50 days in Portland & Bend Itinerary

50 days in Portland & Bend Itinerary

Created using Inspirock United States vacation planner

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Route & dates

50 days in Portland & Bend Itinerary

Start: Redmond
Fly:  11​h 15​min
1
Portland
— 24 nights
+2
bus + foot + Fly:  13​h 30​min
2
Bend
— 24 nights
Drive:  30​min
End: Redmond

24
nights
Portland

Portland ©
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 Boston (Otis House, Freedom Trail, & more), Dolphin & Whale Watching (in Gloucester) and Rockport Breakwater (in Rockport). Next up on the itinerary: appreciate the extensive heritage of Marginal Way Walkway, see the interesting displays at Peabody Essex Museum, take in the awesome beauty at Mount Battie, and contemplate the long history of The House of the Seven Gables.

For where to stay, photos, ratings, and tourist information, you can read our Portland itinerary builder site .

Redmond to Portland is an approximately 11.5-hour flight. You can also drive. The time zone changes from Pacific Standard Time (PST) to Eastern Standard Time (EST), which is usually a 3 hour difference. Expect a bit cooler weather when traveling from Redmond in July: highs in Portland hover around 79°F, while lows dip to 61°F. Cap off your sightseeing on the 25th (Sat) early enough to travel to Bend.

Things to do in Portland

Parks Outdoors Museums

Side Trips

Boston, Salem, North Conway, Ogunquit, Camden
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Dolphin & Whale Watching
Duck Tours

24
nights
Bend

Bend ©
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.
Change things up with these side-trips from Bend: Redmond (Tumalo Mountain & Smith Rock State Park), Dee Wright Observatory (in Blue River) and East Lake (in La Pine). There's lots more to do: get interesting insight from Tours, explore the wealth of natural beauty at Deschutes National Forest, Head underground at Lava River Cave, and get a new perspective on nature at High Desert Museum.

To find where to stay, ratings, reviews, and tourist information, read Bend trip planner .

You can do a combination of bus and flight from Portland to Bend in 13.5 hours. Other options are to fly; or drive. The time zone difference when traveling from Portland to Bend is minus 3 hours. When traveling from Portland in July, plan for somewhat warmer days in Bend, with highs around 85°F, while nights are a bit cooler with lows around 52°F. Wrap up your sightseeing on the 19th (Wed) to allow time to drive back home.

Things to do in Bend

Parks Outdoors Nature

Side Trips

Sisters, Redmond, Sunriver, Oakridge, Prineville
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
River Rafting & Tubing
High Desert Museum ©
High Desert Museum

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