Renowned as the heart of Virginia’s Hunt Country, Middleburg offers a variety of equestrian events throughout the year, including the Middleburg Spring Races, but it’s also a well-known destination for the arts with events such as the Middleburg Film Festival. And, of course, Christmas in Middleburg draws thousands of visitors, who line the streets each year to watch the parade and the Middleburg Hunt & Hounds Review. Check the calendar below to find out what’s happening around town.

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August 2018

Live Music at 50 West Vineyards

August 4 @ 1:30 pm - September 1 @ 4:30 pm
|Recurring Event (See all)

An event every week that begins at 1:30pm on Sunday and Saturday, repeating until August 26, 2018

One event on August 3, 2018 at 5:00pm

One event on August 17, 2018 at 4:30pm

50 West Vineyards, 39060 John Mosby Hwy.
Middleburg, VA 20117 United States
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50 West Vineyards Middleburg VA

Enjoy live music while sipping your favorite 50 West wines! August's lineup includes (all times 1:30-4:30 p.m. unless otherwise noted): Friday, August 3: August Muller (5 -7:30 p.m.) Saturday, August 4: Tyme + Lace Sunday, August 5: Gary Smallwood Saturday, August 11: Pete Lapp Sunday, August 12: Jason Masi Friday, August 17: Jessica Endara (4:30-7:30 p.m.) Saturday, August 18: Laurence McKenna Sunday, August 19: Alex Barnett Saturday, August 25: Shane Gamble Sunday, August 26: David Mininberg

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Live Music at 50 West Vineyards

August 5 @ 1:30 pm - September 2 @ 4:30 pm
|Recurring Event (See all)

An event every week that begins at 1:30pm on Sunday and Saturday, repeating until August 26, 2018

One event on August 3, 2018 at 5:00pm

One event on August 17, 2018 at 4:30pm

50 West Vineyards, 39060 John Mosby Hwy.
Middleburg, VA 20117 United States
+ Google Map
50 West Vineyards Middleburg VA

Enjoy live music while sipping your favorite 50 West wines! August's lineup includes (all times 1:30-4:30 p.m. unless otherwise noted): Friday, August 3: August Muller (5 -7:30 p.m.) Saturday, August 4: Tyme + Lace Sunday, August 5: Gary Smallwood Saturday, August 11: Pete Lapp Sunday, August 12: Jason Masi Friday, August 17: Jessica Endara (4:30-7:30 p.m.) Saturday, August 18: Laurence McKenna Sunday, August 19: Alex Barnett Saturday, August 25: Shane Gamble Sunday, August 26: David Mininberg

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Live Music at 50 West Vineyards

August 11 @ 1:30 pm - September 8 @ 4:30 pm
|Recurring Event (See all)

An event every week that begins at 1:30pm on Sunday and Saturday, repeating until August 26, 2018

One event on August 3, 2018 at 5:00pm

One event on August 17, 2018 at 4:30pm

50 West Vineyards, 39060 John Mosby Hwy.
Middleburg, VA 20117 United States
+ Google Map
50 West Vineyards Middleburg VA

Enjoy live music while sipping your favorite 50 West wines! August's lineup includes (all times 1:30-4:30 p.m. unless otherwise noted): Friday, August 3: August Muller (5 -7:30 p.m.) Saturday, August 4: Tyme + Lace Sunday, August 5: Gary Smallwood Saturday, August 11: Pete Lapp Sunday, August 12: Jason Masi Friday, August 17: Jessica Endara (4:30-7:30 p.m.) Saturday, August 18: Laurence McKenna Sunday, August 19: Alex Barnett Saturday, August 25: Shane Gamble Sunday, August 26: David Mininberg

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Live Music at 50 West Vineyards

August 12 @ 1:30 pm - September 9 @ 4:30 pm
|Recurring Event (See all)

An event every week that begins at 1:30pm on Sunday and Saturday, repeating until August 26, 2018

One event on August 3, 2018 at 5:00pm

One event on August 17, 2018 at 4:30pm

50 West Vineyards, 39060 John Mosby Hwy.
Middleburg, VA 20117 United States
+ Google Map
50 West Vineyards Middleburg VA

Enjoy live music while sipping your favorite 50 West wines! August's lineup includes (all times 1:30-4:30 p.m. unless otherwise noted): Friday, August 3: August Muller (5 -7:30 p.m.) Saturday, August 4: Tyme + Lace Sunday, August 5: Gary Smallwood Saturday, August 11: Pete Lapp Sunday, August 12: Jason Masi Friday, August 17: Jessica Endara (4:30-7:30 p.m.) Saturday, August 18: Laurence McKenna Sunday, August 19: Alex Barnett Saturday, August 25: Shane Gamble Sunday, August 26: David Mininberg

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Cocktails ‘n Charcuterie at Side Saddle Cafe

August 16 @ 4:30 pm - 8:00 pm
|Recurring Event (See all)

An event every week that begins at 4:30pm on Thursday, repeating until January 3, 2019

Side Saddle Café, 7 W. Washington St.
Middleburg, VA 20117 United States
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Cocktails Side Saddle Cafe Middleburg VA

Join us every Thursday evening for Side Saddle Cafe's weekly happy hour! Lovely cocktails and gorgeous Charcuterie plates crafted by Side Saddle's culinary team available for all, so come on out, relax, and chat with the gang over soft tunes floating through the cozy atmosphere.

