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10 fun fall festivals in the Dan River region

September 10, 2019 by Mason Adams

Crackling colors, temperatures that find the right balance between chilly nights and mild days, and perfect-length days come together to make autumn many people’s favorite time of the year.

Here in the Dan River Basin, we know how to celebrate fall. Find yourself in the region and we’ll find you a fall festival. Here are a few upcoming events.

29th Annual Danville-Pittsylvania County Fair

September 13-21, 2019

Pittsylvania County, Virginia

Courtesy Danville-Pittsylvania County Fairgrounds

The fair returns to the Danville-Pittsylvania County Fairgrounds. Don’t miss two nights of Demolition Derby action, Figure 8 racing and ride wristbands offered every day. Other nights include the magic of Lance Gifford and Rosaire’s Royal Racing Pigs. James E. Strates Shows returns with a midway featuring your favorite rides, games, and shows.

Bright Leaf Hoedown

September 21, 2019

Caswell County, North Carolina

The Bright Leaf Hoedown is an outdoor festival filled with arts and crafts, educational booths, and commercial booths. This one-day outdoor festival is held the fourth weekend of September on the Court Square in downtown Yanceyville. It features a multitude of local food vendors, live entertainment, crafters and non-profit organizations, and more than 5,000 guests.

Freedom Park Festival & Cruz In

September 28, 2019

Eden, North Carolina

Find fun for the whole family with free inflatables, mini golf, Zap the Zombie game, Scooby Doo bounce house and slide, games, cake walk, costume contest, Italian Ice and food vendors, band and karaoke.

South Boston Harvest Festival

September 28, 2019

Halifax County, Virginia

Come out and enjoy South Boston’s favorite place to celebrate the fall season. Now in its 28th year, the South Boston Harvest Festival has become a favorite with kids and parents alike. Enjoy the attractions, entertainment, activities, and food that are fun for all ages.

8th Annual River District Festival

October 1, 2019

Danville, Virginia

The River District Festival was formed eight years ago to celebrate the revitalization of Danville’s “river district” and historic downtown, as well as increase awareness and visibility of the area. The festival serves as an event to bring members of the community together to enjoy art, music and learning and to celebrate what is happening in our region.

Oktoberfest International Arts & Culture Festival

October 5, 2019

Martinsville, Virginia

Martinsville Uptown’s 2019 Oktoberfest International Arts and Culture Festival features two streets of vendors offering everything from free balloons to fine art. You can also find lots of kid-friendly activities including inflatable bounce houses and rides. The event offers a beer garden selling craft beer as well as traditional German foods like delicious bratwurst. Loaded with amazing crafters and talented artisans, this street fair has something for everyone. The Rogues will be performing at this year’s event.

SML Fall Fit Fest

October 5, 2019

Franklin County, Virginia

The Smith Mountain Lake YMCA and the Willard Companies present an outdoor festival that samples Smith Mountain Lake’s most fun fitness opportunities. Singer-songwriter Morgan Wade headlines the music performances. This event promises fun for all ages and fitness levels. Bring your lawn chairs and enjoy the music.


Rox’n’Roll Cruise In: Fright Night

October 18, 2019

Person County, North Carolina

Roxboro’s vibrant and family-friendly Uptown District offers high-quality dining that includes an acclaimed farm-to-table restaurant and a craft brewery, unique shopping from high-end gifts to thrifty treasures, and an array of artistic experiences. The third Friday of each month is set aside for a drive-in. Find everything from classic cars and trucks to tricked-out bikes and trikes lining the courthouse square. Guests are invited to “cruise-in” to the Uptown district from 6:00 to 8:30 p.m. Enjoy the sights and all that Uptown Roxboro has to offer. The October event is Halloween-themed.

28th Annual Reidsville Fall Jubilee

October 19, 2019

Rockingham County, North Carolina

The Fall Jubilee draws thousands of people from across North Carolina and southern Virginia for entertainment, food, fun and a car show featuring more than 200 beautifully restored antique cars and trucks, street rods and classics. Find more than 100 vendors offering a mix of art, crafts, jewelry, fashion accessories, pottery, home and garden décor, and more. Eat turkey legs, hot dogs, barbecue, blooming onions, funnel cakes, snow cones, steak and cheese sandwiches, ribs, and sausage dogs. The Kidz Zone features family entertainment, including bounce houses and amusement rides, and Touch A Truck with vehicles from the city’s police, fire, and public works departments.

Apple Dumpling Festival

October 19, 2019

Patrick County, Virginia

The annual Apple Dumpling Festival is held in Stuart’s quaint, historic “Depot” area, where the Danville and Western Railroad once ran the hills and valleys hauling products and people across Southern Virginia. At the festival there will be local and well known bands performing at the Farmer’s Market stage area. Numerous artisans line the streets with unique Southwest arts and crafts. Come hungry and enjoy the abundance of delicious food from apple pies and apple butter to Stuart’s famous apple dumplings.

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