November 15, 2019
More than 10 years later, the infamous Gyspy Run hasn’t lost an ounce of charm.
The Gypsy Run was started in 2007 by a couple guys with good intentions but a lack of capacity. Walt from Kickstart Cycle in New Jersey was one of the handful of us waiting for it to “start” at the west exit of the Holland Tunnel some 12 years ago. Being the motivated individual he was/is, he quickly took the reigns and has been running it ever since. Fast forward to 2019 and the “Gypsy” has become a staple of north east, grassroots motorcycling campouts. I was on that first one on a cantankerous old Triumph chopper, and later on my trusty FXR, a freshly-built shovelhead and several other machines. The last Gypsy for me was 2016 and I felt like I needed to get back to Upstate New York for a little cycle therapy and some time with my buddies from the right coast. I’ve seen most of America from two wheels and driven across it plenty of times but never actually crossed our great nation on a motorcycle in a single trip. Since Biltwell supports Ride 1k in a Day the idea of doing it in a hurry was appealing. We happened to have a perfectly fine 2018 Harley-Davidson Street Bob that we bought last year as a development mule for hard parts. With only 1500-ish miles on it, this machine was the splendid candidate for a cross-country adventure.
I had to add a little detour to make the mileage add up to 1,000 miles every day, but it also made the route a little more fun.
I needed to spend some time with our friends Yeti and Yolo who are working on an LMTV chase vehicle in Iowa for an Arctic Circle trip (#operationnumbnuts) next year anyway, so why not stop there and hang out for a bit? A quick google maps check and the mileage worked out just right. It was about 1000 miles from So Cal to Denver, and if I added a detour through Sturgis, it could be another 1000 to where they were holed up in an old gas station, building crazy Jeeps in Iowa. In a twist of ironic fate, it was almost exactly another 1000 miles from there to Narrowsburg, NY where the Gypsy Run would take place. Trip planning, done!
This was somewhere in Colorado, I think.
I’ll spare you the day-by-day journal of every Flying J truck stop and condense it down to the bare minimum. Day 1, So Cal to Denver took 16 hours and 53 minutes. Day 2 was the longest at 18:36. I detoured up to Sturgis and came back down through Souix Falls and ended in Council Bluffs, Iowa. I spent the next day touring the Brownells facility (mind-blowing) and hanging out with Yeti and Yolo. I hit the road early on Friday and was through Chicago before the sun came up. I lucked out on weather during the whole trip and the two hours of rain through Ohio was really way less than I had expected. That final day I hit the 1000 mile mark about 40 minutes from the Gypys Run at 17 hours, 56 minutes. Ride 1K in a Day was definitely the inspiration and motivation for doing the trip on a crazy schedule like this. Keeping up with Curtis via email required me to shoot a pic of my gas receipt (to prove time and location) next to my odometer (not trip meter) first thing in the morning, a midway update and then another final one at the end of the 1000 miles. It sounds a little complicated but was really easy to keep track of in the same email thread and Curtis was always a cheerleader who would do the math, take the time changes into account, etc. If you’ve ever wondered if you can do it, you can. It takes no special skills, just a little planning and the tenacity to keep going when your body and mind both think it would make more sense to call it a day. I’m already looking forward to doing the next one. I’m gonna work on a new seat for my rigid shovelhead chopper and take one of my favorite routes up the 395 til I hit the 500 mile mark, have an ice cream and a Red Bull and head home. Maybe next spring…
The Street Bob– fast, comfortable and rock-solid.
Our Punisher XL up front and our regular-sized Punisher pegs in back made for two comfortable riding positions.
