
Population: 7,840
Drive time from NoVA: 1 hour, 45 minutes
Small Town Charm
It doesn’t take long to see the highlights of Ashland, but when you dig a little deeper, the town’s true treasures unfold. Henry Clay, an American statesman who served as secretary of state and the speaker of the U.S. House of Representatives in the early 19th century, was born in Hanover County, and Ashland is named for Clay’s Kentucky estate (the county is celebrating its 300th anniversary this year). Located just 20 minutes north of Richmond, Ashland is a college town where students from Randolph-Macon College keep the vibe fresh. Cheekily nicknamed the “Center of the Universe” by a former mayor, Ashland’s historic downtown has two railroad tracks cutting straight through Center Street, making it a “whistle stop” on the Amtrak and CSX lines. Visitors don’t have to be train aficionados to enjoy Ashland, thanks to the quirky shops, farm-to-table restaurants and recently reopened Ashland Theatre. With its historic charm and college town vibe, Ashland has an old-timey feel, with big city perks.

Must-Sees
Go to Ashland car-free on Amtrak’s Northeast Regional Line, or take a quick drive down I-95. Begin your exploration on Center Street, named for the railroad tracks that cut through the center of town. The early 20th-century buildings house an eclectic mix of shops, restaurants and the town’s visitor center inside a 1920s-era train station.
With the train as a centerpiece, there are lots of train-themed places here, like Ashland Museum, housed in a vintage red caboose, and The Caboose Market & Cafe, a restaurant featuring seasonal farm-to-table fare and local beer tap takeovers. Train devotees come from far and away to visit Tiny Tim’s Trains & Toys, stocked from floor to ceiling with railroad gear for building model railways. Also on Center Street is Bell Book & Candle bookstore with children’s books and tomes on Virginia history and its historic railways.

The most recent addition to Ashland’s cultural lineup is the reconstructed Ashland Theatre, a performing arts venue showcasing live music and film. Originally opened in 1948, it was a state-of-the-art theater where people gathered to watch movies and newsreels. The owners operated a second theater that served African Americans in this formerly segregated community. Learn about the history and legacy of Ashland’s citizens of color at the Hanover County Black Heritage Society in the Henry Clay Inn.
Downtown Ashland has several shops of note, especially the Ashland Meat Company at Cross Brothers, a specialty grocer with Virginia-made products, a deli and butcher. Refunkit is a treasure trove of handcrafted art, unique furniture, jewelry and garden sculptures. Sample the town’s best craft beer at Origin Beer Lab, a downtown tasting room specializing in innovative beers and seltzers; Origin is the sister brewery of Center of the Universe Brewing Company, 10 minutes south of Ashland.

You won’t go hungry either. Among the many restaurants on Center Street is Homemades by Suzanne, an Ashland institution with carryout meals, baked goods and Southern comfort food. Occupying two stories of a 100-year-old former department store, Iron Horse Restaurant is an Ashland landmark that serves meals all day and has a patio overlooking the tracks.
Make it a Weekend
The Henry Clay Inn resembles a classic antebellum-style mansion with a porch overlooking the train depot on Center Street. The original hotel was constructed in 1906, but, after a fire, was rebuilt in 1992. The lobby and guest rooms are appointed with turn-of-the-20th-century Americana furnishings. Full breakfast is included in the dining room. Virginia Crossings Hotel & Conference Center is 15 minutes from downtown Ashland. The sprawling resort—from Hilton’s boutique Tapestry Collection—has a swimming pool, golf course, putting green, volleyball court and fitness center.

What the Locals Know
Chris Ray is the owner of Origin Beer Lab and Center of the Universe Brewing Company. As a longtime resident, he can easily articulate Ashland’s allure: “People love watching the 32-plus daily trains that travel through the middle of our town. Whether you are sitting on a restaurant patio, or walking to one of our various museums, it’s always an experience to be so close to those trains rolling down the tracks.” Ray says the town has matured a lot in recent years. “The typical artsy days in Ashland now lead to exciting night life. Several new restaurants have popped up, along with the massive renovation of the Ashland Theatre—it’s now open for business and shows first-run movies, live concerts, comedies and lectures.” He says the town’s residents love welcoming visitors to Ashland to enjoy “some Southern charm and old-fashioned fun.”
This post is a part of our May 2020 print issue‘s cover story, “Small Town Adventures.” For more travel guides, subscribe to our Travel newsletter.