When the leaves start to turn and there’s a chill in the air, Southern Virginia comes alive with fall fun. From hometown festivals to family outings, there’s something for everyone to enjoy. It’s the perfect time to try local treats, celebrate traditions, and spend time with friends and neighbors while soaking in the small-town charm that makes our region feel so special.
Danville-Pittsylvania County Fair
The Danville-Pittsylvania County Fair is a family-friendly event held each fall in Ringgold, VA. The fair features carnival rides, live entertainment, agricultural exhibits, food vendors, and special attractions like bull riding and demolition derbies. It’s a local tradition that offers fun and excitement for all ages.
- Date: September 12 – 20, 2025
- Time: Varies by Day
- Location: 2400 Cavalier Road, Ringgold, VA
- Event Details: Visit the Danville-Pittsylvania County Fair website >
Heart of Virginia Festival
The Heart of Virginia Festival is a free community event held in downtown Farmville, VA. The festival features live music, food trucks, local artisans, craft vendors, and family activities. It kicks off with a Friday evening concert at Riverside Park and continues on Saturday with entertainment and activities for all ages. It’s a celebration of community spirit that brings together residents and visitors from across Southside Virginia.
- Date: September 13 – 14, 2025
- Time: 9:00 AM – 5:00PM
- Location: Downtown Farmville
- Event Details: Visit the Heart of Virginia Festival website >
56th Annual Blackstone Arts & Crafts Festival
Join the Blackstone Chamber of Commerce for a beloved community tradition—the 56th Annual Arts & Crafts Festival! This two-day event features local artists, crafters, and makers showcasing everything from handmade jewelry and home décor to seasonal creations and one-of-a-kind gifts. Guests can also enjoy delicious food from popular trucks, live entertainment, and family-friendly activities in a festive setting. Held indoors and outdoors, rain or shine, the Blackstone Arts & Crafts Festival is the perfect place to shop, connect, and celebrate local creativity.
- Date: September 13 – 14, 2025
- Time: Varies by Day
- Location: 200 High Steet, Blackstone, VA
- Event Details: Visit the Blackstone Arts & Crafts Festival Facebook Event >
South Boston Harvest Festival
The South Boston Harvest Festival is a free community event held in downtown South Boston, VA. The festival features a variety of food, music, pumpkin decorating, vendors, and activities for all ages. It’s the perfect way to kick off the fall season with family and friends.
- Date: Saturday, September 27, 2025
- Time: 9:00 AM – 5:00PM
- Location: Downtown South Boston
- Event Details: Visit the South Boston Harvest Festival website >
Five County Fair
The traditional fair serves the five counties of Appomattox, Buckingham, Charlotte, Cumberland, and Prince Edward. The Five County Fair has games, carnival rides, exhibits, food, beauty pageants, professional wrestling, livestock shows, a petting zoo, team zoom canine entertainment, a power wheels derby, and a pie-eating contest.
- Dates: September 23 – 27, 2025
- Time: Varies by Day
- Location: 209 Fairgounds Road, Farmville, VA
- Event Details: Visit the Five County Fair website >
Henry County Fair
The Henry County Fair is an annual community event held at the Martinsville Speedway in Ridgeway, VA. The fair features amusement rides, games, agricultural exhibits, live entertainment, and a variety of food vendors. With activities for all ages, it’s a celebration of local culture and family fun each fall.
- Dates: September 24 – 27, 2025
- Time: Varies by Day
- Location: 340 Speedway Rd., Ridgeway, VA
- Event Details: Visit the Henry County Fair website >
115th Annual Halifax County Fair
The Halifax County Fair is a beloved tradition featuring amusement rides, games, live entertainment, and delicious fair food.
- Date: September 30 – October 4, 2025
- Time: Varies by Day
- Location: 1188 James D. Hagood Highway (U.S. 360), South Boston, VA
- Event Details: Visit the Halifax County Fair website >
Clarksville Harvest Days Festival
Experience the beauty of fall at the Clarksville Harvest Days Festival. Virginia Avenue in downtown Clarksville will transform into a bustling marketplace, featuring seasonal crafts, antiques, and unique treasures. Local shops will offer special deals, and the event will be filled with games and activities for the whole family.
- Date: Saturday, October 4, 2025
- Time: 9:00 AM – 3:00 PM
- Location: Downtown Clarksville, VA
- Event Details: Visit the Clarksville Lake Country Chamber of Commerce website >
44th Annual Martinsville Uptown Oktoberfest
Oktoberfest is a family friendly event, held annually for the past 43 years. This event has music, craft and food vendors, a beer garden, and children’s activities. For a day full of fun, be sure to attend!
- Date: Saturday, October 4, 2025
- Time: 11:00 AM – 4:00 PM
- Location: Uptown Martinsville, VA
- Event Details: Visit the Oktoberfest Facebook event page >
Autumn Days in Victoria
Celebrate the fall season at the Autumn Days festival in Victoria. This family-friendly event features craft vendors, delicious food, live music, and activities for all ages. It’s a perfect opportunity to explore downtown Victoria and support local artisans.
- Date: Saturday, October 11, 2025
- Time: 9:00 AM – 3:00PM
- Location: 1809 Main Street, Victoria, VA
- Event Details: For more information visit the Autumn Days Festival Facebook Event
A Taste of Brunswick Festival
The Taste of Brunswick Festival is a must-visit for anyone interested in Southern Virginia’s rich culinary heritage. This annual event features the famous Brunswick Stew Cook-Off, where local stew masters compete for the best recipe. Attendees can enjoy a variety of food vendors, browse arts and crafts, and enjoy live music.
- Date: Saturday, October 11, 2025
- Time: 10:00 AM – 5:00 PM
- Location: Brunswick County Airport – 77 Airport Drive, Lawrenceville, VA
- Event Details: Visit Taste of Brunswick Festival website >
Town of Stuart’s Annual Apple Dumpling Festival & Apple Dumpling 5-K
The Apple Dumpling Festival in Stuart is a highlight of the fall season. This festival includes live music, crafts, games, and, of course, delicious apple dumplings. The day kicks off with the Apple Dumpling 5K Run/Walk and continues with festive activities for all ages.
- Date: Saturday, October 18, 2025
- Time: 8:00AM (Race) 10:00 AM – 4:00 PM (Festival)
- Location: Downtown Stuart, VA
- Race Info: Early registration for the 5K is $25 until October 5th; regular registration is $30.
- Event Details: Visit Patrick County Chamber of Commerce website >
Regional Innovation Summit for Entrepreneurs
Calling all entrepreneurs & aspiring business owners across Southern Virginia! Whether you run a business or dream of starting one, the RISE Summit on November 1st in Danville, VA is the event for you! Grow your network of peers and resources to start, grow, and scale your business.
- Date: Saturday, November 1, 2025
- Time: 9:00AM – 3:00 PM EDT (doors open at 8:00AM)
- Location: The Institute for Advanced Learning & Research – 150 Slayton Avenue, Danville, VA
- Event Details: Visit the RISE event website >
Bridge Street Food Truck Rodeo
The Bridge Street Food Truck Rodeo brings together a diverse lineup of food trucks offering mouthwatering dishes from local and regional vendors. Enjoy delicious food, live music, and a fun community atmosphere on Bridge Street!
- Date: Saturday, October 18, 2025
- Time: 12:00 PM – 6:00 PM EDT
- Location: Bridge Street, Danville, VA
- Event Details: Visit the Bridge Street Food Truck Rodeo on Facebook >
These are just a few of Southern Virginia’s favorite fall events! Whether you’re interested in exploring local traditions or enjoying seasonal treats there’s something for everyone to enjoy this fall.