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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November 2018

Holiday Wine Trail

November 27, 2018 @ 8:00 am - January 31, 2019 @ 5:00 pm

Start by purchasing your $16.00 pass at any of the participating wineries! Your pass includes a free tasting at your starting location, a holiday wine glass and passport good for half price tastings and 10% bottle discounts at each additional winery you visit along the trail! 12 participating Wineries! Good through the end of January! PLEASE CHECK EACH WINERY FOR HOURS OF OPERATION! Arterra Wines Aspen Dale Winery at the Barn Blue Valley Vineyard and Winery Boxwood Winery Desert Rose…

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January 2019

Winter Open House at Wakefield School

January 18 @ 1:00 pm - 4:00 pm

Wakefield School, 4439 Old Tavern Rd.
The Plains, VA 20198 United States
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Wakefield School

Thoughtful learning in a caring environment. To learn more about Wakefield School, we welcome you to join them for their student-driven Winter Open House on Friday, January 18th. To RSVP, click on the ticket url or call the Admissions Department at (540)-253-7600.

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$79

Specialty Donuts & Coffee Class

January 19 @ 2:00 pm - 4:00 pm

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

Join Executive Pastry Chef Jason Reaves as he assists you in making yeast raised donuts from scratch with different toppings and glazes. During the class, you will enjoy specialty coffees which pair perfectly with your treats.

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$85

French Wine Dinner

January 19 @ 7:00 pm - 10:00 pm

Salamander Resort & Spa, 500 N. Pendleton St.
Middleburg, VA 20117 United States
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Travel to France from the comfort of your seat at Market Salamander. Our chefs will prepare a succulent four-course French-inspired dinner, paired perfectly with delicious French wine.

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$45

Unicorn Party Drinkware

January 20 @ 2:00 pm - 4:00 pm

Three Fox Vineyards, 10100 Three Fox Ln.
Delaplane, VA 20144 United States
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When you’re in Delaplane or passing by Winchester, looking to mix a little wine and painting together, check out Three Fox Vineyards ). Take in the breathtaking views of the vineyards and valley, enjoy wine tasting and an afternoon of painting with your friends. You'll never forget your experience at Three Fox Vineyards! We provide all the supplies: wine bottle, paint, brushes, apron, twinkle lights and a fantastic time! If you'd like to bring a bottle from home and paint two…

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Family Story Time

January 21 @ 8:00 am - 5:00 pm
|Recurring Event (See all)

An event every week that begins at 8:00am on Monday, repeating until January 28, 2019

Middleburg Library, 101 Reed St.
Middleburg, VA 20117 United States
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Families are welcome to come enjoy a family story hour!

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$85

Wine & Painting Class

January 22 @ 7:00 pm - 9:00 pm
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One event on January 8, 2019 at 7:00pm

One event on January 15, 2019 at 7:00pm

One event on January 22, 2019 at 7:00pm

One event on January 29, 2019 at 7:00pm

One event on February 5, 2019 at 7:00pm

One event on February 12, 2019 at 7:00pm

One event on February 19, 2019 at 7:00pm

One event on February 26, 2019 at 7:00pm

Salamander Resort & Spa, 500 N. Pendleton St.
Middleburg, VA 20117 United States
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Enjoy a fun way to paint and create your own original piece of work while sipping on different local wines.

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Musical Story Time

January 23 @ 11:00 am - 12:00 pm
|Recurring Event (See all)

An event every week that begins at 11:00am on Wednesday, repeating until January 30, 2019

Middleburg Library, 101 Reed St.
Middleburg, VA 20117 United States
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Children are welcome to come to the Middleburg Library for a musical story hour every Wednesday night,

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Digital Marketing Worksop at Mt. Defiance Cider Barn

January 23 @ 6:00 pm - 7:00 pm

Mt. Defiance Cidery and Distillery, 495 E. Washington St.
Middleburg, VA 20117 United States
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Mt Defiance Middleburg VA

TwoSix Digital will deliver an education workshop directed at Middleburg, VA businesses and organizations with the goal of presenting digital marketing strategies. The program will include a two-hour workshop featuring customized content to speak to the unique audience in attendance. Interested local businesses should RSVP/register with Jamie Gaucher - jgaucher@middleburgva.gov

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Paul Bergan Poetry Festival at Foxcroft School: Jan. 25

January 25

Foxcroft School, 22407 Foxhound Lane
MIddleburg, VA 20117 United States
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Foxcroft School Middleburg VA Cherry Blossoms

In the cold winter months, it is essential to warm the soul and keep inspired. The Paul K. Bergan Poetry Festival does just that, and has long been a favorite tradition among students and faculty alike. Renamed in 2007 in honor of beloved English teacher Paul Bergan, the Poetry Festival brings established poets to campus to read, to discuss the writing process with students, and to lead poetry writing workshops.

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