Ride 10: Connecticut
The Constitution State
State: Connecticut (#10)
Area: New Haven
Route: Farmington Canal Heritage Trail
Final Mileage: 50.69
Date: November 20, 2021
The one that got away. Yes, we had planned to do our Connecticut ride much earlier in 2021, pairing it with our New York ride. However, if you have read about that...adventure...you’ll know we were glad just to survive it and live to do Connecticut another day.
As late November rolled around, we discovered we both had a free weekend before the holidays and decided to head back up northeast for each of our first trip ever to the Constitution State. We landed on doing the ride in New Haven (home to Yale), on the city’s Farmington Canal Heritage Trail. As an out-and-back route, there was no need to do much prep work—just show up and find the trail!
We set out for the ride on a crisp, late-autumn day. While much of the surrounding foliage had already fallen off the trees, there were still gold and auburn patches here and there that gave us one last taste of fall for the year.
We began the ride by traversing the historic grounds of Yale University. Although both of us have been out of school for some time now, we were in awe of the gorgeous Gothic buildings and reminisced briefly (and fondly) about our days on our own college campuses.
We then set our sights for the trail, which picked up just on the outskirts of campus.
From there, we headed due north for a little under 25 miles. The ride was pretty easy, minus a few stops and starts early on at spots where the trail crossed main roads.
After about 10 miles or so, we could finally feel ourselves emerging out of the New Haven area and hitting more rural and countryside terrain. For two Midwestern boys who had never set foot in the state before this ride, we enjoyed soaking up our surroundings—even including, at one point, something resembling a mountain.
We continued onward until we reached the town of Southington, which was situated right along the trail. It was here that we pitched camp at an awesome little brewery called Witchdoctor.
After a while, we both must have subconsciously realized it had been a bit colder outside than we’d cared to admit, as we ended up hanging inside Witchdoctor for over an hour. The beers were excellent, so it is hard to complain about the time we spent there. But it did leave us trying to beat the sunset as we headed back to town (Daylight Savings Time had hit just two weeks earlier, leaving us with much less daylight).
By the time we returned to New Haven, the annual Harvard-Yale game had just ended, leaving students milling about the downtown area. Despite Yale’s late-game loss, everyone we crossed seemed to be in fairly good spirits! And while we were forced to walk our bikes for small stretches at a time to avoid the foot traffic, we enjoyed experiencing the downtown atmosphere in what seemed to be its full form on a Saturday evening.
As we made our way back to the cars, we rode past Frank Pepe Pizzeria, one of the most famous pizza places in the country and a staple of the New Haven-style pizza scene. We had looked it up earlier in the ride, and after seeing the line gathered outside, we decided we had to try it ourselves. The verdict: it lived up to the hype, and it was a great way to round out our time in town.
And that’s all there was to this one! A simple, uneventful, but delicious (in both brews and tastes) day—and a great introduction to the state for both of us. There’s no doubt we’d both relish the opportunity to return someday.










