Since 1979, the sign of this family-owned pie shop and diner has coaxed commuters off OR 99W and into the booths of its spacious, retro dining room for diner favorites like omelets, waffles, and burgers. A common finale: a slice of pie from the rotating displays. Like the food and the vibe, the pies here are as sweet and classic as they get, evoking memories of late-night Shari’s trips (RIP) with fluffy banana creams, hearty Dutch apples, and a fun peanut butter, banana, and chocolate number called the Elvis. And while the pandemic put an end to the diner’s 24-hour service, visitors can still find a slice until 10pm on weekdays and 11pm on Fridays and Saturdays.

A homey, bustling café, Bipartisan has served fruit and cream pies to the Montavilla community for 20 years now. Bipartisan’s homestyle pies never get too fussy, with touchstone flavors like banana cream, marionberry, and apple. The fruit pies sport uneven, hand-shaped crusts that are golden and flaky, while its cream pies are stacked high with fluffy whip. A slice is a must to finish a working lunch of panini and coffee. Most days, it’s easy to swing by the store and walk out with a full pie (or three), but during the holiday season it’s best to place a preorder by calling or emailing.

Those in the neighborhood around Caffe Destino know that this cozy little coffee shop doubles as an excellent bakery, particularly for its pies. You’ll find a few different styles, including juicy Oregon berry and a dense butterscotch. But it’s the key lime pie where the baking magic lives: A thick, buttery graham cracker crust supports a sweet-tart meringue, the top dotted with whipped cream, slices of lime, and a sprinkling of zest. It’s not too tart, nor too sweet, and has just the right level of silkiness. The pies are all baked daily, and customers can stop in for a slice with coffee, or take home a full pie for the family. Those planning holiday menus can call ahead or order online up to a few weeks in advance.

There’s no denying that this tiny shop on SE Division Street makes the best pie in Portland, as indicated by the daily lines out the door, customers queuing for its airy, flaky-crusted pastries. Founder Kate McMillen spent decades honing her approach to the craft, including a stint at the now-closed café-bakery Random Order. From there she launched Lauretta Jean’s as a farmers market stand before opening a downtown shop (now closed) and the current iteration on SE Division. The secrets behind her pies: keeping ingredients super cold before baking, only using butter in the crust rather than shortening, and sourcing locally for fillings. The shop offers a large variety of flavors, including seasonals and specials, but there’s nowhere better to start than with one of the classics, like a decadent bourbon pecan or gooey Dutch apple. Lauretta Jean’s also makes take-and-bake savory pies, including chicken pot pie and steak and veggie.

Nestled deep in Southeast Portland, Mehri’s is one part diner, one part bakery (sound familiar?). Alongside an impressive selection of cakes, it bakes old-fashioned-style pies, including peach, sweet potato, and banana cream. And it’s one of the only shops in town to offer a true throwback, that mix of apple and dried fruit called mincemeat. While historically, mincemeat pies occasionally included meat (or at least suet), the ones here are appreciably vegetarian. Less common flavors include blue gooseberry, apple and marionberry, and the Blue Goose, a mix of gooseberry and blueberry. Mehri's offers a daily selection of personal five-inch pies, which guests can enjoy at the bakery or take home. Those looking for the larger, nine-inch versions need to place orders 24 hours in advance, which can be done online.

One of Portland’s oldest gluten-free and vegan bakeries, Petunia’s Pies comes from baker Lisa Clark and her husband and business partner, Jacob Williamson. Clark developed a major gluten and dairy intolerance in college, and started exploring alternative baking options. One farmers market stall and wholesale business later, the couple now operates a brick-and-mortar while still selling celiac-friendly pastries to countless cafés and restaurants across town. Though the bakery is better known for its cupcakes and bars, visitors to the West End shop can find a rotating selection of pies by the slice, including apple crumble, strawberry, and marionberry.

In the complex that houses Friendship Kitchen and Tropicale, the Pie Spot specializes in “cupcakes” of pies, roughly three inches wide, in a kaleidoscope of flavors. There are the traditional ones—marionberry, brown butter pecan, key lime, cherry—but where the Pie Spot has the most fun is with its creations that lean sweeter and richer, encroaching on cake territory. Think banana chocolate, strawberry cheesecake, tiramisu, and the s’more, with chocolate, graham cracker, and toasted marshmallow. Nine-inch pies are available for preorder, but a baker’s dozen of assorted minis is the patrician’s move.