Things To Do
Explore Charlottesville's unique attractions, from Thomas Jefferson's Monticello to the Historic Downtown Mall and Shenandoah National Park
Things to Do While Staying at The 200 South Street
One of the best parts about staying at The 200 South Street is that you're perfectly positioned to experience the very best of Charlottesville. From sipping wine in the rolling foothills of the Blue Ridge Mountains to exploring our vibrant downtown, every adventure is just steps or minutes away. Here's our handpicked list of experiences we think you'll love:
Monticello Wine Tour & Coach Co.
Discover Virginia wine country in style with Monticello Wine Tour, Charlottesville's premier private wine tour company. Relax in luxury vehicles — from Mercedes Sprinters to panoramic Suburbans — as your personal driver whisks you through the scenic Monticello Wine Trail. Each tour is fully customized by a concierge team who can arrange tastings at the region's most celebrated wineries, breweries, and cideries. It's the ultimate way to savor the flavors and views of Central Virginia.
Stroll the Historic Downtown Mall (Steps from Our Door)
Just a short walk from the inn, Charlottesville's Downtown Mall is one of the longest pedestrian malls in the country. Explore locally-owned boutiques, art galleries, and bookstores, or settle in at one of the many acclaimed restaurants. Street musicians, outdoor patios, and historic theaters give this area a charm all its own.
Steps from our door
Thomas Jefferson's Monticello
Thomas Jeffersons Monticello
Short drive from South Street
Hike the Blue Ridge Mountains
Just a short drive west, you'll find countless hiking trails in Shenandoah National Park and along the Blue Ridge Parkway. From leisurely strolls to challenging climbs, there's a trail for every level — and the views are unforgettable.
Short Drive West
Carter Mountain Orchard
In spring and summer, enjoy peach ice cream and orchard picnics; in fall, pick your own apples against a backdrop of panoramic mountain views. The sunsets here are some of the most photographed in Charlottesville.
Short Drive from South Street
The Paramount or Ting Pavilion
Cap off your evening with live entertainment. The Paramount Theater offers an intimate setting for national and local acts, while the Ting Pavilion hosts large-scale concerts under the stars on the Downtown Mall.
Downtown Mall
Plan Your Stay Around Your Adventures
Whether you want a perfectly curated wine tour, a deep dive into Virginia's presidential history, or simply a beautiful walk through our lively downtown, The 200 South Street places you at the heart of it all. Our concierge team is happy to help with reservations, insider tips, and special arrangements to make your visit unforgettable.
