"Rhode Island is neither a road nor an island. Discuss…” This indelible line, uttered by Linda Richman on her show Coffee Talk runs through my head every single time I hear the state's name. Coffee Talk, or more accurately “Cawfee Tawk” was, of course, a skit on Saturday Night Live with Mike Meyers as Linda Richman. The skit was such a hit they did it 17 times with different guest hosts doing horrendous Long Island accents. This was during the second heyday of SNL in the mid-

After a pitstop in Ithaca, I started northeast on my three-state run to close out New England. First up was Vermont. I had been to Vermont a handful of times before, but only for work retreats. I worked for six and a half years for a Boston-based software company. Once a year we would get the company together in Vermont for a week-long retreat. I'd fly into Burlington, grab dinner with the team, then we'd drive about an hour into the country. We’d stay at a place with a summ

As I loaded Pierogi and headed east, I was happy to see Branson MISSOURI receding in my rearview. It was about 900 miles to my next destination, Roanoke, Virginia, so I split the driving across two days and the halfway point was Nashville. I hadn’t really enjoyed Nashville when I stopped there for a night on my way to Memphis during my TENNESSEE week. Maybe I hit it on a bad night the first time, or maybe I hadn’t been in the right mood. Nashville is such a popular spot, I f

I had a religious experience in Missouri, but not in the way that phrase is usually used. I’d been driving since Chicago so I stopped in St. Louis for the evening, just over the border from Illinois. Just outside my hotel was the St. Louis Wheel - one of those giant ferris wheels like the London Eye or the High Roller in Las Vegas. I’d never been up on one of those, so I figured why not? Dusk was settling into night by the time I boarded the wheel, which flashed colorful des

I was now two thirds of the way through the trip. My whole modus operandi was winging it - plan as little as possible and see what happened. What few plans I did make, I mostly stuck to. There was a rough framework for Illinois - pop in to quickly see my friend Sarah, then my friends Doug & Lindsay, then spend the week in Springfield. It didn’t turn out that way at all. LAKE VILLA My first stop was in Lake Villa to see Sarah. I met Sarah through Chris, my close friend, collab

Since I’d mixed up the nights of my booking, I had to drive all evening from Minnesota. It was nearly midnight by the time I pulled into my Airbnb in Viroqua, Wisconsin - the one with the stripper pole in the living room. VIROQUA I had some difficulty finding it because the front of the house was completely obscured by the landscaping. Most Airbnbs are income properties for people or companies. They usually have generic Hobby Lobby decor with no character at all. But it was

I wasn’t going to write about this trip. I had been planning to stay present and just experience it, but I quickly realized it was going to be too good not to share. So this has nothing to do with the 50 States, but I hope you'll indulge me. Truth be told, I had been dreading this trip. For reasons she’s somehow forgotten, my high school bestie and co-instigator Larissa got it in her head that before she turned “milestone birthday” (as she says), she and her husband Jamien we

As soon as I crossed the Red River of the North into Minnesota and passed through Moorpark I saw loads of trees, a welcome sight after the endless North Dakota plains. A gas station that had been converted into a Trump Store for the election stood along the highway, forlorn and empty eight months after the voting. After an hour in the state I cut north off of state route 34 toward Itasca State Park , my first stop and home to Lake Itasca. Minnesota’s state motto is “Land of

I think it’s safe to say that North Dakota has the reputation of being the most boring and drab state in the union, so much so that the state’s tourism board has wittily embraced it. But I’m getting ahead of myself. I pulled off of the road at the border between North and South Dakota. Surrounded on both sides by sweeping green pastures, my only company was the occasional speeding motorist and a scrum of black cows on the horizon. I may have allegedly left another pair of

Somewhere along the line I lumped North and South Dakota together in my mind. I’d been told repeatedly that North Dakota was flat and boring - miles and miles of nothing. I guess I just mentally conflated the two. South Dakota has the highest ratio of cows to people of any state (3.91), so it didn't seem like a huge leap. But everyone I spoke to within three states of the Dakotas was quick to correct me. South Dakota they said is pretty remarkable, and not what I pictured. So

I set out from Laramie in the late morning, groggy and undercaffeinated, and headed east. I’d had a wicked case of insomnia my last night in Wyoming. Sleep and I have always had a complicated relationship. I find it impossible to get into any routine or rhythm. If I manage to get a solid eight hours two nights in a row, the third night is inevitably a disaster. Either I can’t get to sleep or my eyes will pop open at 3:00am. As a kid I had a perpetual case of FOMO at bedtime

It will come as no surprise to anyone who knows me that I can be a bit of a contrarian. Several people have raved to me about the natural beauty of Wyoming and Yellowstone National Park , but I went into the state with low expectations. It’s just mountains, desert, and a dumb geyser, what’s the big deal? If so few people lived in the state (it has the fewest people per square mile in the contiguous 48), I was sure it couldn’t be as special as all that. I was very, very wrong.

Montana was always going to be an emotionally complicated state for me to visit because I first dreamt up the idea of this 50 states trip while vacationing there with my former partner. But first I had to solve the challenge of how to get my car back from Alaska. I had three possible options: 1) drive back through The Yukon and British Columbia, 2) take the ferry down with it, or 3) have it shipped. Remarkably all three options cost around the same. I’d had the luxury of driv

It feels weird to call Alaska a state. It is simultaneously distinctly American and something else entirely. It feels removed from the...

The driving route from Ithaca to Fairbanks, Alaska took me over 4,200 miles through 6 Canadian provinces and territories in sub-zero...

South Carolina marked the halfway point of this trip. It should have been a thrilling milestone. I should have been beaming with pride....

Florida. The name conjures images of bright sunlight sparkling off of aquamarine water, golden beaches, and Disneyland. I experienced...

Little did I know when I set out that a dangerous walk along a breakwater, a Civil War cannon, and a naked sunrise awaited me in North Carolina. I left Annapolis on a sunny Saturday morning. It had crept back up into the mid 40’s and all the snow had started to melt. There was another cold front and potentially more snow on the way, so I didn’t want to dawdle. I had a flight booked from New York to Costa Rica in February which gave me enough time to complete five states befo

Mother Nature finally caught up with me in Maryland... My four hour drive from Pittsburgh to Annapolis was uneventful except for one...

After a five-month hiatus from the trip, I felt conflicted as I pulled onto the highway. It was like starting all over again, but without...