In present day, while using the FM chip on my Motorola made TracFone, the first Portland market signal I'll hear is WHOM-FM 94.9. That's despite the fact that WBLM-FM 102.9 (classic rock) is 100,000 watts.WMTW on Mount Washington NH (COL Poland Spring ME) had cable carriage in Maine, NH, Vermont and parts of northern NY, not to mention across wide swaths of Ontario and Quebec. And you could watch it over the air in all of those places - and even in some corners of Massachusetts when conditions were good.
I sometimes wonder how much coverage WMTW-TV lost when they moved to Baldwin, ME for digital. Even then, they had an in-town Portland translator on channel 26.