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Sayler’s menu
Sayler’s.
Krista Garcia/EPDX

23 Longstanding Restaurants Keeping Old Portland Alive

These restaurants are classics for good reason

by Heather Arndt Anderson, Krista Garcia, and Rebecca Roland Updated
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Sayler’s.
| Krista Garcia/EPDX
by Heather Arndt Anderson, Krista Garcia, and Rebecca Roland Updated

Portland restaurant culture runs deep. And though it's easy to get distracted by the new restaurants opening every week, it's important to remember the city has decades-old classics that have made Portland food what it is today. While many iconic spots have held on through the decades, some have been lost to time like Canton Grill, Jaciva’s, and Claudia’s. On this map, find some of Portland’s longest-running diners, cafes, steakhouses, watering holes, and other historic drinking and dining establishments worth checking out, including Huber’s Cafe, Portland’s oldest.

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Skyline Restaurant

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The ‘50s drive-in vibes at this classic Northwest Portland burger spot remain intact. Skyline first opened in 1935, and the restaurant still serves nostalgic milkshakes blended with pie, half-pounders on sesame buns, and chili cheese tots to eat sitting on the hood of your car or on the patio. It’s the ideal spot for a weekend lunch after a hike in Forest Park.

1313 NW Skyline Blvd, Portland, OR 97229
(503) 292-6727
(503) 292-6727

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The Original Pancake House

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The original Original Pancake House was born in 1953, and the family-owned business that resembles a cozy cottage has since spread its glorious, batter-built gospel worldwide. For decades, hordes of Portlanders have flocked to the Southwest Portland cafe for the giant, puffy, eggy Dutch babies baked with sauteed apples. Those looking for traditional buttermilk pancakes will find those here, as well.

8601 SW 24th Ave, Portland, OR 97219
(503) 246-9007
(503) 246-9007

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Ringside Steakhouse

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Open since 1944, this beautiful, special-occasion steakhouse, replete with fireplaces and table-side lamps, also serves onion rings that were purportedly the best James Beard ever had. It’s also hard to resist the lobster mashed potatoes. The wine cellar — only accessible by elevator and one of just two keys— holds many of the city’s oldest wines.

2165 W Burnside St, Portland, OR
(503) 223-1513
(503) 223-1513

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Goose Hollow Inn

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Bud Clark opened this pub and restaurant in 1967, going on to serve as the city’s eccentric mayor from 1985 to 1992. While Clark has passed away, the restaurant lives on, serving Reubens and pints in the Goose’s poster-lined dining room and outdoor garden. Bands will play out back during summer, and in the winter, there might not be a cozier spot for hot toddies and Irish coffees.

1927 SW Jefferson St, Portland, OR 97201
(503) 228-7010
(503) 228-7010

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Leaky Roof Gastro Pub

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The Leaky Roof started life as one of the city’s original food carts, way back in the 1940s. In 1947, it opened in its current Goose Hollow location and is still going strong as a neighborhood fixture. Diners will find the usual Irish pub food like Guinness stew and shepherd’s pie, plus weekend brunch, and what may be Portland’s largest selection of Irish Whiskey.

1538 SW Jefferson St, Portland, OR 97201
(503) 222-3745
(503) 222-3745

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Jake's Famous Crawfish

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Now owned by McCormick and Schmick’s, Jake’s has become more of a traditional seafood restaurant than a typical spot for peel-and-eat mudbugs. Open since 1892, the shop popcorn-fries its crawfish, stuffed halibut with bay shrimp and Dungeness crab, and ladles a bouillabaisse abundant with shellfish and salmon. During happy hour, Jake’s offers things like crawfish etouffee and garlic steamed mussels for under $10.

401 SW 12th Ave, Portland, OR
(503) 226-1419
(503) 226-1419

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Nite Hawk Cafe and Lounge

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Nite Hawk was built in 1931 as a place to bring in cars for an oil change and chow down on diner food while waiting. It’s since changed many hands, but ever since 1980, it’s been a proper diner serving up chicken-fried steaks and club sandwiches. Visit the Nite Hawk’s lounge for stiff drinks, diner food staples, and pool tables.

