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Local Events in Middleburg

Come & Join the Fun!

Renowned as the Nation’s Horse & Hunt Capital, Middleburg offers a variety of equestrian events throughout the year, including the Middleburg Spring Races and the Virginia Fall Races. It’s also a well-known destination for the arts with events like the Middleburg Film Festival and Art in the Burg.

Christmas in Middleburg draws thousands of visitors, who line the streets on the first Saturday in December to watch the parade and the Middleburg Hunt Revue.

Check the calendar below to find out what’s happening around town.

Audience in lawn chairs clapping in front of National Sporting Library and Museum
Monthly Weekly Daily List
January 2026

Annual Members Exhibit

Join the Artists in Middleburg in celebrating local creativity and art as we host the Annual Members Exhibit. This exhibit is juried and features 53 local artists exhibiting their best work of any subject. See paintings, photography, metal, bronze, ceramic and more. Proceeds from these exhibits help to support local art education.
Jan 08 - Feb 08
All Day
The Artists in Middleburg
102 W Washington St, Middleburg, VA 20117
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Adventures Through Grief

Discover a unique approach to coping with grief through Blue Ridge Care’s FREE tabletop role playing game-based Adventures Through Grief program. Grief counselors act as game masters, guiding participants on a meaningful quest to navigate life after the death of someone significant to them. No prior role-playing game experience necessary. An application is required. Loudoun […]
Jan 27
5:45 pm - 7:45 pm
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Members’ Celebration for Rose Marie Bogley: Elegance Aside

A celebration for NSLM Members in honor of Rose Marie Bogley in conjunction with the exhibition dedicated to her remarkable life. Exhibition Details Rose Marie Bogley: Elegance Aside Nov 7, 2025 – Mar 22, 2026 This fall, the Forrest E. Mars, Sr. Exhibit Hall will feature Rose Marie Bogley: Elegance Aside, an exhibition highlighting the […]
Jan 29
5:00 pm - 7:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
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A Day of Mending: Preservation Through Stitching

Join Oak Spring Garden Foundation for a cozy, hands-on workshop focused on caring for and mending cherished textiles, from family heirlooms to everyday favorites. Participants will learn practical repair techniques, inspired by Bunny Mellon’s thoughtful stewardship of historic fabrics, and enjoy a guided viewing of select pieces from her collection. Open to all skill levels, […]
Jan 31
10:00 am - 4:00 pm
Oak Spring Garden Foundation
1776 Loughborough Lane, Upperville, VA 20184
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Live Music with Gary Jay & the Fire

Join Lost Barrel Brewing for live music, drinks, food and fun! About this event: Lost Barrel Brewing is an all-ages brewery located in Middleburg on a horse farm. LBB welcomes you to enjoy our taproom, porch, stunning yard or private gathering spaces. The music will be indoors when cold and outdoors on the porch weather […]
Jan 31
4:00 pm - 7:00 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117
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February 2026

Crossroads of Liberty

Step back in time at Crossroads of Liberty! Join VPHA for an engaging open house exploring the Virginia Piedmont’s vital role in the early fight for Independence- where bold ideas, local voices, and history itself intersected. Set in early 1776, this event brings to life the push for liberty’s rapidly building momentum. The afternoon includes: […]
Feb 01
2:00 pm - 5:00 pm
Virginia Piedmont Heritage Association
1461 Atoka Rd., Marshall, Va 20116
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Adventures Through Grief

Discover a unique approach to coping with grief through Blue Ridge Care’s FREE tabletop role playing game-based Adventures Through Grief program. Grief counselors act as game masters, guiding participants on a meaningful quest to navigate life after the death of someone significant to them. No prior role-playing game experience necessary. An application is required. Loudoun […]
Feb 03
5:45 pm - 7:45 pm
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