The fair place to meet is Denver, CO — the city closest to the midpoint of Pittsburgh and Portland. From the farther side that’s about 27 hr 38 min of driving.
Recommended midpoint
Denver, CO
From Pittsburgh
27 hr 38 min
1,318 mi to Denver
From Portland
20 hr 34 min
981 mi to Denver
Portland has the shorter trip; the split is off by about 7 hr 4 min. The alternatives below can even it out. Pittsburgh and Portland are about 2,160 miles apart.
Pittsburgh and Portland are about 2,160 miles apart by road. Split the difference and you arrive near Denver, the city closest to the halfway point between them. That puts roughly 27 hr 38 min of driving on the Pittsburgh side and 20 hr 34 min on the Portland side — the fairest single meeting point among the cities near the middle.
Over this distance most people will fly rather than drive the whole way. Denver still makes a fair, central place for Pittsburgh and Portland to converge, splitting the travel instead of asking one side to cross the country.
If Denver doesn't have what you're after, Omaha and Minneapolis are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Pittsburgh and Portland.
Denver is the capital and most populous city of the U.S. state of Colorado. Officially a consolidated city and county, it is located in the South Platte River valley on the western edge of the High Plains, and is just east of the Front Range of the Rocky… Read more →
Pittsburgh is a city in Allegheny County, Pennsylvania, United States, and its county seat. Read more →
Portland is the most populous city in the U.S. state of Oregon. Located in the Pacific Northwest at the confluence of the Willamette and Columbia rivers, it is the 28th-most populous city in the United States, sixth-most populous on the West Coast, and… 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.