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Saturday, October 1:
The 3rd Annual Music in the Plains sponsored by The Plains Community League

Put a big star on your calendar for Saturday, Oct. 1 from 11 a.m. to 6 p.m. for music by Wakefield’s Nova Noce, Sweet Nola’s Po Boys as well as The Crooked Angels, Jaime Pyles and Henry Rust and the Eclectic Company, all sure to produce some toe-tapping music. Add to this a food truck and art walk. And a car show from 8 a.m. to noon. The Plains Community League strives to continue in the spirit of the founders by providing various events and services that will enrich the lives of the residents of the community. Some of the current projects include for Tutoring for 3rd grade through 12th-grade students, a Thanksgiving Basket program that distributes food baskets for neighbors in need and scholarships to help residents further their education. The League also sponsors various celebrations, including community Christmas and Easter parties, complete with pictures with Santa and the Easter bunny. The League maintains a Little Free Library located near the Events Board in front of the John Page Turner House. Details:



October 7 Foxcroft Open House 

For details go to:



October 8 Virginia Fall Races

Post time is 12:30 p.m.

Get your tailgate accessories in order and plan your menu for the annual fall tradition of the 68th running of The Virginia Fall Races at Glenwood Park near Middleburg on Saturday, Oct. 8.

Come sense the history while watching steeplechase action at the oldest continuous race course in Virginia. The 112-acre Glenwood Park was established in 1911 and is maintained  by a private trust left to the people of Virginia by the late Mr. Daniel C. Sands, a local fox chaser and avid sportsman.
The day begins at 9 a.m. with the finals of the Theodora A. Randolph Field Hunter Championship. The flag drops for the first race at 1 p.m. with an afternoon of first-class timber and hurdle racing.

Highlighting this year's meet is the National Sporting Library and Museum Cup with its purse of $30,000. It features the best seasoned timber horses running over the famous Glenwood course against the backdrop of the Blue Ridge Mountains.

With a children's fair of pony rides, a petting zoo and other activities, plus the "Vendor Village" with many tents stocked with enticing attractions, including local artists setting up and working, the afternoon has something for all ages and interests. Details:


October 8 West Virginia Breeders Classic

West Virginia Breeders Classics to Honor Sam Huff

Post time 7 p.m.

The West Virginia Breeders Classics racing series will be held on Saturday Oct. 8 at the Hollywood Casino Charles Town Races and will honor its late co-founder, NFL Hall of Famer Sam Huff, by naming its signature race worth $300,000 as The Sam Huff West Virginia Breeders Classic.

Huff, a long-time Middleburg resident who loved horses and horse racing, died last November at the age of 87. The West Virginia native and son of a coal miner owned horses, and when racing officials in his home state wanted to have a major event centered around the track, Huff took the lead and was instrumental in helping create the West Virginia Breeders Classics racing series, which celebrates its 36th anniversary this year.

"Sam was the driving force behind its creation," said Carol Holden, Huff’s long-time partner and president of the West Virginia Breeders Classic. "He and I had gone to the Maryland Million before, and wondered why we couldn't do this type of event in West Virginia.” 

Onion Juice was the first winner of the West Virginia Breeders Classic in 1987 in a race with a $100,000 purse. The 2022 Classics evening will present $950,000 in purses. Nine races will be contested that night, with a 7 p.m. first-race post time.

"You're going to see a whole lot of good horse racing," Holden said. Details: or 304-725-0709


October 20-22, 1000 Miglia Warm-Up USA October 20-22.

Iconic Italian Car Rally Comes to Middleburg!

The Town of Middleburg is once again hosting the 1000 Miglia Warm-Up USA event.  The event has a storied history in Italy, representing sport, culture, and community. Event participants will be hosted at the Salamander Resort & Spa and will depart each day from The Pink Box, the Town's Visitor Center at 12 N. Madison Street in town.

Thursday, October 20th - 8:00am

On Thursday morning, Oct. 20, the Town of Middleburg will host the “green flag sendoff” to officially begin the race. Join us to wave flags and cheer on the participants as they leave for the first day. This is a fun morning with children from local schools, car enthusiasts, and community partners celebrating.

Friday, October 21st - 5:00-8:00pm:

On Friday, Oct. 21, the race day will also start in Middleburg and will return in the mid-afternoon for a special event in the town, resulting in the award of the inaugural “Middleburg Cup.” This event will conclude with a street festival where the public is invited to see the cars on display, eat local food, and mingle with participants and fellow enthusiasts.    

Saturday, October 22nd:

On Saturday, Oct. 22, the start will again be from Middleburg and the cars will then head to Creighton Farms near Leesburg where they’ll participate in time trials within the community and be on display for ticketed spectators before heading to Maryland and on to D.C. for a stop at the Italian Embassy. 



Saturday, October 22nd The Cherry Blossom Tennis & Pickleball Tournament

The Cherry Blossom Breast Cancer Foundation and The Middleburg Tennis Club are excited to host the 2nd annual Cherry Blossom Tennis & Pickleball tournament. The tournament will be a one-day event starting at 10:30 am and ending at 5:00 pm. There will be live music, food, and fun tennis and pickleball. You don’t want to miss out on a special tournament for a great cause. All proceeds will be donated to The Cherry Blossom Breast Cancer Foundation. Sign up by going online to https://CBBCF-TENNIS.EVENTBRITE.COM.



Saturday, October 22nd

International Gold Cup: A Virginia Fall Tradition

Gates Open at 10 a.m.

A rich history of international involvement characterizes the International Gold Cup races, the highlight of the fall steeplechase season. The event at the gorgeous Great Meadow grounds in The Plains, has had a long and interesting journey en route to its present home.

The first International Gold Cup was held in 1930 at Grasslands Downs in Tennessee over a 4¼ mile brush course, similar to the English Grand National course at Aintree. That year, the King of Spain, Alfonso XIII, then one of the world’s most gallant riders and sportsmen, placed the spectacularly beautiful gold trophy in competition which is still awarded annually to the winner. 

Today, the International Gold Cup attracts more than 30,000 spectators and features the Fegentri World Cup of Nations where the top international amateur jockeys vie for the series title.

Pari-mutuel wagering sites are located all around the property and there are plenty of other diversions during the day.

This year, there will be a return of the tailgate contest. Tailgating at these races is a time-honored tradition, and the best ones have a theme, decorations and special food and drink recipes.

The always popular hat contest on Race Day returns, including several categories for hats that feature the best racing theme, the funniest/most outrageous; most glamorous/elegant; best child (under 18) and best men’s showing.


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