57 days in Oregon Itinerary

Medford is a city in, and county seat of, Jackson County, Oregon, United States. DANCIN Vineyards and Rogue Valley ZipLine Adventure are good opportunities to explore the local culture. Discover out-of-the-way places like Upper and Lower Table Rock and Oregon Caves National Monument and Preserve. Change things up with these side-trips from Medford: Grants Pass (Riverside Park, The Glass Forge, &more), Klamath County Museum (in Klamath Falls) and Cave Junction (Tiger Preservation Center & Great Cats World Park). And it doesn't end there: hike along Natural Bridge Loop, contemplate the waterfront views at Rogue River, do a tasting at Red Lily Vineyards, and stop by Rogue Creamery.

To see reviews, where to stay, more things to do, and other tourist information, use the Medford online travel planner.

San Francisco to Medford is an approximately 4-hour flight. You can also drive. Traveling from San Francisco in March, plan for a bit cooler nights in Medford, with lows around 39°F. Wrap up your sightseeing on the 21st (Sun) to allow time to travel to Eugene.

Eugene is a city of the Pacific Northwest located in the U.S. The Historic Carousel and Museum and Jordan Schnitzer Museum of Art will appeal to museum buffs. Get some cultural insight at King Estate Winery and Shelton McMurphey Johnson House. Change things up with these side-trips from Eugene: Colliding Rivers Viewpoint (in Glide), Roseburg (Stewart Park, Roseburg, Oregon, Abacela, &more) and Wildlife Safari (in Winston). And it doesn't end there: grab your bike and head to Willamette River Trail, stroll around Skinner Butte Park, hike along Mt Pisgah, and look for all kinds of wild species at Cascades Raptor Center.

For more things to do, other places to visit, traveler tips, and more tourist information, you can read our Eugene travel itinerary planner.

Traveling by car from Medford to Eugene takes 3 hours. Expect a daytime high around 57°F in March, and nighttime lows around 39°F. Finish your sightseeing early on the 27th (Sat) so you can drive to 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.

Take a break from the city and head to Newberry National Volcanic Monument and Pilot Butte State Scenic Viewpoint. Get a sense of the local culture at Old Mill District and City of Sisters. Explore Bend's surroundings by going to Sahalie and Koosah Falls (in Sisters), Salt Creek Falls (in Oakridge) and Quail Run Golf Course (in La Pine). There's much more to do: hit the slopes at Mt. Bachelor Ski Area, admire the majestic nature at Tumalo State Park, indulge your thirst for a good beer at Deschutes Brewery, and look for all kinds of wild species at Wizard Falls Fish Hatchery.

To find photos, where to stay, ratings, and tourist information, use the Bend online tour itinerary maker.

Traveling by car from Eugene to Bend takes 3 hours. Alternatively, you can take a bus. Expect little chillier evenings in Bend when traveling from Eugene in March, with lows around 31°F. Wrap up your sightseeing on the 2nd (Fri) to allow time to drive to Hood River.

The city of Hood River is the seat of Hood River County, Oregon, United States. Satisfy your inner culture vulture at Western Antique Aeroplane & Automobile Museum and Columbia Gorge Discovery Center & Museum. Eschew the tourist crowds and head to Horsetail Falls- Columbia River Gorge and Mt. Hood National Forest. You'll find plenty of places to visit near Hood River: River Rafting & Tubing (in Maupin), Trillium Lake (in Government Camp) and Bonneville Lock & Dam (in Cascade Locks). The adventure continues: take in the dramatic scenery at Wahkeena Falls, look for all kinds of wild species at Bonneville Hatchery, stroll through Sturgeon Viewing Pond and Interpretive Center, and learn about winemaking at Mt. Hood Winery.

To find ratings, traveler tips, more things to do, and more tourist information, go to the Hood River online trip planner.

Traveling by car from Bend to Hood River takes 3.5 hours. Alternatively, you can fly; or take a bus. Traveling from Bend in April, expect somewhat warmer with lows of 43°F in Hood River. Wrap up your sightseeing on the 7th (Wed) early enough to drive to Portland.

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.

You'll explore and learn at Live Laugh Love Art and Gilbert House Children's Museum. Give yourself a bit of retail therapy at Northwest (Nob Hill) and Woodburn Premium Outlets. Explore Portland's surroundings by going to Portland Women's Forum State Scenic Viewpoint (in Troutdale), Corbett (Latourell Falls, Vista House, &more) and Oneonta Gorge (in Cascade Locks). There's much more to do: admire the majestic nature at Tryon Creek State Natural Area, surround yourself with nature on Volcano Lands - Private Tours, stroll around Forest Park, and learn about winemaking at Willamette Valley Vineyards.

For ratings, reviews, photos, and more tourist information, you can read our Portland travel route planner.

Traveling by car from Hood River to Portland takes 1.5 hours. Alternatively, you can take a bus; or take a train. April in Portland sees daily highs of 63°F and lows of 45°F at night. Wrap up your sightseeing on the 16th (Fri) early enough to drive to Astoria.

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.

Visit Fort Clatsop National Memorial and Lightship Columbia for their historical value. Your cultural itinerary includes sights like Flavel House Museum and Camp 18 Logging Museum & Restaurant. Explore Astoria's surroundings by going to Cannon Beach (Cannon Beach Gallery, Hug Point State Park, &more) and Seaside (Tillamook Head, Seaside Beach, &more). The adventure continues: hike along Astoria Oregon Riverwalk, stroll around Seafarers' Park, steep yourself in history at Lewis & Clark Salt Works, and don't miss a visit to Goonies House.

