Shannon O'Brien Travel Itineraries

The best destinations

Photo of Oregon
Photo of Oregon

The Best of Oregon

#54 best destination in the world

Map view

Powell's City of Books, Portland

Photo of Portland

Best time to visit: June-Aug

Cost: $

  • Powell's Books is a chain of bookstores in Portland
  • Powell's headquarters, dubbed Powell's City of Books, claims to be the largest independent new and used bookstore in the world
  • The City of Books has nine color-coded rooms and over 3,500 different sections
  • The inventory for its retail and online sales is over four million new, used, rare, and out-of-print books

Clatsop Loop Trail from Indian Beach, Cannon Beach

Photo of Cannon Beach

Walk difficulty: Moderate

Best time to visit: June-Aug

Cost: $

  • Beach famous for Haystack Rock, a 235 ft (72 m) sea stack that juts out along the coast, and is often accessible at low tide, especially in the summertime
  • There is a small cave system that penetrates its igneous rock that can be seen from the coastline

Garfield Peak Trail, Crater Lake

Photo of Crater Lake

Walk difficulty: Moderate

Best time to visit: June-Aug

Cost: $

  • Garfield Peak is a mountain peak on the south end of Crater Lake in Crater Lake National Park, Oregon
  • The top of the peak reaches 7,976 feet (2,431 m) above sea level
  • The peak has a 1,000 feet (305 m) elevation trail to the summit from the Crater Lake lodge, one of the most popular hiking sites surrounding the lake

Lower Macleay Park to Pittock Mansion, Forest Park

Photo of Forest Park

Walk difficulty: Moderate

Best time to visit: June-Aug

Cost: $

  • Forest Park is a public municipal park in the Tualatin Mountains west of downtown Portland
  • It is one of the country's largest urban forest reserves
  • The park is mostly second-growth forest with a few patches of old growth

Hood River Waterfront Park

Photo of Hood River

Walk difficulty: Easy

Best time to visit: June-Aug

Cost: $

  • Hood River offers some of the best spots for windsurfing, kitesurfing, kayaking, standup paddleboarding, skiing and mountain biking
  • The city also features the family- and wind-sport–friendly Waterfront Park, a public pool, a skate park, biking trails, and several small public parks

Captain Cook Trail and Thor's Well

Photo of Thor's Well

Walk difficulty: Easy

Best time to visit: June-Aug

Cost: $

  • Cape Perpetua Scenic Area and the Cape Perpetua Visitor Center were built in the 1960s to highlight the unique beauty of the central Oregon Coast
  • The scenic area includes old growth spruce, Douglas fir, and western hemloc
  • Camping, picnicking, hiking, sightseeing, whale watching, and a visitor center with daily programs are all available within the Cape Perpetua Scenic Area

Shevlin Loop Trail, Shevlin Park

Photo of Shevlin Park

Walk difficulty: Easy

Best time to visit: June-Aug

Cost: $

  • Park located in Bend, first established in 1921
  • Notable natural and manmade features include Tumalo Creek, Aspen Hall, and Fremont Meadow

Oregon Islands National Wildlife Refuge, Bandon

Photo of Bandon

Best time to visit: June-Aug

Cost: $

  • The Oregon Islands provides wilderness protection to 1,853 small islands, rocks, and reefs plus two headlands, of Oregon's coastline from the Oregon–California border to Tillamook Head

Ribbon Trail to Floral Hill, Hendricks Park

Photo of Hendricks Park

Best time to visit: June-Aug

Cost: $

  • Oldest city park in Eugene, which contains mature forest, a rhododendron garden, and a native plant garden
  • The park has trails suitable for hiking, jogging, and birding

Wahkeena Falls Loop Trail, Columbia River Gorge National Scenic Area

Photo of Columbia River Gorge National Scenic Area

Walk difficulty: Moderate

Best time to visit: June-Aug

Cost: $

  • Canyon of the Columbia River in the Pacific Northwest, up to 4,000 feet (1,200 m) deep
  • The canyon forms the boundary between the state of Washington to the north and Oregon to the south

