If you are looking for a historic Virginia getaway where you can park your car once and explore everything on foot, Lexington, Virginia needs to be at the top of your travel bucket list.
Nestled in the southern Shenandoah Valley, Lexington is incredibly walkable. The best strategy for a day trip or weekend visit is simple: just park your car right off Main Street or Jefferson Street, and you can easily walk to almost all of the town’s main attractions.
From striking collegiate architecture to serene riverside nature trails, here is the ultimate guide to exploring the best of downtown Lexington.
My Favorite Things to do in Lexington, VA
🏛️ Historic Highlights & Stunning Architecture
Walking through downtown Lexington feels like stepping back in time. As you stroll around, the gorgeous Victorian houses are incredibly fun to walk by. But the real architectural highlights belong to the town’s two historic higher-education institutions, which sit right next to each other.
Virginia Military Institute (VMI)
The Virginia Military Institute campus is genuinely impressive. It features a historic, fortress-like design that feels so massive it takes up half the town it seems! Walking past the grand barracks gives you a real sense of the deep military history embedded in this region.
Washington and Lee University
Directly across the street from VMI sits Washington and Lee University. The vibe changes instantly as you step onto a beautiful campus defined by classic brick architecture, white columns, and sweeping green lawns.
Oak Grove Cemetery
A short walk away is Oak Grove Cemetery (historically known as the Stonewall Jackson Cemetery), where Confederate General Stonewall Jackson is buried. You’ll find a large, prominent statue of him standing right in the middle of the cemetery grounds.
🛍️ Main Street Shopping & Sweet Treats
After soaking in the history, head straight over to Main Street. The downtown area is lined with incredibly cute shops, local boutiques, and art galleries perfect for an afternoon of window shopping.
Pro Tip: Don’t leave downtown without stopping for a sweet treat! Grab some award-winning, homemade ice cream at Sweet Things Ice Cream Shoppe on Washington Street. Their hand-rolled waffle cones are legendary and make the perfect fuel for a walking tour!
🥾 The Best Walking Trails in Lexington
For nature lovers, Lexington boasts some great walking trails that connect seamlessly to the town. You don’t even have to drive to a remote trailhead to get a dose of the great outdoors.
Woods Creek Trail: A lovely, shaded path that takes you right by a bubbling creek. It runs right through the edges of the university campuses and parks, making it perfect for a casual stroll.
The Chessie Trail: If you want something a bit more adventurous, look for the Chessie Trail. Skirting right along the scenic Maury River under the shade of mature trees, this historic rail-trail goes on for a full 7 miles! It features a flat, easy-to-walk gravel path with beautiful views of old lock ruins, towering cliffs, and local farmland.
🗺️ How to Plan Your Lexington Visit
| Where to Park | Main Street or Jefferson Street parking lots / street spots |
| Walkability Rating | 10/10 — No car needed once downtown |
| Top Photo Spots | The VMI Barracks, W&L Front Lawn, Main Street storefronts |
| Best Season | Spring (blooming trees) or Fall (vibrant autumn foliage) |