Highlands Sky 40 Ultra: Get the Dirty Details From 6 Trail Runners

What's it like to run the Highlands Sky 40 Ultra?

It's an epic race in West Virginia hosted by the West Virginia Mountain Trail Runners that draws about 200 runners to the Monongahela National Forest.

Looking for a Highlands Sky 40 race report?

Here's the dirty details from six trail runners who crossed the finish line...

South Prong Trail, lined by blooming mountain laurel, around mile 18.5 of the Highlands Sky 40. Taken one day before the 2022 race. (Photo/ Brynn Cunningham)

The Highlands Sky 40: Get ready for awesome...

The Highlands Sky 40 is a classic West Virginia point-to-point ultramarathon and the premier race hosted by West Virginia Mountain Trail Runners.

The Highlands Sky 40 consists of:

  • 75 percent trail
  • 15 percent dirt Forest Service road 
  • 10 percent paved road (two miles at the beginning and about four miles at the end)
  • 5,474 feet of elevation gain* 
  • 4,856 feet of elevation loss*
  • 41+ miles total, according to most finisher’s watches at the end of the race*

*Exact elevation loss and gain and mileage varies per GPS device 

Boardwalks abound on the often wet course, including this one on South Prong Trail, the single track that precedes the dirt road section aptly named the Road Across the Sky. (Photo/ Brynn Cunningham)

2023 = The 19th year of the Highlands Sky 40

Held each year on the third Saturday of June, it is a bucket-list late spring race for many trail ultrarunners in the tri-state region and east coast. 

Registration opens before sunrise on Feb. 2, Groundhog’s Day, and fills its 200 spots within hours.

On June 17, 2023, Highlands celebrated its 19th year of taking runners through its magnificent vistas and breathtaking landscapes.

Bear Rocks in the Dolly Sods, around mile 30, taken one day after the 2023 Highlands Sky 40. (Photo/ Eric Harder)

The landscape of the Monongahela National Forest in West Virginia

According to the WVMTR Highlands Sky 40 website

“The course traverses the Roaring Plains and Dolly Sods Wilderness Areas through some of the most rugged and beautiful terrain in West Virginia.” 

Containing the highest plateau in the eastern United States, The Dolly Sods has a landscape of:

  • rocky terrain
  • stunted trees
  • mountaintop meadows traditionally known as ‘the sods’ 
Author Cunningham runs with her sons on the Dolly Sods plateau, the latter section of the Bear Rocks section, nearing Ridge Trail, the day after the 2023 race. (Photo/ Eric Harder)

Dolly Sods is known for pristine vistas and an environment characteristic of more northern latitudes (such as Maine and Canada). 

Race participants are sure to enjoy the varied trail terrain through:

  • northern hardwoods
  • stunted red spruce
  • heath barrens
  • woodland paths
  • ancient sphagnum bogs
  • rocky and boulder-filled plains

Here's a full course description of the Highlands Sky 40.

The 2023 start line at the Red Creek Bridge in Laneville, W.V. (Photo/ Brynn Cunningham)

6 runners share the dirt on the Highlands Sky 40

Wondering what it's like to run the Highlands Sky 40?

We caught up with SIX runners who finished this race:

  1. Caleb Bowen
  2. Jason Cox
  3. Emily Flinn
  4. David Moore
  5. Rob Myers
  6. Aaron Watkins
Caleb Bowen on the Road Across the Sky, Forest Service Road 75, a dirt road section that spans miles 19 to about 26/ 27 of the 40+ mile race course. (Photo/ HollyAnn Swann)

1. Caleb Bowen

  • Runner: Caleb Bowen
  • Finish time: 5:51:20.3 (First overall male)

What did you like most about the race? 

I love how different each section of the course is at Highlands. It has everything! 

  • Paved road sections
  • Six-mile climbs up to 4,770 feet
  • Boulder fields
  • Forest roads
  • Mud
  • Mountain stream crossings, and... 
  • Everything in between. 

Also, you have some amazing scenery! It is so tough but also so rewarding. 

What was the most difficult part for you? 

The most difficult part of the course for me is definitely a one-mile section of trail that's called "Boar's Nest Trail." 