If I had a secret weapon on this trip it was this 2018 Street Bob. Sure, a touring bike would’ve been better, but I already felt like a cheater doing it on a modern bike. Even a cheap windshield would’ve been a good idea, but I didn’t have one and really just wanted to ride a regular ol’ Harley. The only mods were using a bunch of our parts; Murdock 10” risers, Tracker High handlebars, Utility Mirrors, Punisher XL and regular Punisher pegs, Alumicore Grips, our Softail Dash Panel and of course our gear. The bags used were our Exfil-11 tank bag, Exfil-48 backpack and Exfil-7 bar bag with our Exfil-0 tool roll inside. I used our new Borrego Gloves and a Lane Splitter helmet with a prototype Transitions shield (cheater!). See the photos below for the entire gear set up for each bag. Ergonomically, the bike is fine from the factory for a 5’9” fat guy like me. I prefer mid controls and these feel awfully close to the same geometry as my shovel chop. This won’t be everyone’s optimal set up, especially for long-legged tall guys. A set of highway pegs would have absolutely helped with fatigue. I moved back and forth between the regular pegs and the passenger pegs to let my nether-regions get some blood flow. I pivoted our Punishers so they were in a rear-set orientation which was really comfortable and still allowed me to stand on them and have a decent center of gravity. The mids are way too far forward to stand on at high speeds. One thing I learned was that the shape of the tank and position of my feet on the mids at speeds over about 85mph pulled my knees apart so much that my hips actually ached. On a normal day this wouldn’t be a big deal but I rode for hours between 90 and 100mph and after day one had to consciously sit pigeon-toed to keep my knees tucked. Luckily the last couple hundred miles each day was in the dark where I slowed down to about 80mph which offered some relief when I was the most fatigued. The bike never missed a beat. It gets about 150 miles to a tank, so I’d generally look for gas around 120 miles or when the gas light came on. To a chopper rider, it was a little unsettling not to have a manual petcock reserve or an extra gas can on board. Somehow I never ran out of gas but I pushed my luck a few times and where it looked like gas might be a little hard to find, I topped off early and enjoyed the opportunity to hydrate and stretch anyway. The single-disc front brake on this bike is the best I’ve ever used on a stock Harley. The rear, even after adjusting the pedal was one of the worst. I just got used to the extra effort required and will probably adjust the pedal up a little more. Not a single bolt came loose. It used about a cup of oil (I checked it several times a day anyway out of habit) and never required any kind of maintenance. Weird, huh? The most modern bike in my quiver is my trusty 92 FXR and even it requires at least a little wrench spinning on a big trip. To say I was satisfied with the bike’s performance would be an understatement, and I’m not getting paid to say that!
Exfil-11 Tank bag was great to hold the stuff I needed instant access to: map, phone, sunscreen, water, snacks, toll cash all that junk.
The Exfil-36 backpack held everything I needed for the trip and then fly home. Running those lower straps through the passenger grab strap on the Softail made it super-secure and rolling up layers held with the same straps made it a perfect back rest.
The Exfil-7 and Exfil-0 compliment each other nicely since the tool roll fits snuggly inside the other. The straps on front held my Big Agnes sleeping pad and their bikepacking tent clipped right to the MOLLE on top of our bag. This stuff never moved and added a little protection from wind and bugs.
