Stick Season Roubaix

 Oct 28, 2026

I finally got my rear tubeless tire back from the shop after having it retaped, topped with fresh sealant, and fitted with a new valve stem because it stubbornly refused to hold air. I hadn't had a chance to test it out yet, so today I loaded up and headed out to ride some gravel south of Rutland.

After our ride last week, Bruce appears to have officially caught the cycling bug. The other day he rode down to the dirt road and back entirely by himself, and today he accompanied me down toward Walker Mountain Road. He was calling out "car" every time one approached from the rear, so I suggested he switch to the classic "Car Back." He’s got this massive rear-view mirror on his helmet that Ann gave him, so he actually spots cars way before my Garmin Varia even registers them.

After Bruce told us about his solo ride the other day, Ann suggested he try out Strava. Before we rolled out, I asked him if he had the app downloaded, and since he did, he fired it up right at the start of the ride.

When we reached Walker Mountain Road, Bruce turned around and headed back home to the house. I continued down Creek Road toward Wallingford, debating my next move. It was 3:30 PM, the clouds had rolled in, and with the sun blocked out, the temperature immediately took a dive. I was wearing a thermal jersey and a base layer, and I could definitely feel the chill setting in.

Climbing VT 140

I weighed my options. Should I just take the easy way back on East Road, the dirt road connecting Wallingford to the airport? Or climb VT 140, drop down West Hill Road to Dugway, cut across to Hartboro Road, and then hit East Road? I quickly nixed that idea, realizing I didn't have enough daylight left. The final option was to continue up VT 140 past Giant's Table, head north on East Tinmouth Road, and tackle Quarterline Road—a steep ramp I’ve been "jonesing" to climb for a while now.

20 day difference at the apex of VT 140

I took my little gravel shortcut up Memorial Drive to VT 140, started climbing, and decided that hitting Quarterline from south to north was the way to go.

This was only my second time climbing VT 140 in a couple of weeks, and what a climb it is: 2.5 miles long with an average grade of 6% and a few punchy 10% sections. Three-quarters of the way up, I had to stop, strip off my neck gaiter, and unzip my jersey. But once I crested the top and descended into East Tinmouth, I was right back to zipping up and pulling my gloves back on. The sun was peeking out again, but the air was still biting.

Down in the valley, I turned north onto East Tinmouth Road. It's a gorgeous, wide gravel road that climbs for a few miles before rolling down toward Chippenhook. The road surface changes dramatically right at the Clarendon town line—the Tinmouth side features fresh gravel loaded with little stones, while the Clarendon side opens up into smooth, packed dirt.

The views of the Taconic Mountains through the trees were stupendous. 

Many of the surrounding hardwoods have dropped their leaves, but there are still plenty of pockets of late fall foliage. In the fading afternoon light, the remaining oranges and reds really popped.

Quarterline Road starts out deceivingly flat before slamming you with a punchy ramp—averaging a 4.5% grade with a nice little 9% kicker. After cresting that mini-climb, you drop down and hit what I now affectionately refer to as the "Green Monster of the Taconics."

This section looks genuinely daunting, almost demoralizing, making you ask yourself out loud, "I actually have to climb *that*?"

Climb it I did. 

It was slow going, and I definitely found myself wishing I had something lower than my 30:36 gearing. I honestly probably could have walked it faster. To rub salt in the wound, a woman drove to the end of her driveway about 20 feet ahead of me, calmly got out of her car, walked across the road to grab her mail, and strolled back to her vehicle by the time I finally pedaled level with her driveway. Brutal.

It was entirely exhilarating when my Garmin finally chimed: Climb Complete! I stopped to snap a few pictures from "The Money Shot" location. Looking north from here is just as breathtaking as looking the other way.

Right before School House Hill, I ran into my friend Michael, whom I’d met on Quarterline a few rides back. He mentioned that between his son's hockey practices and games, plus the end of Daylight Saving Time, all his riding from here on out will be indoors on Zwift until the spring. Can't blame him, but I'm squeezing out the outdoor miles while I can.

Continuing on, I dropped down to Boardman Hill and decided to push toward West Rutland. I simply can't say no to a little extra dirt when it’s right there in front of me. At the corner, the setting sun was casting a brilliant orange glow on the hills to the north. I tried to capture it with my phone, but I’m skeptical the photos will do justice to what my eyes were seeing. It's moments like this that make me think more and more about picking up a real digital camera. Maybe Santa will hook me up for Christmas.

The sun was dropping fast as I rode Boardman Hill, where I was pleasantly surprised to find that the West Rutland section of the road has recently received a gorgeous fresh layer of blacktop. Where it used to be a patchwork of broken tarmac and dirt, it’s now smooth as silk and ridiculously fast.

I hopped onto the bike lanes on Rutland Road, cut over to Dorr Drive and River Street, and cruised back home—just barely missing a three-handle ride at 29.7 miles. Close enough!

It was a fantastic ride, though it's a good reminder that the trusty CAADx is due for a little workshop TLC soon. Next time I tackle that route, though, I might just have to see how it feels on an e-bike.