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I grew up pretty much exactly in between North Canton and New Philadelphia. Pretty quiet, rural area. Once I graduated and got a job, I purchased a home in Jackson Township which is pretty much the Massillon/North Canton area and I love it here. Very upscale area and from what I hear, the school system is pretty good. Also, there's a lot of stuff around here as far as shopping and restaurants (Belden Village area). I live very close to Stark State college and Kent State University Stark Campus so I'm right in the heart of Belden Village. I'd recommend taking a look around here...
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I'm from Dover. Good HS Football and Basketball Programs, and the Schools are good. You're not going to find much in the way of sports bars in Dover/New Philadelphia, there are a couple though. If the social/night life is more of a priority, I'd look closer to Canton.
I have lived in the New Phila area my whole life (I am 34). I worked in the Massillon area for a few years and know the Canton area well also. The New Phila area is a lot more rural area than Massillon and Canton. There are decent schools in the area, but again the population is smaller so there are no big district 1 athletics. The bars in the area are more small town type. I would agree with magnum that there is much more to do the further north you go. I also agree with aange that I would avoid the Massillon and Canton school districts unless you are enamored with their football programs. There are several nice areas between Massillon and North Canton. Which city would you be working in? If commute is an issue, then specific neighborhoods near your work might be better. Also, what size of city/suburb are you looking for? You can go from Canton/Akron city style to complete country farm life in the areas you are talking about.
I'll be working just outside of New Philadelphia. I'm not at all opposed to a more rural area as long as the schools are good and the commute to work is managable. Night life isn't a big deal, but a decent bar to grab a couple beers and catch a game would be cool.
I live in Uniontown which is probably too far north for you but Lake has the best school district in Stark county.
Tons of sports bars in Belden Village (North Canton). If you want a little more rural, you can head out towards Plain Township which is where Glenoak is (Kosta Koufos and Bri'onte Dunn both went there). Also, it's not too far away from Walsh University and they have a really nice shopping center over there called Washington Square.
If you're a golfer, you'll love the area. Tons of courses.
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