I tend to get a lot of questions about my weekend bike adventures. Cyclists and non-cyclists alike ask about my routes, what I eat on the ride, what I pack, how long the ride takes, if I bike in the rain, etc. I’m going to start doing a better job of documenting all of this, starting with this post about a little trip I took up to the Catskills.

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First: the bike. I’ve been riding a Specialized Tarmac for two years for both recreational and competitive road riding. This summer though I’ve become increasingly obsessed with adventure cycling and bikepacking. I love long endurance rides, I really really love the fun and challenge of riding less traveled dirt and gravel roads, and I’ve been wanting to get out camping more — so bikepacking really is the perfect combination. While there is a trend in ultra-endurance racing to fit out race bikes with frame and saddle bags, I wanted something that I knew I could thoroughly abuse, without worrying about carbon, or without being afraid to lock it up or leave it unattended at my campsite. I found myself desiring something real… something steel.

Specialized’s AWOL fit the bill perfectly, and I had been drooling over the Comp pretty much all summer, so recently I went for it and had my favorite local bike shop build one up for me. This thing is the ultimate zombie-apocalypse ready tank; stable as hell when loaded up with full camping gear, even when bombing a descent at 50 mph, when ripping up a trail over rocks, tree roots, and rail ties, or when dropping the hammer on the road. Simply put – it’s a f***ing sick bike. It likes to go fast, and it likes to go everywhere.

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I set the bike up for covert adventure deployments with a Tubus low rider front rack, as that’s where the AWOL likes its weight. So far I’ve been using classic Ortlieb back rollers (but on front), but am kinda considering going with a rackless setup. I also threw three King Cage titanium bottle cages on, as well as a randonneur bag up front. That’s really all the cargo space I need – even once I start doing trips longer than five days – I firmly believe in packing light and packing smart.

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I was invited recently to spend a few days in the Catskill Mountains with a bunch of far out futurists, tech nerds, and generally awesome people. When I learned I would be camping for three days in the mountains, 150+ miles from home, naturally I decided to leverage this as an opportunity for a bike adventure. I got my rig all packed up on a Tuesday night. Here’s what I brought:


Two spare tubes, one spare tire, five cO2 cartridges, small frame pump, multitool, Garmin, small lightweight bike lock, four tubes of electrolytes, four shot blok sleeves, four energy gels, titanium french press, coffee, lightweight mug, flask full of Kings County bourbon (I may pack light, but I’m not a monster), small backpacking stove and gas, headlamp, small bike lights, auxilary battery for charging USB devices, 100% waterproof phone case with extra battery life, tent, sleeping bag, two shirts, one pair of shorts, extra pair of cycling kit, first aid kit, camp shoes, two USB wall chargers. That’s it! It all adds up to roughly 35 Lbs.

Wednesday morning I commuted in to work on the AWOL with all my gear, and at the end of the day I just hopped on the bike, escaped the city, and embarked on the short first leg of the trip. Destination: a campsite in Harriman State Park, roughly 45 miles from the office.

The name of the game was to try and get to camp before sundown, but I just missed the mark, and rode the final 6 miles in the dark. Turn on the headlamp.
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To polish off the ride, it ended with a nice little 1.7 mile category 3 climb. This was a good warm-up for the suffering that awaited me in the Catskill Mountains the next day.

I set up camp, scarfed down my dinner (I grabbed a burger and fries at The Market on the way out – not the smartest nutrition for the night before a 100 mile ride, should have planned smarter on this point) texted the fam, took a couple swigs from my flask and was off to bed. The tent in case you are wondering is a Tarptent Moment DW.

Made coffee in the morning and then it was off to the mountains.

Starting a ride in the wilderness, rather than fighting through city traffic is pretty magical. This was the view that I started with.

It was about 8 miles through Harriman, and then cutting across route 87, over to Sterling Forrest State Park, at which point I passed this derelict building.

Up through Blooming Grove, up through Walden (where I stopped for lunch and had some KILLER pizza), and on to Wallkill. Just on the outskirts of Wallkill, 40 miles in, the route sent me to continue onto this portion of the Wallkill Valley Rail Trail, which much to my delight was a pretty rough around the edges trail of dirt, gravel, and tennis ball size stones.

