The Ring

p showing the route and elevation of the “The Ring” bike loop.

The Massanutten Trail is a 70-mile loop of the gnarliest trails on the East Coast. The loop is often called “The Ring”. Finishing a lap in one go has become a recognized feat, originally done by runners but completed on mountain bikes for the first time in 2012; by Mike Carpenter in 17 hours and Kyle Lawrence in 19. Since then, 7 more men and 2 women have completed the loop, and a few of the guys have done it more than once! There have been a lot of unsuccessful attempts, only a few of the Ring finishers were able to lace it together on their first try. The sheer ruggedness of the route creates more problem potential than other trails. The luckier riders get away with minimal bike carnage and injury, but many attempts have been squandered by broken bikes, hurt bodies, and bad weather. The feat requires good luck, and major physical readiness. 

The majority of the 70 miles are singletrack trail, with some chunky doubletrack throughout, and about 5 miles of gravel. Elevation gain is around 12,500 feet. 

My boyfriend, Sam Skidmore, set the men’s FKT with Charlie Snyder in 2017, both at 15 hours, 45 minutes.  

On September 27th of this year (2019), I set the women’s FKT and 5th overall fastest time on the Massanutten Ring. I finished in 16 hours, 40 minutes. I was the first female to ride the loop clockwise. Sue Haywood rode it counter-clockwise in 2017. She was the first woman to ride the full loop in one go, finishing in 20-½ hours. Sue is one of my heroes and dear friends, and she gave me constant, positive encouragement over the last few years to try and finish the Ring. 

During my ride, I tried not to use my phone to save battery but whipped my phone out halfway through the downhill from Signal Knob. This was the trail behind and in front of me, actually one of the smoother sections:

Rocky bike trail on a hillside.

The trail before me; chunder-thon!

Bike trail across hillside covered in large, sharp rocks and boulders.

What I had just ridden...

For some more trail beta, here are a few other photos of myself and friends from past rides on the Massanutten Trail.  

Sam carrying his bike uphill on a difficult rocky trail.

Sam Skidmore on the Waterfall hike-a-bike during his record setting ride in 2017...

Nate riding on the trail approaching a large boulder.

Ring finisher Nate Shearer on a Signal Knob group ride last year...

Sam showing Sue the route to take down a rocky portion of the trail.

Sam shows Sue the line during a group ride...

Rider climbing up a steep trail with a scenic valley in the background.

Climbing up Wanoaze last December...

Mike riding down a rocky slope.

Mike Carpenter atop Veach Gap last April...

Lindsay climbing the trail with a fern-covered rock wall behind her.

On the way to Woodstock Tower in December 2018...

Pictures just don’t do it justice; the rocks are constant and relentless. There are tons of mind-blowing sections I don’t have photos of, but even if I did, they wouldn’t capture the rawness of some of the chutes (and ladders) along the orange blaze. Ideally, you stay on the bike as much as possible when riding these trails, but there is definitely some walking. Efficiency is the king of conserving both energy and daylight, so when I dabbed I’d try to be quick and move along to get back on the bike. There were a thousand hike-a-bikes, including one over a mile long. Comfortable shoes are a must, and hiking fitness helps immensely.  

I decided over five years ago that I would do The Ring someday, and it wasn’t until my third attempt that I pulled it off. My first go was in early 2017. I was accompanied by my Dad, and I made it halfway through in 13 hours, definitely slummer pace. The blisters on my heels from walking were what made me pull the plug. I ultimately was not ready and had underestimated the intensity of the course. I was sparked to try again but also a little beat down and intimidated! It took me a few years before I felt like the timing and my fitness were right to try again, and in that time my riding strength and durability excelled greatly. I learned how to fuel properly for my body and diet, and I spent the winter of 2018 mostly trail running to build a base of hiking muscles for The Ring 2019. In May of this year, I was joined by my two buddies Amelia and Dave for my second attempt. We didn’t make it much farther than I did my first try, but we had a really good time riding all day at a party pace, spending a lot of time at our SAG stops and taking some overlook naps. This was great recon, good to familiarize myself with the route and exposure, and I knew that I’d have to keep my stopping time low to save daylight and to avoid eating too much and feeling blah from a full belly. 

Dave flashing a shaka sign while standing with his bike on a rocky outcrop with a beautiful sunrise in the valley below.

Dave on Veach Gap at sunrise...

Amelia pushing her bike up a rocky slope.

Amelia summiting Duncan Hollow...

Rider laying on a large boulder with his bike propped up below him.

