Upcoming Events

Looking for things to do in and around Highland County, Virginia? Would you like 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!



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!


highlandcofairHighland 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.


IMG_1172VAST Rocket Launch

Saturday, September 7, 2019

11 am – 4 pm @ Jack Mountain Village

The Valley AeroSpace Team will hold a Sport Launch on Route 220 South approximately three miles from Monterey. All are welcome to attend and participate or simply watch the activities. Weather permitting with the final go/no-go decision made by 8 pm on Friday evening.  You can check the launch status on the main page of VAST’s website at any time.


Highland Star PartyHighland Star Party

September 27 – 29, 2019

(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

Hands & Harvest

October 11 – 13, 2019

Celebrate the beauty of Autumn at Highland County’s annual Hands & Harvest Festival. Held annually on the second full weekend in October, this event offers two days of activity, entertainment, farm tours, and fall fun. Come and observe the mountain forests of the Virginia’s Western Highlands transformed into a rich palette of russet, gold, and scarlet. Explore local farms, purchase handmade items from crafters and artists, take in a clogging or musical performance, browse local shops, and explore our local Maple Sugar camps!
Seasonal foods, including apple dumplings, apple butter, barbecues, Allegheny Mountain Trout, and homemade baked goods, will be available throughout the county. Take time to explore the back roads on one of Highland County’s Scenic Driving Tours or Barn Quilt Trails. So much fall fun to be experienced!
For more info, visit the Highland County Chamber of Commerce website!



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!



Other Events of Interest…

HC Chamber logo

For more information on other Highland County events, visit the

Highland County Chamber of Commerce website.