6423 N Interstate Ave, Portland, OR
(503) 285-7177
(503) 285-7177

Fuller's Coffee Shop

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Opened originally in Northeast Portland in 1947, Fuller’s Coffee Shop has been a Pearl District holdout on the same corner since 1960 (before there was even a Pearl District). A lunch counter in the true sense of the word, the diner with classic stools and weathered linoleum, serves fare like hash browns and hotcakes, as well as a noteworthy club sandwich layered with chicken salad. 

136 NW 9th Ave, Portland, OR 97209
(503) 222-5608
(503) 222-5608

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Kelly's Olympian

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Kelly’s opened its downtown Portland location in 1902, originally called the Olympian Saloon. Kelly’s remains a spot for burgers, sandwiches, and beer, but its main draw is likely its shows, which range from stand-up comedy to local hip-hop. This is another spot that’s nice to visit for the decor alone, decked out in motorcycle memorabilia and full-blown bikes.

426 SW Washington St, Portland, OR 97204
(503) 228-3669
(503) 228-3669

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Huber's Cafe

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Portland’s oldest restaurant, owned and operated by the descendants of original chef Jim Louie, has served roast turkey and mashed potatoes since 1879, but the famous Spanish coffee, prepared table-side, has only been on the menu for about four decades. Try to sit in the mahogany-filled back room that features handsome cathedral arches and stained-glass skylights.

411 SW 3rd Ave, Portland, OR
(503) 228-5686
(503) 228-5686

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Republic Cafe and Ming Lounge

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Walking into this 100-plus-year-old restaurant and bar in the heart of Chinatown feels like walking into Wong Kar-wai’s In the Mood for Love, all intimate booths and neon red glow. Little wallpapered nooks, a dining room flanked with murals, a back lounge frequented by decades-old regulars, and a hidden banquet-room-turned-venue for concerts and parties make it one of the more compelling spots to grab a no-fuss cocktail and an old-school Chinese American restaurant dish like egg foo young or chop suey. Plus, it’s open until midnight most nights.

222 NW 4th Ave, Portland, OR 97209
(503) 226-4388
(503) 226-4388

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Old Town Pizza

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Old Town Pizza has stood in Old Town Portland since the Accuardi family opened it in 1974. The menu sticks to classics like garlic knots, salad, and pizza, and the more contemporary edition: beer. However, it’s also a destination for the historic tunnels it was built over. The restaurant offers tours of the underground space, complete with a pint.

226 NW Davis St (btwn NW 2nd & 3rd), Portland, OR 97209
(503) 222-9999
(503) 222-9999

Dan & Louis Oyster Bar

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Since the early 1900s, the Wachsmuth family has run this Ankeny seafood restaurant, selling raw oysters, oyster stew, and shellfish cocktails in a space covered in family photos and antiques. The menu has grown since its early days, now encompassing po’boys, gumbo, steamed mussels, and cioppino, served alongside beers and cocktails from the restaurant’s bar.

208 SW Ankeny St, Portland, OR 97204
(503) 227-5906
(503) 227-5906

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Kay's Bar

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Portland’s storied Kay’s Bar first opened in 1934 at the intersection of SE Milwaukie Avenue and SE Bybee Boulevard. Right outside, a bright red neon Kay’s sign hangs above the front door, and green awnings decorate the exterior wall. The interior is dimly lit with red bar stools, and a wood thatched ceiling hanging above the counter. The food menu covers all the bar classics with nachos, burgers, and fries, to pair with beer, cocktails, and more on offer.

6903 Southeast Milwaukie Avenue, OR 97202
(503) 232-4447
(503) 232-4447

Nick's Famous Coney Island

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Opened in 1935, this Hawthorne dive bar happens to have some of the best chili dogs and cheese fries in town. The lived-in space looks its 80-something years, which only adds to the charm of a bar named after a 19th-century amusement park. Keep an eye out for specials, which range from double-stacked burgers to jalapeño margaritas.

3746 SE Hawthorne Blvd, Portland, OR
(503) 235-3008
(503) 235-3008

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Chin's Kitchen

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Dating back to the 1940s, Chin’s Kitchen, with its hard-to-miss neon, is one of the oldest Chinese restaurants in Portland. A few years back, the kitchen got an overhaul, and the restaurant began turning out Dongbei delicacies like handmade dumplings, steaming clay pots of Chinese sauerkraut and pork, and the summery la pi, a chilled noodle salad with a rainbow of julienned vegetables. It’s the ideal spot for a meal ahead of a movie at the nearby Hollywood Theatre.

