Things to Do in Middleburg, Virginia, in May

— May is a busy month in Middleburg, and it’s no wonder. With flowers blooming and the rebirth of spring, it’s a great time to enjoy the countryside. This month, we’ve got everything from the Virginia Gold Cup to community fundraisers, free concerts, Mother’s Day specials, Memorial Day fun and more! Here are our picks for the events you won’t want to miss this month.

1. Virginia Gold Cup at Great Meadow: May 4

Join us in the beautiful countryside of Fauquier County for the 94th running of the Virginia Gold Cup Races. Gates open at 10 a.m. with pre-race activities starting at 11 a.m. Purchase tickets now at

2. Sounds of Salamander at Salamander Resort & Spa: Sundays | 4-7 p.m. 

Sunday has been redefined with Salamander’s weekly event on Gold Cup’s terrace! While enjoying sensational views of the Virginia countryside and the summer sun, feast on Gold Cup’s fresh al fresco menu, spoil yourself with their seasonal beverages and take in the sounds of an acoustic guitarist each week.

3. Cinco de Mayo Culinary Journey Class at Salamander Resort & Spa: May 4 | 2-4 p.m.

Work with Salamander’s trained chefs in this hands-on class and create some of their favorite Mexican dishes from scratch including fish tacos, salsa and guacamole, breakfast chilaquiles and so much more.

4. “Il Fiore” Reception at The Byrne Gallery: May 4 | 5-8 p.m.

The Byrne Gallery is proud to present “Il Fiore, The Flowers of Italy: Nature, Imagery, and Symbolism.” This new exhibition of oil paintings by Sandra Iafrate explores both the wild and cultivated the flowers of Italy that are so much a part of the landscape and culture, and are ever-so-apparent in every Italian art form. This exhibit runs May 1-June 30. The artist reception is Saturday, May 4, from 5-8 p.m. All events are open to the public and everyone is cordially invited to attend.

4. “Cinderella’s Ball” at Middleburg Community Center: May 5 | 1:30-3:30 p.m.

Princes and princesses of all ages are cordially invited to enjoy a royal lunch with Cinderella and her friends and nemeses. As Cinderella’s guest, you will enjoy excerpts from the upcoming Cinderella Ballet. After the performance, all of the fanciful characters will be available for photos, autographs and a special dance. It promises to be a magical afternoon where dreams come true! Tickets are presale only and can be purchased at

5. #HuntCountry Launch Party at Greenhill Winery & Vineyards: May 11 | 6-9 p.m.

Join in on May 11 to launch #HuntCountry, the hashtag of choice to kick off the summer! We invite you to celebrate with us and all of the wonderful people, businesses, and activities within #HuntCountry. Get ready for a fun evening featuring DJ Georgie, Tip Top Photo Booths, a cigar lounge by Middleburg Tobacco Co., and coverage by the area’s top influencers. Complimentary heavy hors d’ouevres and cash bar. This event is 21 and over only.

6. MOMosa Bar & Live Music for Mother’s Day at Greenhill Winery & Vineyards: May 12 | Noon-6 p.m.

Celebrate your mom by treating her to a mimosa bar in the Greenhill tasting room!

On Sunday. Greenhill will be hosting a “Momosa” Bar, featuring your choice of mimosa, juice and garnish. This is an age 21 and over event.

7. “Canter & Crawl” Opening at the National Sporting Library & Museum: May 17 | 6-8 p.m.

Join the National Sporting Library & Museum to celebrate the opening of “Canter & Crawl: The Glass Sculpture of Joan Danziger,” a solo show of the DC-based, contemporary artist’s latest body of work. Stimulating the imagination, Danziger’s vibrant wire and glass-shard sculptures are inspired by the spirit of the horse and the jewel-like nature of insects. Featuring a reception and exhibition viewing from 6-7 p.m. and a lecture by artist Joan Danziger at 7 p.m.

$10 admission, free to NSLM members. RSVP to or 540-687-6542 x4.

Middleburg Community Center Concert on the Steps VA

8. “Concert on the Steps” at the Middleburg Community Center: May 17 | 6-8 p.m.

Join us for an evening filled with free fun, live music, food and beverages, and good company!

9. Art in the Burg on S. Madison Street: May 18 | 10 a.m.-5 p.m.

Join us for Middleburg’s annual spring celebration of the arts! Local and regional artists offering their artwork for sale with live music from the The Glimpses.

10. Land Trust of Virginia’s 21st Annual Garden Party at Hickory Tree Farm: May 19 | 4-7 p.m.

This year’s annual “Garden Party to Save Virginia’s Countryside” will be graciously hosted by Mimi Abel Smith at the stunning Hickory Tree Farm. This event is LTV’s major fundraising event of the year and includes a silent auction full of unusual gifts not found anyplace else. It is the region’s annual party not to be missed! The Garden Party will again feature a “wet paint” auction, “Painting for Preservation,” where artists will create individual and unique artworks from selected locations in the Hickory Tree Farm landscape. Party guests will be able to bid on these works of art during the party to secure their opportunity to take a canvas home.

Please join LTV for an afternoon celebrating efforts to conserve Virginia’s open space, natural resources, and cultural heritage. Purchase your tickets at

Also This Month:

Check out our events calendar for even more events this month!