20+ Things to Do in Middleburg This Weekend

— Check out our round-up of weekend events for Aug. 9-11, including a cardboard regatta at the Middleburg Community Center, Olympian Boyd Martin at Rutledge Farm, a library wine tasting at Cana Vineyards & Winery, a summer pig roast at Greenhill Winery & Vineyards, and more.

Cardboard Regatta & Late Swim at the Middleburg Community Center: Aug. 9 | 5-8 p.m.

Middleburg Community Center’s Doc Saffer Summer Series presents the Cardboard Regatta and late swim.

Build a boat out of cardboard and race your friends down the pool, have a pizza dinner in the park while playing with adoptable dogs from Middleburg Humane Foundation, or have your face painted while eating an ice cream from MooThru!

Event Timeline:

  • 5-5:30 p.m.: Pizza in the park
  • 5-8 p.m.: Middleburg Humane Foundation adoptable doggies in the park
  • 5:30-6 p.m.: Cardboard Regatta
  • 5-8 p.m.: MooThru ice cream truck, bounce house obstacles, face painting and a DJ
  • 6-8 p.m.: Free late swim

This event is free and open to the public. Please register your boat prior to the event if your children plan on participating.

Contact: info@middleburcommuntycenter.com or 540-687-6373 to register your boat. Please provide the boat name and the name and ages of the children participating.

Olympian Boyd Martin at Rutledge Farm: Aug. 10 | 8:30 a.m.-5:45 p.m.

Join Rutledge Farm for a high-performance eventing clinic with PanAm Games gold medalist and Olympian Boyd Martin!

This clinic will offer the following 75-minute training sessions (limited to 4-6 riders):

  • 8:30-9:45 a.m.: Advanced, Intermediate and Preliminary
  • 10:15-1:30 a.m.: Training
  • Noon-1:15 p.m.: Novice
  • 2:45-4 p.m.: BN/N
  • 4:30-5:45 p.m.: Beginner Novice

Sessions will begin with 15-20 minutes of flatwork focused on adjustability for over-fences work. Riders will move from there to over-fences work in the arena (or grass) with heights and questions appropriate to all levels; eventually incorporating related jumping lines. The sessions will culminate with some competition-style questions and XC lines, though these exercises will be done predominately in an arena setting. If decision is made to move part of the clinic to grass, riders will be notified.

Cost is $200 per rider, and $20 per auditor. To register for this clinic and other opportunities from Rutledge Farm, visit rutledgefarm.com/clinics.

Library Wine Tasting at Cana Vineyards & Winery of Middleburg: Aug. 10 | 11:30 a.m.-5 p.m.

On Saturday, Aug. 10, Cana will be conducting a very special library tasting of some of their earliest vintages. They are releasing a small lot of Cana favorites for an exclusive, small-group wine tasting and discussion. Wines will be paired with a delicious charcuterie plate.

Featured wines include:

  • 2012 Barbera
  • 2012 Cabernet Franc
  • 2012 Le Mariage
  • 2010 Tempranillo
  • 2013 Norton

There are three tasting sessions on Aug. 10: 11:30 a.m., 2 p.m. and 4:30 p.m. Each seating has only 20 seats, so book soon! After the tasting, you will have the opportunity to purchase these special library wines. Very limited quantities are available.

Tickets are $35 per person ($30 for Harvest Club members). You can purchase tickets at canavineyards.com.

Summer Pig Roast at the Club House at Greenhill Winery & Vineyards: Aug. 10 | 5-7 p.m.

Join Greenhill Winery on Saturday, Aug. 10, for a summer pig roast! Tickets are $45 per person and include food prepared by Hog Wild Catering, music by the Short Hill Mountain Boys and a glass of wine of your choice! Kick back and enjoy summer overlooking the pond and rolling hillside at Greenhill’s historic club house.

For more information, please contact Greenhill Event Manager Brittany Neilan at brittany@greenhillvineyards.com.

Purchase tickets at greenhillvineyards.com.

Also this weekend

Upcoming events

Bites & Flights at Old Ox Brewery: Aug. 17 | Noon-6 p.m.

Join us at Old Ox Brewery Middleburg on Saturday, Aug. 17, for a food and beer pairing experience. Old Ox’s chef has thoughtfully prepared four delicious bites to pair with four popular beers to create a magical taste sensation. Check out the menu below and buy your tickets now so you don’t miss out!


  • Golden Ox Golden Ale paired with a Chicken Satay with Curry Peanut Sauce
  • Black Ox Rye Porter paired with a Short Rib Braised in Black Ox
  • Down the Hatch Amber Lager paired with Mesa Verde
  • Derailleur Double Dry Hopped American Ale paired with Carrot Cake

Buy your tickets at Eventbrite!

Local Art Show at Boxwood Estate Winery: Aug. 17 | 1-7 p.m.

Enjoy a taste of wine and local art! Featuring Red Fox Fine Art, Amanda Horn and Elizabeth Cosby. Event is free to the public. Art work can be purchased day of the event!

Also upcoming

Remember to check our calendar for even more upcoming events!