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Highland County Chamber of Commerce Calendar

Highland County Chamber of Commerce Calendar

10/24/2026 - 10/24/2027
SAT
October
24
12:00 PM - 2:00 PM

Come to Roots Market to carve a Blue Ridge Greenhouses pumpkin! on Saturday 12-2 We'll have: Local Pumpkins, Cider, Hot Chocolate, Popcorn, BBQ Prizes for Winners Limited Decorating Supplies To Enter: Chose and Buy your pumpkin from Roots Market ✅ BYO ...

MON
October
26
5:00 PM - 6:30 PM

The Highland Tourism Council will host its Fall Lodging Meeting on Monday, October 26th from 5 – 6:30 pm at Big Fish Cider, Co. in Monterey. (You don’t have to be there right at 5 pm to participate, as the first 15 – 30 minutes are time for networking ...

SAT
October
31
2:00 PM - 4:30 PM

Mark Your Calendars 🎃 The Trick Or Treat Trail from the Highland County Recreation Commission will fall on Saturday, October 31st. Please note the adjusted times this year to best accommodate other events happening in the area. Start planning out ...

THU
November
5
10:00 AM - 11:30 AM

LOCAL Caregivers Support Group 10:00am – 11:30am 1st and 3rd Thursdays each month The Mountain View Room at the Highland County Public Library 31 N Water Street, Monterey, VA 24465 FREE AND OPEN TO ALL, NOT JUST HIGHLAND RESIDENTS Need a respite ...

FRI
November
6
5:00 PM - 10:00 PM

It’s that time of the year again for the Blue Grass Ruritans' Consignment Auction! Start searching around through your sheds, barns and garage and turn those unused items into cold hard cash 💰💵 .$$$ The auction will be held on Friday, November 6th ...

SAT
November
7
11:00 AM - 5:00 PM

VAST will be holding a Rocket Launch at the Jack Mountain Village site off of Route 220, 3 miles south of Monterey, Virginia. Everyone is invited to bring their rockets and fly them. The range will be open from 11:00am to 5:00pm but is subject to ...

SAT
November
7
5:00 PM - 7:00 PM

CASINO NIGHT at The Barn! Saturday, November 7th, 5-9pm. ✅ Live entertainment by Lee Dean as Elvis! ✅ Vegas-style unlimited buffet ✅ Your favorite casino games: roulette, poker & blackjack! All money raised from games will go to our local non-profits: ...

SUN
November
8
10:00 AM - 3:00 PM

VAST will be holding a Tripoli Research Launch at the Jack Mountain Village site off of Route 220, 3 miles south of Monterey, Virginia. Range will be open from 10:00am to 3:00pm but is subject to participation and the weather. Typically more flights ...

MON
November
9
6:30 PM - 8:30 PM

A new master plan is being created for our park, and we invite you to a public information meeting where you can learn how to stay informed and involved throughout the process. These plans serve as a guide for park development and conservation, and are ...

THU
November
12
10:00 AM - 12:00 PM

Come connect, make new friends, and enjoy good conversation! Adults 60 and over are invited to gather together every second Thursday from 10:00 AM to Noon at the Highland County Public Library. Come as you are and bring a friend. We’d love to have you ...

SAT
November
14
11:00 AM - 3:00 PM

The FIFTH annual Blue Grass Christmas Bazaar is coming! The bazaar is held at the Blue Grass Ruritan Building, November 14, 11AM to 3PM Please spread the word & reach out to Cassandra Warner if you'd like to set up! For more information contact: ...

SAT
November
14
12:00 PM - 2:00 PM

Highland County Arts Council Membership Meeting Saturday, November 14, 2026 TBD

TUE
November
17
10:30 AM - 12:00 PM

Third Tuesday Bingo Location: Highland Public Library Play begins at 10:30 and ends at 12:15 Pm Free to play Open to community members over 60 years old Call 540-468-2178 for more information

THU
November
19
10:00 AM - 11:30 AM

LOCAL Caregivers Support Group 10:00am – 11:30am 1st and 3rd Thursdays each month The Mountain View Room at the Highland County Public Library 31 N Water Street, Monterey, VA 24465 FREE AND OPEN TO ALL, NOT JUST HIGHLAND RESIDENTS Need a respite ...

