Over Thanksgiving weekend, I had intended to drive out to Western Connecticut while spending the weekend in Manchester and hit a few hills I had heard about in the Northwestern corner. However, I had a mild cold, my toddler had a mild cold and was having some erratic sleep and my wife was having a full on “man cold,” so I found sitting on the couch and eating Pho to be much more attractive options. While I was on the couch I did manage to find some more hills in the area, which got me even more excited about going out this weekend. There had been some discussion of the “meanest mile” in Connecticut on Doug’s recent post about the meanest in MA. The most emphatic post from fredzilla said that Dibble Hill was the meanest. Based on my calculations I was skeptical. Valley Falls/Hatch Hill, though not quite a mile averages a significantly steeper grade and scores 383 vs. Dibble Hill’s 351. Swaller Hill in the same area averages 11.6% (equal to Hatch Hill) for exactly a mile (BRENTACOL: 405) and Great Hill Road, which averages 9.7% nets a BRENTACOL of 416. This means that Swaller Hill is the steepest mile in CT, but as we all know, steepest does not equal hardest. And Great Hill would be the “hardest” according to BRENTACOL rating, but one never knows if the rating/gradient map is accurate until you see the hill in person.
Last weekend, another family discussion found me two more hills to try, which then led me to find a couple more, including Swaller and Great Hill. My brother-in-law is a little obsessed with haunted places and was discussing an abandoned (and off-limits) ghost town in CT named Dudleytown. Some suggest the town’s demise was hastened by pig demons and that the residents went mad, died, etc. Wikipedia is much more sober, but I was intrigued nonetheless. Ghosts or not, abandoned towns and roads are always a draw for me. Looking at the map, the road that gets you closest to the settlement is the sinister sounding Dark Entry Road, and what do you know? It’s a hill, and a pretty decent one it seems. Google maps also showed a road going up Bald Mountain, which looked suspiciously like it might be dirt, as did the Eastern approach, Dudleytown Road. Given that the weather forecast was good for this weekend, and Western CT gets considerably more snow than the rest of the state, I figured this weekend was my last chance until the spring thaw.
Unfortunately, the forecast turned to rain Saturday, which then became snow. Shit. Hoping it would thaw quickly (the roads were already clear in Manchester by 9:00) I decided to head out there anyway. Roads were decent most of the way and I thought I might just sneak in a decent ride. But as I neared Cornwall, the road conditions got much worse. I passed Dibble Hill, and it looked pretty snowy, so I thought I’d check it out in the car and then ride it if it wasn’t too horrible. It was quickly apparent I wasn’t riding Dibble Hill today. When I was almost near the top, I saw a wall I was not expecting, and wasn’t even sure the car would make it up with the snow so I turned around before the steep stuff started. The 25% on the gradient map is for real. The case for Dibble Hill as hardest in CT was improving.
My route was supposed to start just up the road at route 7. I drove up Route 7 to Swaller Hill. The conditions were better on that hill, but still pretty messy. That road seems easier than Dibble Hill Road, but it’s of course impossible to tell. Thinking my day was over, I figured I should at least drive down to Dark Entry and see if I could find some pig demons. By the time I hit Cornwall Bridge, the roads were pretty good, and when I drove by Dark Entry, I was surprised to find it was clear, at least at the bottom. I parked, and rode up it. That’s a nasty little climb. According to BRENTACOL it is slightly harder than Blue Hill and slightly shorter. I agree. It’s gradient is very inconsistent and there are some small sections of really steep (probably 20% or so) that really hurt. I wanted to shift into the 24, but I couldn’t get the chain to drop down, so I was mashing in 36-26.
From there I rode up Warren Hill Road, which is the biggest hill in terms of elevation gain in the area (894 feet). Nice hill, with some steep sections. On the way back down, I turned up Bald hill and was pleasantly surprised to find it was paved all the way to the top. And that one is real kicker as well. Combining Bald Hill (which is 1/2 mile long) with the first section of Warren Hill and it might be in the conversation for meanest mile in CT. I was happy to call it a day and drive to check out the other hills.
Dudleytown Road: Over on the other side, I drove up Dudleytown Road. This one seems like a really nasty hill, and approaches the abandoned Dudleytown from the east. Very pretty and narrow, but paved. The pavement ends at or near the top, which is where I turned around. It didn’t look like there was much more up left at that point. Veloroutes data is horribly inaccurate so don’t pay attention to the gradients or the BRENTACOL rating, but you can take a look at the map, if you like here.
Great Hill Road: Not as hard as BRENTACOL says, because that section of 23% and 19% is pretty definitely bogus. Still nothing to scoff at.