NEW ROAD ADDED!
Like six months ago, I decided that I was going to make a list of cool roads in Connecticut. I started, but the project was too ambitious and too difficult for an idiot like me. Nonetheless, I wanted to start a fascinating discussion of cool roads. Even though it isn't done, I'm putting my draft out there and ask you to contribute to it.
Lists are way in right now. It seems like everything is a list. I have no idea why. I like cool roads and there are many lists of cool roads and even a few for Connecticut. However, the Connecticut ones are all wrong and appear to made by people who have never been to the state. My list may not all be accessible by car or truck, but this is a blog about bikes after all. Actually, some aren't accessible by bike all year either. So, here's my list.
1) Olive St., Hartford
If you've driven on I-84 in Hartford, you've driven over Olive Street. It's nestled into the secret Hamilton St. neighborhood by the Bullpen Cafe. I assume at one point this used to be a pleasant little neighborhood, but 84 came through and now it's generally abandoned. Olive is blocked off on both ends by cement barriers and it's best visited at night. There's broken glass everywhere. From Olive, you can go through this path in a muddy field to get down the Park River banks and ride around on steep sloped concrete. Any urban decay tour of Hartford is incomplete if not visiting Olive Street.
2) Mt. Riga Rd., Salisbury
Lots of people know about Mt. Riga Road, because it's awesome and rumored to be the best hill climb in Connecticut. This guy is into hills and he likes it (Sunset Rock Road is in NY and it's a way harder climb). Once you get to the top, you're in this high valley between the Taconics and the Berkshires. I once broke the exhaust off of my car when it becomes Mount Washington Road. One time when it was still covered in snow, I drove all the way out and there and walked up it with my bike. The snow was deep and it was sort of a stupid waste of time.
3) Millstone Rd., Hartland (north of 20) (nearby Pent Rd. is also cool, but lacks the strange MDC memorials (actually, I have no idea if they have anything to do with MDC))
When I was in high school, I used to drive my Saab 900 up to Hartland to drive around on dirt roads. You can't drive on this one. When I got older and I started riding my bike to Hartland, I went and found out where this one and the others go. In all honesty, I think all the roads in Hartland are awesome, including Rt 20.
4) Cedar Ln., Middletown & Mountain Rd., Newington
These roads are very similar in there spookiness and proximity to closed state run mental institutions. Mountain Road is partially blocked off, but Cedar Lane isn't. Cedar Lane is longer and there are other roads and stuff nearby to explore. Mountain Road is next to Cedar Mountain (and Cedar Lane). Sounds like a conspiracy. Connect the dots.
I'm not sure why I'm counting these as one road, because they're like 20 miles apart.
5) Central Turnpike, Eastford
There used to be a Turnpike that ran from Tolland to Boston. It's still part of the shortest route from Hartford to Boston. Despite these high speed-sounding statements, it's actually a dirt road through the Yale Forest.
6) Schaghticoke Road, Kent
This road goes past the smallest Indian Reservation in the country, is dirt, follows right next to the Housatonic and has some cliffs right on the side of it. I can't believe I forgot about this one earlier. The first I walk down it with Johanna, we had been hiking the Appalachian Trail, which is up the hill from it and it was dark and super spooky. I recommend it at night. I also recommend walking Dark Entry Road at night.