Enjoy a hike or scenic drive in nearby Shenandoah National Park (The Rockfish Gap Entrance is ~30 minutes from Charlottesville). Some of our favorite hikes in the park are Turk Mountain, Blackrock Summit, Jones Run River and Doyles River Falls. For those looking for a longer hike, we recommend checking out the incredible Old Rag Mountain (reservations required).
Humpback rock is one of the most popular hikes in the area. Located off the Blue Ridge Parkway, this moderately strenuous 1 mile hike up to the summit offers some of the best views of Shenandoah valley and the surrounding mountains.
Explore some history at Monticello which was the home of Thomas Jefferson in the late 1700s. Tickets are required and details can be found on the Monticello website.
Go apple picking or enjoy some cider with gorgeous mountain views over the city of Charlottesville. September is the start of the apple picking season. Tickets/reservations are required on certain days in the peak season so we recommend checking the Carter Mountain website before you go.
The downtown mall is a historic brick road with over 100 shops and restaurants to explore. In the mornings, we frequently grab some coffee from Lone light Coffee and take a stroll down the mall. In the evenings you will often find free live entertainment. Some of our favorite stops are The Whiskey Jar (southern food and frequent live music), Bebederos (Mexican food), Millers (the restaurant/bar where the Dave Matthews Band was discovered), The Fitzroy (southern classics), The Alley Light (French speakeasy with great cocktails), and Tillman's (wine and cheese bar with outdoor seating). The Southern Cafe and Music Hall and the Jefferson Theatre are entertainment venues that often offer live music/concerts on the weekends.
Hosted every Saturday from 9 AM to 1 PM.
One of our favorite local wineries which is very popular in the region. Consider checking out their free polo matches on Sundays!
Eastwood winery is one of the closest wineries to town. They're open later than many of the other vineyards and have both an outdoor tent with gorgeous views and a cozy indoor barn.
Jefferson Vineyard is conveniently located near Monticello and Carter's Mountain Orchard. It offers gorgeous mountain views with outdoor seating and frequently hosts live music.
A whiskey distillery located ~10-15 minutes outside of town. The quaint farmhouse overlooks the countryside and mountains and their bourbon cocktails are incredible!
This is the brewery where we discovered our wedding band. They offer a variety of craft brews with indoor and outdoor seating options and frequently host live music.
Enjoy southern comfort food in the quaint Belmont neighborhood. Reservations are recommended.
Grab a warm bagel or sandwich from this Charlottesville staple.