Music·Wed, Jul 1, 2026 – Sat, Aug 15, 2026
Castleton Festival
Castleton Estate (Theatre House and Festival Theatre)
$22-$100+
Events
Festivals, farm tours, races, art tours, and community gatherings across Rappahannock County.
Farm·Sat, Sep 26, 2026 – Sun, Sep 27, 2026
Rappahannock County Farm Tour & Festival
Multiple farms throughout Rappahannock County
Free
Music·Sat, Sep 26, 2026
John Jackson Piedmont Blues Festival
Eldon Farm at Clover Hill, Woodville, VA
Free
food·Sat, Oct 17, 2026
RAPPtoberfest
Wakefield Country Day School
Free (food/drinks for purchase)
Art·Sun, Nov 1, 2026 – Mon, Nov 2, 2026
RAAC Fall Art Tour
Multiple studios and galleries throughout Rappahannock County
Free
Holiday·Sun, Dec 6, 2026
Christmas in Little Washington
Washington (Little Washington), County Seat
Free
Holiday·Sat, Dec 19, 2026
Merry Sperry Christmas Event
Sperryville Schoolhouse Grounds, Lee Highway
Free
Holiday·Sat, Jul 4, 2026
Rappahannock County July 4th Celebration & Fireworks
Ben Venue Farm, Flint Hill
$25 per vehicle
Community·Fri, Jun 26, 2026 – Mon, Jun 29, 2026
Amissville Carnival and Parade
Amissville (14711 Lee Highway)
Free admission (games/food for purchase)
Farm·Sat, May 23, 2026 – Sun, May 24, 2026
Hunt Country Stable Tour
Upperville, Middleburg, and The Plains, Virginia
$35-$50
food·Sat, Apr 25, 2026
SperryFest
Sperryville Main Street and Schoolhouse Field
Free
outdoor·Sat, Apr 18, 2026
Fodderstack 10K Classic Race
Flint Hill to Washington (Fodderstack Road route)
$35-$50
Farm·Sat, Apr 4, 2026
Old Dominion Hounds Point-to-Point Races
Ben Venue Farm, between Flint Hill and Washington, VA
$45–$250 per vehicle (includes admission for up to 6)