Highland County events hold something for everyone year-round. Cyclists should plan to visit for the annual Mountain Mama Road Bike Challenge in August. The yearly event features two states, three counties, nine mountains, 105 miles, and an over 10,000-foot climb.
The Highland County Fair is held over Labor Day weekend and has been bringing farm and family fun to the masses for seventy years.
The annual Hands & Harvest Festival celebrates the beauty and bounty of fall during the second weekend in October. Observe Highland County’s dark night sky as astronomers bring powerful telescopes to share stunning celestial views at a Highland County Star Party. Enjoy the holiday season with Wintertide in December.
The arts are celebrated with second Saturday concerts, workshops to teach skills like basketry or stained glass with the Highland Arts Academy, and an outdoor summer painting event. Plan a weekend trip around other area favorites like Big Fish Cider’s Wassail, an Independence Day celebration in the quaint tiny town of Blue Grass, or the Taste of Highland at The Highland Center.
Highland County is well known for its maple syrup industry, being one of the southernmost places in the U.S. that the sweet “liquid gold” can consistently be produced. Maple syrup producers and their sugar camps dot the landscape, each with their own stories, history, and techniques. Because of the freezing and thawing cycle in late winter, the entire community comes together to host its most popular event with the annual Highland County Maple Festival, which is held during the second and third weekends in March. Thousands attend each year to be a part of this tradition that has been going strong since 1959. Outside of that March timeframe, you can participate in the Virginia Maple Syrup Trail. Several sugar camps are open by appointment for a free tour and local syrup sample. Pick up an official passport, get yours stamped after each stop, and get a free gift if you visit them all!
It’s easy to elevate your travel experience here! One hundred steps up the restored Sounding Knob Fire Tower provides a breathtaking view — and maybe even some wobbly legs! Overlooking Monterey on top of Jack Mountain, hike or drive up the gravel Sounding Knob Road just 1.3 miles south of its intersection with Rt. 250. The tower is open for free from sunrise to sunset every day.
Highland was the first county in Virginia to have its very own Barn Quilt Trail, and you can spend a leisurely day traveling country roads to discover the stories behind these painted wooden blocks. Four Highland County hiking trails are featured in Virginia’s Western Highlands Trail Guide, including the 2.6-mile McDowell Battlefield Trail with interpretive Civil War signs that leads to the core of the pristine McDowell Battlefield. Highland County offers three rivers for public fishing: the Bullpasture, Potomac, and Laurel Fork. The George Washington and Jefferson National Forests feature more miles to explore for outdoor recreation like hunting and camping.
Find your sweet spot in Highland County!
*Highland County Fall photo courtesy Terri Puffenbarger
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