Date Ideas in Wintergreen, VA

  • TripBuzz discovered 51 different types of activities for couples in the Wintergreen area, including Skiing & Snowboarding (like Wintergreen Resort), Waterfalls (like Crabtree Falls), Theaters (like American Shakespeare Center) and Winery/Vineyard (like Blenheim Vineyards), and much more.
  • We discovered a total of 44 date ideas in or near Wintergreen, Virginia, including 41 fun or romantic activities in nearby cities within 25 miles like Staunton, Charlottesville and Waynesboro.
  • TripBuzz discovered 51 different types of activities for couples in the Wintergreen area, including Skiing & Snowboarding (like Wintergreen Resort), Waterfalls (like Crabtree Falls), Theaters (like American Shakespeare Center) and Winery/Vineyard (like Blenheim Vineyards), and much more.
  • We discovered a total of 44 date ideas in or near Wintergreen, Virginia, including 41 fun or romantic activities in nearby cities within 25 miles like Staunton, Charlottesville and Waynesboro.
Showing 31-40 of 135
20.9 Miles
100% 12 votes
Theaters 106 Montgomery Avenue, Staunton, VA 24401 MoreLess Info
Offering interactive, on demand, customizable entertainment, Clever By Half offers murder mystery dinner theater productions, and will travel to perform them on demand. Spectators participate in the mysteries and have the opportunity to solve them.
21.5 Miles
89% 135 votes
Parks 600 Churchville Avenue, Staunton, VA 24401 MoreLess Info
Across 214 acres the Gypsy Hill Park serves as a multi-use recreational attraction. Guests can walk, bike, rollerblade, swim, picnick, and simply play while more advanced facilities are offered for those who want to golf or view extensive gardens.
22.0 Miles
41% 17 votes
Winery/Vineyard 100 Grand Cru Drive, Charlottesville, VA 22902 MoreLess Info
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
74% 304 votes
Winery/Vineyard 31 Blenheim Farm, Charlottesville, VA 22902 MoreLess Info
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
Winery/Vineyard 3550 Blenheim Road, Charlottesville, VA 22902 MoreLess Info
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.
23.3 Miles
91% 124 votes
Historic Sites Charlottesville, VA MoreLess Info
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
80% 471 votes
Winery/Vineyard 3550 Blenheim Road, Charlottesville, VA 22902 MoreLess Info
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
Art Museum 155 Rugby Road, Charlottesville, VA 22904 MoreLess Info
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
90% 10 votes
Sports Stadiums (Professional) 295 Massie Road, Charlottesville, VA 22903 MoreLess Info
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
- 0 votes
Theaters 845 Quicks Mill Road, Staunton, VA 24401 MoreLess Info
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.
Showing 31-40 of 135
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