Solution: Town to Town

Answer: DUO

The first step is to identify all of the images in the puzzle, and index by the number in the squares. This gives the phrase ON COUNTERPARTS.

All of these towns, (perhaps most obviously clued by Toronto, OH) share a name with a town in Ontario, which is also clued because ON is often used as an abbreviation for Ontario. The arrows can then be interpreted as directions travelling away from each city. Each arrow will point to exactly one other town in the list, providing an additional check for the city locations.

Once all the arrows are draw, the following path is produced, which spells the answer DUO.

Author’s Notes

This puzzle was partially inspired by an interaction I had with someone on the first week of classes, and later reinforced by a meme proclaiming a “cross-European road trip without needing a passport”, contained entirely within Ontario. As someone who isn’t native to Ontario, this is a recurring issue whenever I ask people where they’re from– fortunately, it lends itself perfectly to a puzzle mechanism for an Ontario-based puzzle hunt!

During the construction there were a good set of cities I wanted to include but ended up omitting due to their location. Boston, Brisbane, Dover, Essex, Exeter, and Vienna were all candidate cities at one point or another that I ended up not using for the puzzle. However, I hope the selection of cities was diverse enough and had some solvers thinking “wait, that’s also in Ontario?”