Last summer, my very good friend moved from Boston, Massachusetts to Portland, Oregon. He planned to make the drive in 12 days, following U.S. Route 20 from it’s eastern terminus in Boston all the way to Newport, OR (and then jumping on the interstate for the last bit up to Portland. Another friend and I planned to fly out to where he would be on the sixth day and join him, and a third friend planned the same for the same for the eighth day with the three of us flying back to our respective homes in Massachusetts and Maine the day after arriving in Portland.

About two weeks before the trip, I was laid off and suddenly found that I had much more free time than I thought I would, and changed my plans, deciding to join in on the entire trip (minus about the first hour and a half from Boston to where I live in western MA). We loaded up a rented SUV with all of my friend’s worldly belongings and our camping gear while trying to leave enough space to eventually add two more people and their gear.

A short album of highlights can be found here. Our itinerary was as follows:

Day 1: Boston, MA to West Windield, NY - Our camping plans fell through but we were lucky enough to find some couches to crash on at the home of a very understanding old college friend of my wife. Our only detour the first day was to a brewery my friend wanted to visit in Hudson, NY. Any time we detoured from Route 20, we made sure to join back up at the point we left off before continuing further west.

Day 2: West Winfield, MA to Cleveland, OH - Both being from the northeast and having traveled cross-country before seven years earlier, we knew that covering as much ground as possible in the first few days wasn’t going to cause us to miss anything too exciting, so splurging on a cheap hotel room was worth it for the extra driving time it provided. Great Lakes Brewing provided dinner and libations.

Day 3: Cleveland, OH to Warren Dunes State Park, MI. This was the first “new” state for both of us.

Day 4: Warren Dunes SP, MI to Dolliver Memorial State Park, IA.

Day 5: Dolliver Memorial SP, IA to Wind Cave National Park, SD. We left Route 20 around Charon, NE for our biggest detour of the trip, a loop that would take us off the main route for the next several days.

Day 6: Wind Cave NP, SD to Rapid City, SD to Mount Rushmore National Monument to Keyhole State Park, WY. We picked up the third member of the group after he flew into Rapid City.

Day 7: Keyhole SP, WY to Devils Tower NM, WY to Theodore Roosevelt National Park, ND.

Day 8: Theodore Roosevelt NP, ND to Rapid City, SD to Wall, SD to Badlands National Park, SD. We picked up the final member of the group on another trip to the Rapid City airport as we closed in on the end of our detour loop. The stop in Wall just consisted of a quick stop at Wall Drug for a view of some classic Americana.

Day 9: Badlands NP, SD to Cody, WY. We snagged what may have been the last campsite anywhere near the city because we failed to realize that the rodeo was in town and didn’t know how packed the place would be.

Day 10: Cody, WY to Yellowstone National Park, WY to Grand Teton National Park, WY to Jackson, WY to Yellowstone National Park. Spent the day taking our time, driving back and forth through the two nearby parks and getting lunch at a brew pub in Jackson Hole.

Day 11: Yellowstone NP, WY to Burns, OR. Splurged on a motel for the second time in order to cover as much distance as possible and thereby arrive in Portland earlier the following night.

Day 12: Burns, OR to Newport, OR to Portland, OR. Made it into the city with enough time to rent bikes and make it downtown for some Fourth of July fireworks.

All in, Route 20 measures 3,365 miles, but we added in around 1,800 additional miles on top of that for a bit over 5,000 miles in 12 days. Not my most break-neck trip, having done about 7,100 miles in about half a day less back in 2010, but definitely the trip where I felt like I saw the most thanks to traveling entirely on back roads and avoiding the interstate.