23Hoyt
For a bigger breakfast or upscale brunch, 23Hoyt is my go-to. It located on NW 23rd Avenue, a ritzy shopping district in Nob Hill. There may be a line during popular hours on the weekend, but personally I've never needed to make a reservation although it's an available option. I like to order the eggs Benedict with Serrano ham or the Arepa Benedict served on an arepa instead of an English muffin. 23 Hoyt serves dinner as well and has a drool-worthy happy-hour menu, with small bites like marinated olives and bacon-wrapped dates.
Kyra's Bake Shop
Portland has a generous number of specialty bakeries and doughnut shops, including Kyra's Bake Shop.
This gluten-free bakery — a four-time winner of "Cupcake Wars" — is in Lake Oswego, just south of town. You can get gluten-free cakes, cupcakes, and doughnuts colorfully decorated with bright frosting, glaze, toppings, and sprinkles. If you get here early enough, try the hand pies, which are like big Pop-Tarts, with flavors that change seasonally; the strawberry one is my favorite so far.
Le Pigeon
One of my favorite restaurants for a night out is Le Pigeon, which has French-inspired fare by chef Gabriel Rucker, a 2011 James Beard Award recipient in 2011 and 2013. Rucker is also the creative behind the high-end bistros Little Bird and Canard. During lockdowns Le Pigeon offered specialty dinner boxes for pickup, but indoor dining is now open again. There's a chef's tasting menu as well as wine pairings. If you're willing to splurge, I recommend ordering the whole fish presentation — I was dazzled by a delicious halibut during my last visit.
Q Restaurant
Many Portlanders grieve the old Veritable Quandary restaurant, affectionately known as VQ, which closed to make way for the new Multnomah County Courthouse. VQ's chef, Anne Cuggino, who's trained in French and Italian cuisines, is now at the family-owned Q Restaurant. The cuisine is eclectic and globally inspired, with seasonal and local Pacific Northwest ingredients. You won't go wrong with anything you order — I have a particularly fond memory of the lunchtime steak skewers.