Foodies around the world know the name James Beard, one of the most acclaimed American chefs of all time, so it’s a little odd to see a browned-with-age newspaper clipping framed on the wall at Skyline touting Beard’s professed devotion for this tiny retro diner’s burgers.
I happen to share Beard’s devotion to Skyline, and I have been visiting for more than two decades. Even though I don’t live as close as I did growing up, the food and atmosphere keep calling me back and Skyline never fails to satisfy.
Established in 1935, you would guess by looking at the former drive-in that very little has probably changed since the days when teenagers cruised up through the West Hills to enjoy some late-night hamburgers and milkshakes.
The drive-in service is gone, but the burgers and shakes survive. The dining area is a smattering of cozy booths and a handful of stools at the counter, all of which tend to fill up quickly during peak hours. The wood paneled walls are covered with children’s crayon drawings, mementos collected over their years in business and lots and lots of business cards (some pinned to the wall four or five deep). All of which add to the charm of this bygone-era establishment, but also take into account that their bygone-era approach means this is a cash only restaurant. (They do have an on-site ATM.)
The menu is plentiful and retains a definite diner feel with some modern upgrades (like the vegan black bean burger), but the main draw to Skyline is the burgers with their toasted, buttery buns.
I typically go with the regular cheeseburger ($4.15) with a side of fries ($1.25), but for heartier eaters or the more adventurous, there are plenty of burger variation options. Probably the most impressive on the menu are the giant burgers, which are insanely enormous and certainly gut-busting if you can manage to devour the entire thing.
Along with the burgers, Skyline also offers up a remarkable milkshake menu. Beyond your typical chocolate, strawberry or vanilla, you can try the more original flavors like root beer, caramel apple, lime or chocolate covered cherry. There are also seasonal shakes offered, which are listed at your table. To indulge even more, Skyline offers pie shakes, which actually include pie bits and pieces in your shake!
If you aren’t going up to Skyline for a burger and shake, there are many other menu items to suit any taste. They offer salads, soups, chili, hot and cold sandwiches, hot dogs and their Skyline Specialty plates.
Overall, Skyline is a wonderful place to grab an inexpensive, leisurely lunch in Portland. Everyone from young families to hungover downtown hipsters to grandparent-types frequent this hidden-in-the-hills gem, and for good reason. The restaurant is so comfortable, cozy and retro you can’t help but feel the stresses of the modern world just outside the door simply melt away.
http://nonprofitchurchconsulting.com/church-growth/feed/ Pros: Great burgers, fantastic milkshake menu, reasonable prices, charming retro setting, very unique Portland lunch
Cons: Can get crowded, a little off the beaten path, cash only (there is an on-site ATM)