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Best things to do in Winchester

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Where in the world: USA  /  Virginia  /  Winchester

Top 15 things to do in Winchester

1. Stonewall Jackson's Headquarters

Suggested duration: 2 hours
Learn more about Stonewall Jackson's Headquarters

2. Rocking S Ranch

Suggested duration: 2 hours
Learn more about Rocking S Ranch

3. Museum of the Shenandoah Valley

Suggested duration: 2 hours
Learn more about Museum of the Shenandoah Valley

4. 2-Hour Gettysburg Battlefield Guided History Bus Tour with a National Park Guide

FROM $38
Witness landmarks and monuments relating to the Battle of Gettysburg on this guided bus tour of the carefully restored battlefield. Your knowledgeable guide discusses the various phases of this three-day battle that was the turning point in the American Civil War. See significant locations including McPherson Ridge, Culp's Hill, Little Round Top, Devil's Den and the site of Pickett's Charge. Ideal for history lovers, this tour is a somber exploration of one of the most pivotal places in America's past as well as a convenient drive from the nation's capital.
Suggested duration: 2h
Tours from $38 › More about this tour at viator.com ›
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5. Gettysburg National Military Park, Gettysburg

Located on the site of one of the bloodiest episodes in American history, Gettysburg National Military Park preserves the landscape of the historic 1863 battle between the Union and Confederate forces. Though the battle resulted in the largest number of casualties in the entire American Civil War, it became the turning point of the dramatic conflict when the Union army turned back the Confederate attempt to invade the North. The military park contains most of the original battlefield, as well as many support areas, including the supply and hospital locations. Start your exploration at the park's museum and visitor center, where you can see over 40,000 war artifacts and an enormous cyclorama painting of the battle by French artist Paul Philippoteaux.
Suggested duration: 4 hours
Tours from $20 › Learn more about Gettysburg National Military Park

6. Monticello, Charlottesville

For an in-depth look at the private life of the third president of the United States, take a behind-the-scenes tour of Monticello. Jefferson built this estate after inheriting land from his father, eventually creating a vast plantation used primarily for cultivation of tobacco and mixed crops. Utilizing slave labor, Jefferson later switched his production from tobacco to wheat. The main house sits on the summit of a 260 m (850 ft) mountain peak, featuring design elements popular in late 18th-century Europe. The surrounding grounds include several historical outbuildings, including a nailery, slave quarters, and rooms Jefferson used for his plant breeding experiments. Check online for upcoming events and available tours.
Suggested duration: 4 hours
Learn more about Monticello

7. Shenandoah Valley Discovery Museum

Suggested duration: 2h 30 min
Learn more about Shenandoah Valley Discovery Museum

8. Civil War Ghosts of Gettysburg Tour

FROM $30
Visitors to the Civil War Ghosts tour can investigate both the historical and paranormal accounts of each of our carefully chosen tour destinations. Our tour guides will take you securely through the foggy streets while telling you tales of mystery, fear, and tragedy. There will be many chances for you to witness the supernatural force of this ancient city. We are top-rated, scariest, most authenticate, historically haunted tour! 
Suggested duration: 1h
Tours from $30 › More about this tour at viator.com ›

9. Virginia Museum of Veiled History

Suggested duration: 30 minutes
Learn more about Virginia Museum of Veiled History

10. Patsy Cline Historic House

Admission is $8 adults, $7 for seniors 65 and over, and $6 youth ages 12-17. Active duty military free with ID. April 1-October 31 hours Mon-Sat 10 AM-4 PM Sun 1 PM-4 PM November 1-December 15 hours Fri-Sat 10 AM-4 PM Sun 1 PM-4 PM
Suggested duration: 30 minutes
Learn more about Patsy Cline Historic House

11. Harpers Ferry National Historical Park, Harpers Ferry

At Harpers Ferry National Historical Park, you'll see the center of 19th century industry. The park features many small museums and exhibits, battlefields, uninhabited hillside houses, and picturesque streets. Take a guided tour with a ranger and hear about the town's history, which began 8,000 years ago. See galleries such as the wax museum, the blacksmith shop, and the clocks and jewelry exhibit, or visit the bookshop, tavern, and the dry goods store. Plan your visit in advance in order to get the most out of this attraction.
Suggested duration: 8 hours
Learn more about Harpers Ferry National Historical Park

12. BEST Luray Caverns and Shenandoah Skyline Drive All-Day Tour

FROM $166
Experience the cold air rushing out of a limestone sinkhole atop a big hill west of Luray in the Luray Caverns. Take a look at the beautiful scenic views of Skyline Drive! Explore the amazing Shenandoah National Park and all that it has to offer. Experience an unforgettable one-day tour filled with unlimited memories. Itinerary: Luray Caverns (Optional, 120 mins) -- Skyline Drive in Shenandoah National Park(120 mins) Shenandoah National Park Special notes: 1. Due to the Skyline Drive located across Shenandoah National Park, we enter from Thornton Gap and drive to north exit, this is a one-way tour and lasts 120 mins. 2. On the winding driveway on the mountains, we will stop at the overlooks to observe the beautiful Shenandoah Valley. 3. We will also take an easy walk on one of the trails among the mountains. Total 45 for this trail (round trip). 4. If the weather is extreme, the tour leader will cancel the trail trip, and add other stops properly.
Suggested duration: 7h - 9h
Tours from $166 › More about this tour at viator.com ›

14. Luray Caverns, Luray

Take a guided tour of Luray Caverns, subterranean caves that were discovered in 1878 and are now a National Historic Landmark. Your knowledgeable guide will identify and explain some of the caves' most impressive formations, such as Leaning Column, Titania's Veil, Dream Lake, and Double Column. Listen to the song of the Great Stalacpipe Organ, which makes stalactites sing by tapping them. The admission fee includes your tour, as well as entrance to the Car and Carriage Caravan and Luray Valley Museum.
Suggested duration: 2h 30 min
Tours from $166 › Learn more about Luray Caverns

15. Groovy Gettysburg Scavenger Hunt

FROM $20
Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!
Suggested duration: 2h
Tours from $20 › More about this tour at viator.com ›