Labor Day Weekend in Middleburg, Virginia

Kick off a great start to the fall season in Middleburg this weekend! From a one-of-a-kind family movie night at Salamander Resort & Spa to the Virginia Scottish Games at Great Meadow, we’ve got an activity you’re sure to get excited about. Here’s a look at what’s going on this weekend:

Loudoun County Restaurant Week: Through Aug. 30

Are you ready to #TasteLoudoun? The Loudoun County Chamber of Commerce, Loudoun Now and Visit Loudoun teams are excited to present the 2nd annual Loudoun Restaurant Week! Through Friday, Aug. 30, join us as we celebrate the best that Loudoun’s culinary community has to offer! Take this great week-long opportunity to try out new restaurants and gather around the table with your friends and family. From fast casual to gourmet dining, there is something for everyone’s taste buds in Loudoun. For more details and menus, visit and be sure to share your experience on social using #TasteLoudoun! Participating Middleburg restaurants include Gold Cup Wine Bar, Goodstone Inn & Restaurant, Harrimans Virginia Piedmont Grill, Side Saddle Cafe and The Red Fox Inn & Tavern. Reservations recommended. National Sporting Library and Museum Middleburg VA Open Late

Live Music: Aug. 30-Sept. 2

If you love listening to live music, Labor Day weekend is a great time to be in Middleburg. Kick off the weekend with the final “Open Late” concert of the season with the Shenandoah Conservatory at the National Sporting Library & Museum on Friday from 6-8 p.m. This free summer concert series, now in its fifth year, features regional performers, local wine from Greenhill Winery & Vineyards, beer from Powers Farm & Brewery, and delicious concessions from Pirate Rooster Pizza and Blackwater Beef. Attendees are encouraged to stroll through the fine art museum during the concerts, where you can view a selection of pieces from the NSLM’s permanent collection of over 1,200 art objects, as well as changing exhibitions on view. Picnics are welcome and a cash bar will be available — no outside alcohol or glass containers are permitted on the premises. All pets must be leashed. Plus, enjoy extended hours of shopping and dining at over 25 locations, and great fun throughout the town on Friday night! Tell your friends and use #OpenLate in your social media postings! More info at This weekend, Three Fox Vineyards will also feature live music each day, with the Exaggerations on Saturday, Jimmy Lee on Sunday and the Tower Blues Band on Monday. You can also enjoy Jill’s Skrimp Shack on Saturday. Plus, they’ll be doing their annual “Blessing of the Harvest” on Monday at noon with Fr. Mark Moretti, parochial vicar at Christ the Redeemer Catholic Church in Sterling. Play bocce or corn-hole, check out their picnic meadow and hammocks, or stroll their woodland trails or the banks of Crooked Run. You can also enjoy live music on the terrace (weather permitting) at The Red Fox Inn & Tavern on Friday evening, music by Sharif Music at Greenhill Winery & Vineyards from 2-5 p.m. on Sunday, and Sounds of Salamander at Salamander Resort & Spa from 4-7 p.m. on Sunday.

Country Western Night & Chili Cook-Off at Great Meadow: Aug. 31 | 5:30-11 p.m.

On Saturday, Great Meadow will have three polo matches, halftime games, food from Guapos Restaurant, dessert from The Inside Scoop, fun for kids from Funday Packs and wine for sale from Blue Valley Vineyard and Winery. The evening will conclude with dancing in the pavilion after the matches! Gates open at 5:30 p.m. To celebrate Country Western Night, there will be a chili cook-off! Details and rules at Car passes may be purchased online for $25 or $30 at the gate. Each car pass covers entry for all the occupants of the vehicle. VIP reservations, including ringside boxes, entertainment decks and tailgates can be made in advance at General Admission seating is on the grass covered berm overlooking the arena. Guests are welcome to bring a blanket and chairs. Pack a picnic or purchase food and drinks from our on-site vendors. Please leave dogs, tents and grills at home. Virginia Scottish Games

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

Celebrate Scottish and Celtic heritage at this dog-friendly, family-friendly, two-day event. The games include piping and drumming, a British car and bike show, children’s games, fiddling, Highland dancing, Scottish dog events and live music. Gates open to the general public at 9 a.m. and close at 5 p.m. both days. Click here for more information.

End of Summer Bash at Salamander Resort: Sept. 1

Meet us at the culinary garden for Salamander’s end of the summer BBQ and celebration on Sunday! Enjoy the last days of warm weather in Salamander’s culinary garden as they grill traditional BBQ favorites. The resort’s end-of-the-summer bash will also include a giant slip and slide, water balloon fight, plus many more fun family-friendly activities on the Equestrian Center lawn. Reservations required; please call 540-326-4070.

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