The fair place to meet is Columbus, OH — the city closest to the midpoint of Milwaukee and Richmond. From the farther side that’s about 7 hr 12 min of driving.
Recommended midpoint
Columbus, OH
From Milwaukee
6 hr 57 min
331 mi to Columbus
From Richmond
7 hr 12 min
343 mi to Columbus
That’s an even split — both sides drive within 15 min of each other. Milwaukee and Richmond are about 669 miles apart.
Milwaukee and Richmond are about 669 miles apart by road. Split the difference and you arrive near Columbus, the city closest to the halfway point between them. That splits the trip almost evenly — about 6 hr 57 min from Milwaukee and 7 hr 12 min from Richmond.
That's a half-day drive from each side, so Columbus suits an overnight or a weekend rather than a quick coffee — long enough to want a reason to stay, short enough to drive.
If Columbus doesn't have what you're after, Cleveland and Cincinnati are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Milwaukee and Richmond.
Columbus is the capital and most populous city of the U.S. state of Ohio. With a population of 905,748 at the 2020 census, it is the 14th-most populous city in the U.S., second-most populous city in the Midwest, and third-most populous U.S. state capital. Read more →
Milwaukee is the most populous city in the U.S. state of Wisconsin. It is located on the western shore of Lake Michigan at the confluence of the Milwaukee, Menomonee, and Kinnickinnic Rivers. Read more →
Richmond is the capital city of the U.S. state of Virginia. Incorporated in 1742, Richmond has been an independent city since 1871. It is the fourth-most populous city in Virginia, with a population of 226,610 at the 2020 census. Read more →
City descriptions adapted from Wikipedia (CC BY-SA); photos via Wikimedia Commons, credited above.
Estimates use straight-line distance and typical road speeds; real drive times vary with route and traffic.