  • It is the rockiest/rootiest one-mile descent that literally drops more than 1,000 feet down to the Red Creek from Mt. Porte Crayon mountain. 
  • It is just so difficult to run because any time you get into a rhythm you hit a rock or root or twist an ankle. I wish we would run up it rather than down it. 

What did your food, drink, and fueling look like?

My fueling was planned out fairly well I think. I wanted to get roughly around 70 grams of carbohydrates from my gels each hour, and then I also hoped to tack on 20-50 grams of carbs with my electrolyte/liquid fuel drinks each hour. 

So, I would take one Spring Energy Awesome Sauce and one Maurten Gel each hour. I also grabbed a few slices of potatoes and one orange from the aid stations. 

Overall, I think I did a pretty good job as I never really bonked and took in all 10 gels that I brought. 

I probably could have used one more gel in the first 10 miles, but I was flustered from getting lost in the boulder field on top of the first climb (it was foggy, and I was looking down at my feet, and then I looked up and couldn't find any flags). 

The 2023 Highlands Sky 40 was Caleb’s first ultra as a Roam and Run sponsored athlete. (Photo/ Caleb Bowen)

What shoes and gear did you use? 

My gear consisted of: 

  • Hoka Speedgoat trail running shoes (the grip was needed on the slick rocks)
  • My blue UltrAspire Vest that I received in a raffle at the 2021 Rim to River 100 
  • My new Roam and Run racing shirt
  • Blue Rabbit shorts 
  • Compression socks I found at Aldi for $15. The high socks are great for running through stinging nettle in the early miles.

This was my first ultra since being sponsored by Roam and Run, so I definitely wanted to make sure everyone got to see the new kit!

Caleb won first place! Top five are awarded a Patagonia backpack with Highlands Sky 40 embroidery. (Photo/ HollyAnn Swann)

What would you do differently? 

Well, if I were to change anything, it would be to try to look up for the flags better on top of the Roaring Plains boulder field.
I was doing really, really well climbing up the mountain, and I felt great. 

  • But once I got off course, I wandered in the boulder field for what seemed like an eternity (but was actually a little more than three minutes). 
  • Fortunately, my friend Lucas Warner was in second place, found me and got me back on the trail. 
  • From then on I was very frustrated as I knew that mishap cost me a chance at the course record (5:44 held by Joel Wolpert). 

It was difficult to shake off the frustration until I got to the Bear Rocks section at mile 27.

  • Instead of dwelling on the mistake, I made a new goal of just trying to run hard from Aid Station #6 to Aid Station #7. 
  • And I ended up running faster than I had ever before by several minutes. It was as if I had wind in my sails! 

After leaving Aid Station #7, I looked down at my watch and did the math, and I discovered that I was going to run under six hours if I could keep it up. 

While I am still frustrated with my mistake, I am happy that I eventually climbed out of that hole, refocused my goals, and ultimately had a great day!

Why did you choose to run the Highlands Sky 40?

So, I have been doing the Highlands Sky 40 every year since 2017 for a few different reasons. 

The biggest draw is that I absolutely love the community that this race has created. 

It feels like an annual reunion of seeing your friends from all over. I believe we just happen to run a 40-mile race in the wilderness in order to have an excuse to see everyone. 

Another reason that I come back each year...

is because the 2017 race was my very first ultra. 

It was the hardest thing I had ever done in my life up to that point, and that ignited a fire for the sport, and I have loved it ever since. 

This race is also special because it is held in my favorite place in the world, the Dolly Sods Wilderness Area. I absolutely am enamored with the beauty that is up here.

Jason Cox, post-race at the finish line, Canaan Valley Resort (Photo/ Amber Smith)

2. Jason Cox

Runner: Jason Cox

Finish time: 11:44:55.8

What did you like most about the race?

I liked the variations in terrain. There is a nice mix of inclines, declines, switchbacks and flats.

What was the most difficult part for you? 

Butt-slide mountain was the most challenging part by far. The steep decline was matched with rocks and many leaves covering the ground.
What did your food, drink, and fueling look like? 

Jason (far right) with crew and fellow racers at the Road Across the Sky, Aid Station 4, mile 19.7 (Photo/ Brynn Cunningham)

What shoes and gear did you use? 

The Road Across the Sky is a dirt forest service road section that spans seven to eight miles of the course, beginning at mile 19. (Photo/ David Moore)

What would you do differently? 

