30 days in Oregon Itinerary

30 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary builder

Make it your trip
Fly
1
Redmond
— 2 nights
Drive
2
Grants Pass
— 3 nights
Drive
3
Coos Bay
— 3 nights
Drive
4
Florence
— 4 nights
Drive
5
Newport
— 4 nights
Drive
6
Astoria
— 4 nights
Drive
7
Portland
— 5 nights
Drive
8
Hood River
— 4 nights
Fly

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Redmond

— 2 nights
Redmond is a city in Deschutes County, Oregon, United States. Explore the numerous day-trip ideas around Redmond: Wildland Firefighters Monument (in Prineville) and Sisters (McKenzie Pass-Santiam Pass loop & Sahalie and Koosah Falls). There's much more to do: immerse yourself in nature at Smith Rock State Park, indulge in some personalized pampering at Shibui Spa, walk around Sam Johnson Park, and view the masterpieces at The Art of Alfred A. Dolezal Gallery.

For ratings, other places to visit, photos, and more tourist information, read our Redmond tour planner.

Orlando to Redmond is an approximately 9-hour flight. You can also drive; or do a combination of bus and train. The time zone difference moving from Eastern Standard Time to Pacific Standard Time is minus 3 hours. Plan for colder temperatures traveling from Orlando in November, with highs in Redmond at 50°F and lows at 25°F. Finish your sightseeing early on the 3rd (Wed) so you can travel to Grants Pass.

Things to do in Redmond

Parks · Scenic Drive · Outdoors · Nature

Side Trips

Find places to stay Nov 1 — 3:

Grants Pass

— 3 nights
Grants Pass is a city in, and the county seat of, Josephine County, Oregon, United States. You'll find plenty of places to visit near Grants Pass: Ashland (Main Street Adventure Tours & Lithia Park), Angelica Day Spa & Boutique (in Jacksonville) and Rogue River (in Medford). There's much more to do: view the masterpieces at The Glass Forge, take in the views from The Wimer Covered Bridge, see the interesting displays at Schmidt House Museum, and tour the pleasant surroundings at Wildlife Images - Rehabilitation & Education Center.

To see where to stay, traveler tips, and other tourist information, you can read our Grants Pass trip itinerary planner.

Getting from Redmond to Grants Pass by car takes about 4 hours. Traveling from Redmond in November, you can expect nighttime temperatures to be a bit warmer in Grants Pass, with lows of 36°F. Finish your sightseeing early on the 6th (Sat) so you can travel to Coos Bay.

Things to do in Grants Pass

Parks · Wildlife · Tours · Museums

Side Trips

Find places to stay Nov 3 — 6:

Coos Bay

— 3 nights
Coos Bay is a city located in Coos County, Oregon, United States, where the Coos River enters Coos Bay on the Pacific Ocean. You'll find plenty of places to visit near Coos Bay: Bandon (Bandon Historical Society Museum, Face Rock State Scenic Viewpoint, &more). And it doesn't end there: immerse yourself in nature at Shore Acres State Park, tee off at Bandon Dunes Golf Resort, and get engrossed in the history at Coos History Museum.

For more things to do, ratings, maps, and more tourist information, use the Coos Bay attractions tool.

Getting from Grants Pass to Coos Bay by car takes about 3 hours. Plan for a bit warmer temperatures traveling from Grants Pass in November, with highs in Coos Bay at 58°F and lows at 44°F. Wrap up your sightseeing on the 9th (Tue) to allow time to drive to Florence.

Things to do in Coos Bay

Parks · Nature · Outdoors · Golf

Side Trip

Find places to stay Nov 6 — 9:

Florence

— 4 nights
Florence is a coastal city in Lane County, in the U.S. state of Oregon. Get out of town with these interesting Florence side-trips: Cape Perpetua Visitor Center - Siuslaw National Forest (in Yachats), Rochester Covered Bridge (in Sutherlin) and Oakland Oregon Museum (in Oakland). The adventure continues: experience the excitement of Sandland Adventures, take in the pleasant sights at Strawberry Hill Wayside, immerse yourself in nature at Darlingtonia State Natural Site, and make a trip to Siuslaw River Bridge.

