Epic Endurance Test Takes Runners on 30K, 3000-ft Brandywine Valley Climb

The Trail Hipster Handicap may have a name that evokes images of lattes and leisurely urban strolls. But the fifty extraordinarily fit runners who completed the on November 10th will modestly agree it stands atop Delaware endurance contests.

The event celebrated its third anniversary on a chilly November Sunday with its largest group of entrants ever, 50 of the strongest, most experienced trail runners in Delaware and from across the region. The banner crew was drawn to the daunting, beautiful 30 kilometer (18.5 mile) course that snakes its way throughout the Brandywine Valley, taking runners through 3000 feet of ascending and descending terrain.

This is an elite race, requiring strong legs and legit off-road and marathon resumes, but the innovative staggered, handicapped start gives every entrant an equal chance to break the tape first.

Christopher Scarpitti founded the race and is one of its lead organizers. He says the event was conceived as a natural extension of a local running club called “Runner’s High Delaware,” or RHD, that regularly meets to dash along the network of trails carving their way along the Brandywine’s banks.

A Salesianum graduate and WSFS banker by day, Scarpitti gave TSD the scoop on the history of the race, the efforts involved in putting it on and the technology involved in mapping the course and ensuring a competitive sprint to the finish line.


TSD: Tell us about the background of the race.

Scarpitti: The first running was in 2017. So this year was our third year running the Trail Hipster Handicap. Technically I founded the race, but it certainly doesn’t happen because of just my doing. I started RHD on the social media platform called Strava. At its core, Strava is a digital running log that uses GPS and it has “group assembling” capabilities. 

The moniker Runner’s High and the logo came from a homemade wine label I had from 2012. I recycled it into a running group for local trail runners. The first two members were my wife and me, and from there it has grown to 378 people. 

The underlying community was already there albeit a bit fragmented, and it really just needed something to coalesce around. It really is amazing the friendships and comradery that have been developed from that simple start. It has brought a lot of good folks together who are very supportive of each other’s running goals and endeavors.

TSD: Can anyone do this event, or do you need certain times to qualify? 

Scarpitti: Not exactly anyone, and no qualifying times are required.  Our general rule is you need to be a ‘member’ of our trail running group Runner’s High Delaware. Or, at a minimum, someone from the group vouches for you to get you in the Trail Hipster Handicap.

‘Membership’ in RHD is not complicated and it costs nothing. You just need to enjoy trail running, be a good person, be supportive of other’s goals and enjoy the comradery of the group. Strava, a social media platform that tracks individual’s runs, is the most prevalent way runners get plugged into RHD. We host group runs every other week predominantly on the Brandywine Valley trail system.

The Trail Hipster Handicap is the defacto RHD championship. So we like familiar faces in the event and those who participate in at least a handful of group runs throughout the year.  The faces and names cycle through depending on schedules but we routinely have at least 20 folks at group run and sometimes as many as 40. 

We’ve been hosting group runs for four years so there is a big pool of runners who have made connections via RHD.  That said, we had someone from Washington, DC and a couple from Philadelphia this year. 


TSD: How did you map out the course? That must be complex. 

Scarpitti: I was inspired by traveling to trail races around the country.  We may not have large mountains and endless miles of trails like some towns, but I always felt fortunate that we had the trail systems we did here in Delaware in such close proximity to where we live and work. 

I was piecing together a route in my head for years before the first run was ever held. I wanted something that circumnavigated the entire greater Brandywine Valley trail system, and I wanted runners to experience everything the landscape had to offer. Steep climbs, rocky descents, fast running along the flats, single track through the woods, winding paths through the meadows, creek crossings, and so on…. did I say climbs?! 

It’s not an easy course. It measures 30K (18.5 miles) in distance with 3,000 feet of elevation and descent. Once I figured the most efficient, practical and safe way to piece it all together The Trail Hipster course was born. 

And then nothing happened for several years – I wasn’t sure folks would actually want to run it. The first try at hosting the run in March 2017 was canceled because we got hit with an ice storm/blizzard. So, we pulled the plug and tried again in November. That seemed to be the better time in hindsight, so it’s become our fall classic.

TSD: And this was your biggest event yet? 

Scarpitti: Yes, this was our best year. Essentially this is an invite-only event because it is important we keep it small for a variety of reasons, most notably so we can effectively manage the handicapped nature of the run. It has technically ‘sold out’ each year since inception as we capped it to 40 registrants in 2017 and 2018. This year, we increased to 50 as we’ve gotten to know most of the repeat runners better and we’re better at handicapping rookies on this course.  


TSD: Can you explain how the staggered start works?

Scarpitti: It’s akin to a golf handicap. We use ‘time’ to handicap and level the playing field among runners with different talent levels.  We have a secret seven-member Handicap Committee who meet to assess each runner and figure out how long it should take them to run the course. 

It is not an easy task because of the complexity and variant nature of the course but the Committee takes their job seriously.  We just want the run to be competitive and fair. 

Simply put the slowest runner starts first, the fastest runner last, and every other runner is slotted in between based upon a projected finishing time. The delta between that first and last runner is about 75 minutes. 

It is an interesting run because most of the time runners are essentially alone until they approach the end. 

The goal is for that gap to shrink throughout the 18 miles and the entire field is racing up the last climb together.  The first to cross the line is the winner, aka The Trail Hipster. We really celebrate our Top Ten because it is really tough to crack that Top Ten.  It creates for some exciting and wild finishes.  It also makes the race an actual race for every runner in the field no matter their level of talent. 

We have 2:40 marathoners racing 4:00 marathoners and that 2:40 person doesn’t always win.  In 2017 our 41st seed (a slower runner) won the race.  In 2018 our 12th seed won.  In 2019 our 27th seed won.  Consequently, our fastest runner (our #1 seed), has finished 9th, 3rd and 9th, respectively.  If you win, you are affectionately known as The Trail Hipster until the next year and are awarded “the flannel” in a ceremony akin to the Green Jacket being award at The Masters.

TSD: And this race benefits the broader community.

Scarpitti: Yes, we require runners to contribute non-perishable food items which we contribute to Saint Patrick’s Center in Wilmington. A friend is on the board so that is how that connection was made.

We have students from St. Edmond’s Academy on site performing their community outreach who help collect and assemble the food donation to Saint Patrick’s Center. 


TSD: The race isn’t part of an official, sanctioned program or circuit?

Scarpitti: No. In fact, I often remind runners this run will not get you into the Western States 100 or the Boston Marathon. Have fun, be competitive but don’t take it too seriously.  After all, they don’t even start at the same time. That said the contestants are really good runners.  They’ve run and completed countless marathons and ultra-marathons around the country and world. These are hearty runners who definitely like to compete with each other, but are just as likely to be cracking jokes, sharing food and having a beer together the minute The Trail Hipster is over.

TSD: Anything else our readers should know?

Scarpitti: Members of our running club play a key role in organizing the run, officiating the event and leading the group through the day. This year we had 26 volunteers. Many are course marshals who canvass the course to make sure folks remain on the course. It really is an RHD team effort rooted in having fun on the trails we call home.

The Jewish Community Center graciously lets us park on their lot and have our “passing of the flannel” ceremony in their pavilion by the trailhead (the famous flannel says “Respect the Hustle” on the back). We give a small donation to them but they are very kind for sharing with us.

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