How many Yales can fit into one Connecticut? Apparently, two.

There is the Yale we all know and love sometimes, the Yale with phony gothic towers and too many courtyards to count.

But there is another Yale — a bit north of East Rock, a skip up the Wilbur Cross Parkway and just an exit off the freeway, sits the neighborhood, or town, or something, of Yalesville. Many times have I passed this place and wondered whether Yalesville could possibly be as magical as Yale itself, but always I continued on my way, destined to remain ignorant of the wonders that could await me on the shores of the Quinnipiac River.

And so I set off in a Zipcar earlier this week, seeking to uncover whatever diamonds lay hidden in the Yalesville rough.

Yalesville, according to the Wallingford website, seems like it might be steeped in history. This quaint ville actually predates Yale; Wallingford was founded in 1670, according to an 1870 history of the Connecticut commune by Charles Davis that’s stored in a Quinnipiac University library. Yalesville itself can be traced back to the late 17th century, when a mill was constructed at the Quinnipiac River falls. One Charles Yale eventually purchased the mill, and around the turn of the 19th century, the area was renamed “Yalesville.” According to Wallingford’s website, there is exactly one point of interest in Yalesville: an Octagon House — a house shaped like an octagon — built in the mid-19th century. If this was the best Yalesville had to offer, I was in for an interesting trip.

No one seems to know where Yalesville begins and ends. It is a nebulous neighborhood encompassing a large swath of land in Wallingford. It has no official online presence, only a vague Wikipedia page and an elementary school web site. Not far from Choate, it’s a land not of decadence but of decay. In this strange land, “for sale” and “for lease” signs litter the ground like dinosaur bones, hearkening to better times. During a loop around what I think was Yalesville, I passed a boarded-up liquor store, and my heart cried out in agony. I had dreamed of a Yalesville similar to Walden Pond, or perhaps the mythical West in “The Lord of the Rings,” where old elves and old Frodo Bagginses go when they’re washed up or crazy. This faraway land, I thought, was where road weary Yalies spent their happy golden years reading Laura Ingalls Wilder and watching the children play. But there are no children in this town of ticky-tacky, and the people read Thomas Pynchon.

Of course, I knew my fantasy couldn’t be real, but my sneaking suspicions became all too true when I passed my ultimate nightmare: a massive hospital called “Masonicare.” As a devout Roman Catholic, I have a deep-seated fear of the Masons because one time someone told me they hate Catholics, something I am sure is untrue but which has nonetheless colored my view of them and their role in American history. I watched with horror as we passed the monstrous facility — large enough to be described as a campus or compound, filled, no doubt, with hundreds of so-called “Freemasons” plotting to destroy my people by crafting a Constitution built on their dark anti-Catholic, anti-Illuminati agenda. Bastards!

Upon further research, of course, my prejudiced views were proven incorrect — it’s really just a retirement facility, and a nice one at that. But moments after my arrival in Yalesville, my opinion had already soured; what once seemed a land of possibility was now … not. And yet my voyage continued.

The first (and only) stop on my trip was Neil’s Donuts, a mom-and-pop donut shop on the main road that seems to be Yalesville’s biggest attraction. The store has its own page on Yelp, where commenters sing its praises. “Pure bliss in donut form,” one wrote. “I’ve only had their donuts but DAMN are they good. This is coming from someone that doesn’t even have much liking for donuts in general,” added another. I’m a big fan of donuts, so I was obviously excited. The storefront proudly displayed a sign boasting that the Wallingford Record-Journal had named it the town’s top bakery this year. Neil’s did not disappoint; the glazed twist was exquisite.

The whole experience was very Norman Rockwell. There were old men in flannel discussing the day’s news over coffee, laughing with the shopkeepers, probably thinking about Peggy Lee and the upcoming county fair. A wholly American scene. Maybe Yalesville wasn’t so bad after all. I hit the road anew, full of milk and donut, looking for the next great adventure. I passed hill, dale, homes for sale and the Wallingford Church of the Nazerene — a quaint establishment that uses its sign to enlighten weary passersby: “Ashes to fire, we never know the worth of water until the well is dry.”

Seeking clarity, I went not to the doctor or the mountains but to the Yalesville post office. When in doubt, turn to a postal worker, amirite? Unfortunately, they were as ignorant as I: “I don’t know where Yalesville starts and stops,” one worker told me. “It’s all the same zip code — you got Wallingford, then Yalesville, then down the road a little is Tracy.” “No idea about the history,” another offered. What I did find at the post office was direction: one worker suggested I check out the city hall, located not in Yalesville, but in Wallingford. I set off, BlackBerry in tow, sure I could locate this Town Hall via Google Maps. Except my Blackberry crapped out and I had to play it by ear, so instead of making it to the town hall, I ended up in some industrial wasteland. Afraid of getting lost, and with only 20 minutes left until I had to return to New Haven, I headed back to Neil’s for a pick-me-up, and picked up a dozen donuts for all my beautiful friends back in the Elm City. In a last-ditch effort to salvage my trip, I asked a worker if he knew of any must-sees in Yalesville, or, for that matter, any points of interest AT ALL. He said no, adding: “I’m from Wallingford; I don’t even know where it starts and ends.”

As I left town, I could not help but feel that I had missed something. I probably did. Somewhere in this community of doublewide trailers and churches there had to be something compelling, but I left with the distinct impression that Yalesville just wasn’t a real place. After my exhaustive 1.5 hour tour, I found little more than a sad village within a decaying Connecticut community. I left Yalesville with a full stomach and an empty heart.