Renowned for its locavore-driven food scene, independent-spirited shopping and gloriously verdant parks, Portland offers enough cultural and outdoorsy diversions to keep you busy for a week, but it’s also a surprisingly easy city to get to know in a day. Walk through the Pearl District, a former industrial neighborhood that’s now rife with art galleries and modish boutiques. It is also home to legendary Powell’s City of Books, the largest new and used bookstore in the world. As an introduction, we discover Portland with our new best friend, an award-winning "Resident Expert. They live in Portland; they know Portland; they love Portland; and it shows. Allow them to keep you laughing through this easy walking tour. Not only is it fun, but many consider it to be the best tour in Portland.The Best of Portland award-winning walk clarifies why Portland is regularly recognized as one of the best places to live. By the end of your walk, you will want to move here too. You learn about early and modern Portland as your guide shows you an enlightened city rich with artwork, parks, bridges, downtown trains and streetcars, fountains and friendly people. Even locals are amazed and entertained by what they learn. This walk meanders through the most fascinating portions of the city, leading eventually to the waterfront. And don’t forget the camera for your shot of the world’s smallest park! Later, explore leafy Washington Park and tour the Portland Japanese Garden and International Rose Test Garden.
Less than 30 minutes’ drive east of Portland, you’ll enter the spectacular Columbia River Gorge National Scenic Area, an 80-mile (129-km) forested canyon of rugged cliffs and soaring waterfalls, much of which you can tour via the iconic Historic Columbia River Highway. Stop to snap a photo and enjoy a slice of marionberry shortcake in the 1915 lodge at Multnomah Falls; a steep but paved trail ascends to the top of this 620-foot-tall (189-m) cataract. Stop for a brick-oven pizza at Double Mountain Brewery & Taproom in Hood River, a cheerful village famous for kitesurfing and wind-surfing as well as its first-rate culinary scene. The Columbia Gorge contains more than 30 wineries, including Echo Ridge Cellars, whose tasting room occupies a retrofitted grain elevator. In Pendleton, a friendly cowboy town acclaimed for September’s iconic Pendleton Round-Up rodeo, browse the vibrantly patterned blankets and attire at Pendleton Woolen Mills and the handcrafted leather saddles and silver belt buckles at the Hamley & Co. Western store. Then feast on a charbroiled, hand-cut rib-eye steak from ’50s-era Virgil’s at Cimmiyotti’s.
Order a breakfast sandwich and a latte from Pendleton Coffee Bean & Bistro before driving south via Highway 19 and U.S. 26 through the high-desert heart of Oregon, stopping to admire the otherworldly Painted Hills section of the John Day Fossil Beds National Monument. At Smith Rock State Park, one of the nation’s top rock-climbing destinations, embark on a short trek amid the dramatic canyons and fantastic rock spires. Continue toward the majestic Cascades Range to the easygoing mountain hamlet of Sisters, a base for hikers in summer and skiers in winter. Enjoy a frosty mug of FivePine Chocolate Porter at Three Creeks Brewing Co., which also turns out tasty pub fare.
Venture into outdoorsy Bend, one of Oregon’s craft-beer meccas, stopping by Crux Fermentation Project, which has earned a devoted following for its unusual pours, such as Better Off Red, a barrel-aged Flanders red ale. Nearby along U.S. 97, you’ll encounter Newberry National Volcanic Monument, where you can literally get in touch with the region’s ancient, cataclysmic geological history by walking through a lava tube and ascending Paulina Peak for panoramic high-desert views. Allow two to three hours to reach Crater Lake National Park, which is anchored by the nation’s deepest lake. Crater Lake is a must-see for all ages, and what a better way than to enjoy the majestic beauty of one of the “Seven Wonders of The World” than from aboard a historically designed trolley bus. You will enjoy a two hour, Ranger-guided and narrated trolley tours around the Rim of the Lake. The Rangers will talk about the history and formation, answer questions and there will also be 5 to 7 stops during the ride to allow for picture taking or to just take in the unmatched beauty that Crater Lake has to offer.Later, we recommend enjoying dinner and the rustic ambience of Crater Lake Lodge, a classic timber and shingle-roof National Parks hotel built in 1915.
Head for the ruggedly beautiful Rogue Valley and vibrant Ashland, famed for the Oregon Shakespeare Festival, which stages 11 classic and contemporary productions during its mid-February through October season. With its many farm-to-table eateries and the decadent Oregon Chocolate Festival in March, Ashland has become a top destination with foodies. Be sure to check out Noble Coffee Roasting, a third-wave cafe in the historic Railroad District. Also explore downtown’s many galleries and shops, as well as adjacent Lithia Park, an expanse of both groomed pathways and trails through pine forests.
Drive north through the Rogue Valley and its plentiful fruit orchards and grape vineyards, stopping in the endearingly old-fashioned hamlet of Jacksonville, a designated National Historic District with tasting rooms and unique retailers. Continue to Grants Pass, where you can explore the 250-footdeep (76-m) Rogue River Canyon with Hellgate Jetboat Excursions. For a decidedly mellower adventure, book a beer-centric trip with The Paddled Pub, which partners with local Climate City Brewing Co. to provide lazy floats along a relaxing stretch of the Rogue. There are nearly 700 wineries in the state of Oregon. The most popular grapes grown are pinot noir and pinot gris.
Overnight: Grants Pass
En route north to the state’s second-largest city, Eugene, stop in Cottage Grove and rent a bike at Rainy Peak Bicycles to journey along the 36-mile (58-km) round-trip covered-bridge bike route, which traverses some of Lane County’s loveliest countryside. In Eugene walk around the bustling campus of the University of Oregon, home to some outstanding museums and Hayward Field, one of the world’s foremost track-and-field venues. Then head to the bohemian Whitaker neighborhood to sample wine that’s crushed and bottled right in town at Territorial Vineyards & Wine Company, one of the city’s urban wineries.
Start your day with breakfast at Provisions Market Hall, inside downtown Eugene’s handsomely restored Fifth Street Market. Then drive west through Oregon’s forested Coast Range to Old Town Florence, here you can sip a single-origin coffee on the deck at Siuslaw River Coffee Roasters, which overlooks one of the many famous 1930s-era bridges set along scenic U.S. 101, the Oregon Coast Highway. Florence marks the northern end of the massive Oregon Dunes National Recreation Area, the largest expanse of coastal sand dunes in North America. At Florence’s Sand Master Park, you can learn to sandboard or book an extreme dune buggy tour. Follow U.S. 101 north along the Coast, stopping for quick treks at Heceta Head Lighthouse and Cape Perpetua Overlook, and visit Newport’s renowned Oregon Coast Aquarium to view playful sea otters and a giant Pacific octopus. End your day with a walk around Newport’s Historic Bayfront, where you may see (and hear) sea lions barking, and dine on superb Dungeness crab cakes at Local Ocean Seafoods.
Follow U.S. 26 inland, fueling up on strawberry-topped griddle cakes at Camp 18 restaurant and logging museum, before hiking Saddle Mountain, a 5-mile (8-km) round-trip trek with an elevation gain of 1,600 feet (488 m). The views of the Coast and, on clear days, Mt. Rainier and Mt. Hood are well worth the effort. On your way back to Portland, stop by Apolloni Vineyards in Forest Grove to sample outstanding Willamette Valley pinot noir and play on the bocce court as the sun sets over the Coast Range.
Fly out of Portland International Airport.