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Community Events & Calendar

No matter the season, the Highland County community features events that are fun for all ages.  From the arts to food to the outdoors, you’ll find many ways to elevate your travel experience.

The Highland County Chamber of Commerce sponsors the annual fall Hands & Harvest Festival, annual Wintertide, and annual Highland County Maple Festival.

Check out the closest future events to the right, or click the green "View All Events" button for a full community calendar. Below, you’ll find a list of major community events with descriptions and links for further exploration.

*** NOTICE *** Please keep in mind that each organization is solely responsible for following the current state guidelines regarding the coronavirus related to their event.  Plans can change rapidly, so please check with the organizations beforehand to confirm plans.  If you are sick, have a fever or symptoms of COVID-19, have had a positive diagnostic test for the virus that causes COVID-19, or known exposure to a COVID-19 case in the prior 14 days, please stay home.  More information about coronavirus safety and guidelines can be found at,, and


Big Fish Cider Photo

Big Fish Cider’s Wassail

This annual fun re-creation of an old English custom typically takes place in February in Monterey at Big Fish Cider and includes scaring away evil orchard spirits and blessing the apple trees for the upcoming harvest.

Maple Queen Pageant Photo

Maple Queen Pageant

Taking place two weeks before the annual Highland County Maple Festival in March, find out who will represent Highland County in the Maple Queen Court for the upcoming year.  Held at the Highland High School Gymnasium in Monterey, you can then dance the night away at the official Maple Queen Ball held at the Blue Grass Ruritan Building afterwards.

Highland Farmers’ Market

Every Friday from May to early October, come on to The Highland Center pavilion in Monterey to purchase local produce, baked goods and handcrafted items from local farmers and artisans.
Fridays, May 28 - October 8, 2021

Photo by Holly Marcus

Artist’s Weekend

Let the scenic beauty of our mountains, valley views and farms inspire you during this three-day outdoor painting event, typically held in late June.  Artists from all around come to capture Highland County scenes on canvas, capped off by a Wet Paint Show where you can browse and purchase the created artwork.

4th of July Parade Blue Grass Photo

4th of July Children’s Parade and Lawn Party

Celebrate Independence Day with one of the smallest parades in the USA!  It may be small, but its full of fun and excitement.  Held at the Blue Grass Ruritan Building, you can enjoy the parade, lawn party, food and games during the annual summer celebration.

Allegheny Mountain Institute Open House

Allegheny Mountain Institute Open House

Breathe in the summer mountain air on Allegheny Mountain in western Highland County while you tour this educational nonprofit working to cultivate healthy communities through food and education.  Meet the Fellows and enjoy farm fresh appetizers and produce.
Saturday, July 24, 2021 • 1 - 5 pm

Lions Club Street Dance Photo

Lions Club Street Dance

Take part in this small town, summer night celebration held annually in July by the Monterey Lions Club.  You will experience live music, clogging, BBQ chicken, cake walks and square dancing on Spruce Street in Monterey.


Taste of Highland

You have a place at the table for a community meal celebrating the food, drink and culture of Highland County, held annually at The Highland Center in the summer.  Try all the delicious dishes prepared by local culinary talent.
September 18, 2021

Highland Arts Academy

Cultivate artistic learning in a tranquil environment with creative workshops and a farm-to-table style meal.  This multi-day event includes workshops from skilled instructors, where craft your skills in subjects like barn quilt painting, basketry and pottery.  Held in the summer months, take advantage of this unique artistic opportunity.

Mountain Mama Road Bike Challenge

Sponsored by the Highland County Recreation Commission, this annual summer event is a cyclist’s dream, featuring 2 states, 3 counties, 9 mountains, 105 miles, and over 10,000 feet of climb.  This challenge features 5 course of different ability levels in the clean mountain air.
August 7, 2021

Highland County Fair

There’s no shortage of family fun and excitement at one of Virginia’s oldest fairs.  Traditionally held over Labor Day weekend, the multi-day fair features a kickoff horse show, parade, carnival rides, games, demolition derby, truck and tractor pulls, live entertainment and so much more.
September 1 - 4, 2021

Highland County Star Parties Photo

Highland County Star Parties

Observe Highland County’s dark night skies with even greater clarity at these educational and inspiring events.  Astronomers from the Charlottesville Astronomical Society bring powerful telescopes for the public to view nebulas, galaxies, planets and other natural wonders during clear nights in September and October.
Saturday, September 11, 2021
October's Star Party will occur on October 1, 2, or 3, 2021 depending on weather. A final date will be chose in late September.

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