An Insider’s Guide to the Local Side of Portland

The outdoors

Tom McCall Waterfront Park is where the big crowds go to enjoy the Willamette River. Just south of the admired park is the smaller Willamette Park, where you can still soak up the river without a crowd. It also has a dog park for your furry friends.

Forest Park offers fun urban hikes, but Mt. Tabor Park offers spectacular views of the city and Mt. Hood in addition to taking in fresh air.

Pittock Mansion has a great view of the city, but the Portland Aerial Tram is a fun ride up to Oregon Health and Science University with a magical view of Mt. Hood.

You could take the popular Portland Spirit Cruises dinner cruise or you could get closer to both the Willamette and Columbia rivers on a Willamette Jet Boat Excursion.

Entertainment

Punch Bowl Social is great for the whole family, but if you want to act like a kid and play arcade games in an adults-only environment (at night), check out Ground Kontrol.

Living Room Theaters is great for sipping wine and watching independent movies, but try out the Lake Theater & Cafe in Lake Oswego. Before your movie, you can snack on popcorn with a view of the lake.

Uniquely Pacific Northwest

You can’t go too far in Portland without running into a McMenamins, a family-owned chain of brewpubs, event centers and hotels. Kennedy School, part of the McMenamins chain, is a popular location to eat, drink and/or stay the night. If that sounds fun, you might want to try out a companion property, Edgefield. You get the eats, drinks and lodging but also live music in the summer and a country retreat feel. You don’t have to stay overnight to enjoy the ambiance.

Spa and Massage

There are many fancy spas in Portland, but those in the know go to The Everett House to get a soak, steam and massage on the cheap. Please note that the soaking pool and sauna are clothing optional.

Shopping

The Portland State University Farmers Market and Portland Saturday Market draw significant crowds, but the Hollywood Farmers Market, while smaller, is a great place to make local friends and pick up local produce and wares.

Day trips

Check out Hood River along the Columbia Gorge for wineries, breweries and distilleries. You can walk the small, historic downtown in a day and take in magnificent views of the Columbia River.

Coastal Astoria is a little less popular than its Seaside and Cannon Beach counterparts. With no real beach, the community is known as a fishing town with great food, drinks and lodging. Check out my guide to Astoria here.

McMinnville is in the heart of wine country, so it is a wine aficionado’s heaven. It also boasts beautiful countryside as you drive from vineyard to vineyard.

There isn’t much to Rockaway Beach, which is the best part about it. It is a small beach town where you can retreat from the city's heat and crowds.

Cocktails

Fancy libations abound in PDX, so it’s hard to list what is most admired. Ultimately it depends on the vibe you are going for. Here are some places with all the vibes: Abigail Hall is located in the Woodlark Hotel where the original Ladies Reception Hall was established and honors its suffragette roots. Bible Club is a true speakeasy, hidden inside a cozy, nondescript house that you might almost miss. Pink Rabbit lives up to its name with lots of modern pink and has an extensive cocktail list including frozen beverages and shooters. If you are staying at The Nines Hotel, the Departure Restaurant and Lounge offers great cocktails and takes design cues from retro aeronautics.

Beer and wine

Oregon is famous for its wine and beer. You may be able to find Erath wine at most grocery stores, but Fullerton Wines has delightful wine and a fun happy hour. You may have heard of Deschutes Beer, but Sasquatch Brewery is laid back with some fun brews and bites to try.

Brunch

Mother’s Bistro has consistently been THE place to go for brunch in town, but there are a few other places you might want to check out. City State Diner & Bakery offers 10 different types of eggs benedict and their bloody mary could be considered a full meal on its own. GiGi’s Cafe has a variety of brunch options, but specializes in both sweet and savory waffles that are beyond delicious. Salty’s on the Columbia River might have the best buffet brunch ever, especially if you can eat your weight in seafood. The Eastburn has great eats and boozy breakfast flights including their bloody mary and mimosa options.

Dinner

Yes, Portland City Grill has a great view, but there are so many fantastic dinner options to choose from. Eleni’s Philoxenia is a Cretan Greek restaurant with food that will transport you to the clear blue waters of the Mediterranean. Cafe du Berry is an understated French restaurant that sources local ingredients and drinks producing upscale comfort. Jacqueline is inspired by the Wes Anderson movie The Life Aquatic and you will even find a picture of Bill Murray looking at you from behind the bar. They offer a $1 oyster happy hour and their dungeness crab toast is a must. Another stop at The Nines is Urban Farmer Steakhouse. Located in the main aviary-style lobby of the hotel the steakhouse offers a steak-tasting option if you can’t choose which one you want.