22 days in Shenandoah Valley Itinerary

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 much more to do: deepen your understanding at Virginia Military Institute, contemplate the long history of Washington and Lee University, take in the dramatic natural features at Natural Bridge State Park, and identify plant and animal life at Virginia Safari Park.

To see reviews, ratings, maps, and more tourist information, read Lexington trip planner.

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, plan for a bit cooler nights in Lexington, with lows around 49°F. Finish your sightseeing early on the 16th (Mon) to allow enough time to drive to Shenandoah National Park.

Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.

Venture out of the city with trips to Grand Caverns (in Grottoes) and Skyland Stables (in Luray). There's still lots to do: take a memorable drive along Skyline Drive, take your sightseeing to a higher altitude at Hawksbill Mountain, trek along Old Rag Mountain Hike, and skim along the rocks with a canyoning and rapelling tour.

To see ratings, other places to visit, where to stay, and tourist information, use the Shenandoah National Park online trip planner.

Traveling by car from Lexington to Shenandoah National Park takes 2 hours. Alternatively, you can drive; or do a combination of bus and taxi. Prepare for somewhat warmer weather when traveling from Lexington in May: high temperatures in Shenandoah National Park hover around 76°F and lows are around 55°F. Finish up your sightseeing early on the 22nd (Sun) so you can go by car to 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.

Get out of town with these interesting Luray side-trips: Harrisonburg (White Oak Lavender Farm & The Purple WOLF Tasting Room & Edith J. Carrier Arboretum). There's still lots to do: take in breathtaking views at Luray Caverns, take a memorable excursion with Birdsong Pleasure Garden, 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.

Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Winchester is known for museums, sightseeing, and nightlife. Your trip includes some of its best attractions: wander the wide-open spaces of Rocking S Ranch, take in the history at Third Winchester Battlefield Park, contemplate the long history of Abram's Delight, and explore the world behind art at Museum of the Shenandoah Valley.

Klarna Trips's itinerary builder makes planning a Winchester trip simple and quick.

Getting from Luray to Winchester by car takes about 1.5 hours. Other options: drive. In May, daytime highs in Winchester are 73°F, while nighttime lows are 52°F. Wrap up your sightseeing on the 2nd (Thu) to allow time to fly back home.