22 days in Shenandoah Valley Itinerary

22 days in Shenandoah Valley Itinerary

Created using Inspirock Shenandoah Valley trip planner
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Make it your trip
Fly
1
Lexington
— 4 nights
Drive
2
Shenandoah National Park
— 6 nights
Drive
3
Luray
— 6 nights
Drive
4
Winchester
— 5 nights
Fly

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Lexington — 4 nights

Home to two prestigious educational institutions, Lexington was founded in 1778.
Get out of town with these interesting Lexington side-trips: Staunton (Frontier Culture Museum & Woodrow Wilson Presidential Library and Museum). There's still lots to do: take in the dramatic natural features at Natural Bridge State Park, take an in-depth tour of University Chapel & Galleries, steep yourself in history at Washington and Lee University, and deepen your understanding at Virginia Military Institute.

To find ratings, other places to visit, and other tourist information, go to the Lexington attractions tool.

New York City to Lexington is an approximately 3-hour flight. You can also drive; or do a combination of train and bus. Traveling from New York City in May, Lexington is slightly colder at night with lows of 49°F. Finish up your sightseeing early on the 16th (Mon) so you can go by car to Shenandoah National Park.
Historic Sites · Museums · Parks · Nature
Side Trips

Shenandoah National Park — 6 nights

Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Change things up with a short trip to Grand Caverns in Grottoes (about 50 minutes away). There's much more to do: contemplate the waterfront views at Skyline Drive, take in the awesome beauty at Hawksbill Mountain, trek along Jones Run Falls Trailhead, and scramble along the landscape with a canyoning and rapelling tour.

For reviews, maps, traveler tips, and tourist information, you can read our Shenandoah National Park trip itinerary planner.

Drive from Lexington to Shenandoah National Park in 2 hours. Alternatively, you can do a combination of bus and taxi. Plan for a bit warmer temperatures traveling from Lexington in May, with highs in Shenandoah National Park at 76°F and lows at 55°F. Wrap up your sightseeing on the 22nd (Sun) early enough to drive to Luray.
Parks · Nature · Outdoors · Trails
Side Trip

Luray — 6 nights

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.
Get out of town with these interesting Luray side-trips: Harrisonburg (White Oak Lavender Farm & The Purple WOLF Vineyard & Edith J. Carrier Arboretum). There's still lots to do: explore the fascinating underground world of Luray Caverns, sample the fine beverages at River Hill Wine & Spirits, trek along Stony Man Mountain Overlook, and take an in-depth tour of The Car and Carriage Caravan Museum.

For photos, other places to visit, maps, and tourist information, refer to the Luray tour itinerary planner.

Getting from Shenandoah National Park to Luray by car takes about 1.5 hours. In May in Luray, expect temperatures between 75°F during the day and 52°F at night. Wrap up your sightseeing on the 28th (Sat) to allow time to drive to Winchester.
Parks · Museums · Nature · Tours
Side Trips

Winchester — 5 nights

Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Winchester is known for museums, historic sites, and nightlife. Your trip includes some of its best attractions: wander the wide-open spaces of Rocking S Ranch, gain insight at Shenandoah Valley Discovery Museum, admire the landmark architecture of Abram's Delight, and see the interesting displays at Shenandoah Valley Civil War Museum.

To see where to stay, reviews, more things to do, and other tourist information, use the Winchester trip planner.

Traveling by car from Luray to Winchester takes 1.5 hours. In May, plan for daily highs up to 73°F, and evening lows to 52°F. Cap off your sightseeing on the 2nd (Thu) early enough to catch the flight back home.
Museums · Historic Sites · Childrens Museums
Side Trips