Trail napz...

I decided I would try again sometime toward the end of the year, most likely at the beginning of Fall. This way it wouldn’t be too hot, the leaves wouldn’t all be down yet, and the overgrowth from the summer would be dying and beaten down a bit. 

A week prior to my completed Ring lap, my friend Jess Daddio and I wrapped up an epic bike tour, the TransVirginia. We both rode loaded Salsa Fargos with big ol’ mountain bike tires, and made it from Washington D.C. to Damascus, Virginia in 8 days. The tour was 550 miles, with 45,000 feet of climbing. We finished on a Thursday, and Sam picked me up from the Tennessee border and chauffeured me to Snowshoe Resort in West Virginia that night. We did a lot of pre-riding the next two days for the WVMBA Enduro Series Final that Sunday, which Sam and I both won. 

Jess and Lindsay standing with their bikes in from of a red train car.

Jess and I in Damascus after setting the women’s FKT on the TransVirginia bikepacking route...

The winners at the women's podium after the Enduro Series race.

Snowshoe Epic Enduro women’s podium...

I was on a serious roll, I had already ridden almost 100 hours in September before my attempt on the 27th, and Sam and I had spent the last three weeks of August riding and hiking our faces off in Colorado. So much saddle time in the last 6 weeks had me pedaling steady, and my brain and body were accustomed to exposure. I knew I needed to try The Ring before my fitness evaporated, so I jumped at the opportunity to hop in behind my friends Charlie Snyder and Eddie Anderson when I heard they were giving it The Ring a shot on September 27. 

I knew I wanted to try a solo Ring mission, but felt intimidated about starting and riding alone in the dark, so Charlie and Eddie’s presence in the woods made me feel a lot better. We started together and they immediately dropped me, but they cleared all the spiderwebs for me. I owe them!  We had perfect weather topping off around 80 degrees, no gnats or flies to be seen/heard/felt, zero precipitation, and no need for lights from 7am-7pm. 


The Play By Play


Woken by my bladder, I decided not to go back to sleep as my alarm was set for 2:45 and I didn’t want to double the ‘getting out of bed’ torture. This was one of the hardest parts of the day.

3:30 am

Leave the house with eggs and coffee, drive 40 minutes to Moreland Gap, to drop off a resupply bag with snacks and water that I would reach later, around 8:00am.

4:25 am 

We leave the cars in the dark and hop on the Massanutten Trail, marked by orange blazes on rocks and trees that would loom in our visual peripherals all day. The boys drop me after a few minutes, and their lights flicker and then disappear on the way up the long Duncan Hollow climb. I have to stop to pee 10 minutes in; classic. This was good though as I could adjust my wardrobe for easier pants droppage throughout the day. Bib straps over a tucked-in wool base layer so I didn’t have to deal with getting in and out of a wet jersey. Constant animal rustles to the sides and behind me as I spin up the mountain, with glimpses of deer and bats. I started to eat 30 minutes in and kept a steady calorie stream going. Big derailleur smack during the hairy, creek bed descent after Duncan Hollow. This led to some random behind-the-cassette chain drops over the course of the day, but I learned to control my “SRAM slams”, (when you drop 4-5 gears at once to try and get into your Eagle last minute, usually accompanied by loud grinding), and to be extra gentle with my shifting, which kept it from dropping as much the rest of the day. At the bottom of the creek bed descent, the trail drastically ramps upward to kick off the hardest hike-a-bike of the day; 25% grade for over a mile.

6:15 am

Halfway up the hike-a-bike, aka Waterfall trail, my light turns off. I had been greedily running it on medium brightness since the start, and had run out of juice. I had another, bigger battery charged and in SAG for that evening, so I had to make do with my phone’s flashlight feature until sunrise. Thankfully this happened while I was walking uphill, and not in the middle of riding down some technical craziness - which apparently happened to Eddie later that night when his light died mid-East Ridge death chute (yikes!). I knew I still had at least a half hour of complete darkness left and didn’t want to sit and wait for the sun, so I tucked my phone into my bibs on my belly. This worked for the remainder of the push and was only mildly sketchy for a half mile of twisty ridgetop trail through thick laurel, before popping out on the road at the start of Jawbone around 6:40. The sky was getting purple. I stopped here a few minutes to eat a snack and take the light off my helmet, put my phone away and let my eyes adjust to the almost-dawn light. Thankfully the first mile of Jawbone trail is grassy and smooth (a rarity of the Ring), and by the time the gnar ramped back up, the sun had risen. 

