top of page
  • Writer's pictureLisa

The Hike- and Wine-Loving Weekender: Shenandoah and Charlottesville

Updated: Mar 24, 2019

Weekend of hiking through Shenandoah National Park, visiting Monticello, and stopping for some Virginia wine along the way.

I am nothing if not a planner. Whenever we go on trips--or even for our annual weekend-long hosting of our families at Easter, I find making itineraries very useful. They go beyond just picking out what you want to do. They force you to time out how long it will take to get places, and how long you might spend on them. If you do this you can figure out how much you can reasonably fit into a day, a weekend, or a vacation!

Not that he was that surprised, but for our first anniversary, my husband got to see this craziness--and benefit from it--firsthand.

I grew up going to tons of National Parks with my family, and wanted to hit one of the big ones close to DC: Shenandoah National Park. Shenandoah gets a lot of attention during the fall, and for its mega hikes like Old Rag. But our anniversary is in August and I wanted to see more than one trail. Plus, Charlottesville and that area of Virginia are known for their wineries, so we had to save time for that!

Here’s how to do Shenandoah and Charlottesville in one weekend from DC.


8:30am-10:30am: Drive to Shenandoah

10:45-11:45am: Stony Man hike (good ratings, 2nd highest peak; 1.6 miles, easy)

12-1pm: Lunch at Skyland

1:15-2:30: Hawksbill hike (highest pt in park; 1.7 miles, easy)

2:30-3:30: Drive on Skyline Drive to southern part of park

Remaining afternoon: Chimney Rock (3.4 miles, moderate, 2.5 hours) or Jones Run Falls (3.2 miles, 2.25 hours)

7-8: Shower and change, then walk from hotel to downtown

8-?: Dinner and drinks in Charlottesville


9:30-9:50am: Drive from hotel to Monticello

10-12: Monticello

12-1:30pm: Michie Tavern for lunch

Afternoon- Jefferson Vineyards, then Early Mountain Vineyards, then home (2 hrs 40 min drive) plus tasting time

We got up early (but not too early) on Saturday morning to do the two-hour drive to Shenandoah National Park. We started with the Stony Man hike, which is the second-highest point in the park and a relatively easy hike. WW tip: we forgot it was cold and windy at the top of mountains, even in August! Bring some layers--and maybe even a hat!

View from random stop on the way up to Stony Man

This is not even the craziest picture of my hair

After our drive and quick hike, we were ready for lunch. Shenandoah has a few on-site restaurants and we stopped near the trail head at a casual one, Skyland. Check out my fluffy pot pie.

Next we drove to the Hawksbill trail, which was also nearby. Why hike Old Rag when the highest point in the park is an easy 1.7-mile hike?

You can see we picked up some warmer clothes in the gift shop next to our lunch stop!

The other hikes I planned were further south in the park and closer to Charlottesville. We ended up choosing the Jones Run Falls hike, because I had done the Chimney Rock one with my family before. Sadly for a longer hike, the waterfall was a little depleted and disappointing when we got to it. But maybe you'll have better luck!

Jones Run Falls

At three hikes, we felt like we had packed a lot into the day already! So we headed out of the park. One tip: there are many parts of the park where you lose your cell phone signal, which can be scary if you're relying on it for directions! So my advice is to print out directions in the old-fashioned, early 2000's way, ahead of time.

We got to our hotel in Charlottesville, which was a Marriott within walking distance of the downtown restaurant and shops area. After freshening up, we spent a nice night having dinner at Hamilton's in Charlottesville and walking around.

Cute downtown area!

On Sunday morning, we drove from our hotel to Monticello, the home of Thomas Jefferson. We took a great tour of the house and then walked around on our own to see the old slave cabins, gardens, and cemetery.


Right nearby Monticello is Michie Tavern, which is a huge lunch place for "colonial-style" food--AKA self-serve comfort food from a buffet. They have some shopping there too.

After eating, we started the drive back to DC--with a few stops! I did some research about well-rated vineyards along our route. A few tastings were a great way to end our first anniversary trip!

Tasting at Early Mountain Vineyards--we really liked the Five Forks

240 views0 comments


bottom of page