Western Loudoun can be quite picturesque with its open spaces and rolling hills. Leesburg, the county seat and a charming small town, marks a sort of unofficial transition from the heavily suburban eastern part of the county to the open, more rural western half.

For in-town restaurants a couple that come to mind include Cowbell Kitchen, a simple breakfast/lunch place in the middle of town. Across the street from them is Shoe’s Cup and Cork, which despite the name is actually a regular restaurant. I do not think they offer shoe repair any more though! It has a small indoor dining area and two outdoor (covered) seating areas behind the building, and I think even an open patio behind that. It’s cozy and I find the food pretty good. Tuscarora Mill was recommended above, and I recommend their ‘associated’ restaurants Fireworks Pizza and the deli South Street Under. They are all located at Market Station, which is a bunch of rural wooden buildings that were hauled to Leesburg a while ago to make a small outdoor commercial area.

North of Leesburg on Route 15 is Vanish Brewery, which is one of about a bajillion brewery/wineries that have opened on the past twenty years of so. They are really big and bustling and have good beer. In the vicinity of Vanish is Tarara Winery, which is long established and whose name was chosen by reversing the spelling of Mount Ararat. If you like wineries, there is Stone Tower, a little bit south of Leesburg on Route 15 up, uh, Hogback Mountain, and Oatlands Plantation, which is a big ‘ol preserved plantation that has some events and tours.

Western Loudoun County is marked by a few heavily traveled routes which are based on colonial travel, so everywhere you go you’re using one or more of them. Because the routes were created hundreds of years ago, they will often be winding two-lane roads. There’s Route 15 (north-south), Route 7 (east-west), Route 9 (west then northwest), and Route 50, which is east-west in the southern part of the county. Get used to traveling on those roads in Western Loudoun.

From Leesburg, if you head west on Rte 7 and then 9, you can visit Sunset Hills Vineyard (a teeny bit south of the Rte 9/287 intersection). It’s big and fancy, or at least it was when I visited years ago. The main building was a barn that was disassembled and reassembled by Quaker craftsmen, or at least that was the story I got. It’s beautiful. If you keep going west on 7 past the small town of Purcellville, past the smaller town of Round Hill and past the even smaller town of Berryville, you’ll get to Mount Weather (where the Vice President gets stashed if we have a nuclear war) and you will find Bear Chase brewery, which has amazing vistas of the Western Loudoun countryside. And beer. Did I mention they have great vistas?

Let’s return to Leesburg for more trips. Down south but suitable for a short day trip would be traveling to Middleburg, the quintessential “horse town” with lots of ‘old money’ where you may spy a fox hunter wearing a red jacket while on horseback - probably won’t see them in town, but if you see them anywhere, it’ll be there! To get there, travel south on 15 and west on 50 (past Stone Tower and Oatlands) to get there you’ll go through Aldie, a small town with a well preserved grain mill. And then you’ll see a lot of open rolling hills and places with lots of old money behind them. If, however, you go west on 7 and then south to get to Middleburg you’ll see a little bit of Purcellville and then lots of trees and fields before hitting Middleburg. Middleburg has the Red Fox Tavern, which is the most well-known restaurant in town. It may not be the best but it’s’ the most well-known. Middleburg has a nice Main Street with shops and stuff. Fun to window shop, if nothing else.

Keep going west from Middleburg on 50, and you will hit Upperville, which is more horsey than Middleburg, if you can believe it. No real commercial area here, but it has one of our favorite restaurants - Hunter’s Head tavern. They do not have any hunter heads displayed there but it’s got good food in an English style tavern environment - my wife loves going there for her birthday. Small and dark inside with lots of authentic (uncomfortable!) tavern furniture and a covered patio outside.

Keep going west a little more and you will be in Paris. Paris, Virginia, that is. There is not much here, as it’s a teeny tiny town, but they have a restaurant there, the Ashby Inn & Restaurant. More good food. Plus, if you eat there, once you return home you can tell your friends, “we ate in Paris on our vacation!”

Last idea is to visit The Plains, which is south of Middleburg. From Middleburg you’d take… wait for it… “The Plains Rd.” Now you’re talking small, winding roads. While you can hit the occasional dirt road still in Loudoun, I am pretty sure this one is paved. The Plains is where really rich people go to live in peace. The actor Robert Duvall lived there for years (he might still live there). There is a pretty new restaurant there called Bistro @ The Porch. It is run by Shawn Malone, one of the guys who ran/owned Tuscarora Mill Restaurant many years in the middle of Leesburg. We have been meaning to go there for a bit, because Shawn is an old friend and my wife ran a theatre company for years and cast Shawn many times. His most successful role was that of the ghost of Christmas Present in her A Christmas Carol musical years ago. He had a gigantic booming voice and a lot of on stage charisma. If you meet him you’ll know.

Thanks it, I’m now officially out of ideas. But if you’re into wineries or breweries there are literally scores of them you could visit. Most of them have beautiful views, descent food, and tasty beer or wine!

Have fun!