Now that I know the terrain and what to expect, I will push harder on the flats and on the Road Across the Sky. This was my first ultramarathon, and I was mainly focused on keeping my heart rate within a reasonable range and finishing the race – mission accomplished.


Jason (middle) ran most of the race with friends David Moore and Rob Myers. (Photo/ Amber Smith)

Why did you choose to run the Highlands Sky 40?

Running because we can do difficult things – get some!

Emily Flinn enjoys the full splendor of the Dolly Sods, approximately 29 miles into the race.

3. Emily Flynn

Runner: Emily Flinn

Finish time: 9:27:19.4

What did you like most about the race? 

I loved the diversity of the terrain, the AMAZING volunteers, and I see why it is an iconic West Virginia race! 

What was the most difficult part for you? 

It was more technical in sections than I anticipated, including some of the downhills. 

What did your food, drink, and fueling look like?

I mainly used my own nutrition besides some fruit, Coke, Oreos and watermelon… that’s actually quite a lot (LOL). I also used:

What shoes and gear did you use? 

I taped and lined my feet given how wet it was going to be and didn’t switch shoes or socks and didn’t have a blister. 

Entering the Bear Rocks section, about a half mile after Aid Station 5, approximately mile 28 (Photo/ Emily Flinn)

What would you do differently? 

Probably actually train specifically for this race… I’ve been running but prioritizing pacing gigs, and just trail miles not really technical and road miles intermixed.  

Granted, this wasn’t an “A-race”… just looking to have fun and experience the beauty of the course, and I was totally successful in that regard! 


Why did you choose to run the Highlands Sky 40?

It is an iconic WV race and I wanted to experience Dolly Sods in the summer (or a few days shy of). 

David completed the Highlands Sky 40 in 2022 (pictured here) and 2023. (Photo/ Brynn Cunningham)

4. David Moore

Runner: David Moore

Finish time:  11:44:56.5

What did you like most about the race? 

One aspect of Highlands that I particularly enjoy is the variety of environments you encounter along the 40-mile stretch. 

  • Low elevation. The race begins at the Red Creek Trailhead in Laneville, situated at a low elevation point. 
  • Mountains + forest. From there, you'll embark on two challenging climbs up densely forested mountains, the kind of terrain one would expect in West Virginia. 
  • High-altitude plateau. However, as you reach the plateau of the Dolly Sods, your surroundings transform into something very different from typical Appalachia. The Sods is a high-altitude plateau boasting sweeping vistas and an ecology resembling that of Canada rather than West Virginia. This plateau, reaching heights of up to 4,100 feet, stands as the highest east of the Mississippi. It truly is a breathtaking section of the course.
Around mile 17 (Photo/ David Moore)

What was the most difficult part for you? 

The technical nature of the terrain. 

  • I was still in the process of recovering from an ankle sprain and running across rocky surfaces proved to be uncomfortable and demanding.  
  • There were course sections where I had the energy, but lack of confidence in foot placement kept me from pushing myself. 
  • The elite athletes in the field had incredible finishing times, so I believe this just comes down to individual speed and agility.
Boulder garden section of Bear Rocks in the low 30s portion of the race (Photo/ David Moore)

What did your food, drink, and fueling look like?

I tried to eat a mix of fruit, peanut butter and jelly sandwiches and other typical runner fare at aid stations. The aid stations were well stocked, and volunteers did an incredible job. 

  • Sour gummy worms. I carried a large bag of sour gummy worms for the time between stops.  
  •  Saltstick FastChewsI found a new favorite electrolyte replacement in Saltstick FastChews.  
  • Water. I drank water and supplemented four to six Saltstick FastChews and Caps per hour.  I tend to experience cramping during long runs and the FastChews really seemed to help.   

What shoes and gear did you use? 

Another boulder garden in Bear Rocks (Photo/ David Moore)

What would you do differently? 

I would incorporate more training to prepare for the technical terrain. 

There aren’t really similar rocky trails in Northeast Ohio but additional strength training of my ankles or even some practice running along rocky creek beds could’ve been helpful. 

Top of Butt Slide at mile 35. This mile or so of trails is across private property with less routine trail maintenance and more difficult navigation. (Photo/ David Moore)

Why did you choose to run the Highlands Sky 40?

This was my second year running the Highlands Sky 40.  

