here. I was able to go as soon as I woke up the next morning. I was dreading this and if I could go, but was extremely lucky to get that out of the way. Then I worried about when the next one will come and how to manage that. It’s funny that I feel like I’m a dad planning when I need to change my daughter on vacation back when she was a baby.


I was parked next to Tony Taylor. We spoke briefly the night before, but I was extremely tired so we talked more the Friday morning of the race start. I went around and spoke to everyone. One interesting aspect of this race is with the TWOT 200 also going on, guys are getting done with 100 miles or more because they started a two days earlier. Unfortunately, Kevin McCabe had dropped out of the 200. I’m a huge fan of his and was hoping to run some with him.

The Feet of Peter Morgan

There was also another 200-miler runner who was in the TWOT lot this morning. Peter Morgan had done 4 loops and Tony was tending to his feet. Peter kind of stole the show. I was rooting for him to get the 200 done. Lots going on here on TWOT 100 race morning! So, Guy gave us the brief and off we went.

Loop 1

I hung out with Tony and with Jeff Stafford. Last time I ran with Jeff was at the 2018 Barkley Fall Classic. He’s a damn good runner and all-around great dude to talk to out there. The first 7 miles or so you climb Little Bald Mountain. It’s got a lot of vertical but it’s manageable. There’s some flat at times and some downhill, so it’s not just straight up. [Editor’s Note: If you do the loop in the counterclockwise direction, you start with this long climb up Little Bald Mountain. The other two sections are Big Bald, which is in the middle in either direction, and is the shortest of the three TWOT sections; and the longest section comprised of Lookout and Hankie mountains.]

Jeff Stafford and Tony Taylor

Three people deep on a TWOT loop is a luxury, let me tell you. So much to talk about and kill time. We talked about previous TWOT attempts, Barkley, and all the hard races out there.

Tony and I did tell Jeff this race is like Squid Game; you may think someone is totally in control, but they can drop at any time. I told him it could be me or it could be Tony. Never, ever, get too comfortable with someone else. Know they could be gone and do not at all let their dropping influence what you do. Also, if someone does something different than your game plan, then you have to let them go.

It’s rough but as many times as I’ve attempted this race, I’ve seen it all and know better now.

The best thing about the TWOT loop is the climbs are difficult, but the descents down are really nice. We were making up a lot of time going down. The plan was to finish the first loop in around 8 hours or so. By doing this, we would be in the driver’s seat on time. Definitely don’t want to hammer out all fast loops, but if you can do that first one fastish while fresh it sets you up to be able to get some good rest later.

The Little Bald descent is my favorite part of this race. It’s a little technical initially, but on fresh legs it’s fine. Also, you get some excellent running miles in here, too. It goes extremely quick. One really fascinating part is once you get to the road, about 10 miles from the start, there is a check-in sheet. This is your lifeline to the race to see where everyone else is, who’s dropped, and when they checked in here last. It’s one of my favorite parts because it’s so interesting to get caught up.

The crossing of the North River

We made it through the North River crossing at the base of the Little Bald descent, and got to Camp Todd. Guy was there waiting for us to make sure we were okay. We talked a bit and headed up Big Bald Mountain.

This climb is rough; it’s more straight up than Little Bald, not as far, but it’s tough. We kept climbing, talking and being fresh and in good spirits. It was fun. Also, at this point I think it was close to 70 degrees out. We got extremely lucky out there when it comes to mid-February TWOT weather!

I really do not like the next 10 miles or so, after you finish the Big Bald section. You cross the road and get to trails, but it’s weird bike path type stuff. You can run it easily, it’s not technical leading up to the chin-scraper ascent to the top of Hankie. This thing sucks. We did good on it, but I knew it was going to get worse and worse. I was not looking forward to it.

John Calabrese resting on the sign at the top of the Hankie chin-scraper climb

When you get to the top of the chin-scraper, you go to the left and follow the trail, staying to the left. You do a series of climbs, then go into woods. You then get to a gate and it’s like a fire road hunters use. This is a nice part to run if you can. I mostly shuffle it, but you somewhat need to push here because there’s some unfun stuff coming up.

Tony and Jeff got ahead of me here-I don’t go quick on the fire road section. Then once you get done with that, there’s some rocky stuff on what is now Lookout Mountain for about 6 miles. This is the part that in the past has knocked me out of the race. It drags on big time. I took my time. I did not want to push it but at the same time I wanted to catch Jeff and Tony so I could start loop 2 with them.

