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Three main things attract travelers to Charlottesville: history, nature, and the University of Virginia. Friendly locals and amazing dining options are an added bonus. There’s a lot of touring to be done, but we suggest dividing your schedule between tours and outdoorsy activities, especially if you’re visiting with children. Even kids love the historical sites, but two or three days in a row of that stuff can get boring, so don’t try to pack in all the presidents’ homes at once. Bring your walking shoes, and plan to spend plenty of time outside.
Neighborhood: Scottsville Area
On a hot, sticky summer day, nothing feels better than getting in the water here. There are a few public pools, lakes, and swimming holes around town, but tubing on the James River is a favorite activity. James River Runners, located just south of Charlottesville in Scottsville, offer tubing, rafting, kayaking, and canoeing. They provide all the equipment as well as a shuttle to the launch point so you don’t have to coordinate cars for the excursion. It’s a popular weekend and holiday activity, so reservations are strongly recommended. If you want the river to yourself, try going on a weekday. Trip times will vary based on river conditions, but you can rent a cooler tube if you want to pack a lunch. There are plenty of places along the route where you can stop and have a picnic. Two warnings: James River Runners does not accept credit cards, so have cash or checks handy to pay for your trip; also, using a GPS to get you there will put you on the wrong side of the river. Use the directions on the James River Runners website.
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Neighborhood: Massanutten Resort
Massanutten Mountain is about an hour west of Charlottesville (depending on how comfortably you handle mountain driving), home to a four season resort that’s definitely worth a visit, especially if you’re vacationing with kids. The ski slopes and snow tubing at Massanutten are generally open late November or early December through mid-April, but there’s also an indoor-outdoor water park at the resort that’s open year-round. It’s an easy day or half-day trip from Charlottesville, and if you make the trip, be sure to stop at Romano’s Italian Bistro near the foot of the mountain off rt. 33 for lunch or dinner.
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Neighborhood: University of Virginia Grounds
Jefferson put a lot of personal touches into his design of the University of Virginia, and you can feel his passion for the school as you walk around The Lawn and view the gorgeous architecture and landscaping. The Rotunda at the north end of The Lawn is one of the oldest buildings in the University, and it still houses classes today. Jefferson designed The Lawn with student and faculty housing, classrooms, gardens, and a library. This part of Grounds (remember, they don’t say “campus” here) dates back to the University’s founding in 1819, though the Rotunda wasn’t completed until after Jefferson’s death in 1826.
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Thomas Jefferson’s home is the number one tourist attraction in Charlottesville. A skilled architect, Jefferson designed this house that overlooks the university he also designed and founded from a small mountain—“monti cello”—on the east side of town. You may recognize the building from the back of the American nickel. Though Monticello was briefly privately owned, it is now managed by the Thomas Jefferson Foundation, and the house is full of Jefferson’s personal belongings and many of his inventions. Reserve your tour online or by phone to avoid waits, and arrive 30 minutes prior to your scheduled tour. Each house tour lasts 30 minutes, but 45-minute Gardens and Grounds tours and Plantation Community tours are available April through October as well. For a more intimate look at the house, reserve a Signature Tour, available May through early September.
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Neighborhood: North Charlottesville/Hollymead
Before you go here, you have to promise not to tell the locals that we told you about this place. Actually, even most locals don’t know about Sugar Hollow, and we’d all like to keep it that way. Sugar Hollow is a natural area on the Moormans River to the west of town. It’s a scenic 20 or 30-minute drive to get there. Follow Garth Road to a left “turn” at White Hall onto rt. 614 (Garth Road becomes rt. 810 here and curves sharply right. Keep going straight to get to Sugar Hollow). Drive on past the reservoir until you come to a clearing by the river with some space for parking. You can hang out by the water, fish (with a permit), or walk along this side of the water to the edge of the Shenandoah National Park. On a hot day, we recommend crossing the river and finding the fire road/hiking trail on the other side that leads up the mountain (it will be obvious). You’ll work up a great sweat walking uphill in the heat, and your reward will be sweet—after about a two mile hike, you’ll find a very inviting swimming hole with a rope swing, a small waterfall, and some small cliffs you can jump from if you’re feeling daring. The water is very, very cold, but it will feel very, very refreshing after your uphill trek.
Neighborhood: 29 Corridor
It's not quite Napa Valley, but Virginians are proud of their wine, and there’s a lot of it! Charlottesville is surrounded by vineyards on old country estates, and a visit to at least one of these should definitely be part of your itinerary. Most of the 21 vineyards in the group known as the Monticello Wine Trail are small boutique wineries, and the only way to get these wines is direct from the source. The Monticello Wine Trail website offers overviews of each of the local wineries as well as a calendar of special events. You probably won’t be able to see all 21 of them, but you can’t go wrong—each of the vineyards on the Monticello Wine Trail is uniquely beautiful and serves up quality Virginia wine. Find a winery that’s hosting an event while you’re in town, or read the overviews on the website to find the ones that most appeal to you. All these vineyards are within about a 30 minute drive of Charlottesville. Find directions and contact information for each at the Monticello Wine Trail website.
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Neighborhood: North Charlottesville/Hollymead
As the founder of UVA and most the famous Charlottesville resident ever, Thomas Jefferson gets most of the attention, but James Monroe lived practically next door to him, and Monroe’s Ash Lawn-Highland is another beautiful historic site you’ll want to visit. Much more modest than Monticello, Ash Lawn-Highland offers daily tours as well as a calendar packed full of special events including 19th-century craft and educational workshops and summer performances in the Ash Lawn gardens. You can even reserve the grounds for private functions.
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Neighborhood: University of Virginia
JPJ is UVA’s brand new, state-of-the-art arena, located on Massie Road at rt. 29. Thomas Jefferson probably never envisioned anything like this at his university, but he’d probably be proud to see it today. The arena is home to the Cavalier men’s and women’s basketball teams, which are only slightly more successful than their football team of late, but you can also catch some great performances here. Before Charlottesville had the JPJ, there was no good venue for big indoor shows. Now all the hottest names in entertainment play here—Cirque du Soleil, Lady Gaga, Jon Stewart—check out the calendar of events to see who’s here when you’re in town. If you balk at the ticket prices, try showing up 30-45 minutes before the event—scalpers are everywhere.
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Neighborhood: Downtown Mall
If you prefer a more intimate venue for a show, check out The Southern, located on 1st Street just off the Downtown Mall. You’ll find great food, good drinks, and the best of the up-and-coming local artists and nationally touring indie and folk bands. The Southern seats no more than 100, so every seat is the best seat in the house. With all the local musicians that grace this stage, you’ll get a really good taste of the Charlottesville music scene any night you go.
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Neighborhood: Montpelier Station
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James Madison’s Montpelier in nearby Orange, Virginia rounds out the trifecta of Charlottesville-area presidents’ homes. You could easily do Monticello and Ash Lawn-Highland in one day, but Montpelier is a bit of a trek from the other two, so save it for another day. Madison spent his entire life at Montpelier, with the exception of the time he lived in the White House as our fourth president. Mansion tours run regularly each day, but you can also take weekend and quarterly themed tours that explore subjects like slave life, the Civil War, and more. Take the time after your house tour to check out some hands-on demonstrations like brickmaking at the Hands-on Restoration Tent or the hands on cooking exhibit, Dolly’s Kitchen.
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