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May 14, 2022
Charlottesville, VA

Will and Kate

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    Things To Do

Things To Do

Monticello Wine Trail

Monticello Wine Trail

With over 39 vineyards along the Monticello Wine Trail, this is our top recommendation while you are in Charlottesville! Some of the vineyards on the list require reservations a couple weeks ahead of time, so make sure to check out the vineyards' websites. Our personal favorites are King Family Vineyards, Jefferson Vineyards, Blenheim Vineyards, and Pippin Hill.

Historic Downtown Mall

Historic Downtown Mall

Main Street, Charlottesville, VA 22902

A visit to Charlottesville isn't complete without a stop at the Downtown Mall. It is one of the most beautiful and successful pedestrian malls in the nation, and it's located in historic downtown Charlottesville. The Downtown Mall is a vibrant collection of more than 120 shops and 30 restaurants (many with outdoor cafes) housed in the historic buildings on and around old Main Street. A list of our personal favorite restaurants: 1. The Nook (amazing breakfast) 2. Mudhouse Coffee (try the lavender coffee) 3. Citizen Burger Bar 4. Sal's Italian Kitchen 5. The Fitzroy 6. Jack Brown's Beer and Burger Joint (go Dukes!) 7. Chap's Ice Cream

The University of Virginia

The University of Virginia

400 Emmet Street South, Charlottesville, VA 22903

Founded in 1819 by Thomas Jefferson, The University of Virginia (UVA) campus is a designated UNESCO World Heritage site. Feel free to set up an official tour on the UVA website or stroll the campus on your own. We highly recommend touring the famous Rotunda (open from 9:00 am-5:00 pm ET). Designed by the University’s founder, Thomas Jefferson, the Rotunda is the centerpiece of the Academical Village. Modeled after the Pantheon in Rome, it was designed to house the library and be flanked on either side by faculty pavilions, interspersed with student rooms.

Skyline Drive

Skyline Drive

Switft Run Gap Entrance, 22591 Spotswood Trail, Elkton, VA

Though an hour outside of Charlottesville, the drive is totally worth it! Virginia's Skyline Drive is a National Scenic Byway that runs 105 miles along the crest of the Blue Ridge Mountains starting in the north of the Shenandoah Valley at Front Royal to Waynesboro, where it meets the Blue Ridge Parkway. Skyline Drive is Shenandoah National Park’s linear conduit, with 75 overlooks connecting travelers to all the major visitor centers, campgrounds, lodges, picnic areas and most trailheads.

Thomas Jefferson's Monticello

Thomas Jefferson's Monticello

931 Thomas Jefferson Parkway, Charlottesville, VA 22902

We recommend purchasing tour tickets ahead of time and allowing enough time to explore the grounds, as most guests spend an average of 3.5 hours at Monticello.

Carter Mountain Orchard

Carter Mountain Orchard

1435 Carters Mountain Trail, Charlottesville, VA 22902

The Carter Mountain Orchard is on top of a mountain with gorgeous views. While May will be too early in the season for apple picking, apple blossoms will cover the orchard and serve as a beautiful background as you enjoy a glass of wine or cider. The Orchard is also home to a Bold Rock Cider Tap Room.

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