The Weekender: Charlottesville, VA

Stroll Along the Downtown Mall

Charlottesville’s quaint Downtown Mall is a mere 7 red-brick and tree-lined city blocks, but it’s chock-full of local shops and boutiques, restaurants with alfresco dining, and bars. Head downtown on a Friday afternoon, and you’ll find the doors to art galleries thrown open for First Fridays and free concerts at the Pavilion during spring and summer.

Slip on: Some sleek but chic footwear. You’ll thank us later when you see someone stumble in high heels on the uneven brick.

Experience Virginia Wine Country at Its Finest

If sipping wine and gazing out at the rolling countryside with the Blue Ridge Mountains in the background sounds like an idyllic afternoon, you have an option or twp or 20 in Charlottesville. Plan to spend the afternoon at Barboursville Vineyards, a breathtaking 18th-century estate with a year-round tasting room, an elegant library and a flagship Bordeaux, Octagon, that was served at President Obama’s inaugural dinner.

Bring: A picnic tote to carry your favorite Cab Franc (a popular Virginia varietal) while you stroll along the splendid lawns.

Dine at Mono Loco for Not-Your-Average Mexican Cuisine

Just off the Downtown Mall on Water Street, duck into this funky little cantina for hip Latin fare. A Charlottesville staple, Mono Loco serves the requisite chips, salsa and tasty margaritas, alongside specialties such as the Nola Loca Burrito with crispy oysters, pork and jalapeno crema. Of all your options off the Downtown Mall, this one is good for groups, and the ambience is fun.

Wear: A lightweight leather jacket that will stave off any chill so you can dine alfresco beneath the twinkling lights.

Take in the View From Humpback Rock

Since Humpback Rock is best enjoyed in the morning, fuel up with some local favorites, such as bagels at Bodo’s or a sandwich from Bellair Market (don’t let the unassuming gas station fool you), before you hit the road. Take the beautiful Blue Ridge Parkway to Milepost 6, where you’ll find a parking area for Humpback Rock. It’s roughly a mile up and back, but it is STEEP and rocky, so you’ll definitely get in your workout for the day — and be treated to a spectacular view (particularly at sunrise).

Don’t forget: Your trusty, BPA-free S’well water bottle to stay hydrated (especially after all that wine).

Make the Pilgrimage to Monticello

A trip to the ’ville wouldn’t be complete without a nod to its most prolific resident: Thomas Jefferson. You can visit his university or, if you prefer to stay away from the college crowds, venture to Monticello, a popular spot for Charlottesville first-timers. Allow a few hours to take a guided tour of the Founding Father’s house, which is renowned for its neoclassical style, and wander through its grounds, revolutionary gardens and even Jefferson’s grave site.

Top it off: With fall’s must-have hat, the felt fedora.