When you think of Virginia wine country, you probably think of Charlottesville first… and then maybe you’ll think of Leesburg. But nestled halfway between both regions is the gem Sperryville. Sperryville is known but often overlooked. It’s close to Washington, VA where the Inn at Little Washington brings in hundreds of tourists a year. And if you’ve ever hiked in Shenandoah, chances are you have hiked Old Rag, which is right next to Sperryville.
Sperryville, and the surrounding area, deserves more attention. The town is adorable; the food is spectacular; and it has dozens of wineries that are less crowded and more intimate than Charlottesville. If you’re looking for a close COVID-safe trip in the DC-Maryland-Virginia area, Sperryville needs to be on your list.
Where to Stay
We visited two summers ago for Ryan’s birthday. At the recommendation of my bestie, we stayed at Sharp Rock Vineyards, a very rustic and family-owned winery just outside of downtown Sperryville and right next to the Old Rag trail. Sharp Rock has two bed and breakfast options on the property, and we stayed at the Cottage, which was a little bigger with two bedrooms and an upstairs area.
Sharp Rock is owned by Jimm and Kathy, who help make the visit extraordinary. Every morning, you’ll receive a basket full of baked goods from Kathy to start your day, and Jimm is on deck to walk you through Sharp Rock’s award-winning wines. Each stay includes a free tasting and a bottle of wine.
Fair warning that there is no television and limited cell service in the cottage. But it is stocked with a few games and is the perfect place to unwind with a good book or journal. The property itself is also gorgeous and the perfect place for a walk. The Old Rag trail is down the road, but onsite is a creek that cuts through the vineyards. And you’ll definitely find some friendly animals during your stay.
Where to Eat
Sperryville is definitely for foodies. The town has Three Blacksmiths Restaurants, which offers a multi-course tasting menu that changes weekly, and down the road is The Inn at Little Washington, which is famous for its tasting menu.
Both of us are picky eaters, so we steered away from fixed menus (one day!) and opted for some locally loved restaurants. After we checked in at Sharp Rock, we visited Headmaster’s Pub in downtown Sperryville for dinner and frankly had the best cheese fries ever. The pub is large with arcade games and pool tables in one room and has taken bar food up a notch.
Later in the weekend, we visited Griffin Tavern between winery tours and ended the weekend with Tula’s in Washington – both fantastic, filled with locals, and a great menu selection.
What to Do
Even if you’re not staying at Sharp Rock Vineyards, the winery needs to be on your list for a visit. The farm was established in the 1700s, and the barn that serves as the tasting room is more than 100 years old. It is cozy, rustic, and the wines are amazing.
We also visited Rappahannock Cellars, which has a beautiful tasting room and property. While I didn’t like the wines here as much as Sharp Rock, Rappahannock deserves a visit, if only for the olive oil tasting they also offer – so good!
Other notable wineries in the area:
- Little Washington Winery
- DuCard Vineyards
- Mountain Run Winery
- Early Mountain Vineyards
We originally decided on Sperryville not just for wines but to hike Old Rag, which I had never done…. and still haven’t. Our entire visit during mid-July was rainy, cold, and foggy, so we never made it up the mountain. But Sperryville is in the heart of Shenandoah – so close to Old Rag, White Oak Canyon, or you can just drive up and down Skyline Drive and stop at the many, many overlooks.
And no visit to the region is complete without a stop in Washington, VA. While the Inn at Little Washington may get a lot of love, the downtown area is cute and walkable with lots of little shops and art galleries. We ended up booking massages at Little Washington Spa and loved it. There is also a local chocolate and wine store downtown called Wine Loves Chocolate – need I say more?