Charming Virginia Small Towns

These charming Virginia small towns have it all from incredible mountain sceneries to pristine beaches, and just as you’d expect, each one of them has a deeply rooted history. If your experiences with Virginia so far only revolve around Virginia Beach or the cities surrounding Washington, D.C., take the time to check out one or two of these charming Virginia small towns. You won’t be sorry.

Charming Virginia Small Towns


Mention the words “charming Virginia small towns” and you’ll likely hear about Chincoteague, one of Budget Travel’s “coolest small towns in America.” What makes it so is its chill beach experience. This quaint fishing town was established some 300 years ago but wasn’t propelled into the mainstream until the 1960s when the film Misty of Chincoteague was released. It was based on a children’s book of the same title, written by Marguerite Henry when she spent her holidays on the island. In addition to the amazing seafood, pristine beaches, and boat tours that are typical of any beach town, Chincoteague is also known for its wild ponies, many of which are found in the neighboring island of Assateague.

Charming Virginia Small Towns: Chincoteague Ponies
Chincoteague Ponies


If you’re looking for a small town that’s not just rich in history but also upholds many of its traditions, look no further than Abingdon. Tucked in the picturesque Blue Ridge Mountains in the southwestern part of Virginia, visitors will find themselves transported back through time as they walk along the town’s main street or when they decide to spend a night at the historic Barter Theatre where patrons can still barter for their ticket. Nature lovers will appreciate the many hiking, biking, even horseback riding trails located at nearby Appalachian and Virginia Creeper while adventure seekers can follow some of the paths Daniel Boone took when he explored the area near the Virginia and Kentucky border.

Charming Virginia Small Towns: Barter Theatre in Winter
Barter Theatre in Winter


The hometown of the infamous Virginia ham, Smithfield, is likely amongst the top charming Virginia small towns on any traveler’s list not only because it holds the title of being “America’s Happiest Seaside Towns” according to Coastal Living but also because of its traditional Southern hospitality. Smithfield has a thriving community spirit as seen through its many local festivals and events. Spend some time in its Main Street where you’ll come across the historic Smithfield Inn, which has been entertaining guests from out of town for 150 years.

Charming Virginia Small Towns: Virginia Ham Dish
Virginia Ham Dish


Commonly referred to as the “horse and hunt capital of Virginia”, the tiny town of Middleburg is pack with history and beautiful country scenery. With barely a thousand residents, the town most certainly has a small town feel. Many of the buildings in its 10-block area are listed buildings including the Red Fox Inn. Middleburg is also home to the National Sporting Library with books dedicated to hunting, horse sports, shooting, and fishing.

Charming Virginia Small Towns: National Sporting Library & Museum, Middleburg
National Sporting Library & Museum, Middleburg


Just two and a half hours southwest is Lexington, Virginia, a quaint college town that also packs so much history. In this charming Virginia small town, visitors will find the chapel that Confederate General Robert E. Lee is interred as well as museums dedicated to Stonewall Jackson and George C. Marshall, both of whom spent a large part of their adult lives in Lexington. The town also showcases a large number of historic homes, some of which lines up its downtown area where boutique shops and local restaurants now reside. Finally, Lexington is surrounded by gorgeous scenery. The haunting views of the Shenandoah Valley makes it a favorite destination for outdoor enthusiasts as well.

Charming Virginia Small Towns: Lee Chapel and Museum, Lexington
Lee Chapel and Museum, Lexington via Flickr by J. Stephen Conn, CC BY-NC 2.0


Another gem on Virginia’s Eastern Shore is Onancock. Established in 1680 as Port Scarborough, it was a frequent stop for steamboats sailing from Norfolk to Baltimore. Nowadays however, Onancock is a destination for the arts with an award-winning live theater and plenty of local painters, craftsmen, sculptors, actors, dancers, musicians and glass blowers showcasing their work around town. It’s also serves as a great home base for exploring the rest of the Virginia’s Eastern Shore with plenty of accommodation options ranging from budget bed and breakfast to indulgent waterfront inns.

Charming Virginia Small Towns: Charlotte Hotel, Onancock
Charlotte Hotel, Onancock via Flickr by Bill Smith, CC BY-NC 2.0


Staunton is likely the most lauded small town in Virginia, with several well-known travel sites naming it not just one of the most charming Virginia small towns, but also one of the best in America. And it deserves it too. Staunton offers visitors plenty of beautiful natural sceneries thanks to its location right in the heart of the Shenandoah Valley. It’s also home to the Frontier Culture Museum, a great living history museum that tells the story of Old World migrants who took the leap and settled in the New World, and the Blackfriars Playhouse, a classic indoor Shakespearean wooden theatre where you can watch superb performances of the playwright’s work.

Charming Virginia Small Towns: Frontier Culture Museum of Virginia, Staunton
Frontier Culture Museum of Virginia, Staunton

About Iris A


Born in the Philippines, but grew up in Texas, Iris has been traveling and writing about her experiences for well over a decade. Her work has been published on well-known travel sites like Hipmunk (#hipmunkcitylove) and D Magazine Online Travel Club. She has been all over Europe, the US, and has recently started exploring Latin America. She loves trying local cuisine and visiting UNESCO deemed World Heritage sites. Her favourite city is New York, with London, following a close 2nd. You can follow her on Twitter @sundeeiris or through her travel blog, Traveling With Iris.

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  1. Things to Do in St Simons Island GA - Go4Travel Blog

    […] who love the outdoors. It also has plenty of history dating back to the 1700s. Finally, like all quaint small towns, it has boutique shops that sell locally made products and artisan restaurants that feature […]


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