September in Middleburg is brimming with reasons to get out and explore. Start the month with inspiring gallery exhibitions, hands-on art classes, and cozy book signings, then slow your pace with yoga in the crisp autumn air. Mark your calendar for Middleburg Oktoberfest on September 20, when music, food, and cheer fill the streets, and the Rokeby Community Festival on September 27, a celebration of history, heritage, and community spirit. Stroll into town for special shopping events, sip your way through local breweries and wineries, or enjoy Music on the Porch at Emmanuel. Equestrians won’t want to miss the Grafton Hunter Show and the Middleburg Classic Horse Show at the historic Upperville show grounds, two beloved traditions that showcase the beauty and excitement of the sport.
From fine art to fine ales, September in Middleburg is yours to savor!
New events are always being added, so be sure to visit our full Events Calendar and not be left behind!

Nineteenth Annual Summer Sidewalk Sale
Wondering what your collectibles and valuables are worth? Bring them to the Mystique Jewelers Buying Event September 2-4! This special event offers a quick evaluation and payment on the spot for gold, coins, fine jewelry, art, diamonds, sterling silver, watches and more rarities.
For those interested in selling fine jewelry, watches, or diamonds ahead of time, Mystique Jewelers will be accepting items prior to the event for consignment and buying offers.

Grafton Hunter Show at Upperville Showgrounds
The Upperville Colt & Horse Show invites the community to show “Under the Oaks” at the Second Grafton Hunter Show on Saturday, September 6, 2025!
The unrecognized horse show will take place in the main “Parker” Hunter Ring with open Grandstand seating. Classes begin at Hilltopper and run through 2’3″–2’9″, concluding with the 3′ $1,000 Grafton Derby. High point awards will be given to Amateur, Junior, and Professional riders, plus a Grand Champion horse, with a $250 prize for the hunt earning the most points. Proceeds benefit the UCHS Jump In! Capital Campaign.

White Hall Hounds Open House
White Hall Hounds cordially invites you to a special Open House and Meet & Greet at their kennels in the historic Village of St. Louis on Friday, September 12, 2025, from 5:30 to 8:00 p.m
Guests will have the chance to meet the pack up close, speak with the Masters and staff, plus enjoy catering from Lost Barrel!
Whether you are new to foxhunting or simply curious to learn more about White Hall Hounds, this event promises an enjoyable and welcoming atmosphere.
Please RSVP by September 3 to suji@whitehallfarm.us or 571-447-7401.

Visit Loudoun Certified Tourism Ambassador Class
Register today for the Free Visit Loudoun Certified Tourism Ambassador (CTA) class at Middleburg Nomad on September 17th!
The Loudoun County Tourism Ambassador Program is all about turning “hello” into unforgettable experiences. When visitors have a great time, they come back, tell their friends, and boost our local economy, everyone wins: the visitor, the community, and you.
Becoming a Certified Tourism Ambassador™ gives you insider knowledge and tools to wow every guest. Plus, earning your CTA badge is a big accomplishment—and a lot of fun!

Middleburg Oktoberfest September 20th
Prost to five years! Middleburg’s Oktoberfest Returns September 20 from 11 am to 6 pm.
Get ready to raise your steins and celebrate in style when Middleburg’s 5th Annual Oktoberfest returns to South Madison and Federal Streets featuring:
Two festive biergartens, traditional German fare and Oktoberfest favorites from regional vendors, live music, festival games, and fun for all ages throughout the day, plus Artist’s Alley, featuring original artwork, pottery, jewelry, wearable art, and more from local and regional artists.
Click below for more info!

Second Annual Rokeby Community Festival
Celebrate the season at the Second Annual Rokeby Community Festival at the Oak Spring Garden Foundation on September 27!
Enjoy live music from Lua Project and Bramblefoot, delicious food from local trucks like The Roaming Coyote and Red Truck Bakery, plus craft drinks from Powers Brewery and Slater Run Vineyard. Families can explore kids games, inflatables, a scavenger hunt, hay bale competition, and a cover crop maze. Don’t miss plant talks, garden walks, artisan stalls, and educational exhibits from local environmental groups.
Tickets are $10 online or $15 at the gate; kids under 12 get in free.