— Usher in Labor Day weekend with the Boxwood Estate Winery Oyster Riot and make sure you have procured tickets to the September 11th National Sporting Library & Museum Polo Classic presented by MARS Equestrian™ at Great Meadow.

Buckle up your lederhosen as September’s signature event, Middleburg Oktoberfest, returns On September 17 to South Madison and Federal Streets. This year’s Oktoberfest coincides with Oktoberfest in Munich and features two Biergartens, German inspired food, a stein holding contest, local artist showcase, live music, interactive activities for children and much more! Oktoberfest is free to attend and while Bavarian attire is encouraged, it is not required.

Ein Prosit der Gemütlichkeit, everyone!

Second Annual Middleburg Oktoberfest: September 17

Middleburg’s Second Annual Oktoberfest Celebration is September 17, 2022 from 11am-7pm on S. Madison and Federal Streets in downtown Middleburg!

Admission is free and new this year are two biergartens, traditional German food, live music, festival games and Artists’ Alley. Local beer, wine, cider, and traditional Oktoberfest foods will be available for purchase from local vendors.

Middleburg Community Center’s Tenth Annual Art Auction: September 10

The Middleburg Community Center Art Auction serves as a fundraiser for general operations, programs development and community events that are offered throughout the year. The MCC has operated as a nonprofit organization for 74+ years in the heart of Middleburg VA, relying 100% on donations to keep its doors open – as MCC does not receive funding from the county, state, or federal government. We are extremely grateful for your generosity; every donation makes a difference!

Oyster Riot at Boxwood Estate Winery: September 3

Join Boxwood Winery for the Second Annual Oyster Riot in the Vineyard Pavilion 12-3 pm on Saturday, September 3, 2022.

Enjoy lunch from Salerno’s on the Chesapeake Bay with a Boxwood Estate Sauvignon Blanc Half Bottle PLUS an array of other lunch and dessert choices!

National Sporting Library & Museum Polo Classic
Presented by MARS Equestrian™

The NSLM Polo Classic presented by MARS EQUESTRIAN™, is Sunday, September 11 at Great Meadow in The Plains, VA. Proceeds benefit the NSLM in its mission to preserve, promote, and share the literature, art, and culture of equestrian, angling, and field sports, helping to fund dynamic exhibitions, programs, and community events throughout the year.

Tuesdays with Jim Drawing Class: September 6

The Artists in Middleburg presents Tuesdays with Jim on September 6 from 6-8 pm at the Community Center.

Come along and learn techniques on how to visualize, draw and explore the relationship of lines in art! In this class, Jim will guide you through exercises and thought processes

 Small Business Workshop: The Americans with Disabilities Act and Welcoming Your Customers: September 21

Join MBPA and the Town of Middleburg as Lori Daly, President of Diversifi Consulting Group LLC, presents a workshop on The Americans with Disabilities Act (ADA) and Welcoming Your Customers. Learn about the benefits and how-tos of having a welcoming and accessible business for people with disabilities…and everyone!

The workshop is from 5:30-7 pm at the Middleburg American Legion, 111 The Plains Rd.

Land Trust of Virginia Bike the Gravel: Tour de Conservation Easement

The Land Trust of VA is proud to present Bike the Gravel aka Tour de Conservation Easement. Choose your distance: 18-mile, 34-mile or 65-mile, each with an opportunity to ride through private estates and see the very best of the Virginia’s gravel roads.

Hot Jazz and Cool Popsicles at The Parish House: September 25

The ever-popular Dixie Rhythm jazz band will return to Emmanuel Church’s Parish House porch to regale the audience with their toe-tapping repertoire of Dixieland favorites on Sunday, September 25 at 3 pm.

They will be accompanied by The Little Pop Truck, which sells handcrafted popsicles.

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