If you’re heading west this summer, and you have a weekend to spare, a road trip from Bend to Portland, Oregon is a must. To help you make the most of your trip, we’re sharing a foolproof itinerary with the best bites, activities, hotels, and more to explore. These Pacific Northwest enclaves have so much to offer, so schedule a few days in each city—you won’t regret it. Pack your bags—ready, set, go!
The first stop on this two-city tour is Bend, OR. Bend is primarily known for its easy access to myriad outdoor activities and its breweries, but it also has a burgeoning food scene that would impress even the most discerning among us.
Before we get into the details, first thing’s first: getting there. The easiest way to get to Bend is to fly into Redmond and rent a car (this is a road trip after all). From the airport, check into the Oxford Hotel in the heart of Bend. It’s an adorable boutique hotel with a focus on sustainability that takes the term “eco-chic” to new heights with such amenities as organic mattresses, linens, and bath products. If you can swing it, you won’t regret booking a Mountain Suite, where you can enjoy a massive soaking tub, select the perfect pillow from the hotel’s pillow menu, and entertain in your separate living room.
Once you’ve checked in and gotten settled, head to the famed Deschutes Brewery, perhaps one of the most famous purveyors of craft beer in the West. Afterward, grab an easy, early dinner at Bangers and Brews and call it a night.
The next day, get up early and grab some fresh fruit at Newport Avenue Market before heading out to Deschutes National Forest for a hike along the Deschutes River Trail (South Canyon Reach). This easy three-mile hike takes you along the stunning water for which the park is named, and is a great introduction to the natural wonders of the Pacific Northwest. This hike gets bonus points for being close to town while still feeling like you’re getting away from it all.
When you get back to town, head to McKay Cottage Restaurant for a hearty breakfast. We recommend the pecan sticky buns! We also recommend The Sparrow Bakery, where you can feast on a hefty egg sandwich made with a buttery, hand-rolled croissant.
Now it’s time to hit the water with river kayaking tour on the Upper Deschutes River. We recommend the Tumalo Creek Kayak & Canoe. When you get back into town, the Tacos Pihuamo food truck is sure to satisfy your lunch craving. Once you’ve had your fill, make your way to Drake Park and check out the picturesque Mirror Pond. While you’re there, explore downtown’s adorable shops and delightful architecture. For dinner, grab a bite at Zydeco Kitchen & Cocktails, where a local favorite is the BBQ shrimp and the red fish with zydeco sauce.
Start your second day in Bend at a classic spot beloved by locals and visitors alike: Chow. It’s one of Bend’s best-known brunch spots and is not to be missed. Now that you’ve gotten your bearings, spend your second day getting to know the industry for which Bend is best known: beer. A great way to visit several breweries is via a guided tour. We love Let it Ride, which takes you around town on electric bikes and enables you to customize your tour to satisfy every member of your group. You’ll get fresh air, exercise, and (of course) beer all in one go! For lunch, find your way to Bad Wolf Bakery & Bistro for salads, sandwiches, or burgers.
A nice post-lunch spot to poke around is Dudley’s Bookshop Café where you can pick up a good read and a nice cup of tea. After you’ve rested your legs, head to Wabi Sabi where you can find quirky Japanese knickknacks, gift items, and clothing. For dinner, treat yourself to timeless New American fare at Ariana where you’ll find perfectly prepared gnudi, a refreshing radicchio salad, hearty cuts of meat, and some of the freshest fish dishes around.
Kick off your last day in Bend with breakfast at Palmer’s Café where you can dip into a delicious Bloody Mary and classic American fare. After breakfast, pay a visit to the High Desert Museum, which pays homage to nature and wildlife. Grab a sandwich at Planker Sandwiches, a local favorite. You can enjoy an excellent BLT, a mean meatball parm, or a humble but delicious grilled cheese. Up next is a trek on the eastside, where you can hike up to Point Butte to take in the sweeping vistas of Bend and views of Mount Bachelor, the Three Sisters, and the Cascade Range beyond.
Next stop, Portland. This town has come a long way from the hippie enclave it used to be known as. It’s become a jewel of a city in its own right, with some of the best restaurants and cafes in the country. Add to that the fact that it’s just a hop, skip, and a jump from premier hiking and outdoor activities and you’ve got a city whose star is rising.
While a more direct route will get you from Bend to Portland in about three hours, we like the more scenic route that takes you up near Mount Hood to the Hood River, which you then follow Southwest into Portland. It only adds about 45 minutes to the journey and is just gorgeous. Take 97 out of Bend, to 26 and then 35.
If you’re going the hotel route, our two favorites are The Nines and The Ace Hotel. The former is a bit more upscale but worth it if you can splurge. The Ace Hotel is a trendy, affordable spot that won’t disappoint. You’ll probably want to call it an early night, so we suggest an easy dinner with drinks at Pinky’s Pizza and Whiskey Bar, a short 10-minute drive from both the Ace Hotel and The Nines. You’ll have earned your bourbon on the rocks.
