These days Mississippi Avenue is “sleepily trendy,” as a Serious Eats blogger wrote in a review of Interurban when it opened in 2011. The mhoo tom yum soup with flat rice noodles at Mee-Sen Thai Eatery is alone worthy of a date-night. I spent an hour one morning in the Sunlan light bulb shop, where the owner, Kay Newell, rhapsodized on the virtues of rare-earth neodymium and greeted customers with phrases like, “Are you here to get lit?” Just below an apartment occupied in the film by Ms. Strayed’s ex-husband, Paul (Thomas Sadoski), sits a barbershop called the Modern Man, where I sipped Burnside bourbon and got a straight razor shave from a guy named Chachi.

I said goodbye to Ms. Burnett and wandered a few doors down from Interurban to Mississippi Studios, a music venue used in the film for when Ms. Strayed arrives in Ashland, Ore., and meets a handsome guy named Jonathan (Michiel Huisman), who invites her to a Jerry Garcia tribute soon after the death of the Grateful Dead musician. The night I visited, tickets were all sold out for Asgeir, an Icelandic singer-songwriter, so instead I stood near the bar, which affords a perfect view of the stage anyway, drank black ales and listened to the melodic folk music.

Originally I’d hoped to stay at the Hotel deLuxe, one of the city’s finest hotels, used for a quick scene when Ms. Witherspoon’s character picks up a guy in a bar, the Driftwood Room, just off the main lobby. It was booked solid, so I ate a plate of charcuterie six seats down from where the actress sat, and did a 180 for the Courtesy Inn, a dive off Northeast Sandy Boulevard that doubles in the film as a hotel in both Ashland and the Mojave. It was exactly the kind of place you’d stay if you were a poor hiker living off $20 a month 20 years ago. Two of the lamps in my room had no bulbs. The third had a shade that looked as if it had been through a blender. I paid a $5 deposit to get a TV remote.

But as disgusting as this place felt, I liked it. I am who I am thanks to the times I had no money but hit the trail anyway. When I was Ms. Strayed’s age at the time of her hike, I could dance all night in Cuzco with three soles in my pocket. I lived for months on the floor of an unfurnished apartment in La Paz, Bolivia, for $1.25 a day. Six hundred dollars got me 59 days of snorkeling and sun in the Philippines. There will always be a reason you can’t travel but rarely is money one of them, at least not at 26.

On my way back to Bend I took a detour and headed down some winding country lanes to 170-acre Eagle Fern Park, where the movie’s climax unfolds. The rain had started again, but I parked under a massive cedar tree, bundled up and took a short hike.

There wasn’t much of a trail, just a gravel road with some picnic tables under big trees dripping with old man’s beard. But at the far end of the park I found a gap in a white fence and a trail leading beyond it into a small clearing. I couldn’t be sure, but it looked like the spot where Ms. Witherspoon’s character collapses on her knees, sobs and begins to accept herself, her past and her pain. “It was my life — like all lives, mysterious and irrevocable and sacred,” Ms. Witherspoon says in a voice-over, borrowing directly from the book. “So very close, so very present, so very belonging to me.”

I found a log and sat down next to a large fern. The wood was soft and wet and so rotten that new, bright green plants had already taken root in its innards. A small creek tumbled by, but this time I didn’t fish for what I might find. Instead I pointed the car south to what I already had.