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2026 Fall Fairs & Festivals

Illustration shows banners, pumpkins, fireworks and fall leaves. Reads: 2026 Fairs & Festivals Guide

Fall is one of the best times to experience the charm of Virginia’s communities. Throughout the season, festivals, fairs and special events invite visitors to celebrate local traditions, enjoy great food and entertainment, and make lasting memories with family and friends.

 

TASTE OF THE MOUNTAINS | Sept. 5

Taste of the Mountains. Main Street Festival. Madison, Virginia. Saturday, Sept. 5, 2026. 9 a.m. to 4 p.m. Arts, Crafts, Bands, Food, Pony Rides, Family Fun, Wine Tent, Free Parking, Free Shuttle

Madison County — Taste of the Mountains Main Street Festival returns to downtown Madison on Saturday, Sept. 5, from 9 a.m. to 4 p.m. Enjoy more than 150 arts and crafts vendors, regional food, live music, magic shows, pony rides, history exhibits, and a beer and wine tent. Free admission, free parking and continuous shuttle service make this Labor Day weekend tradition worth experiencing. For more information, visit madisonva.com.


THE VIRGINIA PEANUT FESTIVAL | Sept. 25-26

Flyer promoting the Virginia Peanut Festival in Emporia, Virginia, on Friday & Saturday, Sept. 25-26, 2026. Music, free admission, fireworks, arts, crafts, food, parade, car show and carnival. Call 434-634-9441 or go to www.virginiapeanutfestival.com.

Emporia and Greensville County are stoked on peanuts — the 64th annual Peanut Festival, that is. All your favorites will be on hand: a car show, arts and crafts, educational exhibits, a parade, live entertainment, cultural exhibits, a craft fair and plenty of delicious festival food. For more information, click here


SOUTH BOSTON HARVEST FESTIVAL | Sept. 26

Flyer promoting South Boston Harvest Festival, happening September 22, 2026, from 9 a.m. to 5 p.m. Great fun for the entire family!

The 35th annual South Boston Harvest Festival will be held from 9 a.m. to 5 p.m. Saturday, Sept. 26, in historic downtown South Boston. Sponsored by local businesses, industries and community agencies, the free event features shopping, live music, children’s activities, entertainment and food. Throughout the day, continuous live music and entertainment will take place on two stages. For more information, visit downtownsobo.com.


ART AT THE MILL | Sept. 19-Oct. 4 

Millwood, Va. — Art at the Mill is one of the premier art shows in the mid-Atlantic, attracting artists and buyers from more than a dozen states. Three hundred artists will display more than 1,000 works in a variety of media. The show runs from Friday, Sept. 19 through Sunday, Oct. 4. Hours are 10 a.m. to 5 p.m. Saturdays and noon to 5 p.m. Sunday through Friday. For more information, visit clarkehistory.org.


YOUTH FOR TOMORROW’S 41st ANNUAL COUNTRY FAIR | Oct. 3

Youth For Tomorrow’s Country Fair & Auctions, a longtime Northern Virginia tradition, returns for its 41st year with family-friendly activities, entertainment and fundraising events on Saturday, Oct. 3. This year’s fair promises to be the biggest and best yet! For event information and to purchase tickets, visit youthfortomorrow.org.


APPOMATTOX RAILROAD FESTIVAL | Oct. 9-11

The Historic Appomattox Railroad Festival returns to downtown Appomattox Oct. 9-11. Visitors can enjoy local dining, shopping, historic attractions and other events throughout the festival. To find places to stay, look for local eateries and shops, or to discover events happening during the festival, visit experienceappomattox.com.


HANDS & HARVEST FESTIVAL | Oct. 9-11

Fall is unforgettable in Highland County, Va. Experience the Hands & Harvest Festival Oct. 9-11 with a harvest trail, vendors, seasonal treats, entertainment and family fun. Visitors also can enjoy Hayfields State Park, Virginia’s first Barn Quilt Trail, the Sounding Knob Fire Tower and more! For more information, visit highlandcounty.org.


KING GEORGE FALL FESTIVAL | Oct. 10

The 67th annual King George Fall Festival theme is “America the Beautiful: Celebrating 250 Years!” The festival features a craft and vendor show, parade, car show, pageant, races and entertainment. It also includes live music and free rides and games for children. The parade begins at 11 a.m. at King George Elementary School and ends at King George High School. The SkillsUSA Car Show and craft and vendor show begin at 10 a.m. at King George High School in the gym, cafeteria and student parking lot. Food trucks will be on-site throughout the day. For parade, vendor, craft show and food truck information, visit kgfallfestival.com.


RASSAWEK AUTUMN FESTIVAL | Oct. 17-18

The Rassawek Autumn Festival showcases a professional rodeo this year, along with demonstrations that include modern and antique heavy equipment, blacksmithing, welding and carpentry. Guests can also enjoy pig races, bluegrass music, artisan and food vendors, children’s activities, and beer and wine. Purchase tickets in advance to save $5 by visiting rassawek.com.


SPOTSYLVANIA COUNTY 

Experience autumn in Spotsylvania County, Va. Make lasting memories at Belvedere Plantation’s Harvest Festival (Sept. 12-Nov. 7), shop at Miller Farms and Spotsylvania Farmers markets, and explore scenic battlefields and fascinating museums. Plan your fall getaway today by visiting visitspotsy.com.


FRONT ROYAL 

Front Royal, Va. invites you to experience three unforgettable seasonal celebrations. Step back in time at Liberty Day, enjoy fall fun at the Festival of Leaves and embrace holiday magic during Christmas on Main. For more information, visit discoverfrontroyal.com.






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