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10 Best and Fun Things To Do In Upperville, VA


TouristWire Editors

This small town is located in Virginia’s Fauquier County. Upperville is known for its historic homes, quaint shops, and beautiful natural areas.

One of the most popular attractions in Upperville is visiting the Trinity Episcopal Church. The building dates back to the 1800s and has since been restored to its former glory. Visitors can enter the church to admire the well-maintained architecture, or simply walk around the beautiful grounds.

Another popular historic site in Upperville is the Goose Creek Stone Bridge, which dates back to the Civil War era in America.

Read on to discover our list of more great things to do in Upperville, Virginia.

The 10 Most Popular Things To Do In Upperville, Virginia

10. Children’s Discovery Area

4.0 ★★★★☆ (3 reviews)

The Skyline Trail is home to the Children’s Discovery Area, which offers two sections for kids to explore and gain knowledge: the Nature Explore Outdoor Classroom and the Kids in Parks Track Trail. The Trail features four self-guided tours and the Classroom serves as a fun, hands-on learning area with natural materials.

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Credit: Sarah Braxton, Google Maps

Location: Unnamed Rd. Delaplane VA

9. Battle of Upperville | Goose Creek Bridge Historic Park

4.5 ★★★★★ (12 reviews)

This park is one of the most famous battlefields in Virginia, but today also offers scenic woods and hiking opportunities through both nature and history. The two-century-old stone bridge is one of the most beautiful landmarks in the area and is known for the key role that it played in the battle that took place here.

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Credit: Battle of Upperville | Goose Creek Bridge Historic Park, Google Maps

Location: State Rte 832 Middleburg VA

Tel:  703 327 9777

8. Ashby Gap

5.0 ★★★★★ (3 reviews)

The Ashby Gap is a natural windgap between the Blue Ridge Mountains in Upperville, VA. It played an important role during the Civil War, and was earlier used by Native Americans. Today there is a major road that runs through the gap, and the famous Appalachian trail crosses it.

7. Turner Pond

4.2 ★★★★☆ (9 reviews)

Turner Pond is a sought after fishing spot in Sky Meadows State Park. The lake has its own separate entrance and dedicated parking areas. There are programs and activities in and around the lake for all ages to be enjoyed. Among other things there are fishing programs for kids and picnic areas for guests.

5. Lost Mountain

4.6 ★★★★★ (60 reviews)

Lost Mountain is a hiking trail full of beautiful sights and sounds, including an abundance of wildflowers during the springtime. The hike is of moderate difficulty and spans about 4-miles. The total elevation gain is only about 571 feet. The terrain is not difficult as most of it consists of grass and dirt. This trail is also dog-friendly.

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Credit: Belinda Camacho, Google Maps

Location: Upperville VA

4. RdV Vineyards

4.6 ★★★★★ (79 reviews)

RdV Vineyards is one of the jewels of the Blue Ridge wine experience. It is a functioning wine farm that is a fantastic location for photos. Visitors can even buy a bottle to take home. Tastings are open with reservation. Their tasting experience is very extensive, and the price included a guided tour of the farm and the caves on the property. There are also some cheese boards and charcuterie available that is completely seasonal.

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Credit: sheri sipes martel, Google Maps

Location: 2550 Delaplane Grade Road Delaplane VA

Tel:  540 364 0221

3. Arterra Wines

4.8 ★★★★★ (92 reviews)

Arterra is quite an extensive wine farm that is dedicated to preserving the environment. The farm is open to visitors and their pets, as long as the pet is on a leash. There are no food services at the destination, but some snacks are served. Visitors are welcome to bring their own food along. While children are allowed, it is best to remember that the destination is meant to be an adult experience and there are not many amenities available to keep kids occupied.

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Credit: Arterra Wines, Google Maps

Location: 1808 Leeds Manor Road Delaplane VA

Tel:  540 422 3443

2. Delaplane Cellars

4.3 ★★★★☆ (204 reviews)

Of all the wine farms on our list, Delaplane is the most luxurious. They offer wine tasting along with venue hire and events. Over the weekend you will need to book your table for tasting, but walk-ins are welcome during weekdays. There are some summer sunset wine dinners that can be reserved. They also do some private events, including weddings.

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Credit: Delaplane Cellars, Google Maps

Location: 2187 Winchester Road Delaplane VA

Tel:  540 592 7210

1. Sky Meadows State Park

4.8 ★★★★★ (1,252 reviews)

Many of the attractions mentioned on this list can be found in Sky Meadows State Park. It is filled with fun things for the family to enjoy. It is open year-round and is a great attraction to nature enthusiasts while still maintaining the rich history of the area. There are even astronomy programs in the park at night that are open on a monthly basis.

Location: 11012 Edmonds Ln Delaplane VA

Tel:  540 592 3556

Final Words:

Thank you for reading our list of the best things to do in Upperville, Virginia! We hope it helped you plan the perfect itinerary for your next trip to this fantastic destination. Happy travels!

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