Fall Festivals with Something for Everyone

Written by Shayda Windle

Fall is here and there’s no better way to experience the charm of Hunt Country than through the region’s many festivals. Whether you’re drawn to country fairs, family-friendly gatherings, agricultural celebrations, or history-themed and educational events, there is something for everyone. We’ve put together a list of must-attend festivals that highlight the spirit of the season. Pick your favorites and make the most of autumn in Hunt Country!

Fifth Annual Sunflower Festival at The Homestead Farm at Fruit Hill Orchard

Saturday, September 14, 10 a.m. to 5 p.m.

Mark your calendars for a day of family fun at The Homestead Farm at Fruit Hill Orchard’s Fifth Annual Sunflower Festival. Join other festival goers for a vibrant celebration of the fall season with activities for all ages.

A bounce house, face painting, and games are available to the kids, while adults can enjoy live music from the Low Water Bridge Band and explore a shopping experience with over 50 local vendors and crafters. Ticket holders can satisfy their cravings with delicious food trucks, Sugar Shack ice cream, and more.

While you’re there, don’t forget to pick up some festival merchandise and bring home a bouquet of precut sunflowers available for purchase. Please note that sunflowers are not included with your ticket, and while the team certainly hopes to see the fields in full bloom, the recent extreme heat and dry weather may affect their timing. Find more information and purchase tickets at thehomesteadfarmatfruithillorchard.com. 

Fall Festival at Leopold’s Preserve

Saturday, September 21, 11 a.m. to 3 p.m.

Embrace the beauty of autumn at Leopold’s Preserve in Broad Run, Virginia, where local environmental organizations join forces for a day of free fun and learning. Hosted by the White House Farm Foundation and the Northern Virginia Conservation Trust, this gathering is the perfect opportunity to get together with family and friends. 

Leopold’s Preserve is a 380-acre park boasting stunning trails, meadows, and observation areas, all protected under a conservation easement by the NVCT. The seven-mile trail system is free and open to the public year-round, making it an ideal spot for nature lovers.

This family-friendly festival offers a unique opportunity to connect with local environmental champions and explore nature’s beauty. Indulge in mouthwatering BBQ from the Rocklands food truck, enjoy free face painting for the kids, and join guided hikes through the scenic wetland trails. Nature enthusiasts won’t want to miss the raffle, offering fantastic prizes like bird feeders, gift cards, and hiking backpacks from REI and Patagonia. Don’t miss this chance to celebrate fall and support local conservation efforts at Leopold’s Preserve. Learn more at leopoldspreserve.com. 

The Bluemont Fair

Saturday – Sunday, September 21 – 22, 10 a.m. to 5 p.m.

Gather your family and friends for a delightful day at the annual Bluemont Fair, where the charm of a 250-year-old village meets the vibrant energy of a community celebration. This beloved event offers a unique blend of artisan crafts, local wine, beer, live music, and much more all set against the backdrop of Bluemont’s rich history, traditions, and views of the Blue Ridge Mountains.

From pony rides and a petting zoo to barrel rides, games, and face painting, the fair is packed with kid-friendly activities that promise endless fun for the little ones. Meanwhile, adults can savor delicious bites from a variety of food vendors while enjoying tunes from local favorites. Breathe in the crisp mountain air, explore the beautiful village, and start checking off your holiday gift list with one-of-a-kind finds — all for less than the cost of a movie ticket. Admission is just $10, and kids 9 and under get in free.

Staying true to its “country fair” roots, the Bluemont Fair offers an enjoyable, affordable, and informative experience that brings the community together. Don’t forget to bring your tastiest pies and tangiest pickles for the free contest on Saturday — everyone is welcome to participate! Learn more at bluemontfair.org. 

Rokeby Community Festival

Saturday, September 28, 10 a.m. to 5 p.m.

The Oak Spring Garden Foundation is thrilled to announce their inaugural Rokeby Community Festival, a family-friendly event brimming with activities for all ages. Set for September 28 from 10 a.m. to 5 p.m., this exciting festival offers a variety of attractions, including a pickleball tournament on the Rokeby Airstrip, with both competitive and casual matches; live music from local artists; family activities including games and inflatables for the kids; and plant-focused experiences.

Food lovers will have their pick from an array of food trucks, including Divine Swine Barbecue, Big Cheese grilled cheese, Happy Family Ranch, Moo Thru ice cream, and the Mediterranean flavors of Fava Pot. Local libations will also be available.

Throughout the day, educational plant talks and field walks will be hosted every 30 minutes in areas like the vegetable fields, Biocultural Garden, and Wildlife Garden. Guests will also have a chance to participate in a special oak tree walk with Sir Peter Crane, highlighting saplings planted in 2023 as well as older, more historic trees. Additionally, the festival will present a series of Heirloom Crop Talks with three local experts discussing heirloom collard greens, grains, and apples.

Tickets are available online for $10 and may be purchased on Eventbrite. Tickets will also be available day-of at check-in for $15. Children 12 and under are free. Don’t forget to wear comfortable walking shoes — the event will take place rain or shine. 

The Waterford Fair

Friday – Sunday, October 4 – 6, 10 a.m. to 5 p.m.

Come shop, play, and explore during the Waterford Fair, an 80-year-old tradition that captures the essence of fall in the mid-Atlantic. This event offers a unique opportunity to experience 18th-century American heritage, contemporary crafts, living history, a juried art show, historic property tours, local libations, and entertainment for all ages.

The Waterford Fair plays a crucial role in protecting and preserving the National Historic Landmark of Waterford, among the first areas in the United States to receive this designation. The homes in this charming village are lived in by residents who maintain them to historic standards. Once a year, the village comes together to raise funds for the Waterford Foundation, one of America’s first community-based historic preservation organizations whose mission is to protect the buildings and open spaces of this National Historic Landmark.

Visitors will enjoy a fine heritage craft juried show set under tents and interact with artisans in 18th-century costume. Children’s activities include learning about arts and crafts made by hand during the 18th century. Explore three floors of local art, meet artisans in the old mill, visit the fine art show and sale in a nearby barn, and purchase dried flower arrangements just in time for the holidays. Daily entertainment includes historical interpreters, street performers, Americana and bluegrass music, and talks focused on local history.

Relax at Talbott’s Tavern, where attendees can enjoy libations from six local wineries and a special anniversary beer from Wheatland Springs Farm Brewery. Enjoy a variety of food options, from traditional festival fare to gourmet cuisine, and shop at the farmers market for local produce. The Waterford Fair covers nearly 300 acres, will be held rain or shine, and is a walking event, so wear comfortable shoes. Because the village will be closed off, parking will be managed by traffic flaggers. For more details, visit waterfordfairva.org. ML

Featured photo courtesy of the Waterford Fair.

For more Fall Festivals, visit our Calendar of Events. 

Published in the September 2024 issue of Middleburg Life.