10 days in Oregon Itinerary

An old logging town at the crux of the high desert and ponderosa pine forest, Bend melds a love of the outdoors with cosmopolitan flair.

On the 1st (Sun), examine the collection at High Desert Museum and then admire the majestic nature at Smith Rock State Park. Get ready for a full day of sightseeing on the next day: explore the striking landscape at Newberry National Volcanic Monument, then get a taste of the local shopping with Artists Gallery Sunriver, and then take a memorable tour with Tours.

For other places to visit, where to stay, traveler tips, and tourist information, you can read our Bend road trip planning tool.

Jacksonville to Bend is an approximately 12.5-hour flight. You can also drive; or do a combination of train and bus. The time zone changes from Eastern Standard Time (EST) to Pacific Standard Time (PST), which is usually a -3 hour difference. When traveling from Jacksonville in September, plan for slightly colder days and colder nights in Bend: temperatures range from 73°F by day to 44°F at night. Wrap up your sightseeing by early afternoon on the 3rd (Tue) to allow time for the car ride to Cannon Beach.

Cannon Beach is a city in Clatsop County, Oregon, United States. Visiting Haystack Rock and Fort Clatsop National Memorial will get you outdoors. Head to Wheeler Station Antiques and Cannon Beach Bookstorefor plenty of shopping. Step out of Cannon Beach to go to Astoria and see Astoria Column, which is approximately 42 minutes away. Next up on the itinerary: kick back and relax at Cannon Beach, see the interesting displays at Seaside Inverted Experience, admire the majestic nature at Oswald West State Park, and pause for some photo ops at Seaside Beach Lewis and Clark Monument.

For maps, traveler tips, more things to do, and tourist information, go to the Cannon Beach day trip planning website.

You can drive from Bend to Cannon Beach in 5.5 hours. Alternatively, you can fly; or take a bus. Expect a bit warmer evenings in Cannon Beach when traveling from Bend in September, with lows around 52°F. Wrap up your sightseeing on the 6th (Fri) early enough to drive to Portland.

A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.

Head to Powell's City of Books and Northwest (Nob Hill)for plenty of shopping. Take a break from the city and head to Columbia River Gorge National Scenic Area and Multnomah Falls. Explore the numerous day-trip ideas around Portland: Sokol Blosser Winery (in Dundee), Natalies Estate Winery (in Newberg) and Willamette Valley Vineyards (in Turner). It doesn't end there: admire the natural beauty at Portland Japanese Garden and brush up on your knowledge of spirits at New Deal Distillery.

Plan my Portland trip by asking Inpirock to come up with tips and suggestions.

You can drive from Cannon Beach to Portland in 1.5 hours. Alternatively, you can take a bus. While traveling from Cannon Beach, expect a bit warmer days and about the same nights in Portland, ranging from highs of 76°F to lows of 55°F. On the 10th (Tue), you're off to home.