  • The event had caught my attention a couple of years ago, and when I ran it last year, it coincided with my 40th birthday, making it a particularly meaningful experience.  
  • Additionally, I was drawn to the aspect of the Highlands race being a point-to-point course rather than a multiple-loop course. 
  • To me, this adds an element of variety and exploration to the race, which I find appealing.
Rob leaves the Road Across the Sky, Aid Station 4, mile 19.7, with a smile in the 2022 race (Photo/ Brynn Cunningham)

5. Rob Myers

Runner: Rob Myers

Finish time: 11:44:55.2

What did you like most about the race? 

Like is a strong word. ; ) 

  • The best part of this race is the feeling of adventure. 
  • Throughout the 41.3 miles, you feel the constant change of the world around you. 
  • The ups, downs and technical terrain, you look forward to the change under your feet. 
  • Highlands is the most unique and challenging course I’ve run to date.

What was the most difficult part for you? 

Knowing the course from the previous year. 

There are pros and cons to knowing. You know when to conserve energy and when to push! 

With that said, you know the task at hand, and it can be a bit daunting during the first couple hours.

Rob Myers finished his first Highlands Sky 40 in 2022 (pictured here). He loved it so much that he came back in 2023. (Photo/ Brynn Cunningham)

What did your food, drink, and fueling look like? 

I carried salt, gels, peanuts and water. I don’t like to carry a lot of supplies. I rely heavily on aid stations for fuel.

What shoes and gear did you use? 

Rob Myers finished the 2023 race with David Moore and Jason Cox (Photo/ Amber Smith)

What would you do differently? 

Start in the middle of the pack before the long climb up the first mountain. The single track course didn’t leave a lot of room to pass other runners.


Why did you choose to run the Highlands Sky 40? 

Highland was my first ultra in 2022. I ran it last year (and this year, 2023). The beautiful landscapes and location made it the perfect race.

Aaron Watkins cruises through the Dolly Sods section of the course (Photo/ Derek Clark)

6. Aaron Watkins

Runner: Aaron Watkins

Finish time: 9:15:05.1

What did I like most about the race?

This was actually my second go around with this event. I ran Highlands Sky in 2018 as my jump up distance race from 50k (31 miles). 

  • The best part is definitely when you pop up in or on Roaring Planes. 
  • You climb 2,200 feet in six miles as soon as runners hit the actual single track trail. 
  • Roaring Planes sit at the elevation above 4,500 feet. And when you emerge from the woods, you have almost 360° panoramic views. It's amazing.

What was the most difficult part for you?

Probably this very technical descent around mile 36. 

  • It is named “butt slide.” It is an old abandoned downhill mountain bike trail. 
  • t’s basically bushwhacking all the way back down to the valley floor and after running the “Road Across the Sky,” an eight to nine-mile straight-as-an-arrow gravel forest road. 
  • It’s also a dreaded area on the course for a lot of runners with the sun exposure and monotony.  
South Prong Trail, in the first half of the course. (Photo/ Aaron Watkins)

What did your food, drink and fueling look like?

I had one big thing I wanted to stay away from at this race to see if I felt any better than past races. That one thing I did not want any of was cheese.  

  • Skratch Labs. I’ve started to really like Skratch Labs products so I was drinking their hydration drink. 
  • GU Energy Gels: Had a couple of GU Energy Gels and real food like peanut butter and jelly sandwiches. 
  • Maurten. I think I also had a Maurten Solid chocolate oat bar. 

What shoes and gear did you use?

From head to toe:

What would you do differently? 

I had an A+ goal of running sub-eight hours. I went out at that pace when the gun went off. I was in position to do that halfway through the race but paid dearly for it. I don’t really have any regrets in trying, but I need more road running work, honestly!
Why did you choose Highland sky 40?

Last year when I went down to the race to spectate, I got reminded of how beautiful of an area it really is. And the race community is awesome. 

  • I got pulled off the waitlist like two weeks prior to the race. 
  • I looked at the participation list before I made my final decision. 
  • So many familiar names, and that’s what pushed me over the edge to come back. And I will be back again.

It’s truly an amazing event. I feel like we are lucky to be able to run through somewhere that special.

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Brynn Cunningham
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Trail runner, ultrarunner, white water boater, cyclist (mostly MTB), swimmer, triathlete, cross country and backcountry skier...


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