4126 NE Broadway St, Portland, OR 97232
(503) 281-1203
(503) 281-1203

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Otto's Sausage Kitchen

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Otto’s Sausage Kitchen started out as a meat market in Woodstock in 1922, then moved into its current location in 1936. For decades the same family has been making sausages and running the retail store, which continues to sell lovely smoked sausages, wursts and kielbasa, and pastrami. Stop by for lunches of deli sandwiches and wieners grilled outside the shop through the day.

4138 SE Woodstock Blvd, Portland, OR
(503) 771-6714
(503) 771-6714

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Amalfi's Italian Restaurant

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This Northeast Portland Italian restaurant first opened in 1959, one of the first restaurants in the city to serve pizza. The restaurant still uses the same recipe for its pizza dough, topping those pies with alfredo, artichoke hearts, and everything in between. The restaurant also serves a slate of pasta dishes, red-sauce staples, and cocktails, with scoops of spumoni for dessert. Amalfi’s is open for takeout and dine-in, both indoors and outdoors — it can also be a fun spot for outdoor live music, when the weather is nice.

4703 NE Fremont St, Portland, OR 97213
(503) 284-6747
(503) 284-6747

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Clyde's Prime Rib

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Bedecked in wood paneling, chandeliers, and red banquettes, Clyde’s is the place to party like it’s 1955. Juicy, pink slices of prime rib are the historic restaurant’s calling card, but modern touches like kale salad and poke have crept onto the menu, too. Stop by for live jazz in the lounge, paired with a Scotch on the rocks, or pop by for happy hour from 3 p.m. to 6 p.m. daily.

5474 NE Sandy Blvd, Portland, OR
(503) 281-9200
(503) 281-9200

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Cameo Cafe East

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This diner, just across 82nd from the Grotto, originally opened in 1969 next to the motel of the same name, but it wasn’t until 1992, when current owner Sue Gee Lehn took over the space and began introducing Korean dishes to the menu, that it truly hit the city’s radar. The dining room, with grandma’s house vibes and countless family photos, fills most mornings, with visitors ordering pancakes and eggs alongside kimchi and bulgogi.

8111 NE Sandy Blvd, Portland, OR 97213
(503) 284-0401
(503) 284-0401

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Jim Dandy Drive-In

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This Northeast Sandy spot — sporting vinyl booths, black-and-white photos and newspaper clippings, and ’50s memorabilia — hosted illegal drag-races early in its tenure, and now remains one of the state’s oldest operating drive-ins. The restaurant attracts gearheads and locals for its 70-plus varieties of milkshake, and what former Simpsons showrunner Bill Oakley called one of the city’s best old-school cheeseburgers.

9626 NE Sandy Blvd, Portland, OR 97220
(503) 253-2126
(503) 253-2126

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Sayler's Old Country Kitchen

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Opened in the 1940s but tricked out like the 1970s, Sayler’s started out as an East County chicken shack, at a time when the neighborhood was still largely berry fields. Now it’s one of the few restaurants in town that still serves a traditional relish tray, plus 20-ounce T-bone steaks and choose-your-own cuts of prime rib. Meals finish with a scoop of ice cream.

10519 SE Stark St, Portland, OR
(503) 252-4171
(503) 252-4171
Sayler’s menu
Sayler’s.
Krista Garcia/Eater Portland

Heidi's Of Gresham

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Frequent visitors of Mt. Hood will likely recognize the Alpine-themed facade of this Gresham restaurant, off Northeast Burnside on the way to the mountain. In 1968, the late Don and Marie Eklund founded Heidi’s as a drive-in, eventually rebuilding the restaurant into a sprawling homage to Marie’s Swiss roots. Breakfasts here involve Swedish pancakes and cheese blintzes; at dinner, regulars dunk bread into fondue ahead of wienerschnitzel, cabbage rolls, or liver and onions. Stroll through the delightfully kitschy gift shop on the way out.

1230 NE Cleveland Ave, Gresham, OR 97030
(503) 667-4200
(503) 667-4200

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Skyline Restaurant

1313 NW Skyline Blvd, Portland, OR 97229

The ‘50s drive-in vibes at this classic Northwest Portland burger spot remain intact. Skyline first opened in 1935, and the restaurant still serves nostalgic milkshakes blended with pie, half-pounders on sesame buns, and chili cheese tots to eat sitting on the hood of your car or on the patio. It’s the ideal spot for a weekend lunch after a hike in Forest Park.