Cleetwood Cove Trail, Crater Lake National Park

Photo of Crater Lake National Park

Walk difficulty: Moderate

Best time to visit: June-Aug

Cost: $

  • Established in 1902, Crater Lake is the fifth-oldest national park in the United States and the only national park in Oregon
  • The park encompasses the caldera of Crater Lake, a remnant of Mount Mazama, a destroyed volcano, and the surrounding hills and forests

Harris Beach Trail to Harris Butte, Harris Beach State Park

Photo of Harris Beach State Park

Walk difficulty: Easy

Best time to visit: June-Aug

Cost: $

  • Harris Beach State Park is home to Bird Island (also known as Goat Island), which is reported to be the largest island off the Oregon Coast and is a National Wildlife Refuge.
  • The island is also a breeding site for rare birds such as the tufted puffin

Multnomah Falls Trail

Photo of Multnomah Falls

Walk difficulty: Moderate

Best time to visit: June-Aug

Cost: $

  • Waterfall located on Multnomah Creek in the Columbia River Gorge
  • Spanning two tiers on basalt cliffs, it is the tallest waterfall in the state of Oregon at 620 ft (189 m) in height
  • The Multnomah Creek Bridge, built in 1914, crosses below the falls

Oneonta Gorge Trail

Photo of Oneonta Gorge

Walk difficulty: Moderate

Best time to visit: June-Aug

Cost: $

  • Scenic gorge located in the Columbia River Gorge area
  • It has been designated as a botanical area because of the unique aquatic and woodland plants that grow there
  • Exposed walls of 25-million-year-old (Miocene epoch) basalt are home to a wide variety of ferns, mosses, hepatics, and lichens, many of which grow only in the Columbia River Gorge

Timberline Lodge, Government Camp

Photo of Government Camp

Best time to visit: Jan-Feb, Dec

Cost: $$$

  • Ski and snowboarding area of Timberline Lodge, a National Historic Landmark
  • It is one of a few ski areas in the United States with most of the skiable terrain below the main lodge
  • It is located on the south face of Mount Hood

Mt. Bachelor Ski Resort, Bend

Photo of Bend

Best time to visit: Jan-Feb, Dec

Cost: $$

  • Ski resort located in Central Oregon, on the northern side of Mount Bachelor, a stratovolcano rising atop a volcanic shield in the Cascade Range
  • It is the largest ski resort (by area) by more than 1,000 acres (4.0 km2) in Oregon
  • Mount Bachelor offers one of the nation's longest ski seasons, mid-November through the end of May (weather permitting)

Mirror Lake Loop Trail, Mount Hood

Photo of Mount Hood

Walk difficulty: Moderate

Best time to visit: June-Aug

Cost: $

  • Mount Hood is a potentially active stratovolcano in the Cascade Volcanic Arc
  • It was formed by a subduction zone on the Pacific coast
  • In addition to being Oregon's highest mountain, it is one of the loftiest mountains in the nation based on its prominence

Portland Japanese Garden

Photo of Portland Japanese Garden

Best time to visit: June-Aug

Cost: $

  • Traditional Japanese garden occupying 12 acres, located within Washington Park
  • The garden is composed of eight garden spaces and a Cultural Village
  • The desired effect of the garden is to realize a sense of peace, harmony, and tranquility and to experience the feeling of being a part of nature

Crooked River Trail, Smith Rock State Park

Photo of Smith Rock State Park

Walk difficulty: Easy

Best time to visit: June-Aug

Cost: $

  • State park located in central Oregon's High Desert
  • Its sheer cliffs of tuff and basalt are ideal for rock climbing of all difficulty levels
  • Smith Rock is generally considered the birthplace of modern American sport climbing, and is host to cutting-edge climbing routes
  • The trails have viewpoints along the routes that overlook the Crooked River and nearby rock formations

Trail of Ten Falls, Silver Falls State Park

Photo of Silver Falls State Park

Walk difficulty: Moderate

Best time to visit: June-Aug

Cost: $

  • State park that is the largest state park in Oregon
  • Its 8.7-mile (14.0 km) Canyon Trail/Trail of Ten Falls runs along the banks of Silver Creek and by ten waterfalls, from which the park received its name
  • Four of the ten falls have an amphitheater-like surrounding that allows the trail to pass behind the flow of the falls
  • In recent years, Silver Falls State Park has hosted star parties in partnership with the amateur astronomy organization in Salem