9 Picture-Perfect Main Streets In Virginia

Victorian storefronts fill a tight walkable grid along Beverley Street in downtown Staunton. In Abingdon, potters and painters work in the open at The Arts Depot on Main Street. Equestrian shops still line Washington Street in Middleburg beside a tavern opened in 1728. A giant yellow pencil hangs over Main Street in Wytheville above an old office supply store. Preserved 18th and 19th century buildings surround Caroline Street in Fredericksburg by the hundred. These nine main streets each give Virginians a reason to spend an afternoon downtown.

Staunton - Beverley Street

A downtown architectural tour along Staunton's main thoroughfare, Beverley Street, is an absolute must when visiting this historic district, which was added to the National Register of Historic Places in 1982. In particular, it is known for its Victorian architecture, with many buildings dating back to the 1870s and 1920s. Along this street, and worth a visit, is Collins Market, where you'll find local goods, coffee, and deli sandwiches, housed in the 1916 remodeled Clocktower building. Further down Beverley Street, there is what was once a Masonic Temple, dating back to 1896. It is one of the oldest buildings in Staunton and now houses unique local shops, such as the Baja Bean Company and The Split Banana. Beverley Street is also home to the Stonewall Jackson School, which is a must-see.

Abingdon - Main Street

Abingdon is an artsy town with a lively Main Street. Visitors to Abingdon can visit places like The Arts Depot to watch artists painting or molding pottery, or the famous Barter Theater, the longest-running professional theater in the country, for a show to experience the artistic side of the town. But Abingdon is also a historical town. It is home to a 22-block historic district steeped in history. In this area, you'll find the Market District, where the Abingdon Farmers Market takes place on Tuesdays and Saturdays, and where you can find muscadine wine, pickled okra, and other local goods. This historic downtown is also home to the Courthouse Hill area, where locally owned shops and boutiques line the street, as well as one of Abingdon's best restaurants, The Tavern. The Tavern not only serves great food but is also housed in Abingdon's oldest building, dating back to 1779.

Middleburg - Washington Street

Middleburg may be a tiny town, but it has a big personality. Just steps from town, in addition to the Boxwood Estate Winery, several others add to a list that makes this destination worthy of a wine tasting adventure. Much of what there is to see and do right in the town, though, is situated along Washington Street, including The Red Fox Inn & Tavern. This historic inn and dining establishment, opened in 1728, has been serving visitors for almost 300 years. Washington Street is also the perfect place to shop for equestrian gifts, as the town is known for its equestrian identity. Antique shopping is popular in Middleburg, too, with shops like the Middleburg Antique Gallery and Grandeur Antiques just steps from more modern shops like Chloe's of Middleburg and Crème de la Crème.

Culpeper - Main Street

Culpeper's downtown and Main Street are a mix of modern and historic elements that define its personality. Named "The Prettiest Town in Virginia" by Architectural Digest, Culpeper is home to a sufficient number of 18th, 19th, and early 20th-century buildings to satisfy any architecture aficionado. The Burgandine House, a log cabin built in 1749, is now a museum that is worth visiting and sits right on Main Street. Just down the street is Pitts Theater, which dates back to 1938. After taking a walk back in history, visitors can stroll along Main Street and shop in some of the unique boutiques and stores that call the street home. The Chaotic Collector, known for antiques and retro finds, and Quail-At-The-Wood, which sells 18th- and 19th-century antiques, are great places to start for those who like all things old.

Wytheville - Main Street

Not to sound cliché, but unique is the best way to describe the small town of Wytheville, and its Main Street falls right in line with the rest of the town. One of its most notable attractions is the giant yellow pencil that towers over the west end of the street, measuring a whopping 30 feet. For dining on Main Street, the Log House 1776 Restaurant is loved by locals and visitors alike, but for an even more unique dining experience, Wohlfahrt Haus Dinner Theater may be in order. This 27-year-old establishment offers a four-course meal and live theater shows all in one. For those who prefer a different kind of performing art, Seven Sisters Brewery offers live music, and Oracle Books hosts musicians and jam sessions, both located on Wytheville's eclectic Main Street.

Winchester - Loudoun Street

When a town's main street area is called Old Town, like it is in Winchester, it attracts interest and curiosity, and Old Town Winchester will not disappoint. The highlight of the area, Loudoun Street, serves as its main street and is part of the larger Old Town Winchester, a National Register Historic District comprising 45 blocks. Stretching along this street is the Loudoun Pedestrian Mall, flanked by unique shops like the 40-year-old Winchester Book Gallery and favorite dining options like the Village Square Restaurant, housed in a building dating back to the 1800s. For a taste of history on Loudoun Street, a visit to the site of George Washington's Historic Fort Loudoun and the Shenandoah Valley Civil War Museum has plenty to offer.

Lexington - Main Street

The Main Street in Lexington is so much more than just a pretty street. It is the hub of activity for locals and visitors who want to explore the culture and history of this vibrant town. With views of the Blue Ridge Mountains, this Main Street is characterized by its mountain town vibe and eclectic identity. Along it, visitors can stop at unique specialty shops like the Sugar Maple Trading Company to bring home handcrafted items and vintage treasures, and Ladles and Linens, to shop for handmade pottery and gourmet food items. After a day of shopping, dinner al fresco at Juniper Lounge, with outdoor seating overlooking Main Street, or Pure Eats for doughnuts or burgers, is a great way to end the day.

Smithfield - Main Street

The Chesapeake Bay vibes in Smithfield, thanks to its location on the Pagan River, might be what draws many visitors to the town, but its Main Street is an experience worth staying for. Along this Main Street are historic museums and cultural institutions, such as the Schoolhouse Museum, which dates back to 1932, and the Art Center @ 319, which exhibits and sells works by local artists. Follow that up with some craft brews at the Wharf Hill Brewing Company before heading out to try the namesake of the town itself, a slice or two of Smithfield ham. Coined as "The Ham Capital of the World," it is not a surprise that there are several places to get some. On Main Street, the best option is The Genuine Smithfield Ham Shop, where visitors can enjoy delicious ham and purchase a variety of food items to take home.

Fredericksburg - Caroline Street

Diverse, authentic, and historic are just a few of the words that perfectly describe the town of Fredericksburg, and the town's main street, Caroline Street, showcases it all. Caroline Street and the 40-block Old Town area overall are filled with well-preserved 18th- and 19th-century buildings, as many as 350. So, an architectural tour, whether on foot, aboard a trolley, or by carriage through Olde Towne Carriage of Fredericksburg, is highly recommended when visiting the town. Follow that up with shopping for local goods at the Made in Virginia Store and then lunch or dinner with a view. There are around 30 restaurants with outdoor seating in Fredericksburg, and several are right on Caroline Street. Capital Ale House and Sammy T's are just two that locals love.

Where Virginia's History Lives Downtown

Virginia is only the 35th-largest state in the US, but it holds deep reserves of history and culture. The main streets in the smaller towns are where that history and culture can be found and explored. They are where locals gather and where they share their community with visitors from around the world. These nine reward a slow walk and a full afternoon.