1313 NW Skyline Blvd, Portland, OR 97229
(503) 292-6727
(503) 292-6727

The Original Pancake House

8601 SW 24th Ave, Portland, OR 97219

The original Original Pancake House was born in 1953, and the family-owned business that resembles a cozy cottage has since spread its glorious, batter-built gospel worldwide. For decades, hordes of Portlanders have flocked to the Southwest Portland cafe for the giant, puffy, eggy Dutch babies baked with sauteed apples. Those looking for traditional buttermilk pancakes will find those here, as well.

8601 SW 24th Ave, Portland, OR 97219
(503) 246-9007
(503) 246-9007

Ringside Steakhouse

2165 W Burnside St, Portland, OR

Open since 1944, this beautiful, special-occasion steakhouse, replete with fireplaces and table-side lamps, also serves onion rings that were purportedly the best James Beard ever had. It’s also hard to resist the lobster mashed potatoes. The wine cellar — only accessible by elevator and one of just two keys— holds many of the city’s oldest wines.

2165 W Burnside St, Portland, OR
(503) 223-1513
(503) 223-1513

Goose Hollow Inn

1927 SW Jefferson St, Portland, OR 97201

Bud Clark opened this pub and restaurant in 1967, going on to serve as the city’s eccentric mayor from 1985 to 1992. While Clark has passed away, the restaurant lives on, serving Reubens and pints in the Goose’s poster-lined dining room and outdoor garden. Bands will play out back during summer, and in the winter, there might not be a cozier spot for hot toddies and Irish coffees.

1927 SW Jefferson St, Portland, OR 97201
(503) 228-7010
(503) 228-7010

Leaky Roof Gastro Pub

1538 SW Jefferson St, Portland, OR 97201

The Leaky Roof started life as one of the city’s original food carts, way back in the 1940s. In 1947, it opened in its current Goose Hollow location and is still going strong as a neighborhood fixture. Diners will find the usual Irish pub food like Guinness stew and shepherd’s pie, plus weekend brunch, and what may be Portland’s largest selection of Irish Whiskey.

1538 SW Jefferson St, Portland, OR 97201
(503) 222-3745
(503) 222-3745

Jake's Famous Crawfish

401 SW 12th Ave, Portland, OR

Now owned by McCormick and Schmick’s, Jake’s has become more of a traditional seafood restaurant than a typical spot for peel-and-eat mudbugs. Open since 1892, the shop popcorn-fries its crawfish, stuffed halibut with bay shrimp and Dungeness crab, and ladles a bouillabaisse abundant with shellfish and salmon. During happy hour, Jake’s offers things like crawfish etouffee and garlic steamed mussels for under $10.

401 SW 12th Ave, Portland, OR
(503) 226-1419
(503) 226-1419

Nite Hawk Cafe and Lounge

6423 N Interstate Ave, Portland, OR

Nite Hawk was built in 1931 as a place to bring in cars for an oil change and chow down on diner food while waiting. It’s since changed many hands, but ever since 1980, it’s been a proper diner serving up chicken-fried steaks and club sandwiches. Visit the Nite Hawk’s lounge for stiff drinks, diner food staples, and pool tables.

6423 N Interstate Ave, Portland, OR
(503) 285-7177
(503) 285-7177

Fuller's Coffee Shop

136 NW 9th Ave, Portland, OR 97209

Opened originally in Northeast Portland in 1947, Fuller’s Coffee Shop has been a Pearl District holdout on the same corner since 1960 (before there was even a Pearl District). A lunch counter in the true sense of the word, the diner with classic stools and weathered linoleum, serves fare like hash browns and hotcakes, as well as a noteworthy club sandwich layered with chicken salad. 

136 NW 9th Ave, Portland, OR 97209
(503) 222-5608
(503) 222-5608

Kelly's Olympian

426 SW Washington St, Portland, OR 97204

Kelly’s opened its downtown Portland location in 1902, originally called the Olympian Saloon. Kelly’s remains a spot for burgers, sandwiches, and beer, but its main draw is likely its shows, which range from stand-up comedy to local hip-hop. This is another spot that’s nice to visit for the decor alone, decked out in motorcycle memorabilia and full-blown bikes.

