10 Things to Do in Winchester That You Shouldn't Miss

November 27, 2017 Jacquiline Darosa

Sitting at the northernmost corner of Virginia in the Shenandoah Valley, Winchester offers visitors the chance to explore historical sites, museums, vineyards, farmers' markets, and tree-lined Old Town streets once wandered by the likes of George Washington and Stonewall Jackson. The fruitful fields of the surrounding Frederick County have earned the area the title "apple capital of the world," with the city hosting the Shenandoah Apple Blossom Festival annually for almost a century.
Restaurants in Winchester

1. Rocking S Ranch

564 Glaize Orchard Rd, Winchester, VA 22603-2408 +1 540-678-8501
Excellent
97%
Good
2%
Satisfactory
0%
Poor
1%
Terrible
0%
Overall Ratings

5 based on 223 reviews

Rocking S Ranch

Reviewed By sam_svt - Martinsburg, West Virginia

We had a total blast! My cousin is here from England and we really wanted to ride together. The trail ride was amazing and such a good laugh. Especially the jokes told through out! The horses were so sweet and the trail was very pretty. Would defiantly go back again! Plan to go back again soon!

2. Stonewall Jackson's Headquarters

415 N Braddock St, Winchester, VA 22601-3921 +1 540-667-5505
Excellent
73%
Good
22%
Satisfactory
4%
Poor
1%
Terrible
0%
Overall Ratings

4.5 based on 193 reviews

Stonewall Jackson's Headquarters

Season: Open Daily April 1 to October 31

Reviewed By Carolyn B - United States

The docent, dressed in period clothing, presented us with the home's history and explained the artifacts in the rooms and cases. One of her accounts was the connection between Mary Tyler Moore and General Jackson. One of the actress's ancestors (great-great-grandfather, I think) owned the home during the war and offered Stonewall Jackson the use of the home during the winter of 1861-62. During his stay, the general wrote his wife, describing the bedroom's leaf-pattern wallpaper, which he admired. When, next century, a remnant of the wallpaper was discovered, Mary Tyler Moore payed to have it reproduced for the room's restoration.

The artifacts in the home include some of the home's furnishings the time of the general's stay; photos of the Jackson family; silver dishes belonging to General Ewell; and a wood-arch saddle (the only known surviving example of its type) belonging to Turner Ashby.

3. Handley Regional Library

Picadilly St, Winchester, VA +1 540-662-9041
Excellent
76%
Good
20%
Satisfactory
4%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 124 reviews

Handley Regional Library

Reviewed By doowahdiddynotacity - Arlington, VA

Old Town Winchester is a wonderful walking mall with restaurants and neat stores, surrounded by cool historic attractions like the Old Handley library. Like the courthouse and several other sites its free to go in. It has been upgraded but retains its original charm. Nearby metered parking is $.75/hour

4. Museum of the Shenandoah Valley

901 Amherst St, Winchester, VA 22601-3305 +1 888-556-5799
Excellent
68%
Good
26%
Satisfactory
4%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 434 reviews

Museum of the Shenandoah Valley

The Museum of the Shenandoah Valley (MSV) is dedicated to preserving and enriching the cultural life and heritage of the Valley. This regional history complex includes a house dating to the eighteenth century, six acres of spectacular gardens, and a 50,000-square-foot museum featuring changing exhibitions, a permanent display of miniature houses, and an expansive gallery exploring the history and decorative arts of the Shenandoah Valley. The MSV also includes a Museum Store and café (admission not required). The galleries are open year-round; the house and gardens April through October. The MSV sits on land originally claimed by Winchester founder James Wood in 1735. The property was passed through generations of Wood and Glass families until being acquired by Wood descendant and MSV benefactor Julian Wood Glass Jr. (1910–1992) between 1952 and 1955. Glass and his partner at the time, R. Lee Taylor (1924–2000), worked together to transform the site and its Glen Burnie House—built in 1794 by James Wood’s son Robert—into a country retreat where the couple entertained in high style.

Reviewed By Gabriel H - Bellaire, Texas, United States

This Museum is located in a modern building, designed by American architect Michael Graves. The exhibits are beautifully displayed and illuminated. The permanent collection includes a number of items that collectively describe the lifestyle of Virginians living in this area for the past several centuries: furniture, decorative items (paintings, ceramics, glass, etc.), folk art, weapons and household goods. The Julian Wood Glass Jr. Gallery, also part of the permanent collection, includes paintings from well-known 18th and 19th century American artists, as well as furniture ensembles from the same time periods. There is a separate collection of miniatures and changing or traveling exhibits. Associated to the Museum is the Glen Burnie historic house, dating back to the 18th century. While entirely remodeled in the 1950s, it still preserves the original architectural style, furnishings and art work.

