Situated just 13 miles south of Portland, Oregon City sits in the shadow of our beer-loving, weirdo-ridden metropolis. Yet Oregon City happened to play a key role in the establishment of Oregon and, ultimately, Portland's existence as we know it.
Our state's first capital, as well as the first incorporated city west of the Rockies, Oregon City quickly rose as an industrial hot spot after the so-called "Father of Oregon," John McLoughlin, helped pave the way for permanent settlement in Oregon. Oregon City was also the final destination for pioneers traveling the Oregon Trail—an event that has seemingly inspired an entire city motif, where seemingly every other business has the word "pioneer" in its name.
But there's a lot more to this town than just its heritage and historic landmarks. Oregon City has become a cultural hub, with craft brews, an epic waterfall, quality grub, heritage museums, copious amounts of whiskey and perhaps some resident ghosts.
Before heading to Oregon City, it's recommended you pack a comfortable pair of shoes, especially if you're planning to do any of the walking tours. Expect rainier weather during the fall, winter and spring, so bring a good rain jacket. Be sure to download the Heritage Trail app, which provides information about more than 25 heritage sites in Oregon's Mount Hood Territory, including some in Oregon City, such as the McLoughlin House.
IDEAL VISITING TIME
June through October would be the ideal time to visit as the weather will be clearer.
Grab some 'za
You can never go wrong with pizza, and Mi Famiglia Wood Oven Pizzeria (701 Main St., 503-594-0601, mi-famiglia.com) is your best option in town. Think family-style pizzeria but without the red-checkered tablecloths. Rather, the brick-face interior and soft lighting offer more of a cozy Italian bistro vibe, and the wood oven is conveniently set right next to the bar so you can see all the pizza-making happen. In addition to pizza, there are also calzones and lasagna, and a decent beer and wine selection to wash everything down. Save some room for the walnut pie with ice cream because it's probably one of the best desserts you'll ever have.
For a city with such rich history, it's no surprise that Oregon City is home to some hauntings, what with all the creaky old houses and such. Northwest Ghost Tours (503-679-4464, nwghosttours.com) is where you'll learn about the spirits who allegedly still lurk around town—such as John McLoughlin himself. The two-hour walking tour begins at the Oregon City Elevator, and takes you through the city's historic downtown to the Clackamas County Courthouse, the Tunnel and the Old 8th Street Dock, to name a few. This year's Walk With the Spirits tours run from July 13—which just so happens to fall on a Friday—through Halloween. For other tours that run year round, check out Walk Oregon City (503-679-4464, walkoregoncity.com), which includes historic and film tours.
Get the blues
Trail's End Saloon (1320 Main St., 503-656-3031, trailsendsaloon.net) has an old roadhouse atmosphere, with frontier paraphernalia like wagon wheels, saddles, antlers and even a full-on wagon hanging from the ceiling, and the vintage chandeliers give an eerie glow to the otherwise dim bar. The place fills up, so it's likely you'll be having beers with the regulars—and those beers will probably turn into shots later in the night. In addition to being a great community hangout, the venue has won several awards from the Cascade Blues Association, so you're bound to catch some something great when you go there.
Wake and booze
Fuel up with a homestyle breakfast at Yvonne's (818 Main St., 971-322-6613, yvonnes-restaurant.com), a warm and fuzzy brunch spot where the aroma of freshly brewed coffee seems to always linger in the air. Everything is made from scratch, and there are even gluten-free options, as well as a vegan tofu scramble. Most importantly, the place serves several flavors of mimosa. The restaurant is also open for lunch, with a small selection of salads and sandwiches.
Up your pioneer knowledge
Did you play The Oregon Trail computer game as a kid? If you didn't die of typhoid or cholera, among other diseases, you would have made it to Oregon City, where the trail officially ends. The End of the Oregon Trail Interpretive Center (1726 Washington St., 503-657-9336, historicoregoncity.org) teaches you all about the real Oregon Trail, only there are interactive exhibits and candle dipping, which means it's probably a lot more fun than when you learned about it in school. In case you're curious about your roots, the museum also offers genealogy assistance for descendents of pioneers. For even more history about Oregon, visit the Museum of the Oregon Territory (211 Tumwater Drive, 503-655-5574, clackamashistory.org), which also has some cool exhibits like an interactive topographical map.
