Annual Events

Annual Events

Please confirm with each event/venue as to event status due to the impact of COVID-19.


Celebrity Waiter Dinner

Annual themed benefit dinner, with local-celebrity waitstaff whose antics, like the dinner itself, are meant to raise money for the Rappahannock Benevolent Fund. The event is held the last Saturday in January. Contact Berni Olsen at 540-671-0421 for more details.


Fodderstack 10k Classic Race

The annual 10k race course follows the historic hills between the towns of Flint Hill and Washington and has been held for more than 35 years, drawing hundreds of runners of all levels from the region. Usually coincides with art festivals in Washington and elsewhere around the county. Register online at

Old Dominion Hounds Point-to-Point Races

Held at historic Ben Venue Farm, on Route 729 at U.S. 211. Contact the joint-masters at 540-364-4573 or 540-636-1507 or visit

Rappahannock Historical Society Antiques Appraisal

Annual fundraiser for the historical society features appraisers who will tell you what you have (from the item you brought, or some good photos of it); with food and refreshments. For more information, contact Judy Tole at 540-675-1163.


SperryFest is a neighborhood street festival for friends, neighbors, and visitors. Sperryville’s Historic Main Street is closed to traffic, making room for musical acts, stands for local and regional artisans, food, drink, and family activities.  The main activity of SperryFest is the annual Great Rubber Duck Race Down the Mighty Thornton River, featuring 1000 rubber ducks racing from the Main Street bridge next to Happy Camper Equipment Co. to the finish line behind Headmaster’s Pub.  Ducks are available for a $10 suggested donation and will launch at 3:30 PM.  Funds raised by SperryFest are used for Sperryville improvement programs.

Plant Sale

On the last Saturday of April, Waterpenny Farm hosts an annual Plant Sale. Speak with plant experts, buy locally grown plants and see all your gardening friends in the process!  You can buy vegetable plants, annual and perennial flowers, shrubs, trees, fruit trees, mushroom logs, and more. There’s also food, outdoor art and ornaments, and a free Nature Camp for kids. 


American Cancer Society Relay for Life

The Relay for Life is a community event in which teams take turns walking in the relay to raise money in the battle against cancer. For information, contact Ellen Timbers at 540-987-8402.


Amissville carnival and parade

This four-night annual event benefits the Amissville Volunteer Fire and Rescue squad. The event begins with a Fire Parade on Thursday night, kids stay up late, getting the most from the ‘ride all night’ wrist bands, then fall exhausted into bed to rest up for the next night’s excitement. Features include classic carnival games and rides with prizes for games of chance and games of skill, and the ever-popular Bingo pavilion is filled with patrons. Authentic carnival food — burgers, dogs, bar-b-que, french fries and box dinners, and candied apples, funnel cakes and homemade desserts are the icing on the cake. Usually in late June. For information, call 540-937-4218.


Fourth of July Celebration and Fireworks

Held in the green rolling fields of Ben Venue Farm on U.S. 211, just east of little Washington proceeds benefit the Sperryville Volunteer Fire Department. Lots of food, live music, games, and displays. Fireworks start at dusk. Visit for details.

Castleton Fireworks Show

Castleton Festival sponsors a Fourth of July fireworks show, usually a day or two before or after the Sperryville event; generally, the fireworks show follows a performance by a big-name bluegrass act in the Castleton Theatre. Call 866-974-0767 or visit for more information.


Taste of Rappahannock

An annual festival of foods and wine from local chefs and vintners benefits Headwaters, Rappahannock Countyntyns education foundation. To reserve or for more information, contact Headwaters at 540-987-3322 or, or visit

Rappahannock County Farm Tour & Festival

A free, two-day, self-guided, behind-the-scenes look at working farms held the last full weekend of September.  Rappahannock County’s early settlers were farmers, and the county is still deeply rooted in agriculture. This event showcases farms and businesses producing the very best in local food, award-winning wines, and artisanal products, set against the backdrop of the county’s extraordinary beauty, along with an artisans venue at the visitors center. For more information visit

Rappahannock Rough Ride

Multiple bicycle races and events for all levels of fitness and skill. This outdoor challenge benefits the Rappahannock and Fauquier Free Clinics. Call 540-347-0394, or visit

1000 Faces

1000 Faces is a mask theater group that has been performing original plays since 1991. The magical community theater troupe is led by writer and director Peggy Schadler. Local performances are at the Castleton Festival Tent. The troupe also performs on the road at venues such as James Madison University in Harrisonburg. 


End of Oktoberfest

The last Saturday in October heralds the End of Ocktoberfest at Pen Druid Brewery located at 3863 Sperryville Pike in Sperryville, VA. Over 2,000 people typically attend to enjoy wild, wood-fired, spontaneous, and barrel-fermented beers, roasted pig, kombucha, and more so get there early to secure a spot for the day’s festivities!

Oktoberfest: Family Fun Day

Loosen your Lederhosen and get ready for Oktoberfest! Wakefield Country Day School hosts their Annual Oktoberfest on their 12-acre campus in Huntly, VA from 4-8 pm. All are welcome to attend this family-friendly event, featuring festive live music. Food will be available for purchase from a German-inspired menu. Each year a traditional Oktoberfest beer is featured. Children of all ages are invited to play in the kinder zone area with multiple bounce houses, art and crafts booths, face painting, hair braiding, balloon art, potato sack races, pumpkin rolling contests, musical chairs, corn hole tournaments, and more. The entire event takes place outdoors. Presale tickets are $5 until September 25th; $8 at the door— unless you arrive in full Bavarian attire in which case, entry is FREE! Pre-sale tickets are available at Event location: 1059 Zachary Taylor Highway, Huntly, VA (look for the blue and white flags).

Trinity Floral Art Sale and House Tour

For more than half a century, the women of Trinity Episcopal Church in Washington have held this charitable tour of three distinctive and/or historic homes in Rappahannock County. Includes tea at Middleton Inn, and ends with an Evensong service, concert, and reception at the church, which is headquarters for the tour. Call 540-675-3716 or visit for more information.


Fall Art Tour

Sponsored by the Rappahannock Association for the Arts and the Community (RAAC), the tour draws hundreds of art lovers to Rappahannock County. This self-guided driving tour begins at the Washington School, which is set up as an art gallery for the event, with samples of artists’ work. Tour attendees receive a map that directs them to the participating artist studios and the county’s many fine art galleries. For further information, visit or call 540-675-3193.

Typically, over 100 artists, in more than 40 studios and galleries, participate in the tour. Many of these award-winning artists are nationally and internationally recognized.  Creative works include paintings, sculptures, pottery, glass, forged ironwork, jewelry, textiles, and photography. 


Christmas in Little Washington

Described as a Norman Rockwell Christmas, this annual event is held the first Sunday in December and includes a Christmas parade, artisan markets, a visit from Santa, activities, and open houses by local businesses and churches. For more information about the day, one of Rappahannock county’s most popular family-friendly events, visit

Back to top