So my fiancee is helping me out here, and she's pulled up a few towns which are very similar looking to the town I'm remembering, just not in the right area.

It looks a lot like the 'main street' area of both Chester and Grafton, but both of those towns were outside the territory of where I was sent for work. It was more mountainous and further north, but as far as the actual town goes, Chester is the closest I've seen so far, similar architecture and building styles. I'll post the link so you have an idea of the vibe.

https://www.google.com/maps/@43.2641601,-72.5979413,3a,75y,298.73h,97.4t/data=!3m7!1e1!3m5!1sM3xvy3ig8l9sJ6g2sTF6yw!2e0!5s20180901T000000!7i13312!8i6656

I'm assuming the flags were year round because I wasn't there near Independence Day, Memorial Day, or Labor Day. The reason I'm so hung up on it is because the whole place was a weird experience and I'd like to go back to see if it was as weird as I'm remembering it. I was the only person there and the whole town was dead silent. Nothing looked abandoned or blighted, just didn't see any people. All I heard was the wind, and birds as I drove through. I saw a couple of people at the supermarket and there were a few cars parked at the dollar store, but nobody in the rest of the town.

Until I saw the dollar tree/grocery store I thought I may have accidentally driven onto the set of a movie. It would have been creepy if it wasn't so beautiful.

I am totally stumped.