Places To Visit

Top 5 Places to Visit in Winchester

Places to Visit in Winchester, Virginia

Places to Visit in Winchester

When most people think of visiting a city, they usually think of the big, flashy attractions. After all, who wouldn’t want to cruise through that giant yellow happy house, explore a castle full of secrets or see where the witch went off with her gingerbread man? Well, lucky for you and us, Winchendon also has those things! In fact, it has more than that. The small city is home to some really beautiful smaller sites that are just as fun and exciting to visit as any other attraction in the area. So if you’re looking for something a little more off the beaten path this time around but still want to see what Winchester has to offer (without having to venture too far), then keep on reading below for your top 5 places to visit in Winchester, Virginia!

1. Winchester’s Historical District

The first stop on our list is Winchester’s Historical District, which is exactly what it sounds like. Located in the heart of the city, this beautiful area is home to Winchester’s first courthouse and jail, the oldest library in Virginia, a number of Civil War-era buildings, and the site of the city’s original settlement. It’s also where you’ll find the Old Town Market, which is a historic, indoor marketplace that’s been in operation since the 19th century, and the Original Book Shop, which is the oldest operating bookstore anywhere in the country.

As you walk around the district, you’ll also see that Winchester’s Historical District is full of beautiful architecture. A number of the buildings and sites located there are on the National Register of Historic Places, and they’re also all open to the public for touring. So if you’re visiting during the day, you’ll be able to walk around the district and see all of these awesome places for yourself. If you’re visiting during the night, you’ll still be able to see a lot of it, but you can also take advantage of the district’s free self-guided walking tour with audio guides.

2. Hunter-Mason House

Next up on our list is the Hunter-Mason House, which is another beautiful historic building located in the district. The house is open to the public for touring, and it’s also where you’ll find the Winchester Art Gallery and the Winchester Discovery Center. If the Discovery Center sounds familiar to you, it’s because it’s also where the Shenandoah Valley Discovery Museum resides. As for the house itself, it was built in 1857 and was home to the prominent Hunter and Mason families until the 20th century.

3. The Winchester Cemetery

Our next stop is one that might seem a little bit out of place on a list of places to visit, but trust us, it’s a lot of fun. We’re talking about Winchester’s Historic Cemetery, which is the final resting place for 25 notable people, including the city’s first doctor, its first mayor, and the man who designed the city’s beautiful architecture. Winchester’s Historic cemetery is also where you’ll find the grave of John Harper, the man who built the city’s first inn. The inn was quickly converted into a tavern, and thus, the city’s first beer was brewed. You’ll also find the graves of 17 Union soldiers who were killed during the Battle of Millwood in 1864 and reburied in the cemetery.

4. The Winchester Cemetery

Aside from all the history and interesting facts that you can find in the cemetery, it’s also just a really beautiful place to visit. It’s surrounded by lush, green gardens and has a nice view of the city, so you’ll be able to take in both the natural and manmade beauty of the area.

If you visit during the springtime, you can also take advantage of the beautiful Sakura Cherry Blossom Festival that’s held in the cemetery every year. If you visit during the fall, you can take photos at the Harvest Festival, and if you visit in the winter, you can admire the beautiful decorations at the Christmas Festival. So no matter when you visit, you’re sure to have a great time.

The Winchester Art Museum

The Winchester Art Museum is another historic site that you’ll find in the district. This museum is home to a number of different art collections, including works by Picasso and Van Gogh. It’s also one of the only museums in the entire country that features a collection of works by the founder of Impressionism, Claude Monet. The Winchester Art Museum also houses the most famous painting in the entire city, the Sully Portrait.

The George Washington Memorial Chapel

Last but not least, you can enjoy all these other historic sites while also paying your respects to George Washington, one of America’s most famous presidents, at the George Washington Memorial Chapel. The chapel, which is actually a part of Washington and Lee University, is open for public tours, so if you’re visiting Winchester and want to take in this site, you’ll be able to do so.

The chapel is beautiful, and the grounds that it’s located on are also really nice. So if you visit during the day or the evening, you’ll be able to take in some really beautiful sights while also learning a bit more about Washington and his connection to the city.


These places might sound familiar to you because they are mentioned as part of a larger tour. If you are interested in these tours, you can visit the Winchester Visitors Center for all the information you need. With all these beautiful places to visit, there’s no doubt that you’ll have an amazing time while visiting Winchester. So don’t wait any longer, start planning your trip and make sure to visit these places for the best experience.

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