This long, rectangular slice of inner Southeast that stretches from the Willamette River all the way to SE 50th Avenue takes in the quintessential starter Portland neighborhoods. Tourists making their first foray to the city often wash up on lovably scruffy Hawthorne Boulevard, and the side streets teem with apartments for renters looking for a toehold in the city. Plenty of people love it so much they never leave, so when a house does go up for sale there’s some serious competition: prices in Buckman jumped 15 percent between 2018 and 2019, while Sunnyside showed off 12 percent gains, even while prices in surrounding neighborhoods dipped. 

Wander over to the historic Lone Fir Cemetery, the largest patch of greenspace in the two neighborhoods, for some historical reconnaissance. Not only is this the final resting place for many pioneering women’s suffragists and city founders, it’s also home to some of Portland’s grandest trees, without the crowds at the arboretum across town in Washington Park. Keep a sharp eye out for a 100-foot incense cedar, and the cemetery’s namesake Douglas fir. If it’s raining, tour the fun-size Pacific Northwestiana on the nine-hole indoor mini-golf course at the Birdie Time Pub, including a replica of the Fremont Bridge and an intricately carved Sasquatch. 

Just up the road is Movie Madness, a cult video store that was brought under the umbrella of the nonprofit Hollywood Theatre a few years ago with help from a Kickstarter backed by plenty of neighbors. Rent a movie there today, and you’ll often find it’s tagged with the name of a donor. The Hollywood has opened the Movie Madness Miniplex in the back, with a rotating screening-room series that includes cartoons every Saturday morning at 11 a.m. 

The neighborhood has more than its share of great little shops—check out Starflower, on Hawthorne Boulevard, run by a Sunnyside K-8 mom whose flower arrangements approach architectural sculpture standards. Nearby Farmhouse Kitchen, the PDX branch of a hit San Francisco Thai food temple, offers a delightful patio and unfussy platters served family-style. 

Farther down toward the northern fringes of Buckman, the neighborhood transforms when the sun goes down into a chiller alternative to the constant street party across the river in Old Town. A string of iconic bars, dives and otherwise, line lower Burnside—try the live music at the dimly lit RonToms or get sweaty dancing at the Bossanova Ballroom.