This looks like a K-38 cable trailer. And, it is built by the same company (Highway Trailer), but the tag and wheels suggest to me this is a pre-WWII model. The Highway trailer company of Edgerton, Wisconsin, began as a wagon works. In 1917 it shifted to trailers, large and small. This one would look better behind a vintage spoked vehicle from the 1920s.

“$800 OBO
Serious Inquiries Only Please
Must sell!
Excellent vintage condition with original Highway Trailer tag intact. No rusted holes and in great restoration condition or keep as is! Original wheels with Goodyear tires.”

https://fortsmith.craigslist.org/tro/6095915790.html