- TripBuzz discovered 75 different types of activities for couples in the Middletown area, including Theaters (like Wayside Theatre), Historic Homes (like Belle Grove Plantation), Winery/Vineyard (like Bloomery Plantation Distillery) and Movie Theaters (like Alamo Drafthouse Cinema), and much more.
- We discovered a total of 70 date ideas in or near Middletown, Virginia, including 67 fun or romantic activities in nearby cities within 25 miles like Winchester, Front Royal, Berryville and Delaplane.
Showing 91-100 of
344
28.1 Miles
Founded in 1969, the Middleburg Tennis Club is a members-only recreation site with over 10 acres of courts and facilities. Tennis lessons and camps are offered, along with a swimming pool and full size fitness center.
28.9 Miles
The first commercial vineyard in Virginia was the Piedmont Vineyards & Winery. The small and homey winery remains a favorite stop along the Virginia wine trail and holds regular tastings that involve knowledgeable servers.
28.9 Miles
Six main stage productions are performed at the Old Opera House every season. The live performance theater also hosts a summer youth production and one-act play festival annually along with a ballet every other year.
29.0 Miles
Best know for a public swimming pool, Jefferson County Memorial Park is a leisure park that also has two basketball courts, two playgrounds, and four pavilions that are available for rent. The park also has a .7-mile walking trail.
29.1 Miles
Wine tastings at The Boxwood Winery are the main draw to the site since there are no tours of the vineyards or the wine cellar itself. The location also has a wine bar that serves Boxwood wines and other wines from around the world.
29.1 Miles
98%
43 votes
500 N Pendleton Street, Middleburg, VA 20117
MoreLess Info
Guests can coast along the forest canopy at Salamander Tree Top Zip Tour. Packages include zip lining on the 20 acres of land, a rappelling adventure, survival 101, and a leadership odyssey.
29.2 Miles
74%
38 votes
18050 Tranquility Road, Purcellville, VA
MoreLess Info
The Goose Creek Farm and Winery - Otium Cellars produces Chardonnay, Blaufrankisch, Dornfelder, Cabernet Sauvignon, Pinot Noir, and Malbec wines. The location also offers live music performances every other Friday.
29.2 Miles
99%
252 votes
16357 Charles Town Rd, Charles Town, WV
MoreLess Info
Bloomery Plantation Distillery is located in an historic 1840s log cabin distillery. The company creates artesian cordials, including hard lemonade, ginger shine, and peach shine from lemons and raspberries that they grow.
29.3 Miles
Enjoy the beauty of a 56 acre vineyard and sample fine De Chaunac, Seyval Blanc and Marchel Foch wines while enjoying a wine tasting tour of Smith family owned and operated Meredyth Vineyards in the heart of Virginia's wine country.
29.3 Miles
93%
44 votes
18050 Tranquility Road, Purcellville, VA 20132
MoreLess Info
Otium Cellars , Goose Creek Farms is a vineyard that is home to several German varietals of wines. The winery uses three types of grapes in the winemaking process including Chardonnay, Dornfelder, and Blaufrankisch.