2026 Schedule of Events

SATURDAY, AUGUST 29th

8:00 AM:  Fair Set-Up 

9:00 AM:  Horse Show (Grandstand) 

4:00 PM: *NEW* 75th Annual KICKOFF Event-Details to come!
4:00 – 6:00 PM: *NEW* Accepting Specific Exhibit Entries & Pre-Registration (Elementary School Gym)
Arts & Crafts; Art & Photography; Preserved Foods (Not Baked Goods); & Hunter-Fisher Entries
Pre-Registration for: Parade, Kiddie Show & Dog Show (No dogs permitted on grounds during pre-registration)

TUESDAY, SEPTEMBER 1ST

7:00-10:00 AM: 4-H & FFA Weigh-in & Entry of Livestock (Barns)

4:00-8:00 PM: Accepting Exhibit Entries (Elementary School Gym)

WEDNESDAY, SEPTEMBER 2ND

“Family Night” – Valley Amusement rides at reduced rates!!

8:00-9:00 AM: Accepting Flower Exhibit Entries 

9:00 AM-7:00 PM: Judging Exhibits (Gym CLOSED)

10:00 AM: 4-H & FFA Goats & Sheep Livestock Show (Livestock Show Barn)

Goat & Lamb Pet Contest, following Livestock Show

6:00 PM: Parade (Spruce St, Main St, Myers-Moon Rd.)

7:00-9:00 PM: Kimberly’s Kreations Face Painting

7:30-10:30 PM: *NEW* High Carbon Steel, Classic Country Music (Under Big Tent) 

9:00-9:15pm:*NEW* Orion Skys Drone Show (West Side of the Grounds)

ROAMING THE GROUNDS THROUGHOUT THE EVENING: Sky High Skyler

 

THURSDAY, SEPTEMBER 3RD

10:00 AM: 4-H & FFA Hogs & Beef Livestock Show (Livestock Show Barn)
Calf Pet Contest, following Livestock Show

3:00 PM & 5:00 PM: *NEW* Gospel Harmony Boys (Under the Big Tent)

7:00 PM: *NEW* Begoon Brothers Bucking Bulls LLC Rodeo (Grandstand)
Show includes: Mutton Bustin, Junior/Mini Rodeo, Barrel Racing, Rodeo Clowns, & Bull Riding

9:00-9:15 PM (approximate time): *NEW* Orion Skys Drone Show (West Side of the Grounds) 

ROAMING THE GROUNDS THROUGHOUT THE AFTERNOON:  Sky High Skyler

FRIDAY, AUGUST 29th

10:00 AM:  Kiddie Show (Under Big Tent)

4:30 PM:  Sheep Costume Contest & Obstacle Course (Livestock Show Barn)

5:30 PM: Rabbit Race (Livestock Show Barn)

6:00 – 7:00 PM:  Little Switzerland Cloggers (High School Gym)

6:00 PM: Power Wheels Derby, Thomas Motorsport LLC. (Grandstand) 

7 :00 PM: Demolition Derby, Thomas Motorsport LLC. (Grandstand)

9:30-9:45 PM (approximate time): *NEW* Orion Skys Drone Show (West Side of the Grounds) 

ROAMING THE GROUNDS THROUGHOUT THE AFTERNOON: Sky High Skyler 

SATURDAY, 5th September

9:00 AM – 12:00 PM: Dog Show (Grandstand unless raining)

11:00 AM-1:00 PM: *NEW* The Conner Family and Caleb Bailey & Paines Run, Bluegrass Music (Under Big Tent) 

1:00-8:00 PM:  Kimberly’s Kreations Face Painting

1:30-3:30 PM: *NEW* Jacob Tolliver, Multi-Genre-Rock & Roll Pianist (Under Big Tent) 

2:00 PM: 4-H & FFA Livestock Sale (Livestock Show Barn)

2:00 PM: Corn Hole Tournament (High School Gym)

4:00-6:00 PM: Music – To Be Determined (Under Big Tent) 

5:00 PM: Truck, Tractor, & Diesel Truck Pull by *NEW* Dragon Motorsports LLC. (Grandstand) 
10:00-10:15 PM (approximate time): *NEW* Orion Skys Drone Show (West Side of the Grounds) 

ROAMING THE GROUNDS THROUGHOUT THE AFTERNOON: Sky High Skyler

Click Here to for a Printable Schedule! (PDF)

Amusements and rides at the Highland County Fair - Monterey, Virginia
Pigs in the livstock show
A young sheep with a young man at the highland county fair
The Little Switzerland Cloggers performing at the Highland County Fair in Monterey, Virginia
Group of girls who are members of the Little Switzerland Cloggers performing
Cars in the 2025 Demolition Derby at the Highland County Fair

Fairground Regulations

  • All barns close at 11:00pm. Gyms close at 10:30pm, including Saturday when exhibits must be picked up.
  • Handicap bathroom facilities and a nursing and baby changing station is available in the elementary
    school.
  • Only authorized personnel are allowed on the grounds after 12:30am unless grandstand event exceeds
    this time.
  • NO blankets can be left overnight for reserved seating. Blankets left will be discarded by 8:00am.
  • NO pets, comfort, and/or emotional support animals allowed on grounds except dogs during the dog
    show and only at the dog show area. Service dogs are welcome. Handler is responsible for feces clean-
    up.
  • NO camper parking on the grounds except for one barn manager and Amusement Company staff.
  • NO ATVs, golf carts, UTVs, bicycles, skateboards, foot scooters or the like allowed on the grounds,
    including parking areas except authorized personnel. Motorized handicap scooters are permitted. Golf cart
    transportation provided by the Fair is available to all fairgoers.
  • NO drones allowed without written permission from the Fair Association.
  • NO firearms/weapons permitted on school property which includes the handicap parking lot and the high
    school and elementary school gyms. See VA Code § 18.2-308.1
  • Fair Office telephone number during Fair week is (540) 468-2639. The Fair Office is located beside the
    high school gym.
  • ATMs are available on the grounds. The Fair is primarily cash only, to include admittance. ATMs are not
    located outside of ticket booths. Blue Grass Valley Bank and Burke & Herbert Bank are located in
    Monterey which both have ATMs.
  • NO alcohol or drugs permitted on the grounds, including parking areas.
  • Fair management reserves the right to remove violators from the grounds for the remainder of the day or
    week – see Grounds Access policy at highlandcountyfairva.com.