The next day, start off with breakfast at Ovation Coffee and Tea. The Moroccan spiced coffee is the thing to get so don’t miss it. Pair your coffee with an indulgent breakfast pastry or, if you’re hungrier, go for the egg sandwich or the veggie biscuit. Ovation is the perfect jumping off point for exploring the Pearl District, known for its art galleries, great shopping, and home to the legendary Powell’s City of Books. We also love Penzey’s Spices for its high-quality collection of herbs and spices. The perfect place to pick up something for your next dinner party.
Then head into the Northwest neighborhood for some Mediterranean grub at Gastro Mania. Next, amble over to Macleay Park for a postprandial walk along the lush trails for which Portland is known. And if you’re up for it, take the 5-mile hike to Pittock Mansion. For dinner, we recommend Andina, an impressive Peruvian restaurant with an extensive selection of seafood-focused tapas, classic dishes like Lomo Saltado, and carefully crafted cocktails. Follow this up with after-dinner drinks at the Teardrop Lounge, a short five-minute walk away.
The next day, get an early start with coffee and breakfast burritos at Floyd’s Coffee Shop. Then head out to the Columbia River Gorge for a morning hike up Dog Mountain. About an hour outside of the city, this is one of our favorite hikes in the Columbia River Gorge. It tends to be less crowded than a lot of the other hikes the six-mile loop is just long enough to make you feel like you earned it but not so long it takes up your entire day. And though it’s a bit of a steep climb, you’re rewarded with stunning views of the Columbia River Gorge and the Cascade Mountains.
After your hike, head back towards Portland, making time for a pit stop at Walking Man Brewing. Their great sandwiches, artisanal pizzas, and house-made beer are sure to fill you up after your sojourn up the mountain.
Now that you’ve gotten your nature kick, it’s time for a night on the town. And there’s no better place to start than Lantern Lounge for pre-dinner drinks. This new Vietnamese restaurant turns out inspired cocktails, such as the Transcontinental Sazerac Transcontinental Sazerac and the Saigon Scoot Scoot. Once you’ve loosened up your achy joints, head to Revelry. The little sister to the Seattle restaurant of the same name, this eatery serves up inventive Korean food in a very of-the-moment setting. The Kimchi Pancake is to die for while the rice cakes are out of this world. If you have it in you after dinner and you haven’t tried it yet, hop in a cab and make your way to Voodoo Doughnut Too, where your choice of doughnuts is limited only by your imagination.
After your late night out, a hearty breakfast will be just what the doctor ordered. That’s why we suggest you find a table at Kingsland Kitchen. With a solid selection of egg sandwiches and a couple of British staples if some bangers and mash strike your fancy. The best part is, this eatery is located just a short walk from both the Ace Hotel and The Nines—no driving required.
There’s no better way to spend your final morning than at the Portland Art Museum. The museum is one of the oldest in the United States and the oldest in the Pacific Northwest. It houses a collection of over 42,000 objects and a distinctive collection dedicated to Native American art.
For lunch and a classic Portland experience, look no further than The Waffle Window. We know what you’re thinking: Waffles for lunch? But don’t let the name fool you. This place serves more than your run-of-the-mill waffle with butter and maple syrup. Options include waffles with Black Forest ham and cheese, or with balsamic red-wine braised mushrooms, onions, red peppers, and goat cheese, and even bacon, brie, and basil. The choices will have you rethinking the humble waffle’s place in your rotation. And for those craving something sweeter, the Waffle Window’s got you covered with their ice cream sundae waffles. Bon appétit!
After lunch you may be feeling thirsty, so head to 10 Barrel Brewing Co. for a few cold ones. Grab a spot on the patio where you can check out the old warehouses that surround this easygoing spot.
It’s your last night in town, which means it’s time to go big before you go home. That’s why we think you should spend your final meal in the city at Le Pigeon, a legendary Portland establishment. Save room for the Foie Gras profiteroles, a house specialty. If you aren’t craving French food, we’d be remiss if we didn’t mention Pok Pok. Yes, it’s been on everybody’s list for what seems like forever, but there’s a reason: it’s that good. You won’t find Pad Thai on the menu. This is the real deal so be prepared to take your taster on a trip. Just make sure you head to the original location on SE Division St.
Last but not least, and it being Portland and all, here are a few of our favorite coffee shops around town:
Half Pint Café – 537 SE Ash St. Portland, OR 97214
Coava Coffee Roasters – 1300 SE Grand Ave. Portland, OR 97214
Tōv – 3207 SE Hawthorne Blvd. Portland, OR 97214
Saint Simon Coffee Co. – 2005 NE Broadway Portland, OR 97232
Woodlawn Coffee and Pastry – 808 NE Dekum St. Portland, OR 97211
Spunky Monkey Coffee Roasters – 2240a Ne Sandy Blvd. Portland, OR 97232
Spella Caffe – 520 SW 5th Ave. Portland, OR 97204
Olé Latte Coffee – 1003 SW Alder St. Portland, OR 97205
Stumptown Coffee Roasters – 128 SW 3rd Ave. Portland, OR 97204
Coffeehouse Northwest – 1951 W Burnside St. Portland, OR 97209
Deadstock Coffee – 408 NW Couch St. Portland, OR 97209
Nossa Familia Coffee – 811 NW 13th Ave. Portland, OR 97209
Do you have a favorite spot in Bend or Portland? Tell us about it in the comments below!