McMenamins Kennedy School
Hidden in a charming Northeast Portland neighborhood, the Kennedy School is a historic elementary school converted into a funky hotel, movie theater, restaurant, and pub. The school first opened its doors in 1915 and educated local children for over 75 years before closing in 1975. Developer Mike McMenamin transformed the vacant building in 1997, keeping intact many original details like chalkboards, wooden lockers, and mosaic tiled hallways. Today, guests can spend the night in one of 57 guestrooms fashioned from former classrooms, complete with original classroom artifacts. Three bars serve beer brewed on-site, including the Detention Pub in the old principal’s office. Watch a current movie release in the boiler room-turned theater, play pool in the gymnasium, or grab a burger and beer in the courtyard cafeteria. With its whimsical repurposing of a historic neighborhood school, the Kennedy School offers visitors a truly Portland experience.
Address: 5736 NE 33rd Ave, Portland, OR 97211
Phone: (503) 249-3983
Oaks Amusement Park
Located along the scenic Willamette River waterfront and established in 1905, Oaks Amusement Park provides old-fashioned thrills just minutes from downtown Portland. The park boasts classic rides like the wooden Rollercoaster, the craziest bumper cars you’ve ever driven, a 19th century hand-carved carousel, and carnival games of skill. Bring a picnic lunch to enjoy in the shaded picnic groves and don’t miss the park’s famous dance hall. You can also rent pedal boats for a spin around the river or grab some saltwater taffy as a sweet souvenir. Thanks to its vintage rides, picnic grounds, and riverfront location, Oaks Amusement Park has remained a favorite local haunt for over a century.
Address: 7805 SE Oaks Park Way, Portland, OR 97202
Phone: (503) 233-5777
House Spirits Distillery
Portland has long been obsessed with crafting the perfect artisanal cocktail, and House Spirits Distillery played a key role in starting the city’s cocktail craze. Opening in 2004 as Oregon’s first distillery since Prohibition, House Spirits Distillery makes small batches of whiskey, gin, vodka, and liqueurs from locally sourced ingredients. On an immersive distillery tour, you’ll learn all about their award-winning Westward Whiskey and see the distilling process from start to finish. The tour ends with a complimentary tasting of House Spirits’ liquors and cocktails, so you can sip like a true Portlander. For an intimate experience with Portland’s craft distilling scene, don’t miss this hidden gem.
Address: 65 SE Washington St, Portland, OR 97214
Phone: (503) 235-3174
Covering over 5,000 acres, Forest Park is a nature lover’s paradise hiding within Portland’s city limits. Wind your way through nearly 80 miles of wooded trails, keeping your eyes peeled for local wildlife like owls, coyotes, and deer. The Wildwood Trail, the park’s most popular hiking path, meanders 30 miles through Forest Park into Washington Park at the zoo. Bring your dog to roam in the dedicated off-leash area or enjoy a picnic by candlelight at the Stone House event space. For gorgeous Pacific Northwest views without driving hours into the mountains, explore Portland’s beloved Forest Park and its old-growth evergreens towering just above downtown.
Address: NW 29th Ave & Upshur St, Portland, OR 97210
Phone: (503) 823-PLAY
Portland City Grill
While locals love happy hour on the Portland City Grill’s 30th-floor outdoor terrace, the restaurant hides in plain sight on the roof of the city’s second tallest skyscraper. Take an elevator ride up to the top of the US Bancorp Tower, known as Big Pink, for unparalleled views of Portland’s cityscape, bridges, rivers, and mountains. The eclectic Pacific Northwest menu features dishes like cedar plank salmon, Oregon truffle fries, and huckleberry ice cream. With its sky-high vistas and innovative regional cuisine, the Portland City Grill offers visitors a memorable fine dining experience above the Rose City. Don’t forget your camera for panoramic sunset photos!
Address: 111 SW 5th Ave, Portland, OR 97204
Phone: (503) 450-0030
Built in 1914 as a private estate for The Oregonian publisher Henry Pittock, this grand château sits 1,000 feet above downtown with sweeping views over Portland. The 46-room French Renaissance-style mansion features original furnishings, art, and decor. Take a guided tour to see the extensive secret passages, hand-painted Chinoiserie ceiling in the dining room, and Oregon history exhibits. The surrounding grounds provide miles of trails through forested parkland. Pack a picnic or dine at the on-site cafe and witness the Pittock Mansion’s spectacular sunsets over the West Hills. For a glimpse into Portland’s past paired with breathtaking vistas, make your way to this hilltop hidden gem.
Address: 3229 NW Pittock Dr, Portland, OR 97210
Phone: (503) 823-3623
Beneath Portland’s streets lies a network of underground tunnels shrouded in mystery. Starting in the 1850s, an extensive series of basement passages connected the city’s hotels, bars, and brothels to Portland’s bustling port. Local lore says the tunnels enabled a notorious practice called “shanghaiing,” where drunken men were kidnapped through basement trapdoors and forced to work aboard ships. Today, you can take educational Underground Portland walking tours to explore this dark chapter of the city’s history. Tours take you inside passages under hotels and bars as guides shed light on Prohibition and Portland’s underground criminal past. For an intriguing look at Portland’s legendary tunnels, don’t miss these eerie underground walks.
Address: Meet at Doc’s @745 NW Johnson St, Portland, OR 97209
Phone: (503) 490-6882
Columbia River Maritime Museum
Located along the Columbia River in the small town of Astoria, this hidden gem museum memorializes the region’s deep ties to maritime trade and fishing. Exhibits spotlight the history of vessels that navigated from the Columbia River to the Pacific, like piloting ships, steamboats, and World War II liberty ships. Kids can climb aboard a retired Coast Guard rescue boat or watch a blacksmith demonstration at the working boatshop. Afterward, head up the 164-foot Astoria Column tower for panoramic views of the river, Coast Range, and Pacific Ocean. Whether you’re already an old salt or simply intrigued by maritime culture, don’t miss this authentic slice of Oregon’s nautical history.
Address: 1792 Marine Dr, Astoria, OR 97103
Phone: (503) 325-2323
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