18 Things to Do in Middleburg This Weekend

— Check out our round-up of weekend events for Aug. 23-25, including Great Meadow International, a Civil War bus tour with the Mosby Heritage Area Association, a charcuterie tasting at Greenhill Winery & Vineyards, and more.

Mars Great Meadow International: Aug. 22-25

Established in 2015, the Great Meadow International is a three-day eventing competition held annually at the Great Meadow Foundation in The Plains, Virginia. In addition to the international equestrian competition, the event features VIP hospitality, a trade fair, beer garden, and entertainment for the whole family. The 2019 Great Meadow International will take place Aug. 22-25.

Now in its fifth year, the Great Meadow International (GMI) has been repackaged into a larger competitor and spectator-based event offering three levels of international competition. The event features Olympic-level riders and horses in what can best be described as an equestrian triathlon. In addition to the equestrian competition, the 2019 GMI will highlight all things related to our canine companions. Leashed dogs are welcome and can enjoy amenities including a “VIP” (“Very Important Pooch”) cooling tent with swag, treat samples and more especially for your best four-legged friend. Other additions to the event schedule include canine demonstrations and dog-friendly programming and educational events for the whole family.

Tickets to GMI are available here. All grounds admission tickets to GMI include general parking and admission to the venue and Meadow Market vendor village featuring live entertainment, a beer garden, tasty offerings from top local food trucks, and family-friendly games. Tickets also include admission to the Demonstration Station featuring exciting and educational demonstrations. For those seeking options featuring premier Virginia hospitality, special ringside boxes, tailgates and tables in the VIP pavilion are also available.

The Art of War: The Civil War Sketches of James E. Taylor at the Mosby Heritage Area Association: Aug. 24 | 9 a.m.-3 p.m.

As Union forces advanced into the Shenandoah Valley in 1864 they were accompanied by James E. Taylor, a sketch artist working for Leslie’s Illustrated. During his time with Sheridan’s army, Taylor brought the war to life with his detailed sketches that covered all aspects of military life and the surrounding countryside.

Join the Mosby Heritage Area Association for a bus tour that follows in the path of the artist. You will visit some of the locations sketched by Taylor and compare how much these views have changed since 1864. Artists are welcome to bring along a sketch pad and try their hand at recreating these scenes as they appear today!

Bus departs MHAA office at 1461 Atoka Rd., Marshall, VA at 9 a.m.

Lunch included. Seats are limited so reserve your seat today! Get your tickets at mosbyheritagearea.org.

Creminelli Charcuterie Tasting at Greenhill Winery & Vineyards: Aug. 24 | 1-2:30 p.m. & 3-4:30 p.m.

Ever wonder what goes into making the highest quality charcuterie and what wines they pair best with? Join us for a special tasting of Creminelli Fine Meats charcuterie paired with your favorite Greenhill wines. Kristina Siou will guide you through how these specialty charcuterie are created and what sets Creminelli apart.

Tickets are $35 a person and include five different Creminelli selections paired with Greenhill wines and cheese. Purchase tickets via cellarpass.com.

Also this weekend

Upcoming events

“John S. Mosby in Civil War History and Memory” at the National Sporting Library & Museum: Aug. 29 | 6-8 p.m.

NSLM welcomes back 19th century historian David Gerleman, who will discuss the life of John Singleton Mosby. Renowned as the “Gray Ghost,” Civil War partisan leader John S. Mosby was celebrated across the South as a hero for his exploits and dreaded in the North for his military acumen. Yet his bitterest struggles occurred in the years after 1865 when his political stance and refusal to endorse Lost Cause doctrines forced him to abandon Virginia. The presentation highlights Mosby’s tumultuous life and career with particular focus on his transformation from Confederate hero to heretic and back again within the larger context of modern Civil War memory.

This program is hosted by NSLM.

$10 admission. Free for NSLM members. $5 for Mosby Heritage Area Association members.

Limited seating available. RSVP at info@nationalsporting.org or 540-687-6542 x 4.

Open Late in Middleburg: Aug. 30

Join us Friday, Aug. 30, for another concert at the National Sporting Library & Museum, extended hours of shopping and dining at over 25 locations, and great fun throughout the town! Tell your friends and use #OpenLate in your social media postings! More info at middleburgva.gov/openlate.

Virginia Scottish Games & Festival at Great Meadow: Aug. 31 & Sept. 1

The Virginia Scottish Games & Festival returns to Great Meadow in The Plains.


  • Two-day adult: $30
  • Single-day adult: $20
  • Children 5-12: $5 on Saturday, free on Sunday
  • Children under 5: Free

Gates are open 9 a.m.-5 p.m.

Scottish and Celtic heritage is the reason for the celebration, but there is something for everyone at this dog-friendly, family-friendly 2-day event.

Visit vascottishgames.org for more info. Click here to buy tickets online.

Also upcoming

Check our calendar for more information on these and other events!