Upcoming Events

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 Maple Festival

March 10 – 11 & March 17 – 18

Take a step back in time to Highland County, “Virginia’s Sweet Spot”. Travel back roads and mountain byways to the annual Highland Maple Festival. Held on the 2nd and 3rd weekends of March, the Maple Festival has been an annual event in Highland County, Virginia, since 1958.

Each year, thousands of visitors are drawn to this unspoiled, rural region of Virginia to celebrate the “opening” of the trees and observe the process of maple syrup-making. Sugar camp tours provide a unique and educational experience that portrays a rapidly vanishing way of American life.The Highland Maple Festival was designated a “Local Legacy” by the Library of Congress in 1999.


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.

Web site: www.thehighlandcenter.org/our-programs/local-food-agriculture/farmers-market/



Artists’ Weekend

June 22 – 24, 2018

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 14, 2018

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 4, 2018
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 25, August 29 – September 1, 2018
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.


Highland Star Party
Friday, September 7 – Sunday, September 9, 2018
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 – Sunday, October 12 – 14, 2018
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!



Highland County’s Wintertide Celebration
Saturday, December 1,  2018
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!