15 days in Winchester & Medford Itinerary

15 days in Winchester & Medford Itinerary

Created using Inspirock United States visit planner

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Route & dates

15 days in Winchester & Medford Itinerary

Start: Medford
Fly:  11​h
1
Winchester
— 8 nights
Fly:  11​h
2
Medford
— 4 nights
End: Medford

8
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Take a break from the city and head to Stony Man Mountain Hike and Berkeley Springs State Park. Satisfy your inner culture vulture at Little Round Top and Museum of the Shenandoah Valley. Venture out of the city with trips to Shenandoah Caverns (in Shenandoah Caverns), Gettysburg (Lincoln Statue at Wills House, Dobbin House Tavern, & more) and Fredericksburg (Battlefield Fredericksburg, Fredericksburg and Spotsylvania National Military Park, & more). There's much more to do: hike along Old Rag Mountain Hike, contemplate the long history of Patsy Cline House, tour the pleasant surroundings at Great Allegheny Passage, and learn about winemaking at Rappahannock Cellars.

Start your trip to Winchester by creating a personalized itinerary on Inspirock.

Medford to Winchester is an approximately 11-hour flight. You can also drive. The time zone changes from Pacific Standard Time to Eastern Standard Time, which is usually a 3 hour difference. In October in Winchester, expect temperatures between 67°F during the day and 46°F at night. Cap off your sightseeing on the 26th (Fri) early enough to travel to Medford.

Things to do in Winchester

Parks Historic Sites Outdoors

Side Trips

Fredericksburg, Gettysburg, Luray, Berkeley Springs State Park, Great Allegheny Passage
Highlights from your plan
Museum of the Shenandoah Valley ©
Museum of the Shenandoah Valley
Battlefield Fredericksburg ©
Battlefield Fredericksburg

4
nights
Medford

Medford ©
Medford is a city in, and county seat of, Jackson County, Oregon, United States. Step off the beaten path and head to Wildlife Images - Rehabilitation & Education Center and Toketee Falls. Get in touch with nature at Rim Dr and Rogue River Gorge Viewpoint. Get out of town with these interesting Medford side-trips: Crater Lake National Park (Vidae Falls & Pinnacles Trail), Grants Pass (Bear Hotel Artworks Museum & The Glass Forge) and Mount Shasta (in Mount Shasta). There's still lots to do: identify plant and animal life at Great Cats World Park, stop by Rogue Creamery, take in the dramatic scenery at National Creek Falls, and admire the masterpieces at Schneider Museum of Art.

To see traveler tips, maps, where to stay, and more tourist information, read Medford day trip planning app .

The Route module can help you plan travel from Winchester to Medford. The time zone difference moving from Eastern Standard Time (EST) to Pacific Standard Time (PST) is minus 3 hours. October in Medford sees daily highs of 71°F and lows of 44°F at night. Finish up your sightseeing early on the 31st (Wed) so you can travel back home.

Things to do in Medford

Parks Nature Wildlife

Side Trips

Crater Lake National Park, Grants Pass, Prospect, Rogue Creamery, Mount Shasta
Highlights from your plan
Mount Shasta ©
Mount Shasta
Great Cats World Park ©
Great Cats World Park

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