🚴The Phoenix Challenge: Skyline Edition🚴

Date: Saturday June 10th 2023

The Challenge

STEP ONE: Form a squad of four brave souls to tackle this one-day epic ride.STEP TWO: Choose the epic option that fits your ambitions: 100-miles (10,900ft of climbing) or 150-miles (14,600ft of climbing).STEP THREE: Join the Waitlist for an invitation. We will send you a link to register your Squad.

🚨Read the 1st Annual Phoenix:Skyline Report 🚨

Why | The Routes | Register | What's Included | Rules | Strava | FAQs | Hall of Fame | About

Why Take the Challenge?

A PERFECT FITYou don't want to race, but you still want to test yourself. No ordinary challenge will just do -- you want something that will stand out as one of the toughest rides you've done. Our single-day events combine challenging rides with superior SAG and an awesome afterparty, all in a stunning cycling destination.DOING SOMETHING EPICThe Phoenix Challenge takes place on the rolling -- and beautiful -- Skyline Drive. Whether you and your squad come to compete, challenge yourselves, enjoy the scenery, or all three, you’ll go home with a great sense of accomplishment and even better memories.DOING SOMETHING GOODA portion of each entry fee will be donated to a local area Food Pantry to help those who are in need.STRESS-FREE TRAVELOne ride, two directions, and one hotel. The out-and-back format means super simple logistics before, during and after the event!INSPIRING ATMOSPHERESome of the most challenging roads in the US are accessible to the organized and the brave. Don't sit at home and wonder what might have been, pin on a number, ride with and against your friends, test yourself, and enjoy one of cycling’s epic landmarks.

The Routes

We will ride on Skyline Drive. This incredible stretch of road runs through the heart of Shenandoah National Park. We have President Hoover to thank, as he championed the creation of the road seeing as he had a summer home in the region. Construction started in 1931, and now extends a full 105 miles. The speed limit is 35mph and is strictly enforced, making this a super ride-friendly place for an adventure!

The LegendMaker

The Legend Maker: 150 miles + 14,612ft of Elevation

Your ride officially begins once your squad is fully checked in at the ranger station. Point your trusty steeds uphill and get to work.First up, The Gauntlet. The worst part of this day is right here at the beginning. This is a solid 5-mile climb before you get a break, and that repeats for the first 19-ish miles. You’ll enjoy a brief flat section and your first opportunity to rest (and check in) at Elkwallow Wayside📌.Then you enter The Sawtooth. This middle section is punctuated with rolling climbs that will challenge your patience and focus. Check in at Big Meadows Wayside📌 before continuing onwards.The third and final section is The Grind which will take you to Loft Mountain Wayside📌. The name won't make sense on the way to the turnaround, but on the return, you'll see how the climbs will overshadow the descents. Remember to Check In before you leave!All you have to do now is retrace your steps back to the beginning! How hard could that be, you legend? 😱View the Interactive Map.

The MythMaker

The MythMaker: 100 miles + 10,931ft of Elevation

Just like the LegendMaker day, your ride officially begins once your Squad is fully checked in at the ranger station. Point your trusty steeds uphill and get to work.First up, The Gauntlet. The worst part of this day is right here at the beginning. This is a solid 5-mile climb before you get a break, and that repeats for the first 19-ish miles. You’ll enjoy a brief flat section and your first opportunity to rest (and check in) at Elkwallow Wayside📌.Then you enter The Sawtooth. This middle section is punctuated with rolling climbs that will challenge your patience and focus. Check in at Big Meadows Wayside📌 before retracing your steps back to the start. This is where you write your myth, friends. 😱The Bonus Section is added to only this ride, taking you past The Start down to the tollbooth at the entrance of Skyline Drive (don't exit!). Turn around for some extra climbing and bragging rights that those Legends will have to respect.View the Interactive Map.

Ride Start

Who Needs the Phoenix Challenge?

This challenge ride is perfect for adventurous cyclists looking to push their limits in a safe, supported environment. You’ve ridden more than a few century-distance events before, and are a relatively experienced rider. You are looking for a new challenge to jump-start your season.The ride is challenging by design, but we’ve got you. From the group mojo of the event to professional level SAG support and multiple stops built in at official stores along Skyline Drive, you can simply focus on riding. We’ve even lined up a great post-ride celebration to help you recharge!

Great Seasons Are Built Upon Great Ambitions

Sure, you could do the same old local rides you’ve been rolling for years. You can ride with the same folks on the same terrain, telling the same jokes. The catch? You’ll get the same results.Break out of the ordinary to become a Phoenix Legend or Myth! Take advantage of this incredible natural resource of a highway that is eminently rideable. There are only 25 Squad slots available for 4-person teams for this grand adventure, so spread the word and rally your friends -- you have new stories to create!

The Phoenix Code

In the spirit of the mythical creature, riders in the Phoenix Challenge are expected to:Be Resourceful: As a self-supported rider, you must be prepared to fix any issues you have along the way, from flats to nutrition, etc. Stop at each Wayside to purchase additional fuel as needed. In addition to the Waysides, there will be SAG roaming the course to provide emergency help. A good Phoenix never flames out too early.Be Resolute: Not gonna lie. It’s going to be a challenging ride. But that’s the point -- if it was easy, everyone would do it. When the going gets tough, remember that Pain is Weakness leaving your Quads.Be Respectful: Follow the rules of the road with lights and single-file riding; support your fellow cyclists, and of course be kind to the environment.


