We love that there are so many fun events in October in this area. From family-friendly festivals to the Virginia Fall Races, there’s something for everyone. To help you plan out your month, here are our top picks for local events this October in and around Loudoun.

October 3

Mad Cap Puppets: Wizard Of Oz | Purcellville

Travel down the Yellow Brick Road with Dorothy, Toto, and their best friends; Scarecrow, Cowardly Lion, and Tin Man. Madcap brings this epic adventure to life with breathtaking puppets in an enchanting, family-friendly classic. Adapted by Dylan Shelton.

October 5-7

The Waterford Fair | Waterford

Over 100 artisans from across the country gather in the National Historic Landmark of Waterford, Virginia to exhibit and demonstrate jewelry, clothing, furniture, metal, and home decor craft. It’s your chance to touch, feel, and explore high-quality American craft and meet the makers behind the fabulous work.

October 13

The Virginia Fall Races | Middleburg

If you’ve never attended the Virginia Fall Races in Middleburg, you’re in for a treat! This spectacular event has been a local tradition since the 1950s. Join equine enthusiasts from all over, including your neighbors at Middleburg Real Estate | Atoka Properties, to cheer on the participants while they race in front of the backdrop of the Blue Ridge Mountains at the oldest continuous race course in Virginia.

MRE|AP will be there with a tailgate that will feature a delicious spread of local cuisine. It’s a fun, family-friendly event that we love to be a part of – and you won’t want to miss!

October 19

Paint Night at Creek’s Edge Winery | Lovettsville

Come spend a wonderful evening painting, led by talented and local artist, Jill Perla. Your ticket purchase includes a one and a half hour paint session (all materials provided), a Creek’s Edge souvenir wine glass, and a glass of your favorite Creek’s Edge wine.

(Photo source: West End)

October 18-21

Middleburg Film Festival | Salamander Resort

The Middleburg Film Festival offers four days of fantastic films in a spectacular setting, only 30 minutes from Dulles International Airport and just one hour from Washington, D.C. A carefully curated selection of narrative and documentary films screen in intimate theatre venues, followed by fascinating Q and A’s with world-renowned filmmakers, actors, and other special guests. The films include festival favorites, world premieres, first-class foreign films, and Academy Award contenders.

October 20-21

Harvest Celebration & Oyster Throw Down | Purcellville

Breaux Vineyards is partnering with King Street Oyster Bar to bring you over 15,000 oysters in 6 different varieties. From salty to sweet, robust to delicate, you have the opportunity to try them all! Oysters will be sold raw, topped, and grilled. Lobster rolls, crab cakes, and spiced shrimp will be available for purchase as well as salads, BBQ, and some vegetarian options. Everyone knows that oysters pair perfectly with wine! Wine tastings will be available all day with great live music.

Find more September events on these sites:

Salamander Resort | Visit Loudoun | Visit Fauquier

This content is not the product of the National Association of REALTORS®, and may not reflect NAR's viewpoint or position on these topics and NAR does not verify the accuracy of the content.