A sunrise in the distance partially hidden by trees. The tree in the foreground has an orange marker painted on its trunk.

Sunrise on the Orange Blaze...

8:30 am

I pop out of the woods after the heinous Jawbone ridge and descent, not expecting to see Sam and our dog Luna hanging out there. I thought I wouldn’t see him for another 2-3 hours. What a treat to see my pup and person for second breakfast! Almost as nice to see the egg on toast I had in a Tupperware in my drop bag, which Luna immediately licked as soon as I opened. I ate it anyway. Refueled and rehydrated, I started up the quick but steep climb to get on the Short Mountain ridge. This section, and Jawbone before it, were the most consolidated technical parts of the day. I would get in a good groove of riding, and would clear things I’d never done before, then it would switch off and I would bumble and struggle for a little while before grasping how to ride again. I talked to myself a bit, with “LOOK UP!”, “What the f***”, and “This is fine, you are fine” as popular phrases. There were also lots of random Beyonce lyrics.  

Lindsay riding on a trail in a wooded area.

Popping out of the woods at the end of Short Mountain...

10:30 am

Wrapped up Short Mountain! Sam was at the trailhead and my Chipotle barbacoa bowl was in the cooler. Yes! Only a few bites though, as burrito baby bellies are not welcome on the next climb that ensues up Wanoaze Peak. This climb starts out easy, but the last mile is HARD steep tech crazy, and I committed to hike it up to the ridge, which was more efficient and gave me a chance to digest and gave my legs a break from pedaling. The ridge rode really nice, the ibuprofen kicked in, and I rolled the next 12 miles steady and strong. After a loose descent off the ridge down to Mine Run Road, I had five miles of gravel (that was weird but welcome) to the Strasburg Reservoir. A quick diddy of singletrack around the lake, and then onto a few miles of doubletrack up to Signal Knob, with a messed-up headwall in the direct sun for the last ¼ mile. Minor brain meltage here, only to be rebooted by an incredible mile of rock sidewalk off the top of Signal Knob, one of the more rideable sections of major gnar. I blew myself away in this part, I was riding on point and it clicked that I was moving and grooving, and my confidence of finishing the loop grew even stronger. Once I reached the end of that super fun mile, I was at Meneka Peak and then on to the jagged Signal Knob downhill. My triceps were protesting, as were the blisters forming on my hands, but damn was it fun. Even when I pedal strike resulted in a hole in my shin, and blood spurted out of the hole and I got a headrush just looking at it, I was still stoked. 

2:45 pm

Roll into the Signal Knob parking lot, and see Charlie and Eddie with jelly on their faces and slumber in their eyes. I was very surprised to have caught back up to them. I ate some more of my Chipotle and re-upped my Matcha Skratch Labs and snacks as they rolled out. I also put my light and battery back in my bag. The boys had our friend Josh helping them with support, as Sam was doing for me. I ate their leftover Route 11 potato chips and then was out of there by 3:00 and onto the last 20 miles of the Ring. I started up Shawl Gap climb, which is halfway rideable, and was on and off the bike. Once I was up on the East ridge, I conjured the goal to make it past Veach Gap before turning my light back on, and through a particular section of exposed, hardly walkable side trail just before Milford Gap, about 10 miles from the finish. I had fallen off the side of the mountain during this section during my first attempt in 2017 (with no injury besides that of my pride) and knew that it would be especially hard to get through in the dark. 

Charlie and Eddie sitting on the tailgate of a truck taking a break.

Charlie and Eddie at the Signal Knob lot, almost 11 hours in...

Eddie riding downhill on a wooded trail being led by a white dog - Luna.

Luna dog was giving us all pet therapy at the SAG stops, here she is towing Eddie in to Milford Gap...

5:00 pm

Ate some tuna at the Veach overlook. My pace was looking good to reach my goal spot before turning on my light. My body felt alright; my legs were on autopilot. My riding game was on fire, and I felt like I could turn it on for the remainder of the ride and get ‘r done. 

6:30 pm

Arrive at Milford Gap. Sam and Josh had hiked up to meet us on the ridge, apparently Charlie and Eddie had left only a few minutes before I got there. Blessed be my Sam, who hiked up with the remainder of my Chipotle and a Yerba Mate. As I was stuffing my face, it hit me that I’d made it to the homestretch, and I knew this next section very well.