Enjoy a coastal lunch without the drive
Family owned since 1936, Tony's Fish Market (1316 Washington St., 503-655-2488, tonyssmokehouse.com) is a classic lunch spot in Oregon City, with chowders, melts and fish baskets. These days, everything is prepared in an Enviro-Pak smokehouse, although the traditional, smoky woodhouse taste is still there. The old-fashioned market, with its glass counter and shelves lined with canned goods, looks like somewhere your grandparents would have gone back in the day when folks went to speciality shops instead of supermarkets. There's also a small patio outside for dining on warmer days. Don't like smoked fish? Head to Ingrid's Scandinavian Food (209 7th St., 503-744-0457) for lefse wraps and elk sliders.
Take a walk up the street, literally
Oregon City operates one of only four municipal elevators in the world—that is, elevators run entirely by a city or governing body. The Oregon City Municipal Elevator (6 Railroad Ave., 503-594-0521, orcity.org/publicworks/municipal-elevator) is officially named Elevator Street and is the only "vertical street" in the country. Originally constructed in 1915 to ease travel to the upper levels of Oregon City, the elevator connects the city's downtown to the historic McLoughlin neighborhood. You can ride for free to the top of the 130-foot elevator and find yourself enclosed in a flying saucer-like observation deck where you can take in some views of downtown and the Willamette River. It also gives you access to the McLoughlin Promenade, where you can take a free guided tour of the McLoughlin House (713 Center St., 503-656-5146, mcloughlinhouse.org), a colonial-style home with antique furnishings, Victorian-style wallpaper and creaky floors.
Kayak to Oregon's Niagara
Sure, Willamette Falls may look a bit strange plopped in the middle of the river, but it's the second-largest waterfall in the U.S. by volume after Niagara. If you dare venture the waters of the Willamette River, take a tour with eNRG Kayaking (1701 Clackamette Drive, 503-722-1122, enrgkayaking.com), which offers kayaking and standup paddleboarding. The tour covers the history of the area and the Willamette Falls, and you may even see some Native American petroglyphs at the base of the falls. All skill levels are welcome on the tour.
Cool down with a beer
Situated on a busy street corner, Oregon City Brewing Company (1401 Washington St., 503-908-1948, ocbeerco.com) looks like a postcard from Portland with its parking lot patio and boxy structure. The brewery opened in 2014, and offers a solid line of craft beers made in-house, including the flagship Elevator IPA, named after the city's iconic municipal elevator. But the motto here is "Beer for Pioneers"—it's painted in huge lettering across the brewery's back wall—and the Pioneer Pale Ale is subtle enough to offer you a taste of what the pioneers probably drank. OP Wurst also has an outpost here, with its signature classic and creative wursts, but don't spoil your appetite.
Eat tapas in a historic beer bar
Set in the very place where early brewer Henry Weinhard ran his tavern in the 1800s, Nebbiolo Wine Bar & Bistro (800 Main St., 503-344-6090, nebbiolowinebar.com) is now a stylish wine bar and restaurant, but there's still a selection of beer for good measure. After they bought the space in 2012, owners Joe and Yvette Kirwin stripped the walls and carpet only to find original hardwood floors and brick walls, which are now restored to share a bit of the building's history. Come here for a gourmet dining experience and indulge in fine wine with cured meats and imported cheese tapas plates before diving into dinner, where entrees range from mushroom ravioli to roast beef marinated in red wine.
Drink like a Scot
A trip to Oregon City isn't complete without a visit to the Highland Stillhouse (201 S 2nd St., 503-723-6789, highlandstillhouse.com). The well-stocked bar appeases any booze hound, but most come here for the substantial selection of single-malt scotch. If whiskey isn't your thing, no worries—there are also around 60 varieties of Scottish ale and beer taps featuring U.K. brews. The interior has an Old World charm, with dark green walls, well-worn wooden booths and Scottish knickknacks that were probably imported from the motherland. Perched above Willamette Falls, you can enjoy some views on the outdoor patio with whiskey in hand. At some point, you may forget you're not actually in Scotland.
Go bar hopping
While there isn't a ton of late-night bars here, there are enough to keep you out past 2 am. IceHouse Oregon City (1200 Main St., 503-655-6299) is just the kind of divey joint you're looking for to extend your night. Besides the obligatory lottery machines, the bar also has a game room with pool tables, basketball, pinball, darts and golf. There's also some decent bar grub if you need a second dinner. For a less divey experience, head to Midway Historic Public House (1003 7th St., 503-656-9501, midwayhistoricpublichouse.com), where the vibe is more "neighborhood pub." The roomy bar has 11 pool tables along with plenty of seating and a full food menu with burgers, sandwiches, steaks and pasta.