426 SW Washington St, Portland, OR 97204
(503) 228-3669
(503) 228-3669

Huber's Cafe

411 SW 3rd Ave, Portland, OR

Portland’s oldest restaurant, owned and operated by the descendants of original chef Jim Louie, has served roast turkey and mashed potatoes since 1879, but the famous Spanish coffee, prepared table-side, has only been on the menu for about four decades. Try to sit in the mahogany-filled back room that features handsome cathedral arches and stained-glass skylights.

411 SW 3rd Ave, Portland, OR
(503) 228-5686
(503) 228-5686

Republic Cafe and Ming Lounge

222 NW 4th Ave, Portland, OR 97209

Walking into this 100-plus-year-old restaurant and bar in the heart of Chinatown feels like walking into Wong Kar-wai’s In the Mood for Love, all intimate booths and neon red glow. Little wallpapered nooks, a dining room flanked with murals, a back lounge frequented by decades-old regulars, and a hidden banquet-room-turned-venue for concerts and parties make it one of the more compelling spots to grab a no-fuss cocktail and an old-school Chinese American restaurant dish like egg foo young or chop suey. Plus, it’s open until midnight most nights.

222 NW 4th Ave, Portland, OR 97209
(503) 226-4388
(503) 226-4388

Old Town Pizza

226 NW Davis St (btwn NW 2nd & 3rd), Portland, OR 97209

Old Town Pizza has stood in Old Town Portland since the Accuardi family opened it in 1974. The menu sticks to classics like garlic knots, salad, and pizza, and the more contemporary edition: beer. However, it’s also a destination for the historic tunnels it was built over. The restaurant offers tours of the underground space, complete with a pint.

226 NW Davis St (btwn NW 2nd & 3rd), Portland, OR 97209
(503) 222-9999
(503) 222-9999

Dan & Louis Oyster Bar

208 SW Ankeny St, Portland, OR 97204

Since the early 1900s, the Wachsmuth family has run this Ankeny seafood restaurant, selling raw oysters, oyster stew, and shellfish cocktails in a space covered in family photos and antiques. The menu has grown since its early days, now encompassing po’boys, gumbo, steamed mussels, and cioppino, served alongside beers and cocktails from the restaurant’s bar.

208 SW Ankeny St, Portland, OR 97204
(503) 227-5906
(503) 227-5906

Kay's Bar

6903 Southeast Milwaukie Avenue, OR 97202

Portland’s storied Kay’s Bar first opened in 1934 at the intersection of SE Milwaukie Avenue and SE Bybee Boulevard. Right outside, a bright red neon Kay’s sign hangs above the front door, and green awnings decorate the exterior wall. The interior is dimly lit with red bar stools, and a wood thatched ceiling hanging above the counter. The food menu covers all the bar classics with nachos, burgers, and fries, to pair with beer, cocktails, and more on offer.

6903 Southeast Milwaukie Avenue, OR 97202
(503) 232-4447
(503) 232-4447

Nick's Famous Coney Island

3746 SE Hawthorne Blvd, Portland, OR

Opened in 1935, this Hawthorne dive bar happens to have some of the best chili dogs and cheese fries in town. The lived-in space looks its 80-something years, which only adds to the charm of a bar named after a 19th-century amusement park. Keep an eye out for specials, which range from double-stacked burgers to jalapeño margaritas.

3746 SE Hawthorne Blvd, Portland, OR
(503) 235-3008
(503) 235-3008

A post shared by Ted Zahn (@neonhunting) on

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Chin's Kitchen

4126 NE Broadway St, Portland, OR 97232

Dating back to the 1940s, Chin’s Kitchen, with its hard-to-miss neon, is one of the oldest Chinese restaurants in Portland. A few years back, the kitchen got an overhaul, and the restaurant began turning out Dongbei delicacies like handmade dumplings, steaming clay pots of Chinese sauerkraut and pork, and the summery la pi, a chilled noodle salad with a rainbow of julienned vegetables. It’s the ideal spot for a meal ahead of a movie at the nearby Hollywood Theatre.

