Looking for things to do in and around Highland County, Virginia? Looking to add more adventure or entertainment to your stay? Well look no further! Here is a peek at some of Highland County’s upcoming events!
Highland Farmers’ Market
Every Friday, Late May – Mid October, 3:30 pm – 6:00 pm
Local produce, meats, crafts and much more! Drop by to see for yourself. The Highland Farmers’ Market is located in Monterey, Virginia, at 61 Highland Center Drive. Call (540) 468-1922 or email farmersmarket@htcnet.org to learn more about its selection of organic food, local specialties, vegetables, crafts, and fruits.
Bobby BlackHat brings together the finest blues musicians in Hampton Roads to perform classic, modern, as well as original blues tunes that will keep your toes tappin’ and your hips shakin all night long! • Tickets: Adults: $10, Children ages 15-18: $5, Children under 15: free. • For more info, visit the Highland County Arts Council website.
Crooked Road on Tour
Saturday, June 15 @ 7 pm
The Highland Center
Erynn Marshall and Carl Jones are old-time musicians and inspired tunesmiths from Galax, Virginia. They are married – in life and music. Southern song-duets and powerful fiddle, guitar, mandolin, banjo tunes comprise their diverse sets. • Tickets: Adults: $10, Children ages 15-18: $5, Children under 15: free. • For more info, visit the Highland County Arts Council website.
Artists’ Weekend
June 28 – 30, 2019
Held the last full weekend in June each year. Activities begin early Friday with coffee, donuts, and a brief orientation at The Highland Center. Spend Friday and Saturday painting and exploring beautiful Highland County. On Saturday evening, gather again at The Highland Center to share sketches and paintings at the “Wine and Walk Around” followed by dinner. Friends and spouses are welcome to join. Sunday morning provides a final chance to paint before the trip home. Event serves as a fundraiser for the Highland County Arts Council. Registration Form (2018 Deadline TBA) • Email
Lions Club Street Dance
July 13, 2019
Enjoy country entertainment with bluegrass music, cake walks, square dancing, BBQ meals, and clogging at the annual Lions Club Street Dance. Fun for the entire family! Located on Spruce Street next to our historic courthouse.
Other Events of Interest…
Mountain Mama Road Bike Challenge
Saturday, August 3, 2019 Mountain Mama Road Bike Challenge participants enjoy some of the most beautiful rural countryside east of the Mississippi River. Grueling ascents, thrilling descents, rolling valley roads, and breathtaking views from high atop the Allegheny mountains guarantee a challenge for all cycling skill levels. Water and food stops are located every 15-20 miles. SAG support is provided, and a post ride meal is included. For more information on the Mountain Mama Road Bike Challenge including route information, visit the Highland County Recreation Commission website!
Highland County Fair
August 24, August 28 – 31, 2019 An old-time country fair steeped in tradition! The Highland County Fair opens with a hometown parade that makes its way through the streets of historic Monterey on the Wednesday preceding Labor Day. Events include a Horse Show, Demolition Derby, Truck & Tractor Pull, animal shows, amusements, bingo, clogging, musical performances, food, and fun!
For more information on the fair, visit www.highlandcountyfairva.com or call at (540) 468-2225 prior to the event. For more information during the event, call the Highland County Fair office at (540) 468-2639.
(Rain Date: October 25-27, 2019) Highland County will host astronomers from the Charlottesville Astronomical Society for a Star Party. The final decision as to which one of these three possible nights is selected (based on the weather forecast) will be made the Thursday prior. A number of astronomers and some powerful telescopes will set up atop Jack Mountain on the clearest night within the three-day viewing window. The public is invited and will have a chance to view nebulas, galaxies, planets, and other astronomical wonders. There is no charge for this event, which celebrates Highland County’s unique dark sky resource. For more information, contact Michael Bedwell at (540) 468-2316.
Hands & Harvest Festival
Friday – Saturday, October 11 – 12, 2019 Celebrate the beauty of Autumn at Highland County’s annual Hands & Harvest Fall Foliage Festival! This event offers three days of activity, entertainment, farm tours, and fall fun. Explore local farms, purchase handmade items from crafters and artists, take in a clogging or bluegrass show, browse local shops, and try your feet at the Highland Hills Farm 5K Fun Run & Obstacle Course! For more info, visit the Highland County Chamber of Commerce website!
Highland County’s Wintertide Celebration
Saturday, December 7, 2019 It’s like a scene right out of your favorite Hallmark movie – a small town celebrating Christmas, Santa Claus, Christmas lights, good will, and a community coming together to celebrate the season. Enjoy the holiday evening with friends and family – old and new. Even if you’re a visitor to our community, we’ll make you feel right at home in no time!
Take in our area’s nostalgic setting, experience Christmas in a small country town, shop through our local stores and vendors, sip on hot chocolate, and even visit Santa! For more info, visit the Highland County Chamber of Commerce website!
For more information on more Highland County events, visit the
Bobby “BlackHat” Walters Concert
Crooked Road on Tour
Mountain Mama Road Bike Challenge
Highland County’s Wintertide Celebration
