Lovable, occasionally scruffy Woodstock—peep those unpaved side streets—is one of Portland’s up-and-coming neighborhoods, with most of the action happening along SE Woodstock Boulevard between César E. Chávez Boulevard and SE 60th Avenue. Home prices in the area have risen in recent years, but they remain affordable compared to homes in closer-in enclaves. 

The vibe is family-friendly, not cutting-edge trendy, in keeping with the surrounding homes at more affordable price points. Locals start their mornings at Papaccino’s Coffee and Cereal Bar or linger over the Run for the Hills breakfast sandwich at Toast. For lunch, there are many options nearby, including Otto’s Sausage Kitchen, which features an outdoor barbecue that has been serving German sausage since 1929. 

The bucolic Reed College campus is an annex of the hood—hikers and joggers flock to a 28-acre canyon that bisects the campus, which includes the headwaters of Crystal Springs Creek and Reed Lake. Or go fly a kite at the expansive Woodstock Park, often packed with neighborhood families and their four-legged friends. 

Red Fox Vintage on Woodstock Boulevard offers a large selection of clothing, furniture, art, jewelry, records and other nostalgic oddities from Portland’s top vintage vendors. At Piccolina, you can thrift shop for your little one. This secondhand store offers high-quality, gently-used children’s clothing, shoes, toys and accessories. 

Dinner time in Woodstock is as much about the brews as the food. At Double Mountain Taproom, you can enjoy a wide variety of beers on tap with pizza for the family to share. Looking to watch a Timbers game? Head to Proper Pint Taproom where the pints and sports fans are aplenty. Although Proper Pint doesn’t have a kitchen, they have a magical red phone on the wall with a direct line to Bridge City Pizza. A lesser-known drinking spot for locals is the Treetop Bar and Lounge at the local New Seasons Market on Woodstock Boulevard. This rooftop bar includes a kid’s play area, fire pits, cider and beer on tap, and a growler-filling station. 

For those in the area looking to indulge, Bergerac is an intimate French bistro serving authentic cuisine from across the pond. Other ways to indulge? Ice cream! Cloud City Ice Cream is a sleeper candidate for the city’s best scoops.