Top 6 Delightful Ways to Enjoy Fall in Middleburg

— Looking for something fun to do this fall in Middleburg? You’re in luck! However you want to explore the area, we’ve rounded up a list of the best activities in Middleburg this fall:

Middleburg VA Fall

1. Take a Scenic Drive

If you’re looking to get away from it all and enjoy the countryside, Middleburg is always a great place to visit. One of our favorite fall activities is to hop in the car and go for a drive to appreciate the beautiful scenery that surrounds us, especially as the leaves are changing color. If you’d like to take a scenic drive, one of our favorite routes starts right in town at the historic Red Fox Inn and follows a loop along Foxcroft Rd., Mountville Rd., Snickersville Tpke. and Sam Fred Rd. You can find the full route here. Wherever you decide to go on your journey, please be sure to drive safely, obey posted speed limits and be courteous to others on the road. Slow down and enjoy the scenery!

horse ride Salamander Resort Spa Middleburg VA

Photo courtesy of Salamander Resort & Spa.

2. Go Horseback Riding

Middleburg is known as the Nation’s Horse and Hunt Capital for good reason, so if you’re in town, you might as well experience the equestrian life. And what better way to do that than to get on a horse? Salamander Resort & Spa’s equestrian programs provide everything from guided trail rides to riding lessons and horsemanship classes. Not quite ready to get in the saddle yet? Be sure to check out Salamander’s unique Equine Communication program, which focuses on leadership, authenticity, clear communication and the impact of body language and energy.

Greenhill Vineyards Middleburg VA

Photo courtesy of Greenhill Winery & Vineyards. Photo by Jodi Miller.

3. Take a Wine Tour

Did you know that the Middleburg American Viticultural Area is home to 30 wineries? Grapes grown in our region benefit from perennial soft breezes coming from the 1,027-foot Ashby Gap in the Blue Ridge Mountains, which also happen to provide a spectacular backdrop to many of our local vineyards. Three of our favorite Middleburg vineyards are Boxwood Winery, Cana Vineyards and Winery of Middleburg, and Greenhill Winery & Vineyards. If you’re looking for a drive through the countryside, we also recommend stopping in Three Fox Vineyards in Delaplane, which boasts gorgeous mountain views and award-winning wine.

4. Explore Middleburg’s Art Scene

If you’re in town, be sure to swing into Middleburg’s art galleries and the National Sporting Library & Museum, the largest facility of its kind in the United States. With more than 24,000 books dating from the 16th to 21st centuries, NSLM is dedicated to preserving and sharing the literature, art and culture of equestrian, angling, and field sports. The museum, a newly renovated and expanded historic building, houses exhibits of American and European fine animal and sporting art. Current and upcoming exhibits include: “Canter & Crawl: The Glass Sculpture of Joan Danziger” (through Jan. 5, 2020) and “Leading the Field: Ellen Emmet Rand” (Oct. 4, 2019, through March 22, 2020). Remember: museum admission is free on Wednesdays and the last Sunday of the month. Also, the museum also hosts some great free public events, including gallery talks (held every Wednesday at 2 p.m.) and Sunday Sketch, a monthly sketching session led by a local artist or art teacher.

Art lovers will also want to see the 39th American Academy of Equine Art Annual Open Juried Exhibition at the new Masters of Foxhounds Association headquarters in Middleburg. This show, which runs through Oct. 26, features original 2- and 3-dimensional work from the finest equine artists in North America. Get more details at

The Byrne Gallery new “Blue Ridge Harmony” exhibit, which runs until Nov. 9, celebrates Gerald Hennesy’s latest oil on canvas landscapes of verdant pastures, woodland views and the beauty of the Virginia countryside. This exciting one-man exhibition will showcase local scenes of both Loudoun and Fauquier counties and feature Goose Creek, the foothills of the Blue Ridge Mountains, Sky Meadow and the Potomac and Shenandoah Rivers.

At the Artists in Middleburg gallery this month, you’ll find “The Glories of the Untamed: Wildlife Up Close,” which runs through Oct. 27.

Shop Middleburg VA

5. Shop ’til You Drop

If you need some retail therapy, you’ll love Middleburg. We have a wide assortment of shops, including many boutique stores that can’t be found anywhere else. For antiques and art, our favorite is The Shaggy Ram. If you’re looking for clothes, we always find something new to love at Country Classics, Duchessa (women’s fashions), Highcliffe ClothiersLou Lou Boutiques, and Richard Allen Clothing (men’s fashions). For gifts or a little something special, try Les Jardins de Bagatelle for French products; Mystique Jewelers for breathtaking jewelry; Salamander Resort & Spa for unique equestrian-inspired gifts; The Christmas Sleigh for German ornaments and handmade Austrian clothing; The Fun Shop for just about everything (including clothes, housewares and gifts); The Shaggy Ram for antiques;  The Tack Box for equestrian gifts; Kizmetz for eclectic home accents; and Loyal Companion for supplies for dogs, cats and other critters. Make sure to take a trip to nearby Marshall to visit Tri-County Feeds, Fashions, Finds, the most eclectic and unique shopping experience in hunt country.

Red Fox Inn Crab Cakes Middleburg VA

Photo courtesy of Red Fox Inn.

6. Try a New Dish

Middleburg is fortunate to have a wide variety of excellent eateries, with everything from fine dining to a corner café. If you’re looking for a quick bite, we recommend organic and locally grown pub-inspired fare at the family-friendly Hunter’s Head Tavern, gourmet sandwiches at Market Salamander‘s inviting café, or a cup of coffee and locally inspired sandwich from Middleburg Common Grounds (which even has gluten-free wraps). Other favorite spots include the Piedmont-inspired cuisine at Salamander Resort’s Gold Cup Wine Bar, intimate dining at the Red Fox Inn & Tavern, and farm-fresh fare at Side Saddle Cafe. For gourmet fine-dining, try Harrimans Virginia Piedmont Grill at Salamander Resort or Goodstone Inn & Restaurant with its innovative farm-to-table cuisine. And don’t forget to pick up some of The Upper Crust’s famous cow puddle cookies!