I personally design our line of Exfil luggage at Biltwell and trips like this are great to expose weaknesses and flaws. Given the mission at hand, these bags might be considered going lightweight when compared to contemporary baggers and touring bikes. If I hadn’t needed camping gear for two nights on the Gypys Run, I could’ve scaled down even more. I rotated through layers as the weather and altitude changed, but always kept the bed roll behind my lower back at the biggest size the front straps on the Exfil-48 backpack would accommodate. This meant sometimes that I had to actually take stuff out of the bag to make the roll big enough, but that was easy. When I was done with the trip, I put essentials in the back pack and flew home with it as a carry-on. The Big Agnes Fly Creek HL bike packing tent has it’s own straps that made attaching it to the top of the MOLLE on the Exfil-7 look like they were made for each other. Their Air Core Ultra inflatable pad and Anvil Horn 30 sleeping bag fit inside the backpack and once I made it to the Gypsy Run in Narrowsburg, NY, made for the two best night’s sleep during the entire trip. I usually fit in a large pair of our new Borrego Gloves, but chose XL just in case. One night it was a little cold and wet, and I slipped a pair of or our Moto Gloves on as insulated liners. It was a good compromise since most of the weather ranged from warm to downright blazing hot. In the few scattered showers I just rode in the same gear and dried out an hour or two after riding through it. When it looked like Ohio rain wasn’t going to be just a quick shower, I put on some cheap rain pants over my gear and light rain shell under my swap meet jacket and trusty old Biltwell denim vest. I attached an old wash cloth to the tank bag and would wipe the really big chunks off my visor while riding until it got so clogged with bugs and sunscreen that I had to abandon that idea. What didn’t work was my bright idea to drill a hole into the center of the top cap on my Murdock risers and mount a Rok-Form apparatus for my iPhone. Actually, the mount worked out great and looked less lame than a u-bolt holding it to the bars. However, my phone did not enjoy being hard-mounted to the Harley paint shaker. At the first gas stop on day one the sensor in my camera gave up and would not stop vibrating when in camera mode. Not that big of a deal except I had to use the selfie camera to document the gas receipts and odometer three times a day. This had to look super dorky if anyone saw my gyrations to make that happen, but I never stuck around long enough to notice. So, lesson learned, don’t hard mount your sensitive super phone. I had back-up paper maps and the route was fairly simple despite the high miles, but having the phone and the factory USB port up on the neck of the ‘Bob made navigating simple and easy. I used Apple AirPods about 75% of the time. Some podcasts were hard to hear at 95mph, so I mostly played music all day and listened to podcasts at night when I was going slower. I figured out pretty early that the AirPods don’t stay powered all day so I’d keep the case charged and then throw them in that to soak up some energy while I gassed up, hit the head and got a snack. Once I figured that out, it was smooth sailing with my own personal soundtrack.
I thought it would be a good idea to drill my riser cap and hard mount my Rokform mount. It ruined the sensor in my iPhone camera before the first gas stop. Doh! I should have used Rokform’s dampened handlebar mount.
Factory H-D sissy bar worked out great with our Exfil-48 backpack. Simple and strong always wins!
Many riders have logged way more miles than me, so I’m not claiming to be an expert here. But, I’ll share what worked for me as far as pace and stopping go. The biggest contributor to staying on pace is this–you gotta go it alone. Even the best riding buddy will want to stop at times where you don’t need to yet. By traveling solo, it allowed me to skip all meals until the end of the night. I carried RX bars and ate a few of those throughout the day, along with a gas station snack or two. I tried to mow down as many miles as possible early in the day so I had less riding to do at night when fatigue was at it’s peak. I didn’t break for any longer than needed until the 500 mile mark. At that point I’d take a 15 minute rest, maybe eat an ice cream, have a coffee or a Red Bull and lay in the shade if there was grass around. A few yoga stretches and catch up on returning a few texts and I’d be back on the road. Again at the 750 mile mark, I’d allow another quick break, confirm navigation was correct, maybe add a layer and then hammer down for the home stretch. That last 250 was 10x harder than the first 500 and that’s the nature of long days in the saddle. I didn’t overdo it on caffeine, though a had my share of coffees and Red Bulls, but I tried to mostly drink water and Gatrorade. I kept a hydro flask on the bike and topped it off with ice and water first thing in the AM so no matter where I was I’d have some nice, cold water. It fit right in my tank bag so taking a pull whenever was easy. Also, because I know bikes are hard to see in the middle of nowhere in the middle of the night, I added some reflector tape to the sissy bar. It won’t win any bike shows, but it pops from a mile away. I also always bring a cable lock for added security outside crappy hotels in unfamiliar areas.
Now that I’ve done this once, I kinda want to do it again, but faster. I got extremely lucky with weather, deer and cops, so maybe this is as fast as I am capable of doing it safely. Faster is going to have to wait – the next one for me will be 1k in a day on my rigid shovel and I’m absolutely not going for speed records on that. Throw in the needs of a kickstart-only 40+ year old custom and I’ll be lucky to make 1000 miles using the entire 24 hours given.
What are some of your best road trip tips or advice? Share ‘em in the comments below.
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