There is a stage race called the Tour de Burg, based in Harrisonburg, VA, that has a few classic race days and stages. One of those days is a loop including sections of the Massanutten Trail. The first stage is from Wanoaze Peak to Mine Run Road, and then the peloton shoots across the valley and climbs up to the parallel ridge for the second stage - from Milford Gap to Camp Roosevelt. This is the hardest day of the Tour, with at least 4-5 hours of overall race time for the fastest rider, not including party pacing before and in between the race segments. I was almost 14 hours into my Ring attempt upon leaving Milford Gap, and all that was separating me from The Ring was the most challenging stage of the Tour de Burg. I knew exactly what was to come, and I wasn’t intimidated by it - I was motivated. 


Time to put my light on my helmet. The sunset was bangarang, and I made it through the first of the three notorious downhill death chutes before the sun completely disappeared and I had to turn my light on. The trail was lit up with red and pink streaks from the setting sun and the sky and everything around was touched by the best natural effect I’ve ever seen!


Right before the sun sank behind a distant ridge, I had glimpsed Kennedy’s Peak from a high point on the ridge, just a few miles (and bumps) down the way. From Kennedy’s, it was only 3 or 4 miles of mostly downhill to the end. It was dark, I could see the lights from Luray in the distance. I’m riding steady for a while, even more motivated since I’d seen the literal end, and suddenly rolled up on a huge rattlesnake in the trail. We had a moment as neither of us enjoyed the other’s company. We had a stand-off for a few minutes and the snake eventually slithered off. I ended up eating a snack while I was yelling at it during our stand-off, so that probably was a good thing, but it scared me really good. The persistent thought of snakes after that helped me turn over the pedals and tick off the last few ridge miles. On the last hike-a-bike I looked up at the sky and thanked whatever tectonic forces had made that be the last of the major steeps I had to walk up. I turned down Kennedy’s downhill and wanted to cry out in joy, but did not allow myself yet as I knew the next few miles to the car were especially difficult and I needed to keep it together. My arms and hands were feeling rough, my brain felt weird, and my body was ghostly. I made it to the bottom and had a mile of rolling doubletrack to suffer through before popping out on Fort Valley Road. I was one section of orange blaze away from the car, just a mile of superb downhill gnar. Five minutes of line-picking riding and some cyclocross moves later, I was coasting the last few hundred feet of gravel to the parking lot at Camp Roosevelt. 


Charlie and Eddie had gotten in a few minutes earlier. They had stuck together all day, and they hollered at me while I was ugly-crying happy tears on my way toward the van. I’d never felt so good about something I’ve done. It better than any race win or academic graduation. Having the guys there to celebrate with was awesome as they knew how hard it was and what it meant to finish! We all had good luck that day with minimal bike carnage and no flats! Fortunately, also no real injuries, just lots of brier scratches and superficial wounds, plus some very itchy sand flea bites that popped up the next day. This was Charlie’s third Ring lap, and Eddie’s first.

I rode my Salsa Redpoint with 2.6” Maxxis Minion DHRs front and rear. I have EXO+ casing in the front, and an EXO casing with CushCore in the rear. I ran low pressure, around 18 psi. I wore Five Ten Kestrel lace-up shoes and my Osprey hydration pack. I carried one bottle on my bike for sugar drink, and a top tube bag for easy access to my snacks. 

There are definitely one hundred more scratches on my bike than there were before, and lots more wear on my bottom bracket rock guard. My derailleur needs replacing, and the Maxxis logos on my tires are worn and faded. My chamois and seat left their marks for sure; major chafe. Minimal carnage though, considering what I’d put my body through. I ate a lot of food the next few days and recovered fairly quickly.

I had gone through varying waves of both doubt and confidence over the last few years, not sure if I’d ever be able to get through The Ring. To have finished, and to have finished strong with a serious record, was the best feeling I’ve ever had. I’ve been overflowing with happiness since and am ready for whatever is next on my mountain-bike-life journey. Finishing this was my ultimate goal in cycling, inspired by my Dad, Mike Carpenter, the first-ever to ride The Ring.



Salsa Cycles Presents: Foundations East from Salsa Cycles on Vimeo.

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Lindsey Carpenter

Lindsey Carpenter

I love spending time on a bike in beautiful places with my friends. I enjoy challenging myself with technical mountain biking and some racing, but the main reason I ride is to adventure in the mountains surrounding my hometown in the Shenandoah Valley. I look for trails with some history, either because they were CCC projects, or are old logging access roads since made into singletrack trails. Getting to pretty overlooks only accessible by bike or foot is always satisfying, and sharing those moments with all levels of riders and friends is very special.


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