This Unsuspecting Drive-In Has Some Of The Absolute Best Burgers You Can Find In Oregon

by | Dec 1, 2023 | Central Oregon, Eugene, Food & Drink, Restaurants

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I'll never forget the day I stumbled upon this hidden gem while cruising down Highway 58 in the Oregon Cascades. Tucked away in Oakridge, Stewart's 58 Drive-In is a retro diner that's a throwback to the 1960s, and let me tell you, their burgers and onion rings are out of this world! The moment you bite into one of their juicy, grass-fed beef burgers, it's like a flavor explosion in your mouth. And don't even get me started on their onion rings - crispy, golden, and absolutely addictive.

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This place has a rich history, you know. It was once The Big Top drive-in, then transformed into the High Lakes Restaurant, followed by The Trails Head. But since 2014, under the stewardship of Gregg and Shannon Stewart, this spot has become an iconic pit stop. Their passion for top-notch American cuisine is evident in every bite. Whether it's their hefty beef hot dogs, fresh and hearty salads, or the homemade chili and soups, everything screams quality.

stewart's 58 drive-in, oakridge, oregon, best burgers, espresso, homemade, milkshakes, central oregon, eugene cascades, restaurants, delicious food, must try, chili and cornbread, desserts, mom & pop

As Shannon says, "We are a real Mom & Pop shop, and though the work is hard, putting out a quality product is worth it and the smiles on the faces of our customers means everything!"

stewart's 58 drive-in, oakridge, oregon, best burgers, espresso, homemade, milkshakes, central oregon, eugene cascades, restaurants, delicious food, must try, chili and cornbread, desserts, mom & pop

Their menu is a tribute to classic American dining with a modern twist. Those large 1/3 lb beef patties are something else, seasoned to perfection and served on bakery-fresh buns. And for those seeking a meat-free option, the Malibu Veggie Burger is a revelation. Not to mention, their in-house chili is a hearty delight. Served as it should be with cornbread on the side, this bowl is full of comfort.

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As a dessert lover, their Tillamook hard ice cream shakes and malts are a must-try. The Pumpkin Spice Shake and Strawberry Sundae are personal favorites. Their commitment to quality extends to their baked goods too, with irresistible cinnamon rolls and banana nut bread.

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Let's not overlook their savory options. The Mushroom Swiss burger is a crowd-pleaser, while the Chicken Caesar Wrap offers a lighter but equally delicious choice. And for those who enjoy a good sandwich, their Club Sandwiches are packed with flavor.

stewart's 58 drive-in, oakridge, oregon, best burgers, espresso, homemade, milkshakes, central oregon, eugene cascades, restaurants, delicious food, must try, chili and cornbread, desserts, mom & pop

And if you're a coffee lover like me, their full coffee and smoothie bar is a dream come true. Perfect for refueling during a long drive. Plus, their desserts, shakes, and malts are the perfect sweet treats to round off a meal. I mean, you haven't lived until you've tried their desserts!

Their breakfast menu is just as impressive as their lunch and dinner offerings. I often find myself browsing their menu online or drooling over their latest creations on their Facebook and Instagram pages.

stewart's 58 drive-in, oakridge, oregon, best burgers, espresso, homemade, milkshakes, central oregon, eugene cascades, restaurants, delicious food, must try, chili and cornbread, desserts, mom & pop

If you ever find yourself on Highway 58, you owe it to yourself to stop at Stewart's 58 Drive-In. Trust me, you won't regret it. I'm already planning my next trip there on the way to our next skiing adventure. What about you? Have you tried their heavenly burgers and onion rings? If you have, you know what I'm talking about. If not, what are you waiting for?

stewart's 58 drive-in, oakridge, oregon, best burgers, espresso, homemade, milkshakes, central oregon, eugene cascades, restaurants, delicious food, must try, chili and cornbread, desserts, mom & pop

Where is Stewart's 58 Drive-In Located?

Address: 47434 OR-58, Oakridge, OR 97463

Phone: 541-782-7115

Hours: Wednesday-Sunday, 11am-3pm

Web and Menus: 58drive-in.com

Facebook: facebook.com/58drivein

Insta: instagram.com/stewarts58


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Written By Tyler James

Tyler James, founder of That Oregon Life, is a true Oregon native whose love for his state runs deep. Since the inception of the blog in 2013, his unbridled passion for outdoor adventures and the natural beauty of Oregon has been the cornerstone of his work. As a father to two beautiful children, Tyler is always in pursuit of new experiences to enrich his family’s life. He curates content that not only reflects his adventures but also encourages others to set out and create precious memories in the majestic landscapes of Oregon. Tyler's vision and guidance are integral to his role as publisher and editor, shaping the blog into a source of inspiration for exploring the wonders of Oregon.

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