A Local’s Guide to Portland

I’m a rare native Portlander. I lived here before The New York Times ever wrote a travel story about us, and way before the days of Portlandia. The cool part about living here for 30 years is that I’ve been able to watch as the city’s districts have grown and evolved. In the small town where my husband’s from, no one stays around after high school. But I’m proud to be living in my hometown full of ridiculously delicious food and well-curated shops.

Portland has lots of cute shops, but owner Anna Fickle’s impeccable sense for styling and finding unique items—as well as its great location in the underrated Montavilla neighborhood—that make me love hers so much.

Branch & Birdie, 8021 SE Stark

The fact that you get these hot, amazingly delicious waffles through a window right on Hawthorne Blvd. makes them even more of a novelty—but they don’t need novelty to sell me. The banana nutella variety—with freshly whipped cream—is absolutely killer.

The Waffle Window, 3610 SE Hawthorne Blvd

Growing up in Portland, I was told to “lock your doors!” when we drove through this part of town. Over the last 15 years, the West End has transformed completely, and one of the hippest places to hang out now is on this block, near the Ace Hotel and Stumptown Coffee. I highly recommend lunch at Clyde Common. The combination of comfort food plus the beautiful mid-day light streaming in through the windows makes for a perfect Portland moment.

Clyde Common, 1014 SE Stark Street

When walking on NE Portland’s Alberta Street, the average visitor has about 45 choices for seriously good food. But I usually opt for a quick stop to recharge at Random Order, which has a case full of lip-smackingly good pie waiting at just about any time. They even make vegan pie, which is a tall order in a city like Portland. Brandied peach pie, warm and with ice cream on the side? I don’t think I need to say any more.

Random Order, 1800 NE Alberta

Canoe is another example of a well-curated shop that brings its customers coming back for more. From local pottery and kitchenware to furniture and lighting, this is a go-to shop when I need a great gift.

Canoe, 1135 SW Alder St.

This is a shop I stumbled into for the first time recently, and I was so delighted to find such a great selection of beautiful, useful and quirky things here. It’s in a great zone, too—I love to pop in on my way to Kask, the great little bar around the corner, for after-work drinks.

Alder & Co., 537 SW 12th Ave.

This place could not be any more Portland if it tried. It’s one of my absolute favorite places because of the complete originality of programming. We’ve seen art films, silent movies paired with live orchestras and Pee Wee’s Big Adventure. There is just no telling what’s going to come next, and that’s what I love about the Hollywood Theatre.

Hollywood Theatre, 4122 NE Sandy Boulevard

In Portland, we take our ice cream very seriously. Ruby Jewel has two scoop shops in the city, but were originally known for their ice cream sandwiches, available in grocery stores in the area before they started scooping in their shops. Now you can get those original sandwiches made right in front of you—in flavors like honey lavender and salted caramel with dark chocolate.

Ruby Jewel, 3713 N Mississippi or 428 SW 12th Ave

Even if you’re not from Portland, you’ve probably heard of Schoolhouse Electric. I love their stuff—but it’s not the period lighting that draws me back here. The flagship retail store is more of a place to go and seek inspiration. There’s a Ristretto Roasters coffee shop and the workspace of florist Anna Mara inside. I could spend an afternoon—heck, why not every afternoon?—just wandering and being inspired here.

Schoolhouse Electric & Supply Co., 2181 NW Nicolai Street

It’s a little outside downtown Portland, but it’s worth the trek to what is (in my humble opinion) the best bakery in this whole food-obsessed city. Owner Julie Richardson is somewhat of an institution, and the shop’s constant bustle is a testament to that. Try my favorite, the coconut cream pielet (pictured), which inspired me to enter (and win!) the Portland Pie-Off cream pie division in 2009 (Did I say food-obsessed?)

Baker & Spice, 6330 Sw Capitol Hwy

From a funding and planning perspective, I understand this project was a failure of monumental proportions, but I like that it offers an unconventional Portland view and access to the South Waterfront neighborhood. Riding it is fun, and so it standing nearby and taking in the design of the pod-like gondolas and modernist tower.

Aerial Tram, 3303 S.W. Bond Ave.

Sara Gray is a Portland realtor. Tweet with her @segray and follow her new blog, Sara Loves Portland.