Oregon City boasts an impressive list of “firsts”: first incorporated city west of the Rocky Mountains (1844), Oregon’s first capital (before it was even a state) and the country’s first long-distance electric line (Willamette Falls to Portland, 1889).
But it’s actually Oregon City’s last place status that fascinates many modern-day visitors: Located just 15 miles southeast of Portland, alongside the Willamette River and a dramatic, tiered waterfall, Oregon City served as the final wagon stop on the fabled Oregon Trail. And today, thanks to its rich history and recent historic restoration projects, Oregon City remains as much a destination as ever.
At the north end of town, the End of the Oregon Trail Interpretive Center provides an excellent glimpse of life along the historic route. Evoking three giant wagons, the center comes loaded with interactive displays, from learning how to pack a wagon for a 2,000-mile journey to churning butter.
Tucked between the Willamette River and high-rising basalt bluffs, the compact downtown is easily explored on foot. The Caufield House, opened in 2009, has become a local hot spot for Portland Roasting coffee and fresh-baked pastries. Once you’ve fueled up, browse shops like You Can Leave Your Hat On, where you’ll find all manner of hats and other accessories.
A short stroll away, the historic Arch Bridge (Seventh Street/Highway 43) is well worth a visit. Built in 1922, the 850-foot span reopened in 2012 after an extensive two-year makeover, complete with refurbished, monumental columns, gothic-style lighting and wide sidewalks for taking in views of Willamette Falls, the Northwest’s largest by volume.
For an even more expansive vista, head up Seventh Street and board the Oregon City Municipal Elevator. Considered the only “vertical street” in the country, the space-pod-like structure rises 130 feet to an observation deck with panoramic city and river views.
From the elevator, tour the scenic McLoughlin Promenade. Constructed in 1937 as a Works Progress Administration project, the nearly eight-acre linear park overlooks downtown and Singer Falls, another WPA-constructed site that showcases rustic stonework in a series of man-made waterfalls. The adjacent McLoughlin Conservation District includes the McLoughlin House, a manor built in 1846 for Dr. John McLoughlin, the founder of Oregon City.
Nearby the Francis Ermatinger House, erected in 1845, is one of the oldest structures in Oregon. The humble, federal-style residence is steeped in local lore: In 1845 two influential businessmen, Asa Lovejoy and Francis Pettygrove, famously flipped a coin here to decide the name of Portland. (“Boston” was the other choice.)
Returning to the promenade, stroll west, toward the falls, to delve deeper into the past at the Museum of the Oregon Territory, home to an extensive collection of Native American artifacts.
Nearby, the Highland Stillhouse Scottish Pub makes an ideal spot to toast the day. One of the best Scottish-themed bars around, it’s also an homage to yet another one of Oregon City’s firsts: The town claimed the territory’s first moonshine still. Today the Stillhouse boasts the Portland area’s most extensive single-malt selection and an authentic feel, right down to the woolly plaid bar seats. Order up traditional bangers and beans and Scotch eggs. Odds are your first visit won’t be your last.
The pizzas from this family restaurant’s wood-fired brick-oven come with crispy crusts and toppings like prosciutto and fig or chicken pesto and bacon.
This hidden gem plates up authentic Moroccan cuisine. Pick from lamb shanks, oxtail or Cornish hens flavored with an array of sweet and savory sauces.
Sandy Ridge Trail System
Opened in 2009, this purpose-built 12.5-mile (20 km) mountain bike trail system provides a nearly year-round, flowing singletrack experience in the foothills of the Cascade Range.
Take a guided tour of the second-largest waterfall by volume in the U.S. — by kayak. You’ll paddle through natural beauty as well as industry and be rewarded with spectacular views of Willamette Falls.
Dating back to the early 1900s, this two-story B&B delivers a dose of small-town charm, complete with porch swings and free popcorn in the basement movie theater.
A fairy-tale-like abode with Scandinavian-inspired wood interiors filled with vaulted ceilings, vintage claw-foot tubs and no television.