Road Trip: Classic Portland

October 2, 2015 (Updated March 13, 2017)

Portland is full of the new and shiny: There’s a brand new bridge spanning the Willamette River, fabulous breweries like Culmination Brewing popping up every day and award-winning chefs pulling down national awards left and right. But before this town was quirky and trendy, it was the City of Roses, so named for its elegant attachment to gardening in the 19th century. Take this tour of classic Portland to see how the old still shines brightly.

Start with lunch at Fuller’s Coffee Shop, the only remaining old school lunch counter in the downtown core. First opened in 1941, Fuller’s has been operating in its NW 9th Avenue location since 1960. Try the chicken-fried steak, massive club sandwich or enormous breakfast plate (served all day) of omelet, sausage and hash browns. Some people can’t resist the creamy and generous milkshake, no matter the time of day. (Cash only.)


Walk two blocks to Powell’s City of Books for a mandatory browsing session in the largest independent bookstore in the country, family-owned and operated since 1971. Even if you don’t make it past the southeast entrance with its wall of new releases and sale books or the northwest entrance with a vast array of cookbooks and gift items, you won’t leave empty handed. Fiction, nonfiction, kid’s books, travel and mystery — it’s all here.

Take an afternoon stroll through the Pearl District, Old Town and downtown neighborhoods. Head west from Powell’s to Everyday Music and browse a huge selection of new and used vinyl, CDs and DVDs. Then proceed east and north to walk the tree-lined North Park Blocks between Burnside and Glisan streets. Back on Burnside at NW 4th Avenue, check out the massive decorative gate marking the entrance to China Town. Continue south on NW 6th Avenue through the downtown shopping district to Pioneer Courthouse Square (aka Portland’s living room). The South Park Blocks commence just south of here for more urban greenery amid classic buildings.

Cocktails at Portland City Grill start off your classic date night. Located on the 30th floor of the U.S. Bancorp Tower (known as “Big Pink”), this elegant restaurant serves up juicy steaks, seafood and fusion-inspired appetizers. And those stunning nearly panoramic views of Portland and the Willamette River go really well with the grill’s bargain happy hour deals.

Enjoy dinner at nearby Higgins Restaurant and Bar — one of the first to start the farm-to-table dining movement in 1994. Chef Greg Higgins creates a vibrant seasonal menu featuring the finest products from Oregon’s fishermen, farmers and foragers.

Take in a show at the elegant Arlene Schnitzer Concert Hall  (fondly known as “The Schnitz”) with its brightly lit 65-foot Portland sign crowning the neighborhood. First raising the curtain in 1928, the theater hosts live jazz, pop and folk music as well as the Portland Literary Arts and Lecture series and other events. For more live music, look at the latest lineups at the Crystal Ballroom and Roseland Theater.

Enjoy a nightcap at Huber’s Cafe, Portland’s longest-operating restaurant (since 1879) with possibly the best and most dramatic tableside Spanish coffee anywhere. Huber’s is also famous for its full turkey and ham dinners, served with all the fixings.

Turn in at The Heathman Hotel, named one of the “World’s Best Places to Stay” by Condé Nast Traveler, offering elegant stylish service to Portland visitors since 1927. And you’ll fall asleep knowing that you’ve got much more of old Portland to explore.

About The

Eileen Garvin
Eileen Garvin lives and writes in Hood River. When she’s not hunched over her keyboard or digging in the garden, you can find her mountain biking, kiteboarding, hiking, skiing or camping somewhere in Oregon.