5. Shenandoah Valley Discovery Museum

19 W Cork St, Winchester, VA 22601-4741 +1 540-722-2020
Excellent
66%
Good
26%
Satisfactory
7%
Poor
0%
Terrible
1%
Overall Ratings

4.5 based on 149 reviews

Shenandoah Valley Discovery Museum

Our mission at the Shenandoah Valley Discovery Museum is to ignite creativity, spark curiosity and inspire learning in visitors of all ages by providing a rich variety of interactive, hands-on exhibits and programs that focus on the sciences and mathematics, the humanities, and the arts.All exhibits, activities and experiences provided by the Discovery Museum adhere to the following philosophical guidelines:Exhibits, activities and programs are interactive, participatory and informal, and give visitors opportunities to experiment, have fun playing, use their imaginations and share ideas.Visitors are engaged at their own level of expertise and experience.Activities and programs are multi-sensory, authentic, honest, and factual.The Museum works in a spirit of cooperation and partnership with educational, cultural, governmental and community organizations.

Reviewed By Jmuracn - Middletown, Virginia

My nephew loves coming to visit and he loves the museum. Great hands on exhibits that let the kids explore AND help you reinforce learning. You can be there ALL day! just be ready for crowds. it can get really busy on the weekends! but...MoreHands-on learning is what it's all about! Thanks for the great review Jmuracn! We hope to see you and your nephew back again soon!

6. Patsy Cline House

608 S Kent St, Winchester, VA 22601-4664 +1 540-662-5555
Excellent
65%
Good
24%
Satisfactory
9%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 121 reviews

Patsy Cline House

The house stands as an icon for Patsy Cline fans and admirers hoping to know first hand the story of Patsy’s early years. Patsy Cline’s home offers a window on the famed singer’s early road to stardom. TOUR INFORMATION: Opens for tours April 2018.

Reviewed By sc40sumthin - Greenville, South Carolina

As a lifelong fan of Patsy Cline, it was emotional and overwhelming walking through the door of her home. The tour guide was welcoming and had a pleasant demeanor. She shared a lot of history and information. They have done a wonderful job restoring this house and creating a museum to share with all those who love Patsy.

7. Old Court House Civil War Museum

20 N Loudoun St, Winchester, VA 22601-4716 +1 540-542-1145
Excellent
50%
Good
41%
Satisfactory
6%
Poor
2%
Terrible
1%
Overall Ratings

4.5 based on 163 reviews

Old Court House Civil War Museum

Reviewed By atasteofcreole - Fredericksburg, Virginia

we just missed the visit. we were 5 minutes late. I was very disappointed in the times. It is not conducive to any other event going on in the area. But we did walk around the building and read the historical markers

8. Abram's Delight

1340 S Pleasant Valley Rd, Winchester, VA 22601-4447 +1 540-662-6519
Excellent
65%
Good
28%
Satisfactory
6%
Poor
1%
Terrible
0%
Overall Ratings

4.5 based on 66 reviews

Abram's Delight

Reviewed By Dawn M - Vienna, Virginia

This home is across the parking lot from the visitor's center. So is the Hollingsworth Mill.

At the historical society office on the ground floor of the Hollingsworth Mill, you buy your ticket to this home and just walk across the lawn to tour it. If you are going to see Washington's office and Stonewall Jackson's home, be sure to buy a pass for $10 at the mill. It'll save you $5.

My tour guide was terrific. She told the stories of all 5 generations of Hollingsworths who lived in the home and ran the adjacent mill.

The large house was grand in its day. The rooms are furnished in period pieces, including art that was commissioned by the family.

At the end of the house tour, you visit the log cabin that was the first home Abraham Hollingsworth built in 1728.

This is the oldest house in Winchester. The family was very important to the area. It was fascinating to see Winchester through stories of each generation.

Great visit!

NOTE: To view the kitchen, you must go down steep, narrow, irregularly spaced stairs into the basement. I chose to wait on a bench on the ground floor. I could hear others in my group struggling with the stairs going down and coming back up.

9. Kernstown Battlefield and Pritchard House

Battle Park Drive, Winchester, VA 22602 +1 757-593-8227
Excellent
60%
Good
25%
Satisfactory
13%
Poor
2%
Terrible
0%
Overall Ratings

4.5 based on 44 reviews

Kernstown Battlefield and Pritchard House

Reviewed By Neil G

Visited Kernstown battlefield during Civil War trek down Shenandoah. Tucked away but well worth the time. Larry, one of the volunteers, spent an hour with us taking us all over the field and explaining the battles in the context of the overall strategy of the times. They also have an original Napoleon cannon which was very cool. Take the time to stop if you're in the area

10. Stonewall Confederate Cemetery

305 E Boscawen St, Winchester, VA 22601-5014 +1 540-662-4868
Excellent
53%
Good
39%
Satisfactory
5%
Poor
0%
Terrible
3%
Overall Ratings

4.5 based on 53 reviews

Stonewall Confederate Cemetery

Reviewed By jehenson81

My only issue with this place is finding the entrance. We opted to park and walk around. We started by going by the tomb of Major General Daniel Morgan a Revolutionary War hero. Then it was over to the Civil War section. It was divided by state and each had its own monument to commemorate those that were lost. It was a beautiful locale and so peaceful.

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