3 perfect days in Lexington, Virginia

Perched at the junction of Interstates 81 and 64 with the Blue Ridge Mountains as a backdrop, Lexington is anything but a pass-through town.

Nestled along the southern edge of picturesque Shenandoah Valley, this lively small town—originally an 18th-century stopover on the Great Wagon Road—quickly developed into an important crossroads and never looked back. With the founding of Washington and Lee University in 1749 and the Virginia Military Institute (VMI) in 1839, Lexington’s future was cemented.

Today, brick and stone buildings house contemporary galleries, breweries, coffee shops, and restaurants that—combined with several fascinating historic sites—provide ample options for visitors to explore.

If nature is more your speed, nearby attractions are plentiful, including Natural Bridge State Park, the Appalachian wilderness, and lavender fields in the pastoral countryside. Bonus: Breweries and wineries are located all along the way.

Here’s how to take in the highlights in 3 days.

Kick off your visit with an old-fashioned carriage tour. Lexington Carriage Company offers a horse-drawn saunter through the old town, passing by the Jackson House, VMI, Washington and Lee University, and Oak Grove Cemetery.

Guides share local history tidbits along the way: For example, you’ll learn that horse-drawn vehicles couldn’t climb the town’s original steep streets, so residents physically lowered the grade by hand shovel. Public tours are offered April through October.

While taking a stroll, be sure to look down at the sidewalk, where you’ll spot plaques interspersed among the bricks. These “story stones” give a nod to the intriguing people who made their mark on the town, known as the “Righteous & Rascals of Rockbridge.”

Mary McD Greenlee’s stone, for example, reads: “First woman settler, a feisty tavern keeper regarded as a witch, died 1809 at 102 years.” You’ll also find a stone for Patsy Cline: “Country music legend, lived at Wood’s Creek, Lexington, 1930s.” See an interactive map of the story stones.

Feeling fancy? Try the elegant Juniper Lounge at the Gin Hotel, serving classic American dishes beneath crystal chandeliers; or Haywood’s piano bar, named after a man who liked to eat well. Go more casual at Heliotrope, a brewery with yummy pizzas; or Legendary Eats, with sandwiches big enough to share.

There’s no better way to cap off the evening than with a Haunting Tales ghost tour, which takes you through Lexington’s darkened streets before ending up at Stonewall Jackson’s family tomb in Oak Grove Cemetery. The tour is available May through October. Pro tip: Request exuberant tour leader Mark Cline.

Settle in at The Georges, a boutique hotel comprised of 4 historic buildings on and around Main Street. Its 33 cozy rooms, each decorated in a unique style, include in-room amenities like heated floors and towel warmers. Rates start at $289.

In the morning, indulge in a decadent doughnut at Pure Eats, courtesy of the Doughnut Divas—the women bakers who make a mouthwatering selection of sugary treats daily at this former gas station that dates to 1925. The menu has heartier breakfast items as well, including stuffed burritos and egg dishes. Lunch and dinner options are equally good.   

Stroll to Washington and Lee, the nation’s ninth-oldest college. Its brick, white-columned buildings overlook a sprawling lawn. Visit the unadorned University Chapel, built around 1868, with art galleries on the lower level. General Robert E. Lee, once the college’s president, is buried here in a family crypt.

Several small campus museums are worth a peek too, notably the Reeves Museum of Ceramics, displaying a collection spanning 4,000 years; the Watson Galleries, exhibiting international fine arts, including works by Charles Willson Peale and presidential portrait artist Gilbert Stuart; and the authentic Japanese Tearoom, open for viewing and semimonthly tea demonstrations that show the traditional process of making powdered matcha.

Nearby, VMI began at the site of the Virginia State Arsenal in 1839. During the academic year, cadets lead daily tours of the historic VMI Post at 12:15 p.m. The VMI Museum has weapons, clothing, and other artifacts that relay the history of VMI and its illustrious alumni, among them Nobel Prize winners, military leaders, and politicians.

What captures most people’s attention are the bullet-ridden raincoat Stonewall Jackson wore when he was killed in 1863 at the Battle of Chancellorsville and the hide of his horse, Little Sorrel.

Head south on Route 11 and stop for hamburgers, sandwiches, or salads at the whimsical Pink Cadillac Diner, filled with 1950s Elvis memorabilia.

A short but steep jaunt at Natural Bridge State Park leads to the 200-foot limestone arch rising above the gorge and Cedar Creek. Thomas Jefferson bought this natural wonder and the surrounding 157 acres in 1774, with the hopes of someday building a “little hermitage” here, although he never did.

Return to Lexington and call it a day, or stick around for the park’s Dark Sky Program if it’s scheduled. Grab a casual dinner at the Natural Bridge Historic Hotel and Conference Center, then head toward Jefferson Point by foot or hay wagon.

Here, rangers set up telescopes to view the twinkling stars and planets up close. An added bonus: Thousands of fireflies brighten the darkness, creating a magical world of sparkles above and below.

If a ranger-led program isn’t scheduled, take a self-guided hike under the stars on Tuesdays between April and October. BYO binoculars and telescopes.

Enjoy breakfast at Seasons’ Yield Farm at Haywood’s, featuring piping-hot pastries fresh out of the oven, plus sourdough toast piled high with local ingredients. 

Spend the day on a leisurely loop drive that highlights part of the Blue Ridge Parkway and northern Rockbridge County. Get on the fabled parkway via the mountain town of Buena Vista and head north, enjoying breathtaking views of misty peaks, dazzling woodlands, and the Shenandoah Valley far below.

Short hiking trails along the way—including Yankee Horse at milepost 34.4 and Boston Knob at milepost 38.8—entice you to experience this wild beauty on foot.

Spend the afternoon exploring the lovely northern Rockbridge County. Options include wine tasting at Rockbridge Vineyard and Brewery and Ecco Adesso; strolling along scented trails at Lavender Fields at Tantivy Farm; and checking out Wade’s Mill, which has been making stone-ground grits, cornmeal, and flour in the traditional way since 1750. More enchanting activities include hiking the 7-mile Chessie Nature Trail and kayaking the James River.

The Lexington Visitors Center is located at 106 E. Washington Street. For more information, email info@lexingtonvirginia.com or call 540-463-3777.

Barbara Noe Kennedy is an award-winning travel journalist based in Washington, D.C.