NoVA has some of the most beautiful scenery in the world for cycling, and every road along the way is dotted with the perfect stops to explore.
–Victoria Gaffney, Sophia Rutti and Matthew Tracy
Rappahannock County
Start your cycling journey in Little Washington and see the best that Virginia has to offer: fine dining, Virginia wines and postcard-worthy views.
Start at the Winery at Little Washington ⇒ Sperryville ⇒ Skyline Drive
Difficulty: Moderate to difficult; steep incline at Skyline Drive
1. Winery at Little Washington
If wine isn’t what you’re looking for when you start your day, don’t worry. The Winery at Little Washington also boasts one of the top picnic spots in Virginia and allows people to bring their own lunches and refreshments. The winery is available for walk-ins all day on the weekend.
[3.3 miles]
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2. Thornton River Grille
Placed in the heart of idyllic Sperryville, this is the perfect restaurant to stop in and fuel up. The restaurant is open Tuesday through Saturday 11 a.m. to 3 p.m. for lunch and 5 to 9 p.m. for dinner. When you’ve finished your lunch, head out and explore the small town.
[7.4 miles]
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3. Skyline Drive
This unforgettable ride filled with gorgeous foliage and wildlife has overlooks every few miles so you can stop and take it all in. This is the most difficult part of the ride and is not recommended for an inexperienced cyclist, but if you’re up for the challenge, you can experience the beauty of this national park.
Middleburg
Just beyond the town of Middleburg along Lee Jackson Highway, some of the area’s best vineyards await. Begin your cycling tour around noon to try some fine wines and enjoy the beauty of the area.
Start at Quattro Goomba’s Winery ⇒ Cana Winery and Vineyards ⇒ Greenhill Winery and Vineyard
Difficulty: Moderate; mildly uphill along Lee Jackson Memorial Highway
1. Quattro Goomba’s Winery
This laidback winery offers tastings from noon to 6 p.m. Thursday through Sunday. For a $6 tasting fee, try five wines in the bucolic setting of Goomba’s log cabin. For lunch, head over to Quattro for delicious pizza, or picnic on the property while listening to calming music.
[3.8 miles]
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2. Cana Winery and Vineyards
Featuring hillside tasting rooms with breathtaking mountain views, this winery is open from 11 a.m. to 6 p.m. on Saturday and noon to 6 p.m. on Thursday, Friday and Sunday. Live music is every Saturday from 1 to 5 p.m. and tastings are $10 per person.
[2.4 miles]
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3. Greenhill Winery and Vineyard
Nestled on a pastoral road, this winery is open from noon until sunset. Picnic on the green grounds while enjoying some wines on the 128 acres of land, which includes a pond, Little River and a stone house built in 1762.
Ashburn
See the real Ashburn along the Washington & Old Dominion Trail. Enjoy the historic route and stop by some of the mainstays of the area.
Start at Carolina Brothers Pit Barbeque ⇒ Old Ox Brewery ⇒ Green Lizard Cycling & Coffee
Difficulty: Moderate
1. Carolina Brothers Pit Barbecue
Enjoy Old Town Ashburn while munching on North Carolina-style barbecue and cornbread. For $8, choose from pork, beef or chicken barbecue, as well as traditional southern sides. Cool off inside the homestyle eating area or enjoy the scenic view at an outdoor picnic table.
[4.6 miles]
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2. Old Ox Brewery
Adults can make a brewery pit stop right on the trail. Old Ox Brewery is the one of newest family-owned breweries in Ashburn. The establishment is two-wheeler friendly with beer, bike racks, air pumps and food. Try one of their core brews, such as Golden Ox, or their seasonal Hard Way Lager.
[7.1 miles]
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3. Green Lizard Cycling & Coffee
End your ride with a rewarding cup of coffee and the company of fellow bikers. There is a variety of drink options to choose from ranging from espressos to fruit smoothies, and the shop is open Monday through Thursday from 7 a.m. to 9 p.m. and Friday- through Sunday from 7 a.m. to 6 p.m.
Not interested in Cycling alone? Check out these local tours.
