11 Retro Oregon Restaurants Still Serving Like It’s The ’60s
The world spins, trends blaze brightly then fizzle, and yet… some culinary bastions refuse to budge. While kale and quinoa dominate your feed, imagine a place where the biggest debate is whether to have gravy with your fries or fries with your gravy.
In Oregon, a delicious defiance has been simmering since the Age of Aquarius, stubbornly ignoring the passage of time, the rise of fusion cuisine, and the very concept of “new.” We’ve scoured the state, not for relics, but for living monuments to classic comfort food.
Prepare to step back in time, where the milkshakes are thick, the coffee is bottomless, and the ’60s are always on the menu.
1. Skyline Restaurant: Portland’s Neon-Lit Time Machine
Walking into Skyline Restaurant feels like stepping through a portal to 1935. The neon glow bathes everything in a warm, nostalgic light while the sizzle of burgers on the grill provides the soundtrack to your meal.
Families have been sliding into these same booths for generations, ordering thick milkshakes that require both a straw and spoon. The menu hasn’t changed much over the decades – why mess with perfection?
Regular customers often share stories of first dates had here in the ’60s, now returning with grandchildren who order the same classic burger basket their grandparents once enjoyed.
2. The Original Pancake House: Breakfast Traditions Since 1953
Morning sunshine streams through cottage-style windows at The Original Pancake House in Southwest Portland. The family recipes haven’t changed since Eisenhower was president – pancakes still rise to cloud-like perfection using techniques passed down through generations.
Servers know regular customers by name and often remember their usual orders. The wood-paneled walls and old-fashioned decor create an atmosphere that feels wonderfully stuck in time.
Apple pancake, a golden monument to breakfast craftsmanship, emerges from the kitchen puffed and glorious, just as it has for nearly seven decades. The scent alone is worth the often lengthy weekend wait.
3. RingSide Steakhouse: Portland’s Temple Of Old-School Dining
RingSide Steakhouse embodies sophisticated dining as it existed in 1944. Dimly lit by table lamps, the intimate booths have hosted countless anniversary celebrations, business deals, and special occasions for Portlanders seeking classic elegance.
I still remember my grandfather taking me here for my 16th birthday. He pointed out that the onion rings were made using the same recipe he’d enjoyed as a young man. That night taught me what fine dining meant in an era before fusion cuisine and small plates.
Tuxedoed servers still prepare Caesar salads tableside with practiced flourishes. The aged steaks arrive with the same ceremony they did when Frank Sinatra topped the charts.
4. Goose Hollow Inn: Bud Clark’s Time-Preserved Tavern
Political history and pub culture blend perfectly at Goose Hollow Inn. Former Portland Mayor Bud Clark opened this neighborhood tavern in 1967, and little has changed since those days when conversation and community building happened over pints and sandwiches.
The walls remain adorned with vintage posters and memorabilia that tell Portland’s story. Their legendary Reuben sandwich – perfectly grilled rye bread stuffed with corned beef, sauerkraut, and Swiss cheese – continues to draw crowds seeking authentic tavern fare.
The wooden booths have absorbed decades of laughter and debate. Regulars say the place feels like a living museum to Portland’s quirky political past while serving comfort food that defies changing culinary trends.
5. Leaky Roof Gastropub: From 1940s Food Cart To Timeless Haunt
Leaky Roof’s journey from humble food cart to beloved Goose Hollow institution spans over 75 years. The brick-and-wood interior preserves the mid-century charm that made it a neighborhood cornerstone in 1947.
Original wooden beams stretch across the ceiling while the worn bar counter tells stories of thousands of meals shared. The pub grub remains delightfully unchanged – hearty burgers, golden fries, and comforting classics served without pretension.
My father used to bring me here after Little League games in the ’80s, and he’d point out how nothing had changed since his own childhood visits. Today’s customers appreciate that same consistency, knowing they’re experiencing a genuine slice of old Portland.
6. Huber’s Café: Portland’s Oldest Restaurant Frozen In Time
Stepping through Huber’s doors means entering a portal to 1879. The stunning stained glass ceiling, dark wood paneling, and bow-tied servers create an atmosphere that hasn’t changed since your great-grandparents’ era.
