27 days in Colorado Springs & Oregon Itinerary

27 days in Colorado Springs & Oregon Itinerary

Created using Inspirock United States tour itinerary planner

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Make it your trip
Fly
1
Colorado Springs
— 8 nights
Fly
2
Ashland
— 2 nights
Drive
3
Bandon
— 3 nights
Drive
4
Yachats
— 1 night
Drive
5
Astoria
— 3 nights
Drive
6
Hood River
— 4 nights
Drive
7
Portland
— 5 nights

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Colorado Springs

— 8 nights
Stunning Garden of the Gods Park scenery, blue skies and the glory of Pikes Peak-America’s Mountain have attracted visitors to Colorado Springs for more than a century.
Venture out of the city with trips to Golden History Museum & Park (in Golden), Denver (Denver Museum of Nature & Science, Denver Zoo, &more) and Mount Falcon Castle Trail (in Morrison). Pack the 3rd (Mon) with family-friendly diversions at Cave of the Winds Mountain Park. And it doesn't end there: stroll around Garden of the Gods, learn about wildlife with up-close encounters at Cheyenne Mountain Zoo, get your bearings at Glen Eyrie Castle, and expand your understanding of the military at United States Air Force Academy.

To find photos, reviews, where to stay, and other tourist information, refer to the Colorado Springs holiday planner.

Portland to Colorado Springs is an approximately 6-hour flight. You can also drive; or take a bus. The time zone changes from Pacific Standard Time (PST) to Mountain Standard Time (MST), which is usually a 1 hour difference. Expect little chillier evenings in Colorado Springs when traveling from Portland in April, with lows around 33°F. Finish your sightseeing early on the 7th (Fri) to allow enough time to fly to Ashland.

Things to do in Colorado Springs

Parks · Museums · Theme Parks · Historic Sites

Side Trips

Find places to stay Apr 29 — May 7:

Ashland

— 2 nights
Ashland is a city in Jackson County, in the State of Oregon. Kick off your visit on the 8th (Sat): take in the exciting artwork at Gathering Glass Studio, walk around Lithia Park, then catch a live performance at Oregon Shakespeare Festival, and finally relax and float downstream with a rafting and tubing tour. On your second day here, experience rural life at Lavender Fields Forever, relax in the rural setting at Rolling Hills Alpacas, and then don't miss a visit to Art Presence Art Center.

To see maps, photos, traveler tips, and tourist information, go to the Ashland road trip planning site.

Traveling by flight from Colorado Springs to Ashland takes 4.5 hours. Alternatively, you can drive; or take a bus. The time zone difference moving from Mountain Standard Time to Pacific Standard Time is minus 1 hour. Prepare for somewhat warmer weather when traveling from Colorado Springs in May: high temperatures in Ashland hover around 77°F and lows are around 49°F. Finish your sightseeing early on the 9th (Sun) to allow enough time to drive to Bandon.

Things to do in Ashland

Outdoors · Tours · Adventure · Parks

Side Trips

Find places to stay May 7 — 9:

Bandon

— 3 nights
Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. Get out of town with these interesting Bandon side-trips: Coos Bay (Steve Prefontaine Murals & Shore Acres State Park) and Oregon Dunes National Recreation Area (in Reedsport). The adventure continues: admire the majestic nature at Face Rock State Scenic Viewpoint, tee off at Bandon Dunes Golf Resort, stroll around Kronenberg Park, and stroll through Bandon State Park.

For photos, more things to do, traveler tips, and tourist information, use the Bandon trip app.

You can drive from Ashland to Bandon in 4 hours. Alternatively, you can take a bus; or take a bus. Traveling from Ashland in May, expect nights in Bandon to be about the same, around 49°F, while days are slightly colder, around 62°F. Cap off your sightseeing on the 12th (Wed) early enough to go by car to Yachats.

Things to do in Bandon

Parks · Nature · Outdoors · Golf

Side Trips

Find places to stay May 9 — 12:

Yachats

— 1 night
Yachats is a small coastal city in Lincoln County, Oregon, United States. On the 13th (Thu), visit a coastal fixture at Heceta Head Lighthouse, explore the striking landscape at Thor's Well, then take a memorable drive along Cape Perpetua Visitor Center - Siuslaw National Forest, and finally take in the waterfront at Yachats coastline.

Plan a trip to Yachats easily and quickly by telling Inspirock to suggest an itinerary.

You can drive from Bandon to Yachats in 2.5 hours. Alternatively, you can do a combination of bus and taxi; or take a bus. Expect a daytime high around 58°F in May, and nighttime lows around 46°F. Finish your sightseeing early on the 13th (Thu) so you can drive to Astoria.

Things to do in Yachats

Nature · Parks · Scenic Drive · Outdoors

Side Trip

Find places to stay May 12 — 13:

Astoria

— 3 nights

Spirit of the Columbia

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Explore the numerous day-trip ideas around Astoria: Cannon Beach (Ecola State Park, Haystack Rock, &more). And it doesn't end there: steep yourself in history at Fort Clatsop National Memorial, stroll through Seafarers' Park, appreciate the history behind Astoria Column, and admire the majestic nature at Fort Stevens State Park.

To see traveler tips, photos, more things to do, and tourist information, go to the Astoria trip maker tool.

Traveling by car from Yachats to Astoria takes 4 hours. Alternatively, you can do a combination of flight and bus; or take a bus. May in Astoria sees daily highs of 62°F and lows of 48°F at night. Wrap up your sightseeing on the 16th (Sun) to allow time to drive to Hood River.

Things to do in Astoria

Parks · Nature · Historic Sites · Outdoors

Side Trips

Find places to stay May 13 — 16:

Hood River

— 4 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Explore the numerous day-trip ideas around Hood River: Bonneville Lock & Dam (in Cascade Locks), Timberline Lodge and Ski Area (in Timberline Lodge) and Kiyokawa Family Orchards (in Parkdale). There's much more to do: contemplate the waterfront views at Columbia River Gorge National Scenic Area, see the interesting displays at Western Antique Aeroplane & Automobile Museum, learn about winemaking at Wy'East Vineyards, and go for a walk through Rowena Crest Viewpoint.

To find reviews, other places to visit, maps, and tourist information, you can read our Hood River trip itinerary builder tool.

Traveling by car from Astoria to Hood River takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, plan for daily highs up to 67°F, and evening lows to 49°F. Finish up your sightseeing early on the 20th (Thu) so you can go by car to Portland.

Things to do in Hood River

Parks · Nature · Outdoors · Wildlife

Side Trips

Find places to stay May 16 — 20:

Portland

— 5 nights

City of Roses

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.
Get out of town with these interesting Portland side-trips: Wooden Shoe Tulip Farm (in Woodburn), Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). There's much more to do: admire the natural beauty at Portland Japanese Garden, learn the secrets of beer at a beer tour and tasting, have fun and explore at Portland Children's Museum, and admire the landmark architecture of Pittock Mansion.

For photos, where to stay, more things to do, and other tourist information, read Portland road trip website.

Drive from Hood River to Portland in 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 70°F in May, and nighttime lows around 51°F. Finish your sightseeing early on the 25th (Tue) so you can travel back home.

Things to do in Portland

Parks · Museums · Tours · Outdoors

Side Trips

Find places to stay May 20 — 25:

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Oregon travel guide

4.5
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.