4126 NE Broadway St, Portland, OR 97232
(503) 281-1203
(503) 281-1203

Otto's Sausage Kitchen

4138 SE Woodstock Blvd, Portland, OR

Otto’s Sausage Kitchen started out as a meat market in Woodstock in 1922, then moved into its current location in 1936. For decades the same family has been making sausages and running the retail store, which continues to sell lovely smoked sausages, wursts and kielbasa, and pastrami. Stop by for lunches of deli sandwiches and wieners grilled outside the shop through the day.

4138 SE Woodstock Blvd, Portland, OR
(503) 771-6714
(503) 771-6714

Amalfi's Italian Restaurant

4703 NE Fremont St, Portland, OR 97213

This Northeast Portland Italian restaurant first opened in 1959, one of the first restaurants in the city to serve pizza. The restaurant still uses the same recipe for its pizza dough, topping those pies with alfredo, artichoke hearts, and everything in between. The restaurant also serves a slate of pasta dishes, red-sauce staples, and cocktails, with scoops of spumoni for dessert. Amalfi’s is open for takeout and dine-in, both indoors and outdoors — it can also be a fun spot for outdoor live music, when the weather is nice.

4703 NE Fremont St, Portland, OR 97213
(503) 284-6747
(503) 284-6747

Clyde's Prime Rib

5474 NE Sandy Blvd, Portland, OR

Bedecked in wood paneling, chandeliers, and red banquettes, Clyde’s is the place to party like it’s 1955. Juicy, pink slices of prime rib are the historic restaurant’s calling card, but modern touches like kale salad and poke have crept onto the menu, too. Stop by for live jazz in the lounge, paired with a Scotch on the rocks, or pop by for happy hour from 3 p.m. to 6 p.m. daily.

5474 NE Sandy Blvd, Portland, OR
(503) 281-9200
(503) 281-9200

Cameo Cafe East

8111 NE Sandy Blvd, Portland, OR 97213

This diner, just across 82nd from the Grotto, originally opened in 1969 next to the motel of the same name, but it wasn’t until 1992, when current owner Sue Gee Lehn took over the space and began introducing Korean dishes to the menu, that it truly hit the city’s radar. The dining room, with grandma’s house vibes and countless family photos, fills most mornings, with visitors ordering pancakes and eggs alongside kimchi and bulgogi.

8111 NE Sandy Blvd, Portland, OR 97213
(503) 284-0401
(503) 284-0401

Jim Dandy Drive-In

9626 NE Sandy Blvd, Portland, OR 97220

This Northeast Sandy spot — sporting vinyl booths, black-and-white photos and newspaper clippings, and ’50s memorabilia — hosted illegal drag-races early in its tenure, and now remains one of the state’s oldest operating drive-ins. The restaurant attracts gearheads and locals for its 70-plus varieties of milkshake, and what former Simpsons showrunner Bill Oakley called one of the city’s best old-school cheeseburgers.

9626 NE Sandy Blvd, Portland, OR 97220
(503) 253-2126
(503) 253-2126

Sayler's Old Country Kitchen

10519 SE Stark St, Portland, OR

Opened in the 1940s but tricked out like the 1970s, Sayler’s started out as an East County chicken shack, at a time when the neighborhood was still largely berry fields. Now it’s one of the few restaurants in town that still serves a traditional relish tray, plus 20-ounce T-bone steaks and choose-your-own cuts of prime rib. Meals finish with a scoop of ice cream.

10519 SE Stark St, Portland, OR
(503) 252-4171
(503) 252-4171
Sayler’s menu
Sayler’s.
Krista Garcia/Eater Portland

Heidi's Of Gresham

1230 NE Cleveland Ave, Gresham, OR 97030

Frequent visitors of Mt. Hood will likely recognize the Alpine-themed facade of this Gresham restaurant, off Northeast Burnside on the way to the mountain. In 1968, the late Don and Marie Eklund founded Heidi’s as a drive-in, eventually rebuilding the restaurant into a sprawling homage to Marie’s Swiss roots. Breakfasts here involve Swedish pancakes and cheese blintzes; at dinner, regulars dunk bread into fondue ahead of wienerschnitzel, cabbage rolls, or liver and onions. Stroll through the delightfully kitschy gift shop on the way out.

1230 NE Cleveland Ave, Gresham, OR 97030
(503) 667-4200
(503) 667-4200

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