Williamsburg is a wonderful place to experience a lot of great food! During my time living in Virginia, I always enjoyed visiting my mom in Williamsburg, especially when I had the opportunity to take her out for dinner.
Today my visits to this area are less frequent and usually part of a vacation trip via our timeshare at Kingsgate. I've had the opportunity over the years to come to Williamsburg for conferences, but then I've typically been tied to the conference center hotel and its restaurant facilities. I must admit, Kingsmill Resort is outstanding and their dining first class.
While you are in Williamsburg, you owe it to yourself to dine in Colonial Williamsburg at least once! Your meal is as much about entertainment as nourishment. Period costumed servers and staff will add to your colonial moment in history.
Quick Tips:
Let's get the unpleasantries out of the way first. Williamsburg has every chain restaurant known to mankind . . . all the fast food places including McDonalds, Hardees, Wendy's, Arbys, Pizza Hut, Taco Bell, KFC, etc, etc, etc . . . and all of the next step up places like Cracker Barrel, IHOP, Red Lobster, Outback Steakhouse, Olive Garden, etc. This is good news in that if you have picky kids and don't want to experiment with your dining choices, you won't have to. With that being said, however, I encourage you to venture out of your comfort zone and enjoy what the city has to offer!
There are probably no less than 20 waffle and pancake houses. I can't say that I've ever had a bad stack of cakes or a crappy waffle. I would say visit based on convenience as all of the major tourist areas have at least one or two nice breakfast places. All of the breakfast places we've tried have very good southern breakfasts that include biscuits (and gravy if you like), grits and the really good country ham.
For dinner there are a lot of nice seafood and steak places. Many of them are along Richmond Road, which I personally consider the "main drag" of Williamsburg once you are outside of the restored area. Aberdeen Barn has been there for what seems like an eternity and was my favorite place to go with my mom. Today, I must admit that for David and me, Shackleford's II has become a "must do" when we're in town.
Near the restored area, locals and visitors alike enjoy the Cheese Shop for great deli sandwiches . . . or Trellis for fine dining (lunch or dinner).
Whatever you decide, there is rarely a reason to pay full price for your meal. Many, if not most restaurants advertised in the local tourist advertisement magazine. I am also a frequent user of www.restaurant.com for outstanding dining opportunities. Lastly, do not forget about the Entertainment Book. Even if you don't own a local version, owning in your own community will typically afford you the opportunity to get a nice deal through their online program. The one exception here would be the restaurants owned and operated by CW. Everyone pays full price in their taverns. Best Way To Get Around:
If you are going to tour/visit the restored area of Williamsburg (Colonial Williamsburg aka CW), you can park your vehicle at the Visitors' Center and take the free shuttle to the restored area and nearby dining establishments.
There is a public transportation system (buses) that connects at the Visitors' Center but I've never personally used it. For me, I prefer to have my auto and can't imagine vacationing in Williamsburg without my car.
Additionally, with the expansion of the City of Williamsburg and the new suburbs throughout the area, many of the nice restaurants are in outlying areas in shopping areas. Both City Grille and Shackleford's II are examples of places you won't find on the beaten path and will need a car or hire a taxi.
If you are venturing outside of the restored area and need to be back into CW for an evening program, you'll want to plan on dinner for 5:00 or 5:30 so that you have no problem making a 7:00 show. For the later shows (8:30 or 9:00) you can plan on dinner as late at 6:30 but I wouldn't go any later as service can tend to be slow as the night goes on.