I have lived in Williamsburg since I was a small child and have liked it for the most part. There is plenty for the kids to do--multiple county playgrounds, bounce house, Busch Gardens, Water Country, and of course Colonial Williamsburg. There are so many restaurants you could probably go to one every night for 2 or 3 months and not repeat any! The sense of community is nice--lots of stay at home Mom's and retirees who help to keep our area safe and keep everyone in the know of things...every.tiny.little.thing.
There are definitely many pluses to Williamsburg but please make sure you are willing to pay a little(and sometimes a lot) extra for these things. The theme parks around here comes at a hefty price, housing is quite expensive with the HOA's being very strict. The shopping is mediocre at best, we do have the premium outlets with stores that you can find at just about every "city" you visit. The nightlife is almost non-existent..there are a few bars in Colonial Williamsburg but they are usually crawling with students from the local college.
The jist of this is that Williamsburg is a great place if you have a family or if you are a retiree who has the money to throw about for extra this and extra that, but couples or families making a median-to-low salary should probably steer clear or you will end up being stuck in a lovely town with no money to enjoy in it. Another thing I should mention is that Williamsburg is very difficult for teens and they tend to be mischievous since there is not much of a "teen scene." I know this personally from growing up here as a teen.
Be sure to vacation this lovely town first!