May in Middleburg, Virginia, is a vibrant time filled with art, culture, and outdoor charm. Everyone is welcome to stroll Art in the Burg, featuring local artists and live music, or catch thought-provoking films at DocWeek Middleburg. The countryside comes alive with the annual Hunt Country Stable Tour, offering a rare glimpse into some of the community’s most prestigious horse farms. Wine lovers can enjoy tastings and scenic views at nearby vineyards, while families can look forward to community celebrations like Middleburg Day! Whether you’re sipping wine, watching polo, or shopping at the farmers market, Middleburg in May offers the perfect mix of elegance and small-town fun.
New events are always being added, so be sure to visit our full Events Calendar and not be left behind!
Art in the Burg Returns to South Madison and Federal Streets
Art in the Burg, Middleburg’s beloved annual celebration of the arts, returns on Saturday, May 10, 2025, from 11 AM to 6 PM along South Madison and Federal Streets in the heart of downtown. This vibrant festival showcases a diverse array of locally made, handcrafted works—including painting, pottery, photography, jewelry, sculpture, woodworking, leather goods, wearable art, candles, soaps, and lotions. Visitors can also enjoy live music, dance, improv, storytelling, and stunning architecture, all while sipping craft wine, cider, or beer and savoring delicious festival fare. It’s a day full of creativity, community, and Middleburg charm.
Middleburg Farmers Market Kicks Off on Saturday, May 3rd
The Middleburg Farmers Market returns on Saturday, May 3rd, kicking off the 2025 season from 9:00 am to 1:00 pm at the Middleburg Town Hall. Held every Saturday morning through October 25th, the market offers a wonderful opportunity to shop fresh, local, and seasonal goods directly from the farmers, growers, and makers who produce them.
Sponsored by the Town of Middleburg, the market supports local agriculture while giving residents and visitors access to high-quality produce, baked goods, flowers, handmade items, and more. Friendly dogs on a leash are always welcome, and you can stay up to date on specials and weekly highlights by following the Town of Middleburg Facebook page.
Come out and make your Saturdays a little fresher!
Cana Budbreak Festival
Cana Vineyards will celebrate the arrival of spring with its 9th Annual Budbreak Festival—a weekend of wine, live music, food trucks, and local crafts. Guests can enjoy the release of the 2024 Rosé of Merlot and Rosé of Cabernet Sauvignon, alongside tasting flights and seasonal cheer.
Winemaker Melanie Natoli will lead Rosé Around the World, a special guided tasting exploring international rosé styles. Self-guided flights are available without reservations; guided tastings require advance booking through Cana’s website.
The event is family-friendly and welcomes leashed pets on the first floor. Groups of 14+ must arrange space rentals in advance by contacting events@canavineyards.com.
Middleburg Community Center’s Concert on the Hill Series
The Middleburg Community Center’s beloved Free Concert Series is back for its 11th year and offers two shows this month: The Crooked Angels on Friday, May 9 and Bryan Fox on Friday, May 23, 2025
New this year, all concerts will take place in the historic Fox Trap Amphitheater, a venue originally built 77 years ago for performances, films, and community events. As the Center celebrates its 77th year, the series returns to its roots—inviting the community to “fill the hill” once again.
Concertgoers can look forward to live music, great food, and a festive atmosphere as friends and neighbors gather for another season of music and connection.
The Hill School’s 48th Annual Auction “A Black & White Gala”
Mark your calendars for one of the most anticipated events of the season—the 48th Annual Hill School Auction & Gala, taking place on Saturday, May 10th from 6:30 to 10:30 pm in the Hill School gymnasium.
This beloved tradition brings together the Hill School community for an evening of celebration, generosity, and fun. Guests will enjoy a lively atmosphere filled with gourmet food, signature cocktails, and the thrill of silent and live auction bidding on incredible items and experiences.
New this year, guests can also try their luck at the casino game tables—just one more reason this year’s gala is sure to be one to remember. Whether you’re there to bid, play, mingle, or simply soak in the energy of the evening, there’s something for everyone.
Come ready to support a great cause, connect with friends old and new, and make memories that will last long after the final bid is placed.
Community Music School of the Piedmont Mother’s Day Recital
Looking for a fun family activity after Mother’s Day brunch? The Community Music School of the Piedmont invites families to their annual Mother’s Day Recital at Buchanan Hall in Upperville.
The recital will showcase performances by CMSP Faculty & Friends, featuring classical works, selections from Wicked, and other cheerful springtime tunes.
Children and students in the community are encouraged to draw, paint, or color a picture inspired by music or spring. Submissions can be turned in to their teacher or the CMSP office by May 6th. Digital copies of the artwork can also be emailed to piedmontmusic@aol.com.
All submitted artwork will be featured in a slideshow presentation during the recital.
Everyone is welcome to attend and celebrate the joy of music—and moms!
DocWeek Middleburg
DocWeek is a laid-back, local film fest that rolls into Middleburg, Virginia every third week of May. From Tuesday through Saturday, one documentary is screened each evening at sunset—outdoors at the Middleburg Community Center’s amphitheater (as long as the weather plays nice).
This isn’t your typical film festival—DocWeek keeps things cozy, capping the audience at 150 people to keep the vibe friendly and community-focused. It’s all about bringing neighbors together for some thought-provoking, inspiring, and sometimes eye-opening documentaries.
In a time when it feels like everyone’s arguing online, DocWeek is a breath of fresh air—literally and figuratively. Come hang out, watch a good doc, and connect with your community!
Hunt Country Stable Tour May 24th & 25th
Saddle up for an unforgettable ride through the heart of Hunt Country!
Discover the rich equestrian history of this storied landscape—all while supporting Trinity Episcopal Church’s outreach programs and giving back to communities both near and far.
This year’s tour is the biggest yet, with 17 farms, stables, and attractions to explore—including eight brand-new stops that have never been featured before!
What’s new for 2025:
A Sunday-Only Ticket for unbeatable value
Two exclusive VIP experiences for a next-level adventure
Tickets are available online only—so grab yours before they’re gone!
Second Annual Middleburg Day Picnic
The Town of Middleburg invites everyone to the 2nd Annual Middleburg Day on Friday, May 30, 2025, starting at 5:00 pm at Town Hall.
This festive event is all about celebrating the spirit of community—think of it as a big town picnic, complete with delicious food, lively music, fun games, and plenty of good vibes. It’s a chance for neighbors to connect, relax, and enjoy the start of summer together.
Guests can look forward to free food and non-alcoholic drinks, generously provided by beloved local caterer Tutti Perricone of Back Street Catering.
The celebration runs from 5:00–9:00 pm—everyone is welcome!