Southern Loop
DAY 1
STAUNTON
Start your journey in the charming town of Staunton, hailed by Southern Living as one of the South’s Best Mountain Towns. In Staunton, architectural gems sit nestled amidst six historic districts — along with the world’s only re-creation of Shakespeare’s indoor theatre, the Blackfriars Playhouse, and Woodrow Wilson’s birthplace and Presidential Library. Explore all this via the brick-lined main street (Beverley), taking time to sample some wine or coffee at many of the local eateries. Try lunch at Remedy Burger or dinner at farm-to-table restaurants like Zynodoa. Sleep away your food coma at Hotel 24 South or the Blackburn Inn, one of two historic and high-end hotels within walking distance of downtown.
DAY 2
WAYNESBORO & HARRISONBURG
In the morning, cap off your Staunton adventure with some more living history at the Frontier Culture Museum or head straight to Waynesboro on HWY 250 to Farmhaus Coffee for a breakfast sandwich and latte in this charming converted home. Continue through Waynesboro on 250 to reach the Blue Ridge Tunnel Hiking trail. You’ll need a couple of hours to cover this 4.5 round trip historic hike, but the adventure is well worth it.
From Waynesboro, head up Skyline Drive for a strip of road that is a hiker’s heaven. This southern district of Skyline Drive reveals the most untamed side of the park, highlighted by the trails of the Big Run area. Bag three major waterfalls on one loop hike from Browns Gap, milepost 83.0 – two on Doyles River and one on Jones Run. Those looking for their nature fix can walk easily on the 1.2 mile Frazier Discovery Trail or challenge themselves with the very strenuous 9.8 mile Wildcat Ridge Trail. Exit Skyline Drive at Elkton where you can load up on supplies at Appalachian Trail Outfitters or pop over to McGuire’s Country Store for enough Americana nostalgia to last until the Holidays. Fuel up with a burger from Thirsty’s Burgers in Elkton or head to Harrisonburg for the night.
Harrisonburg’s walkable and bikeable downtown district is alive with music, art and history. Locals will urge you to check out the Farmers Market or one of the many art galleries downtown. This writer’s all-time favorite burger is the “Greg Brady” at Billy Jack’s Shack downtown. With monikers like “Virginia’s first culinary district” and “Great American Main Street” Harrisonburg will check all the mountain city boxes on your trip. Stay downtown at the Hotel Madison or treat yourself to a night at Massanutten Resort, a sprawling and breathtaking property with 6000 acres of mountain fun at its very best. The activities at Massanutten are numerous and ready-made. Enjoy golf, a waterpark, or a day at the spa or get back on the Virginia back roads to satisfy the wanderlust.
DAY 3
CROZET & CHARLOTTESVILLE
In the morning, turn around and head south on Skyline Drive or try HWY 810 to Crozet, home to Chile’s Peach Orchard, more delicious wineries, and the widely celebrated Starr Hill Brewery. Just a short drive east is the bustling academic city Charlottesville, home to the University of Virginia and Monticello, Thomas Jefferson’s mountain estate. Charlottesville’s Downtown Mall is the perfect spot for some boutique shopping or alfresco dining on the downtown pedestrian mall that is lined with historic buildings. Treat yourself to a night at the Boar’s Head Resort or the downtown Omni to rest your aching hiking muscles. In the morning, grab a quick bagel from Bodo’s Bagels, a UVA student staple, or find a seat at The Nook for some country cooking (we recommend the chicken and waffles). Direct the car back to 250 toward Afton with a stop at the Rockfish Gap Country Store for the not-to-be missed souvenirs.
