40+ Things to Do in Middleburg in August

— We’re kicking off August with one of the biggest sales of the year, our 12th annual Upscale Sidewalk Sale. The sale will be held Aug. 3-4 from 10 a.m.–5 p.m. and Aug. 5 as posted by shops and coincides with Virginia’s tax-free weekend. We’ve also got some fun free community events in August, including the National Night Out on Aug. 7, Dinner & a Dive-in Movie at the Middleburg Community Center on Aug. 17 and an Open Late concert at the National Sporting Library & Museum on Aug. 31.

1. Fox 5 Zip Trip in Middleburg: Aug. 3 | 6-11 a.m.

Known for its rich history, boutique shops and world-renowned equestrian scene, the iconic town of Middleburg will share its story with the greater Washington, D.C., region on Aug. 3 when Fox 5 broadcasts live from the town’s historic streetscape.

Participate in the live broadcast and show support for the town during this exciting opportunity happening from 6-11 a.m. on S. Madison Street!

Meet Fox 5 anchors Allison Seymour and Tony Perkins as well as Fox 5 weatherman Tucker Barnes, enjoy free samples from Dunkin Donuts and Popcorn Monkey, register to win a 2019 Acura TLX provided by Washington Area Acura dealers and visit with local nonprofits.

During the morning, scheduled guests include Middleburg Humane Foundation, Mayor Bridge Littleton, Red Fox Inn & Tavern‘s culinary director, chefs from Salamander Resort & Spa and Goodstone Inn & Restaurant, Cana Vineyards’ winemaker, Foxcroft School‘s field hockey team, students from the Middleburg Community Charter School, Police Chief A.J. Panebianco, Salamander Resort’s precious pony Cupcake and more!


2. 12th Annual Middleburg Upscale Sidewalk Sale: Aug. 3-5

Hunt for some wonderful bargains for yourself and your loved ones this weekend while experiencing the small town charm of Middleburg during our 12th annual Sidewalk Sale on Aug. 3-5! The sale will be held Friday and Saturday from 10 a.m.–5 p.m. and Sunday as posted by shops.
The sale coincides with Virginia’s tax-free weekend. From Aug. 3-5, you can buy qualifying school supplies, clothing, footwear, hurricane and emergency preparedness items, and select energy-efficient products without paying state and local sales taxes on those items. You can find out more about what items qualify for the tax exemption here.

You can also enter a raffle for a gift basket with a receipt showing $50+ proof of purchase during the sale from a participating store.


3. Beatles & Bubblegum Family Concert at Middleburg Library: Aug. 4 | 2-3 p.m.

Get ready to twist and shout as Raymond Leone Music presents a fun-filled hour of Beatles and 1960s “bubblegum” music and trivia.


4. National Night Out at the Middleburg Community Center: Aug. 7

The Middleburg Police Department and the Middleburg Community Center are joining in celebrating the National Night Out! There will be food, entertainment, music, demonstrations, prizes, games and much more! Also, the Middleburg Police Department “may” be filming that day and you could be in it.


5. National S’mores Day at Gold Cup Wine Bar and Harrimans Virginia Piedmont Grill: Aug. 10

Happy National S’mores Day! Salamander Resort & Spa is recognizing this popular campfire gooey treat by offerings s’mores kits at half-price all day! Each kit is built for two people to be enjoyed at one of Salamander’s outdoor fire pits and includes a Lindt chocolate bar, graham crackers and of course, marshmallows. For more information, please call 540-326-4070.


6. Raid Our Cellar at Harrimans Virginia Piedmont Grill: Aug. 11 | 2-4 p.m.

Stop by Salamander Resort & Spa’s pop-up wine shop and stock up your wine cellar! You will be able to purchase from an exclusive wide-selection of domestic and international wines. For more information, please call 540-326-4070.


7. The Mosby Heritage Area Association Presents A Gospel Concert Fundraiser for Willisville at Buchanan Hall: Aug. 11 | 4-6:30 p.m.

A gospel concert fundraiser for Willisville, titled “The Path Through WIllisville with Carol Lee,” will take place on Aug. 11 at Buchanan Hall.

The Mosby Heritage Area Association has partnered with the residents of Willisville to have the village added to the National Register of Historic Places. Freedmen founded Willisville in southwestern Loudoun County after the Civil War and it is one of the best-preserved villages of its kind. These African-American communities represent a significant part of Virginia’s history, and Willisville would be among the first in the Commonwealth to receive National Register designation.

The final application for its addition to the register must include a well-researched and documented survey of the village’s 15 residences, former schoolhouse and country store, and its Methodist Church. Mosby Heritage Area Association is campaigning to raise $15,000 to fund the professional historical research, facilitate the process, and complete the application.

Join them and the citizens of Willisville for a gospel concert featuring music, food, and refreshments. Performers include: The Gospel Tones of Mt. Olive Baptist Church, The Voices of Agape United Methodist Church, and Sistah of Praise of Middleburg.

Refreshments and light fare will be served. Donations will be accepted to help Willisville reach its goal!

To make a donation, call 540-687-6681 or click here.


Market Salamander Middleburg VA

8. Biz Buzz at Market Salamander: Aug. 14 | 5:30-7:30 p.m.

Biz Buzz is a monthly networking event held by the Middleburg Business and Professional Association on the second Tuesday of the month, except in January. These events bring local business owners and professionals together to network, provide local businesses with an opportunity to showcase their facilities and services, and help to spread the word about interesting news and events in the Middleburg community. Members free, non-members $10. Please RSVP via Facebook or by e-mail to info@visitmiddleburgva.com.



