Things to do in Charlottesville
Explore the Monticello Wine Trail, wineries within a short distance of Charlottesville, but each with distinct features, so read the rules before your visit (for example, some are adults-only, some don’t allow pets, most close by 5 p.m. and post schedules for special events). And do the tastings—especially try the region’s signature grapes Petit Verdot, Cabernet Franc, or Meritage. In terms of dress code, it’s still a college town, so a t-shirt and jeans are usually just fine. Keep in mind the winery you’re visiting may not serve food—if they don’t, check the activities calendar for food truck visits or bring your own picnic, which is generally encouraged.
If you’re traveling around WorldPride, King Family Vineyards resumes free Sunday polo matches on May 25 through October. King has no restaurant on site, but does serve light snacks. Picnics are encouraged (no outside alcohol) and the vineyard schedules food trucks throughout the week. Matches are fun to watch no matter what you know about the game. Some locals say Pippin Hill Farm & Vineyard has the best wine in all the land, and if you want to visit make your reservations well ahead to taste them—veranda tables provide mountain views and much of the seasonal food in the restaurant is grown on the estate.
While most college towns carry their own brand of storied history, in Charlottesville these lessons unfold along vacation-speed rambling walks like those through Monticello. Lesser known are the rustic trails on the former plantation of Jefferson’s fellow founder, James Monroe’s Highland. Peek through the glass doors to see Edgar Allan Poe’s original 1826 restored room in University of Virginia’s West Range of dorms—of course it’s room 13. Locals would send more rugged hikers to Humpback Rocks Trails, off Blue Ridge Parkway, a 35-40 minute drive and roughly an hour to the top and 40 minutes back, with a 360-degree view of the mountains, the Shenandoah Valley, and jagged rock formations. Or make a day of it with Old Rag Circuit, nine-plus miles and a full day of hiking in Shenandoah National Park, about 75 minutes outside of town. Those who wish to skip the sweating and cut right to the scenery drive a stretch of the Blue Ridge Parkway, with its waterfalls, scenic overlooks, and at milepost 61.4 the 215-foot-tall arch of The Natural Bridge, a 30-story limestone formation some 500 million years old.
Where to eat in Charlottesville
Charlottesville’s food scene is super-charged by affordable campus town decadence, a surprising bakery culture, and the yield of Virginia fields. The rich farmland of surrounding Albermarle county supports a robust independent dining scene, including big-portion student hotspots, international fare, well-considered farm-to-table restaurants, and surprising European bakeries. Find some of them on the downtown pedestrian mall, a string of renovated buildings with that distinct college-town mix of smoke shops, traditional haunts, clothing stores, plus Miller’s Bar, where young Dave Matthews formed his band with jazz musicians LeRoi Moore and Carter Beauford.