The AWOL ate this all up and wanted more. The only issue with this trail is the brush gets pretty overgrown in sections and I had to stop three times to remove and branches from my drivetrain. More than once on the road I’ve had a surprise stick in the derailleur, causing it to rip from the hanger, but not today. Lucky. This definitely left me ruminating on the virtues of a belt drive paired with an internal hub.

Sadly, this portion of the trail only lasted about a mile. The trailhead on the other end was pretty ridiculous – it narrows to singletrack, and you’re sent down an extremely steep embankment, and into a ditch. Upon exiting the trail I started to see signs along the lines of “State Correctional Facility Land – No Stopping”. Well then. The route directed me  down a road that was clearly marked *DO NOT ENTER*, which had it not been a prison, I would have considered disregarding. Being the law abiding cyclist I am, I rerouted up to State Highway 208, which I would have wound up on eventually anyway. I noticed Garmin’s battery was below 50% at this point so I decided to try out the backup battery. It worked like a charm, and made me really glad I had recently added the rando bag to my setup.


Moments later, the sky opened up, and I was soaked by what would be the first of at least five thunderstorms that day. It was then 20 miles of flat terrain to hammer through to Rosendale, where I would meet up again with the Wallkill Valley Rail Trail – this section even more epic than the last.

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By now it was steadily pouring rain, and I had a grin on my face as I ripped down the dirt and gravel trail found on the other end of the footbridge. I found myself surrounded by tall trees, splashing through mud puddles, with a steep embankment on the left, and Joppenbergh Mountain on my right. At one point I felt a blast of freezing cold air, and looking to the right realized that it was coming from a huge cave in the side of the mountain – cold air and fog was billowing out of it. Unfortunately I couldn’t get a picture – the waterproof case for my phone allows for it to be used in the rain, but once there is a bit of water on the screen, the phone struggles to register swipes, rendering it difficult to unlock and activate the camera. In any case, pedal on. Don’t want to wait around for the bears.

4 miles later, in Marbletown, after being sent down a gravel private drive, I found my way to Fording Place Rd. The irony of this name was not lost on me as I found myself riding through a 6 inch deep 30ft long puddle that was the entire width of this dirt road. That puddle however was just the warm-up. After turning a corner on the trail I found myself facing the Esopus Creek. So what do you do when you’re faced with fording a 1.5 ft deep creek? You thank yourself for having 100% waterproof paniers, and keep on trucking.

My panniers were about 2/3 submerged but I’m happy to say they held their own and kept my gear totally dry. On the other side of the stream, there is a big corn farm with a nice flat gravel road. On through Lomontville, and Pacama, and before you know it, I found myself at the Ashokan Reservoir – rolling hills  surrounded by seriously beautiful forrest, and occasionally a cute little cabin, or decrepit barn.

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The Forrest eventually gives way to this view from a small bridge.

Shortly thereafter, the road leads to the Ashokan Reservoir itself. Not a bad view here either.

From here it was essentially one grueling 20 mile false flat all the way to the tiny little town of Fleishmans, which was the last civilization I would see until reaching my destination. What came after that 20 mile slog through the false flat, you ask?

Pure. Mountain. Death.

Over the course of the final 10 miles, there were four back to back brutal climbs, as I entered the real mountains. I love climbing, and I enjoy the suffering, but man, when you are hauling 32 lbs of gear – it’s a whole new level of pain. By my calculations, that last 10 miles had around 2,800 feet of climbing. 100% suffering. Here’s the upshot though – one of the climbs had a perfectly straight, incredibly steep descent, with a clear line of sight. I hit it full gas, and broke my own speed PR – 49.45 MPH.

All of this climbing was rewarded by the sudden arrival at my destination – where I was greeted not only by the smiling faces of friends, but the most incredible mountaintop modernist home I’ve ever set foot in.

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And so ensued a weekend of discussions, presentations, debates, and fireside chats on the future of technology and it’s role in society. The weather up in the mountains was incredible – giant thunderstorms would come and go with a moment’s notice.

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… and when Sunday came, I was back on the road. I took the same route most of the way back, but eventually cut over east of the Hudson River so that I could take the train from Beacon. I would have preferred to have ridden the whole way and split it again over the course of two days, but I had to get back to the office on Monday. Here are some photos from the much sunnier (and hotter) return trip.

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Until next time – get out there and ride!

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