Brattleboro has a soft spot in my heart. The first time I ever traveled anywhere even remotely "far" from home alone, was to interview at Marlboro College. I took several buses, leaving from NYC (my first time going there alone, too), and transferring along the way. It was late September and I was staying on campus with a student host overnight.
They billed Brattleboro as this "cosmopolitan" city, which sounded so glamorous to my 20ish year old self. I got out at the bus stop, and was a bit baffled because it didn't seem like much of a city to someone who grew up in the shadow of New York. But it was quaint and charming.
I didn't go to Marlboro (and I believe it no longer exists sadly). But that trip remains something of a defining moment in my life, and this cow parade fits perfectly with the impression the town left on me!