Beautiful Towns in Shenandoah Valley, Virginia

Staunton is a charming small town you can't miss on a trip to Shenandoah Valley
Staunton is a charming small town you can't miss on a trip to Shenandoah Valley | © Pat & Chuck Blackley / Alamy Stock Photo

The Shenandoah Valley is a scenic region in the western part of Virginia, rich in cultural heritage. The valley is dotted with historic small cities and towns – we check out the most beautiful places to visit in this part of the United States.

Winchester

Historical Landmark
Map View
Apple Orchard, Near Winchester, Welltown, Virginia, USA
© Pat & Chuck Blackley / Alamy Stock Photo

Winchester is a small city in the northern part of the Shenandoah Valley. The area was a tribal headquarters for the Shawnee Native American tribe before it was settled by Quakers from Pennsylvania in 1732. Known as the Apple Capital, Winchester is surrounded by orchards and hosts the annual Shenandoah Apple Blossom Festival each May.

Berryville

Historical Landmark
Map View
Berryville Old Book Shop, former First National Bank building, 7 East Main Street, Berryville, Virginia
© Mark Summerfield / Alamy Stock Photo

Just outside Winchester, Berryville is a small community with a historic downtown area and quaint main street. The town, in the northern part of the Shenandoah Valley, is surrounded by beautiful rolling hills and countryside. The nearby Holy Cross Abbey is where monks sell fruitcakes, honey and chocolate truffles.

Luray

Historical Landmark
Map View
Luray Caverns in Luray, Virginia. Image shot 11/2016
© Zoonar GmbH / Alamy Stock Photo

With a population of just under 5,000, Luray is a small town near the famous Luray Caverns – one of the largest caverns in the eastern United States. The caverns are filled with stalactites and stalagmites that make up stunning formations such as the Great Stalacpipe Organ. The town has a charming main street featuring 19th-century architecture.

Dayton

Historical Landmark
Map View
Feeding Dairy Cows, Dayton, Shenandoah Valley, Virginia, USA
© Pat & Chuck Blackley / Alamy Stock Photo

Only two miles from Harrisonburg, Dayton is a small, rural village with a rich history. The farmland surrounding Dayton is owned primarily by the Old Order Mennonite community. One of Dayton’s main attractions is the Dayton Farmer’s Market, which features the best of local food producers and craftsmen.

Staunton

Historical Landmark
Map View
A row of old commercial buildings including Pufferbellies store, Staunton, Virginia, USA
© Washington Imaging / Alamy Stock Photo

Home to about 25,000 people, Staunton has been called one of the ‘Best Small Towns in America’ by Smithsonian Magazine. The area was first settled in 1732, and the town served as the capital of Virginia in June of 1781 – when legislators fled from both Richmond and Charlottesville during the American Revolutionary War. Staunton is the birthplace of president Woodrow Wilson and home to the American Shakespeare Center, the world’s only authentic replica of the Blackfriars Theater.

Lexington

Historical Landmark
Map View
Lexington, USA - April 18, 2018: Washington and Lee University hall in Virginia
© Kristina Blokhin / Alamy Stock Photo

Named for Lexington, Massachusetts – where the first shot was fired during the American Revolution – Lexington in Virginia is home to the Virginia Military Institute and Washington and Lee University. Confederate generals Robert E Lee and ‘Stonewall’ Jackson are both buried in Lexington.

Buena Vista

Historical Landmark
Map View
Sunset, North of Buena Vista, Blue Ridge Parkway, Virginia, USA
© Pat & Chuck Blackley / Alamy Stock Photo

Nestled near the Blue Ridge Mountains, Buena Vista was formed in the late 1800s at the intersection of two railroads and a canal. The Maury River runs through the town, making for a beautiful natural landscape. Buena Vista was known as Green Valley or Green Forest until 1888.

Natural Bridge

Historical Landmark
Map View
Natural Bridge, Virginia
© Zachary Frank / Alamy Stock Photo

Natural Bridge, Virginia, is a small, unincorporated community that has popped up around its namesake landmark – a gorge known as Natural Bridge. Listed as a National Historic Landmark, Natural Bridge is a limestone gorge formed by Cedar Creek, on a piece of land that was once owned by Thomas Jefferson. The landmark is surrounded by several other attractions, including a zoo.

Salem

Historical Landmark
Map View
Virginia Salem Union Street Queen Anne house home, houses homes 1888, American Americans,
© Jeffrey Isaac Greenberg 8+ / Alamy Stock Photo

Salem has a rich Native American history dating back to 8,000BCE. European explorers first came to the area in 1671, when they received guidance from the local tribes. Check out the popular Salem farmer’s market – it’s the perfect place to sample local produce.

These recommendations were updated on July 29, 2021 to keep your travel plans fresh.

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