February in Middleburg may be cold, but the town doesn’t hibernate. This is a month for gathering for dinners that linger, events that bring people together, and the kind of shared moments that turn winter into something to look forward to. From cozy evenings out to meaningful local happenings, February is when love shows up in many forms: friendship, partnership, and pride in the community we call home. And let’s be honest, any month that gives us an excuse to gather, celebrate, and stay out just a little longer is worth embracing!
In the meantime, check out our teeny tiny town’s events that will brighten your winter days ahead!
Be sure to visit our full Events Calendar for the latest updates.
Valentine’s Celebrations in Middleburg
Valentine’s Day in Middleburg is less about one night and more about a full celebration of love!
From Galentine’s Day gatherings and the ever-popular Cupid’s Cave wine pairing at Boxwood Estate Winery, to Galentine’s Day and Mini & Me events at Lost Barrel Brewing, there’s no shortage of ways to celebrate with friends, family, or little ones in tow. Couples can enjoy a romantic Valentine’s experience at The Red Fox Inn & Tavern, while Salamander Middleburg’s Family Sweetheart Dance adds a touch of family fun and nostalgia to the weekend.
Whether you’re celebrating romance, friendship, or community, Middleburg offers something special for everyone.
America’s 250th: Black History Month Celebration
The Town of Middleburg invites all to the Community Center at February 11 at 5 pm to come together for a heartfelt, truly local celebration of Black History Month. Through a partnership with Caandor Ventures, a professional videography firm, the Town captured the oral histories of twelve former congregants of the Asbury Church and members of Middleburg’s African American community.
These powerful videos, each seven to twelve minutes long, share personal stories of faith, family, and life in Middleburg, told in the voices of those who lived them. A special composite video weaves these stories together to highlight the history of the Asbury Church and its lasting impact on the local African American community.
Winter Weekend Sale February 13-15
Join the Town of Middleburg and the Middleburg Business & Professional Association for the 15th Annual Winter Weekend Sale, one of the most anticipated shopping events of the season! It’s the perfect excuse to stroll through town, support local businesses, and score incredible deals you won’t want to miss.
From boutiques and specialty shops to unique gifts and winter favorites, Middleburg merchants are offering amazing savings all weekend long—you’ll be blown away by the bargains! Whether you’re shopping for yourself, picking up Valentine’s Day surprises, or just enjoying a cozy winter outing, there’s something for everyone.
Sale Hours:
Friday, February 14 & Saturday, February 15: 10:00 am – 5:00 pm
Sunday, February 16: Hours vary by shop
Mark your calendar and come experience the charm, savings, and community spirit that make Middleburg shopping so special.
Bundle up, bring and friend, and shop small!
Cooking Class Weekend at Briar Patch B&B
Briar Patch’s Cooking Class Weekend is February 14 & 15, 2026!
What’s Included
Two-night stay with hot breakfasts Saturday and Sunday
Friday night wine tasting with a local winery expert and hors d’oeuvres
Saturday evening cooking demonstration and four-course dinner with wine
Experience
Arrive Friday to meet the chef, enjoy appetizers, and sample Virginia wines paired for Saturday’s meal. After breakfast Saturday, explore Middleburg at your leisure. Saturday evening, gather for a hands-on cooking demonstration and four-course dinner with recipes provided. Enjoy a final hot breakfast Sunday morning.
Expect a relaxed weekend of great food, wine, and company. Limited spots are also available for the cooking class only, without overnight accommodations.
Young Voices at Emmanuel Parish House
It’s easy to think that our area’s most talented singers are mostly found in local choral groups, churches, bands, and performance venues. Meanwhile, right under our noses, there’s a wealth of singing talent flourishing in our area schools!
For the fourth consecutive year, At The Parish House is bringing together local school choruses so we can all hear and celebrate their talents on February 22, 2026, at 3 pm at Emmanuel Parish House. They will showcase their wide-ranging repertoires with genres ranging from Renaissance madrigals to pop, Broadway, folk, contemporary, international favorites, and more.
Come enjoy and support our talented local students!
Environmental Film Night at The Hill School
On February 27 at 5:30 pm, step into the hidden history of the Chesapeake Bay watershed at the Goose Creek Association and Land Trust of Virginia Environmental Film Night, featuring the documentary Water’s Way: Thinking Like a Watershed, produced by The Bay Journal.
Once shaped by beaver ponds, wetlands, and forested streams that naturally filtered water flowing to the Bay, the Chesapeake region has been altered by development, agriculture, and stream channelization—creating what scientists call an “ecological amnesia.” This visually compelling film explores how restoring beavers, trees, and wetlands can help heal these systems and improve water quality today.
Before and after the screening, connect with local conservation professionals to learn more about watershed health and practical, community-based ways to support restoration efforts close to home. Light refreshments will be served.