Often appearing on “best small towns in America” lists, Staunton, though not technically a small town, has the neighborly charm of one, with the cultural cache of a much larger metropolis. Where else can you find the world’s first re-creation of Shakespeare’s original indoor theater, a museum dedicated to the life and work of Woodrow Wilson, and a world-class international chamber music festival? Here’s what you’ll find in this college-town gem. This story is part of our July Explore Virginia by Train issue. Check back as we share additional weekend trips in Virginia that are just a train ride away.
Travel Time: About 3.5 hours by train from Alexandria
What to Do
This small city has become an unassuming epicenter of classical music in Virginia. Whether you’re an orchestral aficionado or an early-stage enthusiast, you’ll appreciate the community-focused devotion to the art of classical music in Staunton. The annual Staunton Music Festival, held every August (this year it’s August 15 to 24), brings more than 90 international artists to the city for 10 days of vocal, orchestral, and chamber music events. Expect pre-concert talks, intimate venues that make for excellent acoustics, and historical performance traditions. One of the best parts? You can bring the kids. Most festival events are open to all ages. Plus, every summer, the prestigious Heifetz International Music Institute hosts exceptional young string musicians from around the world. They fill the city with music nearly every night at events that are free for kids 12 and under.
Theater enthusiasts are also in for a treat. Staunton is home to a re-creation of Shakespeare’s indoor theater at Blackfriars Playhouse at the American Shakespeare Center, where actors often take on multiple roles within the same production. Pre-show and intermission music invite audience participation, and house lights remain on throughout to foster an authentic, communal experience.
The city is filled with unexpected delights, like the quirky Camera Heritage Museum with its collection of more than 6,500 cameras, the majority of which are antique. At the Woodrow Wilson Presidential Library & Museum, walk through the 28th president’s home and take a self-guided tour through seven galleries, where eye-catching artifacts include his restored 1919 Pierce-Arrow limousine. Learn about the origins of the region at the family-friendly Frontier Culture Museum, a large open-air living history museum where costumed interpreters and hands-on demonstrations bring you back in time. Walk down Beverley Street for more historic sites, art galleries, and independent shops featuring local makers.
Where to Stay
The Blackburn Inn and Conference Center, constructed in 1828, was once a mental health hospital and then a penitentiary. Now, it’s an elegant 49-room hotel a quick walk from downtown, inviting guests with its neoclassical red-brick facade, natural light, vaulted ceilings, local artwork, and coffee and wine bar. Ironically, the former prison boasts plush, welcoming accommodations, as well as a spa with a wide range of pampering services including Ayurvedic treatments. Its “Stay, Ride, Relax” overnight package includes tickets to the Virginia Scenic Railway. If you want to stay right in the heart of downtown, check out Barristers Row, the town’s newest boutique hotel featuring seven stylish suites with kitchenettes and contactless check-in.
Where to Dine
A semi-finalist for Best New Restaurant in the 2025 James Beard Awards, Maude & the Bear serves a seven-course tasting menu Thursdays through Sundays. Seasonal produce and artful presentations shine in the destination restaurant opened by chef Ian Boden and his wife, Leslie, where influences range from Jewish-Ashkenazi to Appalachian. Housed in a 1926 Montgomery Ward kit house, the restaurant comes with an upscale inn attached, and lucky guests get the benefit of a multicourse breakfast. Looking for a pre-theater meal? Find farm-to-table Southern food with ingredients from regional suppliers at Zynodoa, adjacent to the Shakespeare Center. For a more casual dining experience, try authentic hand-crafted Salvadoran food at Gloria’s Pupuseria or pies on the patio at Pizza Luca.
Feature image of Blackfriars Playhouse by Marek Kunicki
This story originally ran in our July Issue. For more stories like this, subscribe to Northern Virginia Magazine.
