50 days in Portland & Bend Itinerary

50 days in Portland & Bend Itinerary

Created using Inspirock United States vacation planner

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Make it your trip
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Portland
— 24 nights
Fly
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Bend
— 24 nights
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Portland

— 24 nights

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Explore Portland's surroundings by going to Dolphin & Whale Watching (in Gloucester), Rockport Breakwater (in Rockport) and Boston (Otis House, Freedom Trail, &more). Next up on the itinerary: get to know the fascinating history of Marginal Way Walkway, enjoy the sea views from Nubble Lighthouse, explore the galleries of The House of the Seven Gables, and indulge your thirst for a good beer at Allagash Brewing Company.

To find ratings, where to stay, and tourist information, you can read our Portland planner.

Redmond to Portland is an approximately 11.5-hour flight. You can also drive. The time zone difference when traveling from Redmond to Portland is 3 hours. When traveling from Redmond in July, plan for slightly colder days and a bit warmer nights in Portland: temperatures range from 79°F by day to 61°F at night. Wrap up your sightseeing on the 25th (Sat) early enough to fly to Bend.

Things to do in Portland

Parks · Outdoors · Historic Sites · Museums

Side Trips

Bend

— 24 nights
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.
You'll find plenty of places to visit near Bend: Redmond (Tumalo Mountain & Smith Rock State Park), East Lake (in La Pine) and Dee Wright Observatory (in Blue River). The adventure continues: let the river carry you with a rafting and tubing tour, cruise along McKenzie Pass-Santiam Pass loop, explore the activities along Deschutes River, and see what you can catch with a fishing tour.

To find more things to do, other places to visit, reviews, and other tourist information, you can read our Bend travel itinerary planner.

Getting from Portland to Bend by flight takes about 12.5 hours. Other options: drive; or do a combination of bus and train. Due to the time zone difference, you'll gain 3 hours traveling from Portland to Bend. Traveling from Portland in July, you will find days in Bend are somewhat warmer (85°F), and nights are little chillier (52°F). Finish up your sightseeing early on the 19th (Wed) so you can go by car back home.

Things to do in Bend

Parks · Outdoors · Nature · Trails

Side Trips