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Feel-Good Gatherings this Holiday Season

Feel-Good Gatherings this Holiday Season

Written by Shayda Windle | Photos courtesy of Foxcroft School

December is here, and what better way to celebrate the magic of the season than through the gift of giving back and supporting the community? From Christmas caroling to toy drives, holiday concerts, and more, we’ve curated a list of some of the best charitable events in and around Hunt Country this season. Embrace the holiday season in Middleburg — where warmth, community, and the spirit of giving come together in perfect harmony. 

Loudoun County Holiday Toy Drive – now until December 18

For the eighth year in a row and over 14,000 toys later, Loudoun’s Sheriff’s Office will partner with Cole’s Closet to help collect toys to fill “closets” for children at the hospital during the holidays. Cole’s Closet was created in 2002 by Ellen and Steve Tomczyk after they lost their 6-month-old son to an undiagnosed brain disease. The Tomczyks spent four months in and out of hospitals where they experienced the anxiety and fear families face when a child is hospitalized. The couple began a toy drive at a family holiday party a year after Cole passed. For more information about Cole’s Closet, visit Donations will be accepted until December 18, 2023, and toys can be dropped off at any Loudoun County Sheriff’s Office.

Foxcroft School’s Christmas Pageant – December 3

Bring the entire family to Foxcroft School for this classic holiday tradition with live animals, chorale, and a special visit from Santa Claus. Presented annually by Foxcroft’s New Girls, the pageant is a perfect ending to your “Christmas in Middleburg” experience. All are welcome. Admission is free; seating is limited. To RSVP, please call 540-687-4510. 

English Tea at Oatlands Historic House and Gardens in Leesburg – December 3

Take part in the English tradition of a holiday-themed tea at Oatlands Historic House and Gardens. Traditional English Tea will be held in the historic Carriage House where you will enjoy English scones, Devon cream, classic tea sandwiches and sweets, local preserves, and Oatlands’ exclusive tea blend. Guided Mansion Tours are available at an additional charge. Enter the code “teatour” at checkout to receive a 50% discount on a tour with tea. Oatlands Historic House and Gardens is an independent 501(c)(3) nonprofit organization 100% dependent on your generous donations to preserve the 200-year-old property. To purchase tickets, visit:

Piedmont Symphony Orchestra Holiday Concert: Handel’s Messiah – December 10

In conjunction with the St. James Church Choir of Warrenton, the Piedmont Symphony Orchestra will present the concert version of Handel’s Messiah on Sunday, December 10, at the Michael A. Hughes Center for the Arts at Highland School. For over 25 years, PSO has been enriching, inspiring, and transforming lives through performances and educational outreach within the local community. To purchase tickets, visit:

Mobile Hope’s Christmas Village for Children in Need – December 15 & 16 

This year, Mobile Hope will serve more than 2,500 children in need with new, wrapped toys, bikes, stuffed animals, diapers, food, and seasonal clothing. But your help is needed; collecting toys for these deserving kids takes a village! While the elves are working, kids will be entertained by Santa Claus, the Grinch, holiday music, festive lights, and delightful decorations. The gifts will be collected, wrapped, and distributed with the help of volunteers, corporate partners, civic groups, faith-based groups, small businesses, individuals, and families. For more information about how you can contribute, visit:

Lessons and Carols at Trinity Episcopal Church – December 17

December opens the Masters Singers of Virginia concert season, with the first concert highlighting the season’s meaning with sacred and secular music. Enjoy the energy in Psalm 96 by Merrill Bradshaw and “Alleluia” by Jake Runestad. “Three Christmas Alleluias” by Andre Arnesen is MSVA’s major work and will feature solo harp accompaniment and vocal solos. The group closes with the King’s Singers arrangements of “The Christmas Song (Chestnuts Roasting on an Open Fire)” and “Jingle Bells.” Visit for more information. ML

Published in the December 2023 issue of Middleburg Life.

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