Middleburg’s Oktoberfest is One of Northern Virginia’s Best Fall Attractions

Posted by Lauren Weiner on Thursday, September 25th, 2025  5:55pm.


Middleburg’s Oktoberfest is One of Northern Virginia’s Best Fall Attractions

Here’s What You Need to Know

Autumn is near, and with it comes orange hues, chilly weather, and best of all, fall festivities. If you don’t have plans yet to celebrate the change in season, come to Middleburg’s Oktoberfest for unique activities, lively music, and warming food. This is the fifth year of the event, and it takes place on September 20th from 11 a.m. to 6 p.m.;  it’s completely free to attend. Below is a rundown of what you can find at the celebration. 

 

 

Food and Drink 

 

Food can be found at vendor stands, which are local to the area. There will be fourteen vendors selling a variety of cuisine, from authentic German eats and street food classics to popular snackable bites. Oktoberfest will also have locally sourced beer, wine and cider, particularly at their Biergartens. I’m going to go over a few fan favorites of each. 

 

King Street Oyster Bar is a well-loved local restaurant. As a vendor you won’t have to deal with long waits or reservations, making Oktoberfest the best place to try out this trending spot. Based on their last attendance at an Oktoberfest in Chantilly, they will probably be selling fresh and grilled oysters, buttery lobster rolls, crab cake sandwiches, and sausages for the German theme of the event. They will also be serving up beers. 

 

 

Little Austria is my recommendation for a sweet treat. Austrians Berni and Helene established this rustic bakery to create the perfect strudel. Little Austria was the first brick-and-mortar place in Sterling. Check their website (which is linked below) which has a recipe for their delicious apple strudel.

 

For a drink or two, Greenhill Winery and Vineyards has got your back. Offering 100% Virginia wine made from local terroir, this winery has excellent wines. Their grapes are locally sourced as well, and some of their vineyards are the oldest in Northern Virginia, beginning in 1762. 

 

Maybe you’re looking for a different taste or drink— if you are, I’m sure Oktoberfest has it. Check out Big Kyle BBQ if you’re craving barbecue, and if you’re looking for a burger, 50 West has it. For quick snacks, there’s Family of Nuts, Top Shelf Jerky, and the Preppy Pretzel have you covered.  These are just a few mentions, and there’s plenty more delicious eats at Oktoberfest. 

 

 

Live Music

Music will be taking place on Federal Street, and S. Madison St and a variety of different musicians will be taking the stages. 

 

On Federal Street, the opening act is Blaskapelle Alte Kameraden. This mouthful is also called “the Old Comrades” as a shorthand, and they are a German wind band that follows the styles made in Bavarian alpine villages. Founded in 1977,  Blaskapelle Alte Kameraden is the very first American band to be inducted into Bavaria’s association of village bands. Two years later, they were accepted into Germany’s honorary society for bands and military music. They start at 11 a.m. and are not a show to miss. 

 

At 2:00 p.m., Something Brewing will be performing. Based out of Leesburg, Something Brewing is a cover band that covers anything rock, though they add a bit of a bluegrass-folk twist with banjo and mandolin players. They cover oldies by Allman Brothers, Bob Dylan, Bruce Springsteen, Dave Matthews Band, Jimi Hendricks, and Pink Floyd. They also cover young hits by Pearl Jam, Red Hot Chili Peppers, Weezer, 311, Blink-182, and more. With the range they have, there’s sure to be at least a few songs for every type of music lover. 

 

On S. Madison St, Justin Paschalides Music is the main show. This group included an accordion pianist, a tuna player, and a trumpeter. They vary in what styles they do and usually cover well-known songs from every genre, though it depends on the show and setting, and what general aesthetic they will go for. For Oktoberfest, they tend to wear traditional German clothing and play traditional polka music. 

 

Alt Washingtonia will also be performing. The group is a Bavarian folk dancing and cultural group, with the full title ‘Alt Washingtonia Schuhplattler Verein’. For over 40 years, the group has performed songs and dances of authentic Bavarian Alpine folk culture. They wear traditional outfits entitled Trachts, which include skirts, suspenders and knee-length socks shaded in bright reds, deep blues and rusty oranges. A bonus of this is that you won’t be able to miss them! 

