- Our list of the best things to do in Wintergreen, Virginia, features the top 56 nearby activities — including 26 great attractions with user approval ratings of 90% or more!
- Wintergreen, VA has a variety of great sights and experiences nearby. Top categories include: Museums & Galleries, Entertainment & Shows, Outdoor Places, and Sights & Landmarks.
- The results below include the top 5 things to do within the city of Wintergreen, VA , followed by 51 popular activities in nearby cities, including Staunton, Charlottesville and Waynesboro
Showing 41-50 of
173
22.0 Miles
41%
17 votes
100 Grand Cru Drive, Charlottesville, VA 22902
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Known for large pours during tasting, Trump Winery offers visitors a selection of red, white, and sparkling wines to sample. Visitors can choose from a self-guided or guided wine flight, and can pair it with a cheese plate.
22.1 Miles
Several red and white wines are produced by Blenheim Vineyards. While there are no tours offered, guests can participate in tastings and view the wine production facility through the paneled glass floors.
22.2 Miles
60%
52 votes
3550 Blenheim Road, Charlottesville, VA 22902
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Wine aficionados can please their palates with samplings of sparkling, red, or white wines amongst acres of beautiful scenery at the Trump Winery Tasting Room. Located near historic Monticello and Ash-Lawn Highland, Trump is the state's largest vineyard.
22.6 Miles
94%
31 votes
410 Golf Course Drive, Charlottesville, VA 22903
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Since 1984, Birdwood Gold Course at The Boar's Head has been challenging and delighting golfers of all skill levels. The course features 18 holes, a pro shop and professional lessons.
23.3 Miles
For a look at personal history of slavery in America, guests visit Mulberry Row. The property where Thomas Jefferson's slaves lived shows the conditions slaves were kept and serves an important reminder of how far the country has come.
23.9 Miles
Located on 1,300 acres, the Trump Winery is one of Virginia's most notable wineries. Visitors cannot view the fields, but they can access the Tasting Room with tastings held daily and food offerings in the form of a regionally-inspired gourmet menu.
24.1 Miles
72%
46 votes
155 Rugby Road, Charlottesville, VA 22904
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Also known as the Fralin Museum, the on-campus University of Virginia Art Museum has an extensive permanent collection made of roughly 13,000 objects. Highlights of the collection include African art, Native American art, European paintings, and photographs.
24.1 Miles
Located on the campus of the University of Virginia is the prestigious John Paul Jones Arena. The arena features a wide selection of sports and entertainment events throughout the year including basketball, wrestling, music concerts, symphony presentations and more.
24.2 Miles
The University of Virginia can be a very relaxing place to both walk and bike. Almost all the buildings remain in their classic stone architecture forms with extensive manicured lawns and gardens for public viewing.
24.2 Miles
A local favorite since 1954, Oak Grove Theater presents a number of funny, daring, and thoroughly entertaining shows throughout the year. Past shows include Corpse!, Monte Python's Spamalot, and Don't Dress for Dinner.