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I have been to both, Roanoke moreso than Wheeling because I have family down there. If it were me I would choose Roanoke hands down. Wheeling is a rather economically depressed area, some people will say otherwise but simply looking at population stats will reveal that there has been massive population decline throughout the Northern Panhandle over the past 30 years.
Roanoke is the economic and cultural magnet of SW Virginia, it is close to the mountains, several beautiful lakes, and A LOT closer to the beach than the Wheeling area. The downtown area has several great museums for a city of Roanoke's size along with a wide assortemnt of restaurants. It has a fairly diverse economy and seems to be quite a progressive area, very laid back yet with somewhat of a city feel to it.
If you like warmer weather you won't find a lot of it in Wheeling. Winters will be cloudy, cold, and just downright dreary most of the time. Roanoke will be milder with less snowfall, not to say it doesn't get cold there too but it will be far less extreme. Summers in Roanoke however will be much more humid and uncomfortable than Wheeling.
Diversity...neither seems exceptionally diverse, but then again I live in the DC area where you are constantly surrounded by people from all over the world. Roanoke probably has the most simply because it is a larger city. Wheeling has a lot of 2nd and 3rd generation Italian Americans, I don't really consider that anything great on the diversity scale, but they do make some EXCELLENT FOOD.
One advantage Wheeling has (aside from the states newest casino) is being an hours drive from Pittsburgh which is a very nice city to visit. If you ever felt you needed a culture fix all you would have to do is hop in the car and head to the Burgh to visit its many museums, ethnic restaurants, and of course awesome professional sports teams.
Good luck with your decision!
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Wheeling vs. Roanoke Va
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