Delaplane is a beautiful area it has great wineries and beautiful countryside especially with the leaves changing. I would recommend Barrel Oak Winery which has great outdoor seating, yummy wine and good snacks. Sometimes on the weekends they have live music. There are also a number of other wineries around the area too. I have been to few but like Barrel Oak the best. I would not recommend Three Fox Vineyards for wine wasn't good but it does have nice picnicking grounds and activities like bocci. I also really love  Hollin Farms where you can pick your own field greens and other things they just had pumpkins. Both are nestled in the blue ridge and not terribly far from  Shenandoah Skyline Drive There are multiple places to get on to skyline drive so there is a closer entrance near Delaplane. 

Here's a list of wineries close to Charlottesville. Barboursville Vineyards is probably the most recognizable name in the area - the grounds are neat, but it tends to be crowded. DelFosse, Prince Michel, Horton (try the Norton!), and Blenheim are good options.

If you guys haven't been to Monticello, I'd make a point to visit, along with taking a walk around UVA (check out Edgar Allan Poe's old dorm). Shenandoah National Park runs along the mountains to the west, and has hiking trails of varying difficulty.

If you want to take the scenic route between DC and C'ville and really want to splurge on a meal, then make reservations for The Inn at Little Washington. In Charlottesville, C & O Restaurant is supposed to be good.

C'Ville is a mecca for restaurants.  Dining out is very popular.  Call ahead to check for seating. There are so many great places, but I know these are good.

The Local http://www.thelocal-cville.com/  (located in the Belmont area which has several great restaurants)

Mas http://www.mastapas.com/   If you like tapas meals this is the best!

Baja Bean http://www.bajabean.com/cvmap.html   At The Corner on Main St.- Great Mexican food

The Shebeen http://www.shebeen.com/index.php  excellent! Some of the best food I have had.

King Family Vineyards http://www.kingfamilyvineyards.com/About-Us/Visiting     Gorgeous!

Keswick Vineyardshttp://www.keswickvineyards.com/

http://www.visitcharlottesville.org/visitors/things-to-do/vineyards-and-breweries/   Take your pick....they are everywhere!

Charlottesville Historic Downtown Mall https://www.google.com/search?q=charlottesville+va+downtown+mall&ie=utf-8&oe=utf-8&aq=t&rls=org.mozilla:en-US:official&client=firefox-a&channel=sb   The Downtown Mall is full of life, especially in the evenings. Several excellent restaurants.  A couple serve breakfast.

Bluegrass Grill & Bakery http://www.yelp.com/biz/bluegrass-grill-and-bakery-charlottesville  Good food and the have Chocolate Covered Bacon!!!! omg!

Humpback Rocks http://www.realcentralva.com/2012/07/19/a-few-of-my-favorite-hikes-around-charlottesville/   Humpback view is awesome. 

Saunders Monticello Trail http://www.monticello.org/site/visit/overview-saunders-monticello-trail    Leads to Monticello ticket office area.  My daughter hiked this daily when she lived in C'ville.

Carpe Donut http://www.carpedonut.org/

Spudnuts http://www.urbanspoon.com/r/108/853318/restaurant/Spudnut-Shop-Charlottesville   The last place my daughter visited when she drove out of C'Ville in early 2014 was Spudnuts.  They are fresh cake donuts. Cash only. I like yeast donuts best, but I have to admit that warm chocolate cake and  blueberry Spudnut was delicious!