For reviews, more things to do, traveler tips, and tourist information, you can read our Astoria trip planner.

You can drive from Portland to Astoria in 2 hours. Another option is to take a bus. Traveling from Portland in April, you will find days in Astoria are a bit cooler (58°F), and nights are about the same (43°F). Finish your sightseeing early on the 21st (Wed) to allow enough time to drive to Tillamook.

The city of Tillamook is the county seat of Tillamook County, Oregon, United States. Escape the urban bustle at Cape Lookout State Park and Cape Kiwanda State Natural Area. Your cultural itinerary includes sights like Cape Meares Lighthouse and International Police Museum. Get out of town with these interesting Tillamook side-trips: Oswald West State Park (in Cannon Beach), Kelly's Brighton Marina (in Rockaway Beach) and Nehalem Bay State Park (in Nehalem). The adventure continues: stroll through Rockaway Beach Wayside, trot along with Green Acres Beach & Trail Rides, admire the sheer force of Munson Creek Falls, and take a peaceful walk through Tillamook Forest Center.

Plan a Tillamook trip in moments using our itinerary builder.

Getting from Astoria to Tillamook by car takes about 2 hours. Other options: take a bus. The time zone difference when traveling from Astoria to Tillamook is 1 hour. In April, daytime highs in Tillamook are 58°F, while nighttime lows are 41°F. Cap off your sightseeing on the 25th (Sun) early enough to go by car to Newport.

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.

Your itinerary includes some good beach time at Nye Beach and Taft Bay. You'll discover tucked-away gems like Yachats coastline and Prehistoric. Explore Newport's surroundings by going to The Sparks Gallery (in Depoe Bay), Lincoln City (Connie Hansen Garden Conservancy, Mossy Creek Pottery, &more) and Earthworks Gallery (in Yachats). The adventure continues: take in the dramatic natural features at Cape Foulweather, engage your brain at Hatfield Marine Science Center, make a trip to Boiler Bay State Wayside, and cruise along Otter Crest Loop.

To see photos, reviews, maps, and tourist information, refer to the Newport trip itinerary planning app.

Getting from Tillamook to Newport by car takes about 2 hours. Other options: take a bus. The time zone difference when traveling from Tillamook to Newport is minus 1 hour. In April, daytime highs in Newport are 55°F, while nighttime lows are 42°F. Finish your sightseeing early on the 1st (Sat) so you can drive to Florence.

Florence is a coastal city in Lane County, in the U.S. Get some cultural insight at Umpqua River Lighthouse, Museum,and Gift shop and Oregon Coast. You'll explore the less-touristy side of things at Devil's Churn and Heceta Beach. You'll find plenty of places to visit near Florence: Reedsport (Dean Creek Elk Viewing Area & Oregon Dunes National Recreation Area) and Umpqua Triangle Oyster from Aquaculture (in Winchester Bay). Next up on the itinerary: stroll through Hobbit Trail, immerse yourself in nature at Darlingtonia State Natural Site, take in the views from Siuslaw River Bridge, and get the adrenaline pumping with Sandland Adventures.

To find more things to do, other places to visit, ratings, and other tourist information, read Florence day trip site.

Traveling by car from Newport to Florence takes 1.5 hours. Alternatively, you can take a bus. In May in Florence, expect temperatures between 62°F during the day and 49°F at night. Wrap up your sightseeing on the 5th (Wed) early enough to drive to Bandon.

Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. Get outdoors at Shore Acres State Park and Bandon Dunes Golf Resort. Satisfy your inner culture vulture at Cape Blanco Lighthouse and Coquille River Lighthouse. Explore Bandon's surroundings by going to Port Orford (Humbug Mountain State Park & Cape Blanco State Park), Betty Kay Charter (in Charleston) and Coos Bay (Cranberry Sweets, Cape Arago State Park, &more). There's lots more to do: explore the striking landscape at Face Rock State Scenic Viewpoint, stroll around Bandon South Jetty County Park, identify plant and animal life at West Coast Game Park Safari, and stop by Face Rock Creamery.

To see ratings and other tourist information, read our Bandon route planner.

Traveling by car from Florence to Bandon takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 62°F in May, and nighttime lows around 49°F. Wrap up your sightseeing on the 9th (Sun) to allow time to travel to Brookings.

Brookings is a city in Curry County, Oregon, United States. Relax by the water at Lone Ranch Beach and Myers Creek Beach. You'll explore the less-touristy side of things at Harris Beach State Park and Azalea Park. Explore the numerous day-trip ideas around Brookings: Ophir Beach (in Ophir) and Gold Beach (Cedar Bend Golf Club, Geisel Monument State Heritage Site, &more). The adventure continues: cruise along Samuel H. Boardman State Scenic Corridor, tee off at Salmon Run Golf Course, see what you can catch with Brookings Fishing Charters, and enjoy the sand and surf at China Beach.

To see reviews, maps, traveler tips, and other tourist information, read our Brookings tour planner.

You can drive from Bandon to Brookings in 2 hours. In May, plan for daily highs up to 63°F, and evening lows to 48°F. Wrap up your sightseeing on the 13th (Thu) early enough to travel back home.