This Small Virginia Town Has The Best Downtown
Lexington is a town in the Commonwealth of Virginia that is as much defined by history as by its claim to one of the best downtowns. While it never hurts to have your community up against the gorgeous hills of the Shenandoah Valley, the star of Lexington is its carefully planned downtown layout, which allows rapid access to shops, dining, entertainment, and attractions, and lets you get by without a vehicle. Here, you can not only experience structures that have stood nearly as long as the settlement has, like Stonewall Jackson House and Miller’s House Museum, but you can also see the transformation of the community with two major institutions calling Lexington home: Washington and Lee University and the Virginia Military Institute. Tour Lexington and experience Virginia’s best downtown for yourself.
Where Lexington Began

One of the appeals of Lexington is that little has changed structurally in its downtown since its founding in the late 1700s. The settlement began in 1778, and over the centuries, the compact, walkable grid has shaped what visitors can find here today. The 18th and 19th-century architecture reflects the growth and expansion of Lexington through decades of change and reform, especially with the inclusion of the campuses of Washington and Lee University and the Virginia Military Institute, bringing a lively vibe to the area's entertainment, athletics, educational opportunities, and annual community events.
Dining in Downtown

Dining is a big part of why Lexington is deemed one of the best downtowns in the state. While there are multiple options in this compact assortment of packed city blocks, many locals point visitors to Haywood’s. There is a two-part dynamic to this establishment, the first being a successful daytime café serving fresh, seasonal options. Most nights of the week, the place transforms into an elegant dining establishment and piano bar, offering upscale dishes like Mushroom Tagliatelle and Snapper with Baby Kale.

Just down the road and still on Main Street, Niko’s Grille is another popular destination to stop and grab a bite. This Greek-inspired spot is on a similar scale to eating at Haywood’s in the evenings, offering hearty, sit-down dinners that make it one of the most frequented stops in downtown Lexington. Favorites include the Greek salad with gyro, the Gyro Platter, and the walnut baklava.
Locally Owned Shops

A good part of what makes downtown Lexington special lies in its collection of small, independently run stores. Inside Just Games, visitors enter a space built entirely around tabletop games and roleplaying adventures from Magic: The Gathering to Dungeons & Dragons. The only standout thing from the central theme here is the business’s love of disc golf, even going so far as to sell equipment for the sport in the store for use on the local Washington and Lee University-run course.
Gift shops like Sugar Maple Trading Company on Main Street offer an authentic look at the whole of Rockbridge County. The selection of niche craft items, home décor, and home goods means a shopper can find everything from specialty balms, lotions, and soaps to puzzles and toys. Having this in the heart of downtown means visitors can experience the fame of historic downtown structures while selecting from carefully curated products and items that best represent central Virginia.
Attractions You Cannot Find Anywhere Else

History is one of the alluring qualities of downtown Lexington, and it has many stories to tell in this concentrated group of blocks. Start with the exploration of Confederate Lieutenant General Thomas “Stonewall” Jackson’s home. While the renowned military strategist was born in Clarksburg, West Virginia, the only home he would ever own was at 8 East Washington Street in Lexington, while he taught at the Virginia Military Institute. Those interested in the artifacts and stories of the figure’s life can visit his former home, now the Jackson House Museum.

To further help visitors explore the history of Lexington, many schedule a carriage ride with the Lexington Carriage Company. These are guided tours with drivers providing narration that highlight multiple factors, from the architectural feats of some buildings to their unique histories. Whether referring to the Miller’s House Museum or Oak Grove Cemetery, the historical foundation of Lexington is well documented and discussed on one of these guided adventures.
There is often more happening in downtown Lexington than its walkable layout. Gatherings and festivals play a big part in the community's personality, ultimately drawing thousands throughout the year to events such as The Rockbridge Community Festival, which has been held in late August since 1976. From arts and crafts to family fun and countless food vendors, this free festival draws a substantial crowd, and proceeds help local non-profit charities continue operating.
Lexington’s Downtown Stands Out in Virginia
Since the late 1700s, little has changed in the layout of Lexington’s center, making it a convenient, historic, and attractive destination for those seeking a truly all-in-one downtown setting. Between annual events like the Rockbridge Community Festival and historic properties right in the action, like the Jackson House Museum, Lexington is a compact city that is more than just shopping and dining, though it certainly shines in those areas as well. Those looking for an authentic look at central Virginian hospitality, historical significance, and the kind of liveliness that comes with being a multi-institution community, start in downtown Lexington.