Famous for tableside Spanish coffee preparation – complete with dramatic flames and flair – Huber’s traditions remain gloriously intact. Turkey dinners, served with all the trimmings year-round, have sustained Portlanders through two world wars, the Great Depression, and countless local changes.
The historic cash register still chimes with each transaction. Photographs of old Portland line the walls, reminding diners they’re participating in a living tradition that spans three centuries of the city’s history.
7. Sayler’s Old Country Kitchen: Home Of The 72-Ounce Steak Challenge
Sayler’s red leather booths have supported hungry Portlanders since Harry Truman occupied the White House. Founded in 1946, this family-owned steakhouse maintains its mid-century charm with wood-paneled walls and vintage decor that transport diners to simpler times.
The famous 72-ounce steak challenge has remained unchanged for decades – finish the massive porterhouse plus all the sides within an hour, and it’s free. Black-and-white photos of successful challengers line the walls, creating a hall of fame spanning generations.
Servers still deliver relish trays before meals, a dining tradition largely forgotten elsewhere. The massive portions and no-frills approach to quality steaks reflect values from an era before small plates and deconstructed cuisine.
8. Nite Hawk Cafe & Lounge: North Portland’s Roadhouse Since The 1930s
Nite Hawk’s neon sign has guided hungry travelers to this North Portland landmark since the Great Depression. The checkerboard floor, chrome-edged tables, and swiveling counter stools remain perfectly preserved from decades past.
Truckers, night shift workers, and early risers have relied on their 24-hour breakfast service for generations. The massive pancakes, served on the same heavy ceramic plates they’ve used for decades, arrive at the table with a nostalgic aroma that instantly triggers childhood memories.
I once met a 90-year-old woman who told me she’d been eating the same Denver omelet here since 1955. “They haven’t changed a thing,” she said with satisfaction, “and that’s exactly how I like it.”
9. Cadillac Cafe: Breakfast With A Pink Cadillac
The fully functioning pink 1961 Cadillac parked permanently inside Cadillac Cafe serves as both decoration and dining booth. This Irvington neighborhood staple embraces 1960s kitsch with unapologetic enthusiasm – from the vintage automobile memorabilia to the retro color scheme.
Morning light filters through windows onto formica tables where plates of classic breakfast fare arrive steaming hot. Their signature Cadillac Coffee comes in mugs large enough to require two hands, just like diners served in the Kennedy era.
Families often compete for the coveted seats inside the pink Cadillac itself. Children press pretend buttons on the dash while parents enjoy benedicts and hashes prepared using recipes that haven’t changed since the cafe’s inception.
10. Dutch Mill Diner: Tillamook’s Checkerboard Floor Classic
Dairy country’s favorite retro eatery, Dutch Mill Diner in Tillamook, celebrates the golden age of American dining. The black and white checkerboard floor squeaks pleasantly underfoot as servers in classic uniforms deliver comfort food to red vinyl booths.
Chrome-trimmed milkshake machines whir constantly, transforming Tillamook’s famous local dairy into thick, frosty treats served in tall glasses with the extra in metal mixing cups. The jukebox in the corner still works, playing everything from Elvis to Buddy Holly for just a quarter.
Travelers along the Oregon coast make special detours to experience this deliberately preserved slice of Americana. The menu reads like a greatest hits collection of roadside dining – patty melts, blue plate specials, and pie that makes you close your eyes when you take the first bite.
11. Heidi’s of Gresham: Swiss-German Comfort Since 1968
Cuckoo clocks tick methodically on the wood-paneled walls of Heidi’s, a Swiss-German diner that hasn’t redecorated since the Summer of Love. The Gresham institution proudly maintains its European-inspired roadside restaurant charm through meticulously preserved decor and recipes.
Hearty schnitzel and potato pancakes arrive on the same patterned plates they’ve used since opening day. The restaurant’s multi-generational staff includes grandchildren of original employees, trained in preparing family recipes exactly as they were in 1968.
Regulars claim the restaurant’s secret lies in refusing to update or “improve” anything. The hand-written specials board, the vintage coffee machines, and even the staff uniforms remain frozen in time, creating an authentic experience increasingly rare in our chain-dominated restaurant landscape.