8 Most Charming Town Squares In Virginia

The state of Virginia stretches from the Atlantic Ocean to the Appalachian Mountains and is famous as the "Mother of Eight Presidents." The commonwealth has produced more presidents than any other state and is full of fascinating history. The small towns embrace the best elements of Old Dominion, and these eight charming downtown districts show the community's pride.

Traditional commercial structures line the compact streets and are home to galleries, museums, and other unique finds. The modern amenities merge seamlessly with the historic and natural scenery, making these towns among the best to visit. Towns like Staunton are famous for their historic structures and schools, while others are known for their vibrant art scene. Check out these best town squares in Virginia.

Middleburg

Charming and picturesque, Middleburg's downtown section is a vibrant district with small-town charm. Founded in 1787, the area boasts more than 160 historic buildings on the National Register, featuring brick-lined streets and fascinating sites. Sophisticated lodging is available at the Red Fox Inn and Tavern. Sit in a quaint setting and enjoy four-course meals or visit the bar for pub fare.

Brick and Mortar Mercantile is another landmark downtown that transforms the shopping experience. Along with selling books and home goods, the venue hosts community events like Paint a Pint nights and live music events. Antiquing is popular here, especially at the Middleburg Antique Gallery. The gallery features over 45 local, national, and European dealers, and one could spend an entire day here, and many do.

Onancock

Historic Onancock traces its roots to the 1600s, and it is filled with historic charm mixed with modern amenities and a fantastic dining scene. North Street Playhouse is a must-see live performance theater, the only year-round venue on Virginia's Eastern Shore. The district also has historic homes, such as Ker Place.

Tours are available at the Georgian-style mansion, which allows visitors to see the 19th-century furniture. The Eastern Shore Maritime Museum shines a bright light on the region's nautical history, a pivotal part of the area's economic prominence. There are many other interesting things to do and see, and one visit will more than likely lead to more.

Wytheville

Downtown Wytheville is a fun and charming district with a vibrant community spirit and many festivals that celebrate the unique region. Mayhem on Main in October promises to be a fun event where the residents and visitors put on their Halloween best and gather in the streets. Other interesting venues include Oracle Books, a used book and record store that consists of a listening room.

There are also sophisticated lodging options on Main Street, like the Trinkle Mansion Bed and Breakfast. The luxurious inn was finished in 1912 and includes seven fireplaces and elegant furnishings that make any visit to Wytheville complete. Finishing the day at one of the numerous restaurants, including Graze on Main, serving Southern cuisine and offering outside seating.

Williamsburg

Historic Williamsburg is a stunning town filled with living history events and venues. The walkable district offers modern shopping experiences and historic homes, such as the Armistead House. Boutiques include Blink and Brick and Vine. Merchant Square is a must-see area in historic downtown with over 40 stores and restaurants, and a significant draw for many.

The Williamsburg Manor Bed and Breakfast is a fine example of Williamsburg's architectural elegance. The estate was built in 1927 during the Rockefeller reconstruction period. The rooms offer a glimpse into the past while offering modern conveniences. It is also a short distance from the heart of downtown and a transformative experience.

Fredericksburg

Historic downtown Fredericksburg has more than 350 18th and 19th-century buildings in its 40-block district. Unsurprisingly, there are many historic inns available for lodging, such as the Richard Johnston Inn and 1890 Caroline House. The inn was built in 1770 and is only one block away from the Caroline House. Both offer elegant furnishings that reflect the historic spirit of the town.

Fredericksburg Square on Caroline Street is a timeless wedding venue that must be seen to be believed. The 1854 brick building can accommodate up to 275 guests. Summer is a special time to visit during the annual Twilight in Downtown event every Wednesday. Shops stay open later, with sales and happy hour events, providing a unique time to explore the district.

Abingdon

Many people visit Abingdon's downtown district for its charming atmosphere, shops, and restaurants. The brick sidewalks of the 20-block section have many unique finds, including Siegner's LTD and Abdingdon Olive Oil Company. After a day of exploring the venues, stop at the Sweetbay Brewing Company for a craft brew and a relaxing evening, or another of the many available options.

Courthouse Hill, named for the local courthouse, is worth seeing. The 1868 courthouse is a remarkable structure, and the area includes several boutiques, coffee shops, and interesting venues. There are several other districts to explore, each with its own characteristics and charm. This is a great town to explore on foot, with a pleasant combination of fascinating history and shopping options.

Staunton

Staunton's historic downtown is a Virginia Main Street district with 270 businesses and 30 restaurants, many of which are housed in Victorian architecture. Unique attractions include the Blackfriars Playhouse and the American Shakespeare Center.

Walking around the historic architecture will whisk you away to a different era. The Woodrow Wilson Museum should not be missed. It interprets the history of the 28th president and other famous townspeople. This is one of the most charming districts in the state, with an abundance of cultural attractions and a historic atmosphere.

Winchester

Downtown Winchester, known as Old Town, has been a pivotal marketplace for over 250 years, encompassing an astounding 45-block area. The vibrant district, filled with traditional brick storefronts, is a walkable area featuring many shopping and dining options. The Loudoun Street Pedestrian Mall has earned a listing on the National Register of Historic Places Travel Itinerary and is considered a must-see hallmark of the area.

There are many festivals and events celebrating the community. Events include the Shenandoah Apple Blossom Festival and Winchester Winter Village, two spectacular times to plan a visit to Old Town. While in town, check out George Washington's Office. The fascinating log cabin was Washington's office from 1775 to 1776 while Fort Loudoun was being constructed, and it is only one of many American history sites to explore in Winchester.

From scenic Staunton to the amazingly historic Williamsburg, these are the best town square areas in Virginia. The state is known for its diverse topography and history, and these areas reflect the best aspects of its beauty and charm. The historic venues and modern amenities combine to make scenic districts and memorable visits.

Towns like Middleburg are reminiscent of small-town Americana, and the sights and attractions are unbeatable. For those seeking a tranquil retreat with unique venues, these are the town squares to visit. There is everything from exquisite dining options to vibrant art scenes in these districts, making them unbeatable for any visit.