36 Hours in Oregon City

The country’s only vertical street, the Oregon Trail’s terminus and excellent beer

By Michelle Harris July 7, 2022

Kayakers in front of Willamette Falls

Just 13 miles south of Portland, it’s easy to overlook Oregon City as a destination. But let’s put some respect on its name; Clackamas County’s government seat is plenty worth the drive. 

Our first state capital and the first incorporated city west of the Rocky Mountains, Oregon City was the final stop for pioneers traveling the Oregon Trail. But before being overtaken by Euro-American settlers, the area was a hub for fishing and trading among Native Americans and a home to the Clowwewalla, Cashooks, and Molalla tribes.  

It’s also where Portland got its birthname off the back of an alleged coin toss between Asa Lovejoy and Francis Pettygrove. According to legend, the two men were attending a dinner party at Ermatinger House in Oregon City and couldn’t agree on a name — Lovejoy wanted Boston and Pettygrove wanted Portland. Needless to say, this squabble resulted in the famous penny flip (and we all know how that ended).  

History aside, you can easily while a day away by exploring Oregon City’s parks, dining spots, shops, and museums — the town also boasts a brewery named after the mighty coin toss.   

Where to Play 

For those of you who grew up playing the Oregon Trail computer game, a visit to the End of the Oregon Trail Interpretive Center might jog some memories (assuming you made it to the end without dying from typhoid, that is.) The Interpretive Center includes interactive exhibits and fun-for-the-whole-family history-themed activities including candle dipping and making a rag doll. The museum also offers genealogy assistance in case you want to trace your roots. 

Did you know that Oregon City is home to the country’s only vertical street? (Take that, crookedest street in the world.) The 130-foot Oregon City Municipal Elevator was constructed in 1915. Named Elevator Street, it connects downtown Oregon City with the historic McLoughlin neighborhood. Hitch a free ride up to the top and you’ll get panoramic views of the Willamette River and downtown. From the elevator you can stroll along the McLoughlin Promenade, a linear park situated above the bluff that overlooks the Willamette, a great place to score some snapshots for your next Instagram post. A little over a mile from the promenade is Canemah Bluff Nature Park, which has over a mile of trails if you’re looking to extend your walk. 

In warmer months, you can get up close and personal with Willamette Falls by taking a guided kayaking tour with eNRG Kayaking, who provide kayak and/or SUP rentals, paddles, and a lifejacket. Plopped in the middle of the river, Willamette Falls is the second largest waterfall by volume in the United States (after Niagara Falls, and a whole lot closer). The tour covers the history of the area and there’s a chance you may spot osprey and heron. 

Last but certainly not least, consider booking a ghost tour with Northwest Ghost Tours, which runs from July through December. Led by historian and paranormal investigator Rocky Smith, there are a few different two-hour walking tours to choose from, including a tour of the historic McLoughlin neighborhood, where you’ll learn the history and ghost stories behind some of the creaky old homes (where perhaps some resident haunts still reside) or you can tour downtown Oregon City, where you’ll hear all about the town’s haunted landmarks. 

Early evening on Main Street in Oregon City


Where to Eat/Drink 

Start the day off with fluffy waffles and creamy coffee lattes at The Hive Social, a cozy nook that serves seed-to-plate scratch-made bites and is also open for dinner. Alternatively, Ranee’s on Main is where to go for comfort food fare, with all day breakfast and boozy drinks to pair it with. For something simple, Singer Hill Café serves pastries and bagel sandwiches in an airy plant-filled space that also has a garden patio.  

Way closer than road-tripping to the Coast, Tony’s Smoke House has chowders, melts, and baskets, along with canned seafood sold in the market to take home. For a family-friendly outing, Mi Famiglia Wood Oven Pizza offers crispy pies as well as other Italian comforts like lasagna and calzones. Hoping to impress a date? Nebbiolo Wine Bar & Bistro is a stylish wine bar and restaurant that’s been restored since its former days when brewer Henry Weinhard ran a tavern at the location in the 1800s.  

For tasty soups and noodle dishes, Vietnamese spot Pho Thi, right along Main Street, has flavorful bowls of pho as well as a full bar. Fans of steam burgers and soft-serve at Canard will be happy to know that another outpost is opening on July 10 in Oregon City with some exclusive dishes created just for the new location. And if you’re simply indecisive, Corner 14 is a food cart pod with a full bar, fireside dining, live music, and axe throwing with Celtic Axe Throwers, which you can book ahead of time. 

But sometimes you just want to chill with a beer in hand. The town’s namesake beer spot Oregon City Brewing honors its locale with tasty craft brews such as the Elevator IPA and Pioneer Pale Ale and also has food carts on site. Not far from Oregon City Brewing is Trails End Saloon, a local roadhouse-style watering hole with kitschy frontier-themed décor (peep the full-sized wagon hanging from the ceiling). The venue puts on regular blues concerts. And don’t miss out on The Highland Stillhouse, a Scottish pub with an extensive collection of single malt Scotch whiskey and live Celtic music on Sunday evenings. 

Where to Shop 

Retro is not an understatement in Oregon City, which has enough antique shops dotted along downtown that you can spend an entire afternoon perusing. Just off Main Street is vintage toy nirvana Coin Corner and Hobbies; find everything from a Pee Wee’s Playhouse set to Trolls and Ninja Turtle figures, as well as comic books, vinyl records, and other collectibles.  

If your reading collection needs a revamp or you’re out of ideas on what to gift your quirky aunt with 10 cats, independent and family-owned bookstore White Rabbit Books & Gifts has a thoughtfully curated selection of books, as well as locally made items like artisan soaps and candles. While you’re at, grab a cup of coffee or tea from Black Ink Coffee, who shares the space.  

Find a perfect windowsill plant at Root + Stem, a women-owned and operated plant shop with everything from succulents to jumbo-sized fiddle-leaf figs. And located in mid-town Oregon City, World HeARTS Fair Trade has ethically produced items such as jewelry and clothing made by artisans from all over the world 

Where to Stay 

What’s a vacation without cool overnight digs? Spend your down time at Clackamas River House, a quaint bed and breakfast that’s just seven miles from Oregon City. You've got a choice between a rustic log cabin-themed suite, where you can warm up by the electric fireplace, or the a suite that comes equipped with a Jacuzzi, perfect for a long soak after a busy day.  

If you’ve ever dreamed of living in a houseboat, this tiny floating vacation home set along the Willamette River is just one mile south of Oregon City. The best part? You can wake up just steps away from your own private deck with river views. Canoes and kayaks are also provided (just bring your own life vest). 

If you’re hoping to crash somewhere more off the grid, book a stay at this very mod shipping container cottage set in the forest, complete with chicly minimalist furnishings and plenty of places to curl up with a good book. Or if you’re looking to unwind, this pet-friendly home is just a mile from downtown Oregon City and features a wood-barrel sauna, hot tub (which in the summer becomes a soaking pool) firepit, and a fully enclosed patio in which your fur babies can let loose. 

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