Back at Camp

I was kind of stupid here, once we got back to the TWOT lot. I had a quick turnaround so I could go out on the loop with them. I know better than this, but I slammed food. Got on fresh clothes, headlamp, etc., got supplies and it just worked that they were ready to go. Should I have stayed in the TWOT lot longer? Maybe, but I was committed to this plan.

Loop 2

This was my hardest loop. It’s knocked me out most in the past and I do not remember parts of it well. Tony Taylor remembers it a little differently.

Tony, Jeff, and I headed up Little Bald. We were in time-saving mode. Tony really was strategizing. We all were because once we got done with this loop it was nap time. We needed to get this one done and manage the carnage. Early on this loop something bad started happening. We were starting to lose Jeff.

Jeff was fighting the climb, but we had to keep moving. I hate this aspect of the race. I’ve been Jeff before on loop 2 in previous years and I know how it feels.

Tony and I pressed on. We totally lost sight of Jeff at this point-not even a headlamp in the distance.

Tony and I got to the top and made the descent, it’s harder at night but we moved pretty good and made it to Camp Todd. Amanda Womack was there volunteering with her son. We talked to her for a bit. Fixed ourselves up, waited for Jeff, but there were no signs. We had to move on.

Going up Big Bald was much rougher this time and we were now getting tired. I don’t remember much of this loop; in fact, out of all 4 loops, this one is the loop I’m the most foggy on.

Tony remembers this section differently, but I swore he was with me or nearby. I could see his headlamp in the distance or something.

I believe once Tony and I got done with the Hankie chin-scraper I really took my foot off the gas. I tried to keep up with Tony but I couldn’t. This is my weakest area of the loop. I could see Tony in the distance for a while but eventually I lost him. I just did my absolute best to get back to the TWOT lot to get sleep.

I believe I came back about 30 minutes or so after him. My plan was to take 2 hours, get organized for loop 3, eat, clean up, put on fresh clothes and then with whatever time was left over, sleep.

For some reason I woke up and saw someone headed back out on the trail. I assumed it was Tony and I’d be alone. I knew at this point I was going to have to be comfortable being alone out there.

The alarm clock woke me up, but Tony was still there. He gave me a part of a Jersey Mike’s sandwich and I drank some coffee. Amazing!

I must have been confused and saw someone else head back out. So, I got to start the loop with Tony, but I knew he was stronger than I was out there. I understand he just was in “get it done” mode, and that’s how everyone in the race needed to be because the weather was incredible. We had to take advantage! It may not come again or for a long time in this race.

Loop 3

This was all new. I had never made it to this point in previous TWOT attempts! Feeling great from a little nap — and another really cool thing on this loop was the one-loop TWOT runners were about to have their Saturday morning start. For me, that meant there would be people out there to talk to and get motivation from, and I would not be alone! Also it’s daylight! All around much better situation than loop 2!

I believe Tony went ahead towards the top of Little Bald. Rick Kwiatkowski was out there, and we talked for a minute. It was really cool to see him-I ran the loop with him a few years back. A little while later I ran into Zach Weinberger. It was great to see a fellow VHTRC friend out there who I’ve done many races with. We talked briefly and he went on.

Headed down the mountain into Camp Todd, and it was then that some rain started. I was dreading this, but also we were very lucky up until now, so I couldn’t be too annoyed. I got ready at Camp Todd, and then proceeded up Big Bald. I had a coat with me, but I was still too warm from climbing to put it on yet. This part was kind of miserable, but once I got near the top I put on my coat and shuffled down the nice runnable area. Once I got to the checklist below, I met up with a one-looper. I forget his name, but he was extremely nice and got me motivated for my least favorite stretch.

By this time the rain had stopped completely, so I was really happy. I took this last big section of Hankie and Lookout extremely slowly.

The bridge over the North River that signals the runners’ approach to the finish at the end of a counter-clockwise loop of TWOT

I believe I got in from Loop 3 of TWOT just as it was getting dark. Tony and another runner named Jason (who was doing the two hundred miler) were about to head out. I made sure I had everything I needed. Got comfortable clothes for the loop, ate, and then I headed out. I knew this was going to be a weird, lonely loop so I prepped as best as I could. It was at this point I found out that Peter Morgan had to drop. I was really saddened by this as he was looking great, had a great routine down, and I fully expected him to get it done. Peter is one of my favorite runners at Wild Oak. I feel like he’s the blueprint of what a Wild Oak runner should look like and conduct themself! Super cool guy.

