Community Health Fair

10:00 AM - 2:00 PM

Free admission and giveaways for first 100 attendees to the Barn at Monterey Inn's first Community Health Fair! Saturday, January 17, 10am-2pm. We are also now accepting vendor applications. If you have a product or service in the health and wellness ...

Valentine Pet Photos

10:00 AM - 2:00 PM

The Highland County Humane Society presents Valentine Pet Photos! Bring your pet for a lovely Valentine's photo at The Recorder Office at 108 W. Main Street in Monterey, Virginia between 10 am and 2 pm! $25 donation (cash, check, Venmo or Paypal) ...

Allegheny Mountain Institute ~ Garden Mastery Series: Pruning Trees & Shrubs

9:00 AM - 1:00 PM

Garden Mastery Series: Pruning Trees & Shrubs Feb 07, 2026, 9:00 AM – 1:00 PM 2599 Bear Mountain Rd, Monterey, VA 24465 Join us here at The Village as we host Master Gardener Emeritus Pamm McDowell for a series of educational workshops. It may be cold ...

Girls Night Out - Highland County Humane Society Fundraiser

6:00 PM - 9:00 PM

Save the date for a casual Girls Night Out to benefit the Highland County Humane Society with DJ Scott Smith at the Barn at Monterey Inn at 32 West Main Street in Monterey! - Night of dancing, ladies only, 21 and up please - Bar menu and cash bar - ...

Big Fish Wassail

5:00 PM - 9:00 PM

Big Fish Cider will be hosting its annual Wassail! event! Guests will follow the old English custom of walking to an orchard at night, scaring away any evil spirits, and waking the tree spirits with gifts and a blessing.

March Madness Basketball Tournament

Highland County Recreation Commission host a March Madness Basketball Tournament on March 7. For more information: Director@highlandcountyrecreation.org (540)468-2978 office

2026 Maple Festival Weekend #1 of 2

Get the full details at www.highlandcounty.org/maple-festival/! Take a step back in time to Highland County to enjoy Virginia's sweetest event of the year!

2026 Maple Festival Weekend #2 of 2

Get the full details at www.highlandcounty.org/maple-festival/! Take a step back in time to Highland County to enjoy Virginia's sweetest event of the year!

Easter Egg Hunt

10:00 AM - 12:00 PM

Highland County Recreation Commission hosts the great Easter Egg Hunt on Saturday, April 4, 2026. For more information: Director@highlandcountyrecreation.org (540)468-2978 office

Foraging Classes

10:00 AM - 4:00 PM

A Guided Walk through the gardens, meadows and woodlands at Emerald Mountain Sanctuary, Highland County, Virginia. Discover the abundance of edible and medicinal plants that grow in the lush bio-diverse region of the Virginia Western Highlands. We ...

Summer Kick-off Party

12:00 PM - 6:00 PM

Highland County Recreation Commission invites you to start your summer off right at the Summer Kick-off Party! Join in the fun on Saturday, June 13, 2026. For more information: Director@highlandcountyrecreation.org (540)468-2978 office

Youth Drama Camp - 2026

10:00 AM - 5:00 PM

Students learn behind the scenes of theatre acting, culminating in a performance on Friday, June 19, 2026. Camp will be held Monday-Thursday from 10am-2pm, with Friday's class time TBD, and a performance is tentatively scheduled for Friday, June 20th ...

Artists' Weekend

The Highland County Arts Council invites you to join other artists for a weekend of plein-air painting that culminates in a Wet Paint Show and sale. The event occurs county wide on the weekend of June 18-21, 2026 Registration form will be added at a ...

Wet Paint Show from Artists' Weekend

2:00 PM - 4:00 PM

Sunday, June 21, 2026, artists set up for the highly anticipated “Wet Paint Show” and sale at the conclusion of the Artists' Weekend. The Wet Paint Show & Sale open to the public at the Highland Center from 2pm-4pm. For more information: ...

4th of July Parade & Lawn Party

5:00 PM - 7:00 PM

Happy 4th of July! You are invited to celebrate Independence Day in Highland County, Virginia! The Blue Grass Ruritans will present their annual Parade and Lawn Party today at the Blue Grass Ruritan Building at 2724 Blue Grass Valley Road. Parade ...

Momentum in the Mountains 2026

Momentum in the Mountains 2026 is a one day health retreat in Highland County, Virginia from Positive Momentum, LLC that will take place this Saturday, July 25th . The goal is to empower you to take charge of your health through world-renowned speaker ...

26th Mountain Mama Road Bike Challenge

The Mountain Mama Road Bike Challenge is scheduled to take place on the first Saturday in August in beautiful Highland County, Virginia. The yearly event features 2 States, 3 Counties, 9 mountains, 105 miles, and over 10,000 feet of climb. The ...

Taste of Highland

5:00 PM - 9:00 PM

The 2026 Taste of Highland fundraiser will take place on Saturday, August 15th. When you attend the Taste of Highland, you’re helping The Highland Center grow and flourish. This hallmark event supports the Highland Farmers' Market, Youth Employment ...

75th Annual Highland County Fair and Horse Show

12:00 AM

Horse show, August 29, 2026 Fair, September 2-5, 2026

18th Century Trades Fair

3:00 PM - 12:00 PM

On Labor Day weekend Fair Lawn Farm will be hosting it’s Eighteenth Century Tradesmen Fair. Come see and experience nationally recognized artisans plying their trade on the beautiful grounds of the family farm in beautiful Highland County Virginia. ...

Highland County September Star Party

7:30 PM - 11:59 PM

Plan to attend the September 2026 Highland County Star Party on Friday, September 11th. The “rain date” is Saturday, September 12th. The public is invited, at no charge, to celebrate Highland County’s unique dark sky resource. The event will be held ...

Hands & Harvest Festival

12:00 PM - 2:00 PM

Highland County, Virginia's Hands & Harvest Festival returns October 9 - 11, 2026! The Highland County Chamber of Commerce invites you as we welcome back our annual celebration of the beauty and bounty of fall in our rural mountain community!

Highland County October Star Party

7:30 PM - 11:59 PM

Plan to attend the October 2026 Highland County Star Party on Friday, October 9th. The “rain date” is Saturday, October 10th. The public is invited, at no charge, to celebrate Highland County’s unique dark sky resource. The event will be held at the ...

Fall 5K Color Run during The Hands & Harvest Festival

10:00 AM - 12:00 PM

Color yourself through out this five-kilometer, untimed event, October 10, 2026 at 10:00am. Color Runners are covered from head to toe in fall colored powder. Participants wear white at the starting line and finish the race plastered in fall color ...

Wintertide

9:00 AM - 8:00 PM

Join Highland County, Virginia during the holiday season each year on the first Saturday in December. Slow your pace, and enjoy the sights, sounds, and tastes of this very special time!

Christmas Parade

5:00 PM - 6:00 PM

The Highland County Christmas Parade in Monterey, brought you by the Highland County Recreation Commission. is held on Saturday, December 5, 2026 starting at 5 pm during Wintertide! Beginning at the VDOT Parking lot at 1005 Fleisher Avenue in Monterey, ...