10 days in Shenandoah Valley Itinerary

10 days in Shenandoah Valley Itinerary

Created using Inspirock United States trip itinerary planner

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Route & dates

10 days in Shenandoah Valley Itinerary

Start: Chicago
Drive:  11​h
1
Winchester
— 1 night
Drive:  1​h 15​min
2
Luray
— 2 nights
Drive:  1​h 15​min
3
Staunton
— 2 nights
4
Roanoke
— 3 nights
Drive:  11​h 45​min
End: Chicago

1
night
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Start off your visit on the 1st (Fri): admire the masterpieces at Museum of the Shenandoah Valley, experience rural life at Marker-Miller Orchards, and then admire all the interesting features of Rocking S Ranch.

To see traveler tips, photos, ratings, and more tourist information, use the Winchester planning site .

Chicago to Winchester is an approximately 5-hour combination of flight and taxi. You can also do a combination of flight and car; or drive. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. In March in Winchester, expect temperatures between 50°F during the day and 31°F at night. Cap off your sightseeing on the 2nd (Sat) early enough to go by car to Luray.

Things to do in Winchester

Museums Breweries Shopping

Side Trips

Catoctin Creek Distillery, Bloomery Plantation Distillery
Highlights from your plan
Bloomery Plantation Distillery ©
Bloomery Plantation Distillery
Rocking S Ranch ©
Rocking S Ranch
Museum of the Shenandoah Valley ©
Museum of the Shenandoah Valley

2
nights
Luray

Luray ©
Nestled in the heart of the valley formed by the Shenandoah River, Luray draws visitors with a vast underground cavern system adorned with stalactites, stalagmites, and mirrored pools.
Keep things going the next day: learn about winemaking at River Hill Wine & Spirits, get engrossed in the history at The Car and Carriage Caravan Museum, examine the collection at Luray Valley Museum, then have fun at Garden Maze, and finally Head underground at Luray Caverns.

Find out how to plan Luray trip without stress by asking Inspirock to help create an itinerary.

You can drive from Winchester to Luray in 1.5 hours. In March, daytime highs in Luray are 54°F, while nighttime lows are 32°F. Wrap up your sightseeing on the 4th (Mon) early enough to drive to Staunton.

Things to do in Luray

Parks Outdoors Nature

Side Trip

Skyline Drive
Highlights from your plan
Luray Caverns ©
Luray Caverns
Skyline Drive ©
Skyline Drive
Stony Man Mountain Hike ©
Stony Man Mountain Hike

2
nights
Staunton

Staunton ©
Staunton is an independent city in the U.S. On the 5th (Tue), see the interesting displays at Camera Heritage Museum, admire all the interesting features of Virginia Military Institute, then get engrossed in the history at Lee Chapel and Museum, then steep yourself in history at Stonewall Jackson House, and finally get a taste of the local shopping with Earth, Fire, & Spirit Pottery. On your second day here, examine the collection at Woodrow Wilson Presidential Library and Museum, then contemplate the long history of Frontier Culture Museum, then relax in the rural setting at White Oak Lavender Farm, and finally steep yourself in history at Woodrow Wilson Birthplace.

For where to stay and other tourist information, read Staunton online road trip planner .

Traveling by car from Luray to Staunton takes 1.5 hours. In March in Staunton, expect temperatures between 53°F during the day and 30°F at night. Finish your sightseeing early on the 6th (Wed) so you can drive to Roanoke.

Things to do in Staunton

Historic Sites Museums Outdoors

Side Trips

Lexington, White Oak Lavender Farm & The Purple WOLF Vineyard
Highlights from your plan
Frontier Culture Museum ©
Frontier Culture Museum
Virginia Military Institute ©
Virginia Military Institute
Lee Chapel and Museum ©
Lee Chapel and Museum

3
nights
Roanoke

Roanoke ©
Roanoke is an independent city in the U.S. Roanoke is known for museums, shopping, zoos & aquariums, nature, and nightlife. Your plan includes some of its best attractions: admire all the interesting features of Mill Mountain Star and Park, indulge your taste buds at Food & Drink, explore the world behind art at Taubman Museum of Art, and sample the tasty concoctions at Big Lick Brewing Company.

To see maps, where to stay, traveler tips, and other tourist information, go to the Roanoke trip planning app .

Getting from Staunton to Roanoke by car takes about 1.5 hours. Other options: take a bus; or take a train. Traveling from Staunton in March, expect a bit warmer with lows of 36°F in Roanoke. Wrap up your sightseeing on the 9th (Sat) to allow time to travel back home.

Things to do in Roanoke

Museums Tours Shopping
Highlights from your plan
Virginia Museum of Transportation ©
Virginia Museum of Transportation
Beer Tastings & Tours
Mill Mountain Star and Park ©
Mill Mountain Star and Park