One thing to always remember around Williamsburg and most of Virginia: No road runs compass-straight. Ever. The hilly, river-crossed terrain doesn’t lend itself to it. Locals joke that some roads run the way they do because some native or settler wandered crookedly centuries ago.
So remember that Williamsburg, Jamestown, and Yorktown are small, and roads in the heart of the localities are paved versions of the early paths of the colonists: quaint, sometimes narrow, and often congested. Give yourself plenty of time to make it to your destination at the desired hour.
Before you can hope to find your way around, it’s essential you get a brief geography lesson.
Williamsburg is the northwestern-most city in a region called the Virginia Peninsula. The peninsula also includes the cities of Hampton, Newport News, and Poquoson, and the counties of James City and York.
Across the York River to the north is Gloucester County. Across the James River to the south is South Hampton Roads or Southside—the cities of Norfolk, Portsmouth, Chesapeake, Suffolk, and Virginia Beach. Taken together, the Virginia Peninsula and South Hampton Roads make up a geographic area dubbed Hampton Roads, which is also the name of the harbor at the mouth of the James River around which most of these cities are located.
With a population of almost 1.7 million, Hampton Roads is the nation’s 35th-largest MSA, about the same size at Charlotte, North Carolina, or Austin, Texas.