One of the benefits of growing up/living/working in the Washington DC area. is that sooner or later a friend, acquaintance or colleague is going to grow tired of the rat race and "follow his/her dreams" and open up a winery out in the northwestern portion (what we like to call the Hunt or Horse Country) of Virginia along the Shenandoah Valley. This provides plenty of excuses to head west and check out their operations virtually every year (sadly, some after significant capital outlay and mind numbing effort, don't survive, but many after the inevitable tough start up, thrive).
Now I'm not calling it Sonoma or Napa, Williamette or Columbia Valley or anything like that, but I guarantee that you can certainly have as much entertainment and taste some terrific wines. Going west out Interstate 66 there are also some excellent restaurants, many supplied by the local farmers.
http://www.railstoprestaurant.com/ is a good example (Robert Duvall used to be one of the owners and has since left, but the quality remains as high)
http://girasole-panino.com/ another fine dining experience
and where we dined today, http://www.ashbyinn.com/ make up three of the examples of good food experiences all along the area (Front Royal and Warrenton Va. has some tasty places as well)
Indoor was packed, patio filled up after photo (beer from merb's Mt. Hood)
There are scores of wineries and a trip down the Skyline Drive to take on the views and fall foliage (it hooks up with the Blue Ridge Parkway and runs all the way to the Great Smoky Mountains in Tennessee) in the Shenandoah National Forest makes for a great weekend experience; pumpkin and apple pie, festivals with great music including some excellent blue grass, chocolates and cheeses, and of course delicious wines. You may even bump into vaboywonder as he works his way northward from Charlottesville Va. Trump bought the Kluge estate and actually turns out a nice product as well as several other wineries up and down US 29.
The Fairfield Inn in Strasburg, Va. is a nice stay (could enter Skyline at Front Royal and thirty miles later exit at Thornton Gap) as is the one in Winchester Va (home of Patsy Cline) and there are nice Marriott properties in Charlottesville Va near the University. Another possibility which is very pleasant (stayed several times) is the Marriott Ranch Bed and Breakfast in Hume Va. A bit of history for Insiders: This was JW's (senior) family farm (called Fairfield Farm) and used to be the site of the Marriott company picnic decades ago. We used to enjoy the time the Marriott family spent with employees each year (especially the hayrides with Uncle Woodrow, JW's brother) and as you might imagine, the food was fantastic!
Along with a nice patch of wineries around Williamsburg, Virginia also has distilleries (legal and illegal), and breweries out in them thar hills, but that's a story for another time.
Views of some wineries