18 days in Mount Hood & Columbia River Gorge, Yellowstone National Park & Regent Itinerary

Start off your visit on the 11th (Fri): relax in the rural setting at Kiyokawa Family Orchards and then fly down the slopes at Timberline Lodge and Ski Area.

To find maps, where to stay, and tourist information, read Timberline Lodge road trip website.

Des Moines to Timberline Lodge is an approximately 27-hour car ride. You'll gain 2 hours traveling from Des Moines to Timberline Lodge due to the time zone difference. Expect little chillier weather when traveling from Des Moines in September: highs in Timberline Lodge hover around 71°F, while lows dip to 57°F. Cap off your sightseeing on the 11th (Fri) early enough to go by car to Troutdale.

Kick off your visit on the 12th (Sat): take a memorable excursion with Envi Adventures, contemplate the long history of Columbia River Highway, then take an in-depth tour of Sandy Area Historical Museum, and finally admire the sheer force of Multnomah Falls. Here are some ideas for day two: see human ingenuity at work at Bonneville Lock & Dam, trek along Oneonta Gorge, and then admire the striking features of Vista House.

To find more things to do, traveler tips, maps, and other tourist information, use the Troutdale trip planner.

Traveling by car from Timberline Lodge to Troutdale takes 1.5 hours. In September, daily temperatures in Troutdale can reach 76°F, while at night they dip to 54°F. Cap off your sightseeing on the 13th (Sun) early enough to go by car to The Dalles.

On the 14th (Mon), examine the collection at Columbia Gorge Discovery Center & Museum, stop by Big Winds, then see the interesting displays at Western Antique Aeroplane & Automobile Museum, and finally trek along Historic Columbia River Highway State Trail. On the next day, don't miss a visit to The Dalles Murals, contemplate the waterfront views at Trillium Lake, then contemplate the geological forces at Mount Hood, and finally examine the collection at Fire Museum in City Hall.

To find where to stay, maps, photos, and more tourist information, refer to the The Dalles day trip website.

Traveling by car from Troutdale to The Dalles takes 1.5 hours. September in The Dalles sees daily highs of 80°F and lows of 54°F at night. Wrap up your sightseeing by early afternoon on the 16th (Wed) to allow enough time to drive to Yellowstone National Park.

Yellowstone National Park is known for nature, wildlife, and sightseeing. Your trip includes some of its best attractions: explore the stunning scenery at Grand Canyon of the Yellowstone, take in the natural beauty of Grand Prismatic Spring, explore the activities along Yellowstone Lake, and identify plant and animal life at Lamar Valley.

To see where to stay, more things to do, other places to visit, and tourist information, go to the Yellowstone National Park visit planning tool.

Getting from The Dalles to Yellowstone National Park by car takes about 13 hours. Due to the time zone difference, you'll lose 1 hour traveling from The Dalles to Yellowstone National Park. Traveling from The Dalles in September, expect Yellowstone National Park to be much colder, temps between 60°F and 33°F. On the 26th (Sat), wrap the sightseeing up by early afternoon so you can drive to Regent.

On the 27th (Sun), contemplate the long history of Petrified Wood Park, then see the interesting displays at Grand River Museum, and then take a memorable drive along Enchanted Highway. Keep things going the next day: take in the spiritual surroundings of Assumption Abbey.

To find traveler tips, maps, where to stay, and more tourist information, read our Regent online journey planner.

You can drive from Yellowstone National Park to Regent in 9 hours. In September, Regent is somewhat warmer than Yellowstone National Park - with highs of 73°F and lows of 46°F. Wrap up your sightseeing by early afternoon on the 28th (Mon) to allow enough time to drive back home.