This is one of the most challenging cycling events on the East Coast and if you sign up, you are expected to finish by 5pm. We do not offer SAG wagon service to the finish, you must finish on your own except under extreme circumstances (medical emergency). If you do not think you can complete the entire ride on your own, you should not sign up!Waitlist: This event is by invitation only.
You need to sign up for the Waitlist as a Squad Leader or Squad Member to get more details.
Forming Squads
You will create, register and ride in 4-person Squads. You are expected to ride with your Squad across the day and your finish time is noted by the fourth and final rider in your squad checking in at the end. Ride as a team, finish as a team!
The LegendMaker 150
Squads check-in and depart between 6am and 7am based on your estimated time to complete the course.
The MythMaker 100
Squads check-in and depart between 8am and 9am based on your estimated time to complete the course.

What's Included

Well, we created this torture chamber, so there’s that. To make things up to you, we have recruited world-class support to make sure you’ll have what you need in case of a mechanical emergency.We’ve also organized lodging discounts you can choose from. Lodging is recommended unless you prefer to sleep in the fetal position post ride (not recommended).Support
There is a SAG vehicle that can help with extreme mechanical issues and pre-ride check ups.
Participants are expected to carry cell phones, spare tubes, and tools.
Please be courteous, and aid your fellow participants as needed.
There are two designated water break areas. Participants are encouraged to stop at stores along the route as needed for additional refueling.
The full list of items provided include:- Lodging Discounts in Front Royal as needed.
- Massive Quantities Of (Your Own) Blood, Sweat, And Tears
- Emergency Ride Support
- 2 Designated Check Ins (plus self-serve on the route)
- A refreshing post ride celebration beverage.
- Finisher Shirt
- Additional Epic Swag
- Recognition in Phoenix Challenge Hall of Fame

What's Not Included

- $15 entry to Skyline Drive Park (order online, instructions to follow).
- Dinner in Waynesboro (or excessive beverages).
- Lodging.
- Sympathy.


- All entries are final; no refunds. If we can't hold the event due to the conditions listed below, we will make a donation to the NPS after our expenses have been recovered.
- The Challenge Ride will be held rain or shine. Normal amounts of rain will not cancel the event.
- However, in the event of Extreme Weather (such as impassable roads, named storms, or Official Weather Warning), other emergencies, or situations beyond the organizers’ control, the organizers reserve the right to cancel the event or reschedule it to a date of their convenience. If you cannot attend the rescheduled date, your entry will be forfeited, and a refund will not be issued.
- Should the event be canceled for reasons of force majeure, entry fees will not be refunded.
- Registration Insurance is available on BikeReg at the time of registration.
- All riders are required to check-in prior to the ride, and sign a waiver.
- This is a timed ride, not a race.
- The roads are open to vehicular traffic; all rules of the road must be obeyed. Participants are responsible for their own safety
- VA Traffic Laws recommend that riders ride Single File.
- Lights are required on the front (white) and back (red) for tunnels and low visibility conditions.
- Helmets are required to be worn at all times participants are on the bike
- Participants should ride in a safe and courteous manner; please stay to the right, except when passing.


Join the WeRideWeRise Strava Club to connect with fellow riders that you'll meet on event weekend. We will be doing regular challenges to help spread the word -- and to get you fit -- we hope you play along!


What if the rides seem too far?
That's part of the adventure! We have excellent support, plenty of fuel, and your Phoenix finish legacy on the line. We got you!
What about safety / COVID?
Our event is complete outside to limit the risk of sustained exposure. Everyone is encouraged to regularly wash their hands; hand sanitizer will be available at all official stopping points along your ride. Finally, stay home if you are sick.
What if I need fuel / fluids during the ride?
No worries, there are rest stops on Skyline Drive in each direction. You won't go more than 30 miles (2 hours max) without the chance to completely refuel as needed! 🍰

June 2023 Will Be Epic

Smash Your Limits.
Meet us in Front Royal, VA for the ride of your life.

Hall of Fame

Carl AlleyneEndurance NationWashingtonDC20211
Dennis CruffEndurance NationPoquosonVA20211
Sean HyltonEndurance NationMobileAL20211
Stefan JudexODZPort JeffersonNY20211
Allison LeeEndurance NationWashingtonDC20211
Edward LefrakReston Bike ClubMcLeanVA20211
Suzanne PorterN/ARestonVA20211
Kori RetzbachEndurance NationNoviMI20211
Robert SaboEndurance NationMargateNJ20211
Kate SitlerEndurance NationStowOH20211
Bret SlaterVeloLabs RacingSpringfieldVA20211
Narr SunkaraRestonVA20211 
Jason TomR-Hill Road WarriorsRound HillVA20211
Justin WagnerTeam ODZMidvaleUT20211

About Us

We Ride We Rise is a movement about movement. Our mission is to provide epic experiences for adventurous cyclists. We find great, accessible locations that fit our unique event model. We partner with local professionals to create an incredible vibe and experience that will last much longer than the fatigue in your legs. Have a great destination in mind? Email us!