Chappaqua, NY to Bridgeport, CT

46.8 mi / 10.4 mph / 2011 ft. climbing
Home: Steve’s WarmShowers House

We always get good send-offs when we finally depart from our families’ homes, but it’s going to be tough to beat a 7- and 5-year-old hugging, waving, shouting goodbyes, and then running after us up the driveway and into the street, only turning around when called back by mom since Sydney was wearing nothing but her underpants!

The goodest of goodbyes from Sydney and Robin.

We had six miles of New York to pedal, and while the roads hadn’t gotten much wider or straighter during our time off, leaving mid-morning at least made the traffic less-treacherous. Still, Rett was very excited to cross the (totally invisible) Connecticut border, where she perceived an immediate improvement in driver behavior. And, honestly they did seem more-relaxed, though it’s difficult to explain how the artificial straight line drawn through this contiguous population could be a cause of that.

And here we were in state #17 of our nomadacy! That puts us more than 1/3rd of the way to 50. Maybe more-special, it’s a state I’ve never been in in my life until now, and leaves Nevada as the only “new” state for me that Rett has beaten me to.

The Greenwich sign stands in for the absent “Welcome to Connecticut” sign that didn’t exist on this minor residential street.

We’re heading for the coast via the town of Greenwich, one of the wealthiest towns in the United States. That of course brings impressive houses, but we also passed a mile worth of the grounds of The Bruinswick School, a $52k school you can send your 1st-grader to if you’d like (and if he’s a boy!)

A castle under repair?
Crossing the Norwalk River as it heads to sea.

The built-environment became significantly less-upscale as we headed east, winding in and out and up and down to cut across the lobes of land poking into Long Island Sound (we crossed over and under I-95 eight times today!) We were heading into a steady east wind, but all the turns and small climbs meant that it didn’t really affect us like the same wind on the Great Plains might have.

At one point a driver stopped and said that he’d seen us in Stamford, and asked where we were headed. “Bridgeport? Good luck, don’t get shot!” I was pretty skeptical that we’d be at any risk of getting shot, and assumed the guy was just a rich racist. Norwalk at least just showed that towns with large black populations can be a lot more fun: on an obviously-poor but busy street, two guys cheered us on as we passed, and a block later a teenage girl waiting for the bus did a little dance when she saw us. Earlier in the day at a light, a woman in the SUV in front of us hauled herself completely out of the passenger-side window, to ask what we were up to. Connecticut is amazing for getting reactions from strangers!

Wealth cycles as unpredictably as the turns and hills here, however, and by the time we approached Southport, we were again in a Hamptons-like area of grand oceanfront properties, most hidden behind gatehouses themselves fancier than many castles. But of course then there was no one to wave to us, no human energy, barely sights of humans at all.

Waterfront riding.
Stone walls are everywhere in this part of the country, but we’ve never seen one quite like this!
We’re heading for New Haven, partly because we both love Gilmore Girls and Rory went to Yale. But her high school was “Chilton”. Hmm!
The hazy form of Long Island across the sound.
I self-portraited myself without realizing it.
“Downtown” Southport.
In Southport, they put their office buildings on little islands in the harbor connected by bridges on both sides.

When we arrived to Black Rock, an outlying neighborhood of Bridgeport where our WarmShowers host lives, we found a perfect combination of the day’s economic extremes. The vitality and humanity that was present in the poorer neighborhoods, and with higher-culture opportunities for those with means. Like a cool neighborhood nightclub (that reminded me of Evanston’s SPACE). Or a variety of world cuisines (like the Mediterranean takeout place we could walk to) served by immigrants on their way up.

We saw all of this from our host Steve, on a short walking tour of the neighborhood strip, which was a wonderful way to learn about the place with a local’s eye, and with much more depth than we ever gather when spending a night on our own in a town.

We were going to go to a brewery, but ended up just bringing dinner back to Steve’s gorgeous garden-roofed backyard and talked bikes and life (the inside of his perfect-sized house made Rett and I both independently decide that we’d love it for our own. Maybe if Steve ends up liking his first bike tour so much that he wants to do it full-time (and can convince his wife to do the same!), we could switch places!


by

Last Updated:

Comments

Leave a Reply

Your email address will not be published. Required fields are marked *