9. Dinner & Dive-In Movie at the Middleburg Community Center: Aug. 17 | 6:30 p.m.

Join us for MCC’s final summer event! Chick-fil-a dinner at 6:30 p..m, Captain Cookie and the Milkman Ice Cream Truck from 6:30-8:30 p.m., various amusements in the ball field from 6:30-8:30 p.m., and closing with a showing of “Moana” poolside at 8:30 p.m.!
This event is free and open to the public, and made possible by the Luminescence Foundation.


10. Spanish Wine Dinner at 50 West: Aug. 18 | 6:30-9:30 p.m.

An evening celebrating the release of the 2017 Albariño with Spanish cuisine and music!

Te amo Albariño! In honor of 50 West’s 2017 Albariño release in the tasting room, 50 West invites you to join them for a Spanish wine dinner.

Gaze at the beautiful hills of Middleburg and imagine you are in Galician, Spain, overlooking the sloping vineyards full of Albariño vines. During this Spanish wine dinner, you’ll enjoy five courses of Spanish cuisine paired with a variety of Spanish wines. Spanish guitar will be played during the dinner to enhance the ambiance and every ticket holder will go home with a bottle of Spanish Albariño.

Get your tickets today!

11. Legends by Lanternlight: Using a County Seat to View the War: Aug. 18 | 7:30-9:30 p.m.

Partnering with the Clarke County Historical Association, the members of the Mosby Heritage Area Interpretive Group, in a twilight-lanternlight walking tour, will bring alive the memorable experiences of Berryville during the American Civil War through costumed first-person interpretations in the historic downtown. Learn how our preserved landscape still tells us stories.

The program will start at 7:30 p.m. at the Clarke County Historical Association. Participants will view the Civil War experience of Berryville and how the war affected life in the Shenandoah Valley. The period-dressed Mosby Heritage Area Interpretive Group will offer their story-telling ability against the backdrop of historic Berryville, featuring stories of Clarke County’s commissioner to the Virginia Secession Convention, the visits of two famous Civil War generals, Mosby’s Wagon Train Raid in Berryville, and the story of Eugene Ferris, a Medal of Honor recipient from his days of fighting Mosby’s Rangers.

Tickets are $15 for adults and $8 for students and can be purchased in advance or at the door. Walking is involved; dress comfortably. For more information: 540-687-6681 or kpawlak@mosbyheritagearea.org.

This program is sponsored jointly by the Mosby Heritage Area Association and the Clarke County Historical Association.


12. Le Marche Comes to Girasole: Aug. 23 | 6:30 p.m.

Here’s an exceptional opportunity to learn about and taste the dishes of Le Marche. Lydia’s relatives, Paola Alessandroni and her daughter Marta, will host a cooking class at Girasole.

Many from Lydia’s tour groups to Italy will know Paola and Marta as the groups stayed and dined at their bed and breakfast, called an agriturismo in Italy. On their property, they grew their own food, raised livestock, cured meats, and prepared delicious, authentic dishes from the region that stretches along the Adriatic coast. The undulating hills of its interior are rich farming terrain and only sparsely peppered with market towns and one-street villages. The land is dotted with small picturesque cities like Urbino, an UNESCO world heritage site.

Since the time of the ancient Romans, many different cultural and political factors have shaped the character of the Marche. Both the landscape and the gastronomic traditions of the Marche are a reflection of the region’s long history.

The influence of the neighboring regions and the proximity of both the mountains and the sea give Le Marche region a unique blend of the best of Italian flavors. Join us for the unique opportunity to learn about and taste the cuisine of this often-overlooked region of Italy without leaving Virginia! The cost is $95 per person, exclusive of tax and gratuity and includes dinner and wine pairings. To make a reservation, please call 540-253-5501.


Open Late Concert National Sporting Library & Museum Middleburg VA

13. “Open Late” Concert at the National Sporting Library & Museum: Aug. 31 | 6-8 p.m.

Join us for the “Open Late” summer concert series at the National Sporting Library & Museum. Bring a picnic blanket and your dancing shoes for a fun-filled evening of music by Piedmont Symphony Orchestra. Concerts are FREE and open to the public, and you can take advantage of free museum admission at the same time!


Twilight Jumpers Great Meadow The Plains VA

14. Twilight Jumpers at Great Meadow: Aug. 31 | 7 p.m.

Twilight Jumpers at Great Meadow is an evening event held on a series of Friday nights under the lights at Great Meadow. This will be the last Twilight Jumpers of 2018, so don’t miss out!

Modeled after Great Meadow’s highly successful Twilight Polo event, Twilight Jumpers offers two invitational classes each night. Proceeds benefit the nonprofit High Performance Equestrian Foundation.

Gates open at 6:30 p.m. The first class ($500 Child/Adult Amateur Class at 1.05m) begins at 7 p.m. The second class ($5,000 at 1.30m) will start at 8:30 p.m. The class size is limited to 20 competitors, by invitation only. The evening features top competition, intense tailgating, and dancing in the pavilion after the competition.

Whether you want to compete, reserve a rail side box for 6, tailgate, or just picnic on the grass for $40/carload, it’s a great way to support a worthy nonprofit organization and enjoy the show jumping at Great Meadow!

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