trippin' on roads

Growing up with a mother with an entire phone book of family ties in CT, we would venture down to the nutmeg state at least once every two months. Or maybe that's revisionist history -- maybe it was once every three months. Anyhow. With or without us, though, she would slip out to see her parents, sisters, brother-in-laws, nieces and nephews quite often. I remember her excitedly telling my dad that she had made it in only one pitstop, in only five hours, before it got dark, etc. It was always a challenge: to find the best, easiest, and most scenic way.

Last Friday afternoon, RJ and I made the trek from Watertown to Mount Kisco, a sleepy little town filled with sprawling estates and equestrian farms for a family function. As we got closer and the roads got twistier, the sun was setting and the moon roof was open and I felt like we were in a commercial for Volkswagen. Really, how great can (some parts) of (some) roadtrips be?

Sunday morning, we got up early and did sort of a repeat of this whole vibe. Heading southeast to Fairfield, we avoided major highways (looking at you, 95) and meandered through small villages and bits of the Merritt Parkway until we literally hit the beach.

Now it's Monday, and I'm still daydreaming about that road tripping feeling. So it was super convenient that I have my dear friend N is planning a road trip from Old Greenwich to Chaumont in the coming weeks.  So I got to spend some time out of my day mapping out our route Sunday. Here's how I'd do it.