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Local Events in Middleburg

Come & Join the Fun!

Renowned as the Nation’s Horse & Hunt Capital, Middleburg offers a variety of equestrian events throughout the year, including the Middleburg Spring Races and the Virginia Fall Races. It’s also a well-known destination for the arts with events like the Middleburg Film Festival and Art in the Burg.

Christmas in Middleburg draws thousands of visitors, who line the streets on the first Saturday in December to watch the parade and the Middleburg Hunt Revue.

Check the calendar below to find out what’s happening around town.

Audience in lawn chairs clapping in front of National Sporting Library and Museum
September 2026

“Horizons: Where Earth Meets Sky” Exhibit

The Byrne Gallery proudly presents Horizons: Where Earth Meets Sky, the new exhibition for the month of September. Local artists Laura Bollettino, Katie Flack, and Gerald Hennesy will explore the timeless beauty of the landscape and the quiet wonder found where land and sky converge. Through scenes of coastlines, fields, marshes, and mountains, the exhibition […]
Sep 02 - 27
All Day
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117
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Fall Paint & Sip

Celebrate the start of fall with a cozy afternoon of painting at Cana Vineyards on Saturday, September 20, from 1:00 to 3:00 PM! Enjoy the breathtaking views at one of Virginia’s most beautiful wineries while creating a festive fall-themed painting. No experience is needed. Your ticket includes all painting supplies, step-by-step instruction, and one glass […]
Sep 20
1:00 pm - 3:00 pm
Cana Vineyards & Winery
38600 Little River Turnpike, Middleburg, VA 20117
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Beyond the Gates of Farmer’s Delight

Join VPHA for a special tour of historic Farmer’s Delight, a Federal-style home built in 1791 by Revolutionary War veteran Colonel Joseph Flavius Lane. Explore the house, gardens, and arboretum while discovering the property’s rich history, from its early years as a Virginia plantation to its later role as the home of diplomat George C. […]
Sep 20
2:00 pm - 4:00 pm
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“How Can I Help?” An Evening with Douglas Tallamy

Back by popular demand, the National Sporting Library & Museum welcomes renowned author and wildlife ecologist Douglas Tallamy. Tallamy will discuss his new book, How Can I Help? which offers practical ways everyday gardeners and homeowners can make a meaningful difference for local ecosystems. The evening includes a reception, discussion, Q&A, and book signing. Come […]
Sep 24
5:00 pm - 7:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
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Free Concert with The Plate Scrapers

Join the Middleburg Community Center for a free outdoor concert featuring The Plate Scrapers, a high-energy progressive bluegrass band that blends traditional Appalachian sounds with a refreshingly modern spirit. Expect hard-driving bluegrass favorites, heartfelt country ballads, original songwriting and outstanding musicianship. Bring a picnic and the whole family for a lively evening of music at […]
Sep 25
6:00 pm - 8:00 pm
Middleburg Community Center
300 W Washington St, Middleburg, VA 20117
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Rokeby Community Festival

The Oak Spring Garden Foundation invites you to the third annual Rokeby Community Festival, a celebration of agriculture, art, learning, and community in the heart of Virginia’s beautiful Piedmont. Bring the whole family for a fun-filled day featuring live music, local food trucks, beer and wine from Powers Brewery and Slater Run Vineyard, kids’ activities, […]
Sep 26
10:00 am - 4:00 pm
Oak Spring Garden Foundation
1776 Loughborough Lane, Upperville, VA 20184
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Sunday Sketch

Held the last Sunday of every month. Participation in the program is free and open to the public: no sign-up is required, and all necessary materials are provided. Visitors may also enjoy free admission to the Museum on these days, regardless of participation in the program. The NSLM reserves the right to cancel or reschedule […]
Sep 27
2:00 pm - 4:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
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Free Film Screening of “Hamnet”

Join Middleburg Library for a free screening of Hamnet (PG-13, 125 minutes) and enjoy refreshments while supplies last. In 16th-century rural England, William Shakespeare and his wife Agnes are confronted with the death of their only son.
Sep 28
6:00 pm - 8:45 pm
Middleburg Library
101 Reed St, Middleburg, VA 20117
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October 2026
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