Exploring the Oregon Trail

  • Columbia River Gorge
  • Multnomah Falls
  • Hood River
  • Wallowa Mountains
  • Wineries


August 25 – September 2, 2025


  • Portland’s hip vibe; and the fabulous Japanese Gardens
  • Exploration of the natural and human history of the Columbia River Gorge
  • Stories: Chief Joseph (namesake of the Oregon town, near the chief’s tomb); the Oregon Trail; Sam Hill; natives and early settlers; the river, then and now
  • Guided tour of the historic Timberline Lodge; drives on Oregon’s scenic byways
  • Outstanding inns in lovely locations; delicious local food and drink

Trip Description

Let’s pack our bags for more of the great American West, as we explore upstream on the impressive Columbia River! We’ll begin our trip in Portland, Oregon . . . and fly out of Boise, Idaho, at trip’s end. In between, we’ll encounter highlights on a day-in, day-out basis. The Columbia, itself: North America’s third largest river by volume; the Columbia Gorge Scenic Byway (one of the nation’s first); Multnomah Falls; the Bonneville Dam; and the riverscapes that border arid Sam Hill Country, east of the Cascade Mountains. Mountain majesty: from views of Washington’s big Mt. Adams (and Mt. Saint Helens), to the Timberline Lodge on Mt. Hood, and one of America’s best-kept secrets – the Wallowa Mountains of northeast Oregon. Cultural trappings of the region: Portland’s Japanese Gardens; the old western town of Dufur (OR); Columbia River and Walla Walla wineries; artsy, escape-from-it-all Joseph, Oregon. We’ll spend one night in each of our bookend cities (Portland and Boise), and two nights each in Hood River (OR), Walla Walla (WA), and on Lake Wallowa (close to Joseph, OR). Bring your explorer’s hat, a thirst for adventure, and a mind-set to encounter plenty that will surprise you!

What's Included

  • Comfortable ground transportation
  • Accommodation with breakfast for 8 nights
  • 5 lunches and 5 dinners
  • All activities/admissions per the itinerary
  • Guide and concierge service throughout the trip

Trip Price

$6,630 / person (double occupancy; single supplement, $1,195)

What's Not Included

Price does not include airfare, alcohol, other meals, optional activities, or optional trip insurance.

Couldn't have asked for more in terms of weather, accommodations and scenery. Can't wait to go on another adventure with Explore Up Close!
My husband and I love the attention to detail. We always have a wonderful experience: visiting new and interesting places, eating lots of good food, making new friends, and exploring new places!
..well-planned, from interesting and fun excursions planned each day, to comfortable lodging and transportation. Our trip leaders, Chumley and Khal, were impressive with their knowledge of each area we explored and gracious in their planning of every aspect of our trips.

Trip insurance safeguards your travel investment, your belongings, and most importantly, you. Though trip insurance is optional, we strongly encourage travelers to purchase trip insurance in the event you have to cancel or leave a trip for any reason. Please note, all trip participants should wait for confirmation from Explore Up Close that the trip has the minimum sign-up required to be a “go” before purchasing travel insurance or airline tickets. Please confirm with Explore Up Close before making any additional travel arrangements.

Once you have received confirmation from Explore Up Close, we recommend contacting a travel insurance provider directly to request a quote and compare pricing and features. You can find other providers that may fit your needs at www.insuremytrip.com, or we can gladly connect you with our travel agent.

Please note, all trip participants should wait for confirmation from Explore Up Close that the trip has the minimum sign-up required to be a “go” before purchasing airline tickets.

Explore Up Close will provide a recommended flight itinerary for your consideration, which is intended as a helpful suggestion. We encourage travelers to choose airfare depending on their personal preferences, as some travelers may prefer to travel independently and meet at our destination, or may wish to extend their travels at the beginning or end of the trip. Our travel agent is available to assist you with booking flights and trip insurance.

Again, please confirm with Explore Up Close before purchasing your airline tickets or making additional travel arrangements!


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