Fifth stop: New Haven, CT

Across the street

As the days started to dwindle in Livingston Manor and we faced the reality that we needed to find a stopover between there and Maine, some friends came to the rescue with great ideas. Our first plan was to go through Vermont as we’ve both always wanted to experience that state and the awesome Bailey from Jackalope Brew came through with some amazing recommendations. Sadly, though, we were so last minute about it all that we were having trouble finding lodging that would accommodate the whole menagerie and had just started rethinking our plan when I happened to be emailing with colleague-turned-friend, Heather, about the upcoming Artist Thrive meet-up. She asked if New Haven was on the way for us. Turns out, New Haven was RIGHT on the way and saved us almost a whole day on the road. We found an incredible AirBnB (more on this shortly), so that pushed us over the edge and we headed out to New Haven!

Shortly after arriving, we enjoyed a lovely, leisurely sushi dinner with Heather who gave us the scoop on all things New Haven, and gracefully laughed while we talked over each other for hours (we’re bad about this at the best of times, but it had kinda been awhile since we’d seen other people at this point…). It was great to catch up with a friend, especially one willing to bust your chops when needed (one great Heather quote of the evening as I rattled off a laundry list of desires for my next job—“wow, you sure have a lot of expectations for this job you don’t have yet.” Ha! Well said, my friend).

After a fun night of dinner and exploring downtown New Haven, we headed back to the AirBnB in the historic City Point neighborhood that we were soon becoming smitten with. Our house was the Willis Smith Oyster House, a true historic treasure with a gorgeous view of the water. And to top it off, the hosts turned out to be two of the funnest people we’ve met. We had a great evening of drinks and dinner with them at the Pequonnock Yacht Club across the way.

Listen up on this part, Nick, Kix and Dween: we used the old trick we learned from my Uncle Bill—a yacht club membership ANYWHERE is typically reciprocated by all yacht clubs across the US. Woah. So we reciprocated our way right up in that incredible yacht club on the water and enjoyed a fine meal (at a steep yacht club member discount). See pic of us looking smug on the patio below. Go out and try this yourselves soon.

Anyway, it was a night of great conversation as our hosts seemed almost comically well-matched for our interests. The guy, a Yale grad, headed up greenways, bicycle paths, parking, sidewalks, etc. for the city of New Haven, and the gal was a lawyer who is also chairing an arts nonprofit board. We could have talked to them for days.

Maddie and Zeke really loved this stop, too. (Yes, both are still alive and in great health, for those of you following the progress of our 20-year-old cat and 12-year-old dog with baited breath). Maddie took in the countryside on the drive and once we got to the house, she curled up by the windows enjoying the sea breeze and didn’t really move for three days, but she seemed quite content. Zeke enjoyed strolling around the beautiful, historic neighborhood (see excessive pics of the neighborhood below), looking out at the view off the porch, barking at anything that moved, and eating shellfish off the sand.

This ended up being one of our favorite stops along the way. We only wish we could have stayed longer. Trent would like to add: Shout out to my boy, Larry the chef, who served me the breakfast special (biscuit, homemade sage sausage, egg, cheese, and coffee) each day for $4. Come on. Talking to him was worth the $4 alone. What a cool guy. Visit City Point Kitchen (pictured above) if you’re ever in the neighborhood.