It’s a testament to a city that you can love it even in lousy weather.

And for sure, Eugene, Oregon at the tail end of winter can be socked in with rain clouds. But with truly delicious food options, evergreen-lined streets, and—more than anything—rich cultural heritage, it’s easy to be reeled in.

This is the kind of place where turkeys roam freely in the outlying neighbourhoods. It’s the birthplace of Nike, The Simpsons, and the probiotic yogurt craze. It was on the cutting edge of sustainability, launching one of the United States’s first recycling programs and bike lane networks way back in the sixties. It offers that same sense of heady progressivism as Portland, but without any of the bustle or grime (God love it). Eugene restaurants offered farm-to-table cuisine long before it became a trend. The locals here simply called it “food.”

The city’s agricultural roots are made plain on the drive into town. I fly from Vancouver to Portland and drive south. As I pass through Salem, the sky suddenly opens wide, unimpeded by any mountains or evergreens, with the flats of the Willamette Valley stretching out on either side. Just south of Albany, the prairie eventually runs into a  small mountain range to the southwest and, aside from the odd car passing by, hardly any indication of modernity, conjuring visions of the old Western trails.

Skinner Butte Park, which sits directly north of downtown Eugene, offers sweeping vistas of the mountains that surround it. But looking east, there’s a startling site: the neighbouring city of Springfield and a view that looks almost exactly like the Springfield from the opening credits of The Simpsons—which is no surprise when you consider that creator Matt Groening, originally from Portland, based the cartoon family’s fictional home on this real-life place.

But the true cultural heart of Eugene might very well be located at Willamette Street and Broadway, where The Storyteller lives. It’s a sculpture of author Ken Kesey reading to his three grandchildren.

Kids these days have no real idea who Kesey is, but his influence is significant in American culture. He wrote the novel One Flew Over the Cuckoo’s Nest, the basis for the movie that made Jack Nicholson famous. He’s also responsible in no small way for the popularization of psychedelic drugs along the USA’s West Coast, as detailed in Tom Wolfe’s The Electric Kool-Aid Acid Test. The book documents Kesey and his Merry Prankster’s LSD-fuelled bus trip across America—which directly inspired the Beatles’ Magical Mystery Tour, among other notable artworks, as well as Kesey’s Acid Tests events—which birthed, among other things, the career of the Grateful Dead.

The Dead roots run deep, due in part to Kesey’s connection. The community is out in full force on my first night in town at a gig for Lukas Nelson (Willie Nelson’s son) with his band, Promise of the Real, at McDonald Theatre. The theatre is owned and operated by Kesey Productions, which was founded by Kesey’s nephew Kit. Tie-dye shirts and wild manes of white hair abound.

At the entrance of the venue hangs an enormous portrait of Kesey, who died in 2001, with one of his quotes inscribed below: “The answer is never the answer. What’s really interesting is the mystery.” It’s a memorial for the man, but also something of a tone-setter for the city. Things can get weird here. In fact, they had better.

WHERE TO STAY

Graduate Eugene — Designed with ephemera from Oregon’s history and cultural lore, each room is designed as a rustic cabin, right down to the wooden-panelled walls. It also includes Easter eggs from Eugene’s past, including a waffle iron lamp that pays tribute to the waffle press that was used to make the soles of the first batches of Nike shoes.

WHERE TO EAT

5th Street Public Market — The market is home to independent boutiques and a food court with local and independent eateries, including some of the best BBQ I’ve ever had.

Black Wolf Supper Club — Located next to Eugene Station and a short walk from the hotel, it offers high-quality Southern-inspired cuisine with urban millennial flair.

Magpie Coffee Shop — Seriously, all the coffee in Eugene is superb, but this place takes the leading edge for its gobsmackingly delicious biscuits. Worth the cost of the trip alone.

Plank Town Brewing Co. — Located a short drive across the Willamette River in Springfield, the brewery helped spur the revitalization of Main Street. It also offers elevated pub fare and quality takes on classic Pacific Northwest beer styles. Take some time to walk around the neighbourhood to view the numerous Simpsons murals—paid for by the city and painted by actual Simpsons artists—as well as the massive mural of Kesey on the side of the brewery.