 

 

Festivities 

Festival attendees will be able to compete in traditional German games like the pretzel toss, a ring toss game using soft pretzels.  One of the quirkier and more well-loved activities of Oktoberfest is the corgi race. This race, featuring furry friends of the specified corgi breed, is a highlight of the fall event. Corgi contestant applications have already been finalized, and sixteen dogs will compete. The dogs will run ‘heats’, which are preliminary races, followed by the course race, where the grand prize will be given. Local and regional artwork will be available for purchase at Artist’s Alley. This regular annual Oktoberfest feature is hosted by Middleburg’s art council, and there will be plenty of handcrafted artwork to peruse and buy. 

 

Side note: The Middleburg Arts & Community Events Committee is being held in conjunction with Oktoberfest and Artist’s Alley. This is a juried event where artists of all types come to compete. There will be fifteen spots featuring various arts like sculpting, painting, fashion, pottery and more. If you’re an artsy type, Oktoberfest will be your jam. 

 

 

If you’re looking for delicious bites, refreshing drinks, arts and crafts or fun activities, Oktoberfest is for you. Welcoming guests of all ages, the event is cherished in Middleburg and brings about the holiday spirit.

Middleburg VA

Sort by:
35771 Snake Hill Rd, MIDDLEBURG

$2,675,000

35771 Snake Hill Rd, MIDDLEBURG

3 Beds 4 Baths 3,839 SqFt Residential MLS® # VALO2106308

Thomas and Talbot Estate Properties, Inc.

23117 Pantherskin Ln, MIDDLEBURG

$2,500,000

23117 Pantherskin Ln, MIDDLEBURG

4 Beds 4.5 Baths 5,223 SqFt Residential MLS® # VALO2105130

Thomas and Talbot Estate Properties, Inc.

21497 Hibbs Bridge Rd, MIDDLEBURG

$2,495,000

21497 Hibbs Bridge Rd, MIDDLEBURG

4 Beds 4.5 Baths 3,727 SqFt Residential MLS® # VALO2106494

Corcoran McEnearney

Seabiscuit Park Pl, MIDDLEBURG

$2,495,000

↑ $50,000

Seabiscuit Park Pl, MIDDLEBURG

4 Beds 4.5 Baths 4,430 SqFt Residential MLS® # VALO2091788

Pearson Smith Realty, LLC

35653 Millville Rd, MIDDLEBURG

$2,390,000

↓ $100,000

35653 Millville Rd, MIDDLEBURG

4 Beds 3.5 Baths 3,520 SqFt Residential MLS® # VALO2099874

Thomas and Talbot Estate Properties, Inc.

New
35162 Notre Dame Ln, MIDDLEBURG

$2,290,000

35162 Notre Dame Ln, MIDDLEBURG

4 Beds 3.5 Baths 7,167 SqFt Residential MLS® # VALO2108538

TTR Sotheby's International Realty

36775 Leith Ln, MIDDLEBURG

$1,925,000

36775 Leith Ln, MIDDLEBURG

4 Beds 3.5 Baths 4,555 SqFt Residential MLS® # VALO2107656

Thomas and Talbot Estate Properties, Inc.

21056 Beaverdam Bridge Rd, MIDDLEBURG

$1,899,900

↓ $99,100

21056 Beaverdam Bridge Rd, MIDDLEBURG

4 Beds 3.5 Baths 3,707 SqFt Residential MLS® # VALO2069944

Keller Williams Realty

23400 Melmore Pl, MIDDLEBURG

$1,790,000

↓ $60,000

23400 Melmore Pl, MIDDLEBURG

4 Beds 2.5 Baths 3,808 SqFt Residential MLS® # VALO2100804

Sheridan-MacMahon Ltd.

W-10-121 On Beaverdam #lot 10 & 11, MIDDLEBURG

$1,699,890

↓ $10

W-10-121 On Beaverdam #lot 10 & 11, MIDDLEBURG

0 Beds 0 Baths 0 SqFt Residential MLS® # VALO2100822

Fairfax Realty Select

6437 John S Mosby Hwy, MIDDLEBURG

$1,595,000

6437 John S Mosby Hwy, MIDDLEBURG

3 Beds 2.5 Baths 2,832 SqFt Residential MLS® # VAFQ2018402

Thomas and Talbot Estate Properties, Inc.

39434 Snickersville Tpke, MIDDLEBURG

$1,350,000

39434 Snickersville Tpke, MIDDLEBURG

4 Beds 4 Baths 4,308 SqFt Residential MLS® # VALO2104064

Sheridan-MacMahon Ltd.