8 days in Asheville, Shenandoah Valley & Richmond Itinerary

8 days in Asheville, Shenandoah Valley & Richmond Itinerary

Created using Inspirock United States trip planner

Make it your trip
Fly
1
Asheville
— 2 nights
Drive
2
Lexington
— 2 nights
Drive
3
Winchester
— 1 night
Drive
4
Richmond
— 2 nights
Fly

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Asheville

— 2 nights

Land of the Sky

Asheville nestles between two major mountain ranges in the scenic western section of North Carolina.
Popular historic sites such as Grovewood Village and Thomas Wolfe Memorial are in your itinerary. You'll discover tucked-away gems like Asheville Pinball Museum and Woolworth Walk. The adventure continues: view the masterpieces at New Morning Gallery, wander the streets of River Arts District, let the river carry you with a rafting and tubing tour, and get a taste of the local shopping with American Folk Art & Framing.

To see where to stay, traveler tips, other places to visit, and tourist information, read Asheville sightseeing planning app.

New York City to Asheville is an approximately 3.5-hour flight. You can also drive; or take a bus. Expect a bit cooler evenings in Asheville when traveling from New York City in July, with lows around 65°F. Finish your sightseeing early on the 2nd (Mon) to allow enough time to fly to Lexington.

Things to do in Asheville

Museums · Shopping · Historic Sites · Neighborhoods

Side Trip

Lexington

— 2 nights
Home to two prestigious educational institutions, Lexington was founded in 1778.
Start off your visit on the 3rd (Tue): steep yourself in history at Lee Chapel and Museum, then steep yourself in history at Stonewall Jackson House, and then explore the striking landscape at Natural Bridge State Park. Get ready for a full day of sightseeing on the next day: contemplate the long history of Woodrow Wilson Birthplace, steep yourself in history at Frontier Culture Museum, and then learn about winemaking at Veritas Vineyard & Winery.

To see more things to do, other places to visit, and tourist information, you can read our Lexington tour builder site.

You can fly from Asheville to Lexington in 4.5 hours. Alternatively, you can drive; or do a combination of bus, train, and taxi. In August, Lexington is slightly colder than Asheville - with highs of 71°F and lows of 57°F. Wrap up your sightseeing on the 4th (Wed) to allow time to drive to Winchester.

Things to do in Lexington

Historic Sites · Museums · Nature · Parks

Side Trips

Winchester

— 1 night
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. On the 5th (Thu), take an in-depth tour of Stonewall Jackson's Headquarters, then explore the world behind art at Museum of the Shenandoah Valley, then steep yourself in history at Historic Fort Loudoun Site, and finally get a taste of life in the country at Rocking S Ranch.

To find photos, ratings, reviews, and other tourist information, refer to the Winchester online trip planner.

Getting from Lexington to Winchester by car takes about 2.5 hours. Other options: do a combination of bus and taxi. When traveling from Lexington in August, plan for a bit warmer days and about the same nights in Winchester: temperatures range from 82°F by day to 62°F at night. Finish your sightseeing early on the 5th (Thu) to allow enough time to fly to Richmond.

Things to do in Winchester

Museums · Historic Sites

Richmond

— 2 nights

The River City

The capital city of Virginia, Richmond has diverse architecture, a large collection of monuments, and world-class museums that reveal the city's important role in American history.
Start off your visit on the 6th (Fri): get engrossed in the history at American Civil War Museum- Historic Tredegar, learn about all things military at Tredegar Iron Works, explore the different monuments and memorials at African Burial Ground, then contemplate the long history of Edgar Allan Poe Museum, and finally see the interesting displays at Pocahontas Island Black History Museum. Here are some ideas for day two: pause for some serene contemplation at St. John's Episcopal Church, then take an in-depth tour of Virginia Holocaust Museum, then learn about all things military at White House of the Confederacy, and finally explore the different monuments and memorials at Hollywood Cemetery.

To find traveler tips, where to stay, other places to visit, and other tourist information, go to the Richmond trip planner.

Fly from Winchester to Richmond in 2.5 hours. Alternatively, you can drive; or do a combination of taxi, train, and bus. Traveling from Winchester in August, you can expect nighttime temperatures to be a bit warmer in Richmond, with lows of 68°F. Cap off your sightseeing on the 7th (Sat) early enough to catch the flight back home.

Things to do in Richmond

Museums · Historic Sites

Side Trip