Most of this was shot in and around the town where I grew up. Some 9th graders tried to beat Macauley up outside a sub shop during the shooting but he was too fast for them.
Not this scene, though, the closest cliffs like that I know of would probably be in Nova Scotia or something.
Nice. The only one I can think of was that Burt Reynolds movie Breaking In, which was filmed at an amusement park just blocks from where I grew up, and seemed to frequent the same restaurants that my parents took us kids to. Mr. Holland's Opus was also filmed here (and I was an extra in the orchestra) but it was on the opposite side of town and apparently Richard Dreyfuss was kind of a pompous dick who never left the trailer unless he had to.
Sounds like what happened to Macauley is what's been happening to Fred Armisen when he just goes to the bar in his downtime: like, maybe not "beat up" but he's generally ostracised at this point by pretty much everyone in Portland, even folks who might've moved here after Portlandia came out. I've seen him at a few bars over time and he's just sitting there all alone. It's actually kinda sad but he brought it on himself.