Embark on a picturesque day trip along the Columbia River Gorge.

Kick off with a tasty frozen treat at Sugar Pine Drive Thru. Then, continue the journey with breathtaking views at the Vista House, explore the waterfall corridor along Historic Columbia River Highway. Don’t forget to snag a permit for Multnomah Falls, you might need one. If you continue your journey all the way to Hood River for a leisurely lunch, consider stopping by Pfriem Tasting Room for a barrel aged beer. On your way back into Portland, see where Caroline works and stop by Wood Village’s Donald L. Robertson Park and then grab something to eat next door at McMenamins Edgefield. We like to sit by the fire and sip cocktails in The Little Red Shed.

Live like locals and spend an afternoon in St. Johns.

Check out the famous Cathedral Park after you grab a coffee from Two Strokes and pastry from Sparrow Bakery.Or for a more substantial start to your morning sit down for breakfast at Paiku or John Street Cafe. Walk and shop along Lombard at Two Rivers, Revolutions, Rōm, and Vinyl Resting Place. For a pre-dinner snack, make sure to grab a candy bar from Bees and Beans. Then, walk to Pastificio d'Oro or Gracie’s Apizza for dinner. Grab a post dinner drink at Mosaic Taphouse or a cocktail at The Garrison.

Spend your Sunday in Southeast Portland.

Grab a tea at Smith Teahouse and be sure to check out 20th Century Interiors to browse their vintage MCM furniture, sample vermouth at Kabinett PDX, and grab cheese and Italian cold cuts for an afternoon (or late night) snack at Cowbell. For lunch, head to Güero for our favorite torta and mezcal margarita. Walk off your mid-day margarita at Music Millennium, before visiting Up Up Books. Venture over to SE Hawthorne where you’ll find a Powell’s Books (hot take: this shop is smaller but better than the famous Powell’s on Burnside), Jackpot Records, and a handful of vintage shops and cafes to pop in and out of. End your day sipping a glass of wine on Company’s patio or enjoying a fresh plate of pasta at Luce.

Hike the hills on Portland’s west side.

But first make a stop at our favorite coffee shop, Electrica, for a mochi donut and cortado. Make your way to the visitor center at Hoyt Arboretum where you’ll take a short 0.5 mile hike to the Redwood Deck to see some big ole trees. Don’t miss the Rose Garden or the Japanese Garden while you’re in Washington Park. Head down to NW 23rd Ave. for some light shopping and then walk two blocks to NW 21st Ave for an amuse bouche and a glass of wine at NĂ©gociant. 

Take in the views along historic highway 101.

Drive up Highway 26 through the Clatsop State Forest for a dreamy drive through Oregon’s big trees. Take the Historic-101 to Cannon Beach to see the famous Haystack Rock and explore the shops and restaurants like Ecola Seafood Restaurant & Market and Pelican Brewing. Hike some of Oregon’s most scenic areas at Ecola State Park just a few minutes away. If you’re staying overnight on the coast, be sure to check out our favorite coastal stay, The Drifthaven at Gearhart. Enjoy your morning coffee on the beach, and then pop-over to the Osprey Café in neighboring Seaside for breakfast. Keep heading north to Astoria to see the Bridge to Nowhere and the Goonies House. Visit Lonely Crab Records and the many antique and vintage shops before checking out the Astoria Column for the best view of the city and the spot where the Columbia River meets the sea.

What else is there to do in Portland?