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Free

Scenic Cinema at Salamander Resort & Spa

August 17
|Recurring Event (See all)

An event every week that begins at 12:00am on Friday, repeating until August 31, 2018

Salamander Resort & Spa, 500 N. Pendleton St.
Middleburg, VA 20117 United States
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Salamander Resort Spa Middleburg VA Outdoor Cinema

Grab your family, friends and a blanket for a movie under the stars this summer. Join us on Salamander's Grand Lawn for their weekly family-friendly film with complimentary popcorn, lawn games and so much more. Movies start at 8:30 p.m. Also, don't forget to pre-order your very own Salamander picnic! To order, please call 540-326-4070. June 1: The LEGO Ninjago Movie June 8: Despicable Me 3 June 15: Cars 3 June 22: The Nut Job 2: Nutty by Nature June…

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Live Music at 50 West Vineyards

August 17 @ 4:30 pm - 7:30 pm
|Recurring Event (See all)

An event every week that begins at 4:30pm on Sunday and Saturday, repeating until August 26, 2018

One event on August 3, 2018 at 5:00pm

One event on August 17, 2018 at 4:30pm

50 West Vineyards, 39060 John Mosby Hwy.
Middleburg, VA 20117 United States
+ Google Map
50 West Vineyards Middleburg VA

Enjoy live music while sipping your favorite 50 West wines! August's lineup includes (all times 1:30-4:30 p.m. unless otherwise noted): Friday, August 3: August Muller (5 -7:30 p.m.) Saturday, August 4: Tyme + Lace Sunday, August 5: Gary Smallwood Saturday, August 11: Pete Lapp Sunday, August 12: Jason Masi Friday, August 17: Jessica Endara (4:30-7:30 p.m.) Saturday, August 18: Laurence McKenna Sunday, August 19: Alex Barnett Saturday, August 25: Shane Gamble Sunday, August 26: David Mininberg

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Dinner and Dive in Movie

August 17 @ 6:30 pm - 9:30 pm

Middleburg Community Center, 300 West Washington Street
MIddleburg, VA 20117 United States
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Join us for MCC’s final summer event! Chick-fil-a dinner at 6:30 p..m, Captain Cookie and the Milkman Ice Cream Truck from 6:30-8:30 p.m., various amusements in the ball field from 6:30-8:30 p.m., and closing with a showing of “Moana” poolside at 8:30 p.m.! This event is free and open to the public, and made possible by the Luminescence Foundation.

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$25

Twilight Polo at Great Meadow

August 18
|Recurring Event (See all)

An event every week that begins at 12:00am on Saturday, repeating until September 15, 2018

Great Meadow, 5089 Old Tavern Rd.
The Plains, VA 20198 United States
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Twilight Polo Great Meadow

Twilight Polo celebrates its Silver Anniversary in 2018! Since 1993, Twilight Polo has bought the community together to watch fast-paced arena polo here at Great Meadow. Join us at Greenhill Stadium in The Plains Saturday nights for Twilight Polo at Great Meadow! They will have THREE polo matches and halftime games for kids and adults. The evening will conclude with dancing in the pavilion after the matches! Arena polo is like hockey on horseback! It is fast paced and easy…

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Live Music at 50 West Vineyards

August 18 @ 1:30 pm - September 15 @ 4:30 pm
|Recurring Event (See all)

An event every week that begins at 1:30pm on Sunday and Saturday, repeating until August 26, 2018

One event on August 3, 2018 at 5:00pm

One event on August 17, 2018 at 4:30pm

50 West Vineyards, 39060 John Mosby Hwy.
Middleburg, VA 20117 United States
+ Google Map
50 West Vineyards Middleburg VA

Enjoy live music while sipping your favorite 50 West wines! August's lineup includes (all times 1:30-4:30 p.m. unless otherwise noted): Friday, August 3: August Muller (5 -7:30 p.m.) Saturday, August 4: Tyme + Lace Sunday, August 5: Gary Smallwood Saturday, August 11: Pete Lapp Sunday, August 12: Jason Masi Friday, August 17: Jessica Endara (4:30-7:30 p.m.) Saturday, August 18: Laurence McKenna Sunday, August 19: Alex Barnett Saturday, August 25: Shane Gamble Sunday, August 26: David Mininberg

Find out more »
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