To find traveler tips, ratings, where to stay, and other tourist information, go to the Florence holiday website.

Traveling by car from Coos Bay to Florence takes 1.5 hours. Expect a daytime high around 58°F in November, and nighttime lows around 44°F. Wrap up your sightseeing on the 13th (Sat) to allow time to drive to Newport.

Things to do in Florence

Outdoors · Parks · Nature · Scenic Drive

Side Trips

Find places to stay Nov 9 — 13:

Newport

— 4 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Explore the numerous day-trip ideas around Newport: Yachats coastline (in Yachats) and Lincoln City (Beachtown Charities Thrift and Gift, Lincoln City Glass Center, &more). There's much more to do: tour the pleasant surroundings at Yaquina Head Outstanding Natural Area, get up close to creatures of the deep with a dolphin and whale watching tour, enjoy the sea views from Yaquina Head Lighthouse, and meet the residents at Oregon Coast Aquarium.

To see more things to do, traveler tips, ratings, and other tourist information, you can read our Newport trip planner.

Getting from Florence to Newport by car takes about 1.5 hours. Other options: take a bus. In November, plan for daily highs up to 54°F, and evening lows to 43°F. Finish your sightseeing early on the 17th (Wed) so you can drive to Astoria.

Things to do in Newport

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Nov 13 — 17:

Astoria

— 4 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 (Haystack Rock, Cannon Beach, &more) and Seaside Aquarium (in Seaside). Spend the 21st (Sun) exploring nature at Fort Clatsop National Memorial. And it doesn't end there: contemplate the waterfront views at Columbia River Maritime Museum, immerse yourself in nature at Fort Stevens State Park, and pause for some photo ops at Astoria Column.

For photos, other places to visit, maps, and more tourist information, go to the Astoria trip planner.

Drive from Newport to Astoria in 3.5 hours. Alternatively, you can take a bus. In November, plan for daily highs up to 55°F, and evening lows to 42°F. Wrap up your sightseeing on the 21st (Sun) to allow time to drive to Portland.

Things to do in Astoria

Parks · Nature · Historic Sites · Beaches

Side Trips

Find places to stay Nov 17 — 21:

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: Evergreen Aviation & Space Museum (in McMinnville), Cellar Door Wine Tours (in Lafayette) and Vista House (in Corbett). The adventure continues: look for gifts at Powell's City of Books, get to know the resident critters at Oregon Zoo, hike along Forest Park, and get a tailor-made plan with Volcano Lands - Private Tours.

For where to stay, maps, ratings, and more tourist information, refer to the Portland online trip itinerary builder.

You can drive from Astoria to Portland in 2 hours. Alternatively, you can take a bus. Expect a daytime high around 53°F in November, and nighttime lows around 42°F. Wrap up your sightseeing on the 26th (Fri) to allow time to drive to Hood River.

Things to do in Portland

Parks · Tours · Museums · Outdoors

Side Trips

Find places to stay Nov 21 — 26:

Hood River

— 4 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. You'll find plenty of places to visit near Hood River: Cascade Locks (Bonneville Lock & Dam & Punchbowl Waterfall). Next up on the itinerary: stroll through Columbia River Gorge National Scenic Area, trek along Historic Columbia River Highway State Trail, view the masterpieces at Art on Oak, and do a tasting at Sunshine Mill Winery.

To see photos, maps, and other tourist information, read Hood River trip site.

Traveling by car from Portland to Hood River takes 1.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Portland in November, Hood River is a bit cooler at night with lows of 36°F. Wrap up your sightseeing by early afternoon on the 30th (Tue) to allow time for the flight back home.

Things to do in Hood River

Parks · Museums · Outdoors · Nature

Side Trips

Find places to stay Nov 26 — 30:

Oregon travel guide

4.4
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.