Posted by on September 13, 2019

17 Things to Do in Middleburg this Weekend

— Check out our round-up of weekend events for Sept. 13-15, including The Fox Trail, Debbie McDonald’s dressage clinic at Rutledge Farm, the Polo Classic at Great Meadow, and more.

The Fox Trail: Through Sept. 15

Middleburg Life has teamed up with Boxwood Estate Winery, Cana Vineyards and Winery of Middleburg, Chrysalis Vineyards, and Greenhill Winery & Vineyards in celebration of October’s Virginia Wine Month. Sip and sample along Route 50 for a chance to win a case of Virginia wine! Participate in the challenge Thursday, Sept. 12-Sunday, Sept. 15.

To participate, please follow the instructions below:

  • RSVP on Eventbrite.
  • Visit the wineries on the list.
  • Check-in on Facebook at each winery.
  • Tag each winery and add your location on Instagram.
  • Once the above are completed, DM @middleburglife to let them know you’ve completed the challenge and to become eligible to win one of 3 prizes!
    • 1st place: a mixed case, to include 2-3 bottles from each participating winery
    • 2nd place: 6 bottles of wine
    • 3rd place: 3 bottles of wine
  • These prizes are valid ONLY with a purchase. (Winners must provide a receipt upon selection.) Winners will be chosen and notified on Monday, Sept. 16.

Questions? Email info@middleburglife.com.

Olympic Bronze Medalist Debbie McDonald Dressage Clinic at Rutledge Farm: Sept. 14-15

Rutledge Farm invites riders to apply to ride in this unique two-day high performance dressage clinic with Olympic Medalist and US Dressage Technical Advisor/ Chef D’Equipe Debbie McDonald.

Riders will be notified of acceptance and be provided a passcode with which to submit full details & payment via Event Clinics. A waitlist will be maintained.

Cost is $900 for full clinic participation, including two private lessons. Auditors may purchase tickets at $40/ day or $65 for the duration.

Lessons will be 45-minute private sessions. Please ensure early arrival so that you are ready for your assigned lesson time.

Click here to register.

Polo Classic at Great Meadow: Sept. 15 | 10 a.m.-5 p.m.

This event is fun for the whole family with pipes and drums, the parade of hounds, and more. Food and drink will be for sale at the event.

As the sole fundraising event for the National Sporting Library & Museum each year, the Polo Classic supports everything NSLM does. From exhibitions to educational programs to preservation of NSLM’s collections and more, your ticket purchase helps NSLM fulfill their mission: to preserve, promote and share the literature, art and culture of equestrian, angling and field sports.

For more info, visit nationalsporting.org or call 540-687-6542 ext. 35.

Also this weekend

Upcoming events

Lucy Stomp at Three Fox Vineyards: Sept. 21

Let out your inner Lucy or Ricky! This is the original northern Virginia wine country “stomp like Lucy” event. This is fun, competitive grape stomping in cut-down barrels with two-person teams.

Three Fox will have several heats and then the championship round. There will also be a “Lucy-Ethel-Ricky-Fred” look-a-like costume contest after the championship round.

To energize you, Three Fox will have the Gentle Harvest Food Truck, a selection of sweets from Teapot & Cake and live music by the Exaggerations. Pam Anderson from Stella and Dot will have cool fashion jewelry, accessories and clothing for sale. Carly Prow from Rodan and Fields will be presenting a full line of high-quality cosmetic and skin care products. Register online at threefoxvineyards.com.

Oktoberfest & Art in the Burg: Sept. 21 | 10 a.m.-8 p.m.

Art in the Burg returns this fall bigger than ever, as it coincides with the Town of Middleburg’s first-ever Oktoberfest! Please plan to join us on Saturday, Sept. 21, in downtown Middleburg on S. Madison Street for a celebration of regional artists. This year’s event will include jewelry, pottery, textiles, photographs and one-of-a-kind original canvases showcasing the history and beauty of Virginia’s hunt country.

Art vendors will be on-site from 10 a.m.- 8 p.m.

Oktoberfest will run from noon-8 p.m., with a traditional German biergarten, live music, feats of strength, craft beverages and German-inspired food.

This event is free and open to all ages!

Gallop Gala at Sprout Therapeutic Riding and Education Center: Sept. 21 | 6-11 p.m.

The Gallop Gala is an annual celebration of service and high-impact fundraiser that provides critical support to Sprout’s programs, students and horses. Funds raised through this event make dreams come true.

In honor of their Horse of the Year, David, they’re rolling out the red carpet and putting on the ritz! Glitz, glamour, classic cars, swinging jazz, cocktails and diamond dig along with dinner and a live auction will keep everyone jiving all night!

Prepare yourself for a night of vintage elegance as Sprout transports you to “The Golden Age of Hollywood!”

Get your tickets at bidpal.net. Tickets are $195 per person or a table of 10 for $1,850.

Harvest Experience at Boxwood Estate Winery: Sept. 22

Curious about what happens behind the scenes during harvest? Well, now is your chance to experience first-hand with a vineyard tour, fruit and wine tasting! Get your tickets before they sell out! Get your tickets at boxwoodwinery.com.

Also upcoming

Check out our calendar for more information about these and other upcoming events!


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MBPA, P.O. BOX 1384 Middleburg, VA 20118 | info@visitmiddleburgva.com


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