Get breakfast at an art-filled cafe
If there's a cafe in town perfect for lingering away the morning, this is it. The family-owned Singer Hill Cafe (623 7th St., 503-656-5252, singerhill.com) not only serves breakfast stuff like bagel sandwiches, quiche and pastries, you can also get your caffeine fix thanks to the full coffee bar, which you'll probably need after last night's bar prowl. Vertical gardens dot the interior space and outdoor patio, and you'll definitely want to check out the art gallery operated by Three Rivers Artist Guild.
Buy a stuffed Garfield
Downtown Oregon City has some quirky shops, and they're worth a visit before leaving. Coin Corner and Hobbies (215 7th St., 503-656-1835, facebook.com/coincornerpdx) has an entire collection of your favorite childhood toys, such as Hot Wheels and even an entire bin of stuffed Garfield dolls, as well as old movie posters and video games. Even if you don't end up buying anything, the place is worthy of a browse. Christmas at the Zoo (524 Main St., 503-223-4048, christmasatthezoo.com) is where you go if you want to stock up on odd tree ornaments whose themes range from Halloween to the Fourth of July.
Get buzzed and learn something
Oregon City is where Asa Lovejoy and Francis Pettygrove supposedly tossed a coin to determine the name of Portland, so it's only right that Oregon City has a brewery to commemorate this event. On your way out of town, be sure to make a stop at Coin Toss Brewing Company (14214 Fir St., Suite H, 503-305-6220, cointossbrewing.com). Burrowed inside a lackluster industrial park about 5 miles from downtown Oregon City, it's one of the city's newer breweries. The taproom has a plaque detailing the history of the Portland penny, and the room is adorned with earthy copper tones. The vibe here is overwhelmingly friendly—you'll probably hear a fellow barfly's life story before you're even halfway into your first beer. Speaking of which, the craft beers are great, too, so you might as well order a flight and try them all. Try the flagship brew Black Hohl, a dark and hoppy beer with some malts peppered in for a subtle sweetness.
WHERE TO STAY
Clackamette RV Park
About a mile from downtown Oregon City, Clackamette RV Park (1955 Clackamette Drive, 503-496-1201, orcity.org/parks/clackamette-rv-park) resides at the confluence of the Clackamas and Willamette rivers and will run you $25 to $30 a night. The park accommodates up to 40 RVs, and water and electricity hookups are available. However, the park itself has enough amenities to keep you occupied in case you're just looking for some outdoor time, including a boat launch, horseshoe pit, beach access to the rivers, and a skatepark.
Bed and Breakfast:
Clackamas River House
If you prefer the serenade of frogs over the sound of street traffic, consider the cozy Clackamas River House (178850 S Clackamas River Drive, 503-502-8478, clackamasriverhouse.com), located about 7 miles from downtown Oregon City. Run by Marc and Beverly De La Bruere, the two-story home is within arm's reach of a peaceful wooded area sprawled right in back of the house. Only two rooms are available, so you'll be staying in either the rustic Log Cabin Room, a pine-paneled room with fireplace, or the Oregon Room, a glorified honeymoon suite with ruffled bedding, flowers and a Jacuzzi. The cost for either is $90 a night. Breakfast is served in the dining room, or the patio on nicer days. As for perks, you'll have views of the Clackamas River from your guest room, and the backyard has a small pond, gazebo and fire pit.
Portland Oregon Vacation Rental
Located right on the Willamette River in Oregon City, these three floating homes offer something for everyone. The three-bedroom Main House (903 S McLoughlin Blvd., 503-656-3132, floatinghomevacations.com), which looks like a miniature version of a Barbie Dreamhouse painted white instead of pink, is best suited for large groups or families, while the Bungalow House, which has two bedrooms, is better for those who enjoy more rustic, wood-paneled accommodations. And then, for parties of one or two, there's the Minnow, a little cabin that resembles a tiny home. Sure, staying at one of these might put a hole in your wallet. But just imagine sipping that morning coffee while taking in views of the Willamette River and surrounding mountains. Like to fish or water ski? You can do it right from your deck. Each floating home ranges from $150 to $400 a night, plus a cleaning fee. So if you have the money to spend, it really can't get much better than this.