Annual Events

Annual Events

Please confirm the event status with each sponsor/ venue.


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. 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.

Waterpenny 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’ wristbands, 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

The Rappahannock County Annual Farm Tour is a free, two-day, self-guided tour offering a behind-the-scenes glimpse of our working farms. With around 15 venues on the tour each year, you’ll experience a wide range of agriculture – from beekeeping to organic vegetable farms, not to mention goats, chickens, and cows, as well as local artisans selling their wares. The Rappahannock County Farm Tour is always the last full weekend in September. For more information visit

RAPPtoberfest: Rappahannock County’s Very Own Oktoberfest

Join us for this fun family day in Huntly, Virginia. Hosted by Wakefield Country Day School. Bounce houses, arts and crafts, German food, bier, and wares. Featuring live Bavarian music by the Edelweiss Band.  September 24, 2022, from 4-8 pm. All proceeds benefit student scholarships. Tickets available at

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!


Fall Art Tour

One of the premier events in Virginia, the annual Fall Art Tour, produced by Rappahannock Association for Arts and Community (RAAC), takes place the first weekend of November. Many Tour participants are nationally and internationally recognized, award-winning artists, presenting a diverse range of creative works, including paintings, sculptures, pottery, glass, forged ironwork, jewelry, textiles, and photography.   

During the Tour weekend, visitors will be able to meet and talk with artists and gallery contacts. And, follow-up visits can be scheduled right through the holidays!  After November 1st, those planning to attend the Tour in person can access a printable, online program guide listing all studios and galleries open during the Tour weekend. Visitors will be able to access and print an online map for their scenic, self-guided tours, making for a totally flexible and individualized experience.  Visit, and for the latest Tour information.  


Christmas in Little Washington (1st Sunday in December)

Described as a Norman Rockwell Christmas, this annual event includes a Christmas parade, artisan market, Santa and Mrs. Claus, activities for all ages, and open houses hosted by local businesses and churches. For more information about the day, one of Rappahannock county’s most popular family-friendly events, visit

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