58 days in Southern Oregon Itinerary

58 days in Southern Oregon Itinerary

Created using Inspirock Southern Oregon tour planner

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Route & dates

58 days in Southern Oregon Itinerary

Start: Tampa
Fly + Drive:  9​h 45​min
1
Jacksonville
— 12 nights
Drive:  1​h 15​min
2
Cave Junction
— 11 nights
Drive:  2​h
3
Winston
— 11 nights
Drive:  2​h 30​min
4
Crater Lake National Park
— 12 nights
Drive:  1​h 15​min
5
Klamath Falls
— 11 nights
Drive + Fly:  11​h
End: Tampa

12
nights
Jacksonville

Jacksonville is a city in Jackson County, Oregon, United States, about 5mi west of Medford. Get in touch with nature at Wildlife Images - Rehabilitation & Education Center and Upper and Lower Table Rock. You'll explore and learn at The Glass Forge and Crater Rock Museum. Venture out of the city with trips to Ashland (Dana Campbell Vineyards, North Mountain Park, & more), Grants Pass (Bear Hotel Artworks Museum, Rogue Creamery Dairy Farm, & more) and Plaisance Ranch (in Williams). Next up on the itinerary: stroll the grounds of Jacksonville Cemetery, explore the activities along Rogue River, do a tasting at LongSword Vineyard, and get lost in a book at Jacksonville Library.

For where to stay, maps, traveler tips, and other tourist information, refer to the Jacksonville trip builder .

Tampa to Jacksonville is an approximately 10-hour combination of flight and car. You can also drive. The time zone difference when traveling from Tampa to Jacksonville is minus 3 hours. When traveling from Tampa in October, plan for little chillier days in Jacksonville, with highs around 71°F, while nights are colder with lows around 44°F. Cap off your sightseeing on the 18th (Fri) early enough to go by car to Cave Junction.

Things to do in Jacksonville

Wineries Parks Museums

Side Trips

Ashland, Grants Pass, Medford, Gold Hill, Central Point
Highlights from your plan
River Rafting & Tubing
Rogue River ©
Rogue River
The Glass Forge ©
The Glass Forge

11
nights
Cave Junction

Cave Junction ©
Cave Junction, incorporated in 1948, is a city in Josephine County, Oregon, United States. Step out of the city life by going to Oregon Caves National Monument and Preserve and Great Cats World Park. And it doesn't end there: identify plant and animal life at Eight Dollar Mountain Botanical Area, look for gifts at Taylor's Sausage Country Store, and examine the collection at Siskiyou Smokejumper Base Museum.

For maps, ratings, reviews, and more tourist information, refer to the Cave Junction day trip planning app .

Traveling by car from Jacksonville to Cave Junction takes 1.5 hours. Traveling from Jacksonville in October, expect nights in Cave Junction to be somewhat warmer, around 50°F, while days are a bit cooler, around 64°F. You'll set off for Winston on the 29th (Tue).

Things to do in Cave Junction

Parks Wildlife Nature
Highlights from your plan
Eight Dollar Mountain Botanical Area ©
Great Cats World Park ©
Great Cats World Park

11
nights
Winston

Winston ©
Winston is a city in Douglas County, Oregon, United States. Satisfy your inner culture vulture at Oakland Oregon Museum and Douglas County Museum of History & Natural History. Escape the urban bustle at Wildlife Safari and Clearwater Falls. Venture out of the city with trips to Roseburg (Reustle Prayer Rock Vineyards, Susan Creek Campground, & more) and Rochester Covered Bridge (in Sutherlin). There's lots more to do: do a tasting at HillCrest Winery and Distillery, see the interesting displays at Noah's Ark Biblical History Museum, stroll around Stewart Park, Roseburg, Oregon, and try to win big at Seven Feathers Casino Resort.

For ratings, maps, more things to do, and other tourist information, read our Winston online trip planner .

Drive from Cave Junction to Winston in 2 hours. In October, daytime highs in Winston are 69°F, while nighttime lows are 48°F. On the 9th (Sat), you'll travel to Crater Lake National Park.

Things to do in Winston

Parks Wineries Trails

Side Trips

Roseburg, Rochester Covered Bridge, Seven Feathers Casino Resort, Oakland Oregon Museum
Highlights from your plan
Wildlife Safari ©
Wildlife Safari
Oakland Oregon Museum ©
Oakland Oregon Museum
Watson Falls ©
Watson Falls

12
nights
Crater Lake National Park

Crater Lake National Park ©
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Get in touch with nature at Crater Lake National Park and Garfield Peak. Change things up with these side-trips from Crater Lake National Park: Prospect (Union Creek Trail, Mill Creek Falls, & more). The adventure continues: take a memorable drive along Rim Dr, trek along Castle Crest Wildflower Trail, head off the coast to Wizard Island, and stroll through Cleetwood Cove Trail.

To see traveler tips, maps, more things to do, and tourist information, you can read our Crater Lake National Park trip builder .

Traveling by car from Winston to Crater Lake National Park takes 2.5 hours. In November, daytime highs in Crater Lake National Park are 55°F, while nighttime lows are 38°F. You'll set off for Klamath Falls on the 21st (Thu).

Things to do in Crater Lake National Park

Parks Nature Outdoors

Side Trip

Prospect
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Rim Dr ©
Rim Dr
Cleetwood Cove Trail ©
Cleetwood Cove Trail

11
nights
Klamath Falls

Klamath Falls ©
Klamath Falls is a city in and the county seat of Klamath County, Oregon, United States. Get outdoors at Moore Park and Badger Run Wildlife Rehab. Appreciate the collections at Klamath County Museum and The Favell Museum Native American Artifacts and Contemporary Western Art. Change things up with these side-trips from Klamath Falls: Diamond Lake (in Medford) and Historic Pinehurst Inn (in Ashland). The adventure continues: ride a horse along OC and E Woods Line State Trail, enjoy some diversion at Klamath Falls Skatepark, identify plant and animal life at Klamath Fish Hatchery, and play a few rounds at Running Y Ranch Golf Course.

To find ratings, traveler tips, and other tourist information, refer to the Klamath Falls travel route planner.

You can drive from Crater Lake National Park to Klamath Falls in 1.5 hours. Traveling from Crater Lake National Park in November, things will get a bit cooler in Klamath Falls: highs are around 50°F and lows about 27°F. On the 2nd (Mon), you'll travel back home.

Things to do in Klamath Falls

Parks Outdoors Museums

Side Trips

Diamond Lake, Historic Pinehurst Inn
Highlights from your plan
Moore Park ©
Moore Park
Badger Run Wildlife Rehab ©
Badger Run Wildlife Rehab
Klamath County Museum ©
Klamath County Museum