Look left-you’ll spot a stately brick mansion with arched entries, turrets, and more chimneys than a Sherlock Holmes novel; the arched brownstone doorway and intricate brickwork really make this one stand out from its neighbors.
Alright, what you’re looking at isn’t just another campus house, but the Xi Chapter of Psi Upsilon-home to quite possibly the most ambitious group of students to ever hold a toga party in the United States. Built in the early 1890s, this was the very FIRST house in the country designed specifically for living and fraternizing, all under one impressively expensive roof. Back then, it cost $40,000 to build-these days, that’s getting close to $1.4 million. Definitely not your average college housing.
Picture Wesleyan in the late 1800s: students often wore starched collars, football meant something awkward with leather helmets, and the Psi U boys were basically the influencers of their day-top of the sports leagues, racking up academic awards, leading all the clubs. The fraternity itself started at Union College in 1833, but when it opened the “Xi Chapter” here around 1843, it became the first national fraternity chapter at Wesleyan. Kind of the original out-of-town social network.
Now, about the building-it was crafted by Colin C. Wilson, a young English architect who, frankly, was a bit of an underdog. He got the gig thanks to a well-connected alum living all the way in London. The design is a mash-up of Richardsonian Romanesque (think bold, rough stonework and heavy arches) and Jacobethan style, so you get a sort of castle-with-a-hint-of-Hogwarts vibe: sturdy yellow brick, brownstone, and terracotta trim; steep, slate gables; a big Roman arch that looks like it’s holding secrets; and even some half-timbering in the gables for that “old English inn” flourish.
Check out the iron porch on the north side and those fancy brownstone carvings-like the architects just couldn’t resist adding one more little detail. Inside, it has a grand wooden dining room with colonnades, and, rumor has it, plenty of secret fraternity traditions.
Psi Upsilon even went co-ed in 2015-so the legacy continues, just with a bit less pipe smoke and a lot more WiFi.
Ready to keep strolling? Richard Alsop IV House is just a five-minute walk north up High Street.




