15 days in Central Oregon Itinerary
Created using Inspirock Central Oregon holiday maker
Start: Kansas City
Fly
1
Bend
— 3 nights
Drive
2
Madras
— 4 nights
Drive
3
Terrebonne
— 1 night
Drive
4
Prineville
— 2 nights
Drive
5
Redmond
— 1 night
Drive
6
Sunriver
— 3 nights
Drive to Roberts Field, Fly to Kansas City
End: Kansas City
Mon, Nov 7 - Mon, Nov 21
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Bend — 3 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.Step out of Bend to go to Sisters and see Proxy Falls, which is approximately 1 hour away. There's lots more to do: admire the sheer force of Tumalo Falls, examine the collection at High Desert Museum, contemplate the geological forces at Newberry National Volcanic Monument, and trek along Falls Creek Trail to Green Lake.
To find other places to visit, ratings, more things to do, and tourist information, read our Bend trip builder tool.
Kansas City to Bend is an approximately 7-hour flight. You can also drive; or take a bus. The time zone changes from Central Standard Time (CST) to Pacific Standard Time (PST), which is usually a -2 hour difference. November in Bend sees daily highs of 48°F and lows of 28°F at night. Wrap up your sightseeing on the 10th (Thu) early enough to drive to Madras.
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Madras — 4 nights

Madras is a city in Jefferson County, Oregon, United States. Get out of town with these interesting Madras side-trips: Hood River (Mount Hood & Mirror Lake Trail) and Government Camp (Little Crater Lake & Trillium Lake). And it doesn't end there: explore the activities along Columbia River Gorge National Scenic Area, admire the majestic nature at The Cove Palisades State park, and see the interesting displays at Erickson Aircraft Collection.
To see more things to do, reviews, other places to visit, and other tourist information, read our Madras holiday website.
Traveling by car from Bend to Madras takes an hour. Alternatively, you can drive. November in Madras sees daily highs of 50°F and lows of 25°F at night. Finish up your sightseeing early on the 14th (Mon) so you can go by car to Terrebonne.
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To see more things to do, reviews, other places to visit, and other tourist information, read our Madras holiday website.
Traveling by car from Bend to Madras takes an hour. Alternatively, you can drive. November in Madras sees daily highs of 50°F and lows of 25°F at night. Finish up your sightseeing early on the 14th (Mon) so you can go by car to Terrebonne.
Side Trips
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Terrebonne — 1 night

Terrebonne is an unincorporated community and census-designated place (CDP) in Deschutes County, Oregon, United States. Kick off your visit on the 14th (Mon): witness a stunning natural landmark at Cougar Hot Springs.
For ratings, other places to visit, more things to do, and other tourist information, read Terrebonne vacation planner.
Terrebonne is just a short distance from Madras. November in Terrebonne sees daily highs of 50°F and lows of 25°F at night. On the 15th (Tue), you're off to Prineville.
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For ratings, other places to visit, more things to do, and other tourist information, read Terrebonne vacation planner.
Terrebonne is just a short distance from Madras. November in Terrebonne sees daily highs of 50°F and lows of 25°F at night. On the 15th (Tue), you're off to Prineville.
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Prineville — 2 nights

Prineville is a city in and the county seat of Crook County, Oregon, United States. Explore Prineville's surroundings by going to John Day Fossil Beds National Monument (in John Day) and John Day Fossil Beds National Monument, Painted Hills Unit (in Dayville). There's more to do: take a memorable drive along Crooked River Scenic Drive and admire the majestic nature at Prineville Reservoir State Park.
For other places to visit, maps, where to stay, and tourist information, go to the Prineville trip itinerary maker.
Prineville is just a stone's throw from Terrebonne. In November, daily temperatures in Prineville can reach 50°F, while at night they dip to 25°F. Wrap up your sightseeing on the 17th (Thu) early enough to drive to Redmond.
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For other places to visit, maps, where to stay, and tourist information, go to the Prineville trip itinerary maker.
Prineville is just a stone's throw from Terrebonne. In November, daily temperatures in Prineville can reach 50°F, while at night they dip to 25°F. Wrap up your sightseeing on the 17th (Thu) early enough to drive to Redmond.
Side Trips
Highlights from your trip
Redmond — 1 night

Redmond is a city in Deschutes County, Oregon, United States. Kick off your visit on the 18th (Fri): admire the majestic nature at Smith Rock State Park.
For photos, ratings, maps, and tourist information, read our Redmond travel itinerary planner.
Redmond is just a short distance from Prineville. November in Redmond sees daily highs of 50°F and lows of 25°F at night. Wrap up your sightseeing on the 18th (Fri) to allow time to drive to Sunriver.
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For photos, ratings, maps, and tourist information, read our Redmond travel itinerary planner.
Redmond is just a short distance from Prineville. November in Redmond sees daily highs of 50°F and lows of 25°F at night. Wrap up your sightseeing on the 18th (Fri) to allow time to drive to Sunriver.
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Sunriver — 3 nights

Sunriver, Oregon is a census-designated place and 3300acre planned residential and resort community in Deschutes County, Oregon, United States. On the 19th (Sat), see the sky in a new way at Oregon Observatory and then tour the pleasant surroundings at Trail to Benham Falls. On the 20th (Sun), you'll have a packed day of sightseeing: take in the dramatic scenery at Salt Creek Falls and then look and learn at Dee Wright Observatory.
To find photos, other places to visit, traveler tips, and other tourist information, refer to the Sunriver trip planner.
Drive from Redmond to Sunriver in an hour. In November, plan for daily highs up to 48°F, and evening lows to 28°F. Wrap up your sightseeing on the 21st (Mon) to allow time to drive back home.
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To find photos, other places to visit, traveler tips, and other tourist information, refer to the Sunriver trip planner.
Drive from Redmond to Sunriver in an hour. In November, plan for daily highs up to 48°F, and evening lows to 28°F. Wrap up your sightseeing on the 21st (Mon) to allow time to drive back home.
Side Trips
Highlights from your trip
Central Oregon travel guide
The Cascade Mountains catch most of the precipitation from the Pacific Ocean, leaving residents of Central Oregon on the mountains' eastern side with an average of 300 sunny days per year for hiking, mountain biking, fishing, kayaking, whitewater rafting, golfing, skiing, and rock-climbing. The weather and terrain are so inviting for outdoor activities that many people have moved to the region specifically for this purpose. The combination of plentiful sunshine and volcanic soil from the Cascades has given rise to a booming wine industry, and you'll find scenic wineries throughout the area. Bend serves as the de facto capital of Central Oregon, which encompasses three counties and numerous small towns, and offers a mix of fine dining, microbreweries, and lively pubs.