Loop 4

I knew this final TWOT loop was going to be an adventure. I was exhausted, but I was so motivated to get done. I couldn’t drop at this point! I’d done so much and who knows if there would be another TWOT this good, weather-wise!

I could see headlamps in the distance, so I knew I wasn’t too far behind other runners, but I wasn’t near them either. I thought a lot about horror movies and things I really should not have been thinking about. I was so sleepy that certain trees and leaves were looking like faces, monsters, people, etc. At one point I swore I saw Pokémon. I kept pressing on. I found myself humming and singing Oliva Rodrigo songs that my daughter likes in order to ward off demons. I thought a lot about my daughter out there (as a baby, and how she’s grown since).

I got to Camp Todd, and I really can’t remember much of what I did here. Just headed up Big Bald. The rain started again at some point. It was misery but also may have helped me not want to take any dirt naps because everything was wet. Also, the rain helped keep me awake.

Off on the side of the trail I saw Jason. I hung out with him a bit. I needed to talk to a human and was happy. We talked a lot of sports. I needed someone like him who was into the same stuff as me to be able to have a conversation with, to get my mind working again and get in a better place. Jason started having issues as we started the descent. His feet were trashed, and the extreme wet downhill here was not good for him. I felt kind of bad here, and I didn’t say bye or anything — we just sort of parted ways. He knew I stayed as long as I could, but we had different cutoffs, so I had to move it to make mine.

Alone Again

I also knew this was basically the race, right here. What came next wasn’t going to be easy. The Hankie Chin-Scraper and a lot of annoying wet rocks.

Tony had left me a present. A black rifle can of coffee with an obscene amount of caffeine. I took that shit to the head, and it was on. I ran faster than I had in a while and actually moved up the Chin-Scraper faster than my last loop (in reality I probably didn’t, but it sure felt like it). Once I got up there, I was creeped out. The caffeine and fear kept me moving, but I was getting tired. The woods were foggy. It looked very unpleasant. I kept thinking about serial killer movies and other bad things, so I moved as fast as I could to the fire road section.

At the gate I felt relieved, but it wasn’t over yet. I tried to make the best I could of the road running when I could. I was genuinely worried about the next section. Also, like a complete jackass I switched shoes on the last loop to the ones with the least amount of tread (and extremely worn).

I got to the rocks, and I was sliding everywhere. I don’t even understand what happened, on some spots as soon as I stepped on certain rocks my feet went out from under me. I was passing out and falling on rocks. It felt like Neo getting his ass kicked in the beginning of the Matrix - just relentless. After multiple falls, I woke up and got it together. As slow as I was moving, I now at least had it together.

From this point on, I just pushed as hard as I could. It wasn’t pretty, but I wanted to be done and sleep. I had been gone from home for days and I missed everyone.

The Twitterverse is alerted to John’s finish!

Headed into the TWOT lot and I saw Guy. It was very quick. He was so happy I made it and I was, too. But it was also pouring rain, so we both just talked for a second, and then I went to triage, taking care of my carcass.

Post Script

If you do this race, after it’s over you may want to just bite the bullet and get your car detailed - it will be in bad shape all around. Everything will be a mess, so be ready for that.

I didn’t have cell service, so I slept, and then headed out after an hour or so and called my girlfriend, Denise Freeman, to discuss the race. I also called my mom, and finally I ate the closest available breakfast, McDonald’s! It was delicious. I also have no idea where I ate this meal, but I made it!

For anyone serious about doing this race, my advice is: Do the Massanutten Training Academy Run #1 and the Waterfall 50k back to back on MLK weekend as ideal prep for TWOT. I pretty much owe this finish to the VHRTC for that amazing training weekend in the mountains. If you can finish both runs on MLK Weekend, then you are absolutely 100% TWOT-ready. Also, a good last prep race is the Willis River 50k, especially if there’s bad weather in late January for that race, as it will get you tough if you need it! I know it helped me at Wild Oak!

Thank you to TWOT RD Guy and volunteer Amanda for helping all of us out there. That was an incredible amount of work you did, and it’s obvious how much you love this race.

I know this long-established, low-key race is going to continue to thrive. I hope more people come out for it next February. I’m in for the 200 miler! So, please join me out there! Let’s talk sports and ward off evil spirts and serial killers together!