Beautiful Towns in Shenandoah Valley, Virginia

Staunton is a charming small town you cant 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
Ann Marshall-Thomas

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.

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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.


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.


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.


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.


Home to a four-year college – Bridgewater College – Bridgewater was established in 1880. Scotch-Irish settlers first moved to the area in 1740, closely followed by Germans. Bridgewater’s historic Main Street was revitalized in the early 20th century.


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

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

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 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.


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.

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