THU
December
3
10:00 AM - 11:30 AM

LOCAL Caregivers Support Group 10:00am – 11:30am 1st and 3rd Thursdays each month The Mountain View Room at the Highland County Public Library 31 N Water Street, Monterey, VA 24465 FREE AND OPEN TO ALL, NOT JUST HIGHLAND RESIDENTS Need a respite ...

SAT
December
5
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!

SAT
December
5
10:00 AM - 2:00 PM

Get Ready! Get Jingly! Get to Holiday Shoppe! Saturday, December 5th, 10AM to 2 PM --Free admission --Secret Shopping area for kids --Holiday vendors for adults --Hot Chocolate Bar --Arts & Craft activities for kids --NEW THIS YEAR: pancake breakfast ...

SAT
December
5
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, ...

SUN
December
6
3:00 PM - 4:00 PM

Highlands Community Orchestra Holiday Concert Sunday, December 6, 2026 The Highland Center, 3 pm TBD, 7 pm ​Free admission, donations accepted

THU
December
10
10:00 AM - 12:00 PM

Come connect, make new friends, and enjoy good conversation! Adults 60 and over are invited to gather together every second Thursday from 10:00 AM to Noon at the Highland County Public Library. Come as you are and bring a friend. We’d love to have you ...

TUE
December
15
10:30 AM - 12:00 PM

Third Tuesday Bingo Location: Highland Public Library Play begins at 10:30 and ends at 12:15 Pm Free to play Open to community members over 60 years old Call 540-468-2178 for more information

THU
December
17
10:00 AM - 11:30 AM

LOCAL Caregivers Support Group 10:00am – 11:30am 1st and 3rd Thursdays each month The Mountain View Room at the Highland County Public Library 31 N Water Street, Monterey, VA 24465 FREE AND OPEN TO ALL, NOT JUST HIGHLAND RESIDENTS Need a respite ...

FRI
December
18
5:00 PM - 8:00 PM

Join us for a family style Christmas Dinner at The Barn and enjoy live entertainment by Lee Dean as Frank Sinatra & Elvis and sing along to your favorite holiday tunes! Friday, December 18, 5 to 8 PM TICKETS: https://square.link/u/G67Q58WD

THU
Dec Jan
31 1
7:00 PM - 12:30 AM

Let's ring in the New Year together with Highland County Humane Society at the Monterey Inn Barn! PAWty starts at 7PM! This night will feature DJ Scott Smith, guaranteed great dancing tunes! Food, drink, tickets, and details to come. See you there! ...

THU
January
14
10:00 AM - 12:00 PM

Come connect, make new friends, and enjoy good conversation! Adults 60 and over are invited to gather together every second Thursday from 10:00 AM to Noon at the Highland County Public Library. Come as you are and bring a friend. We’d love to have you ...

TUE
January
19
10:30 AM - 12:00 PM

Third Tuesday Bingo Location: Highland Public Library Play begins at 10:30 and ends at 12:15 Pm Free to play Open to community members over 60 years old Call 540-468-2178 for more information

TUE
February
16
10:30 AM - 12:00 PM

Third Tuesday Bingo Location: Highland Public Library Play begins at 10:30 and ends at 12:15 Pm Free to play Open to community members over 60 years old Call 540-468-2178 for more information

SAT
March
13 14

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!

TUE
March
16
10:30 AM - 12:00 PM

Third Tuesday Bingo Location: Highland Public Library Play begins at 10:30 and ends at 12:15 Pm Free to play Open to community members over 60 years old Call 540-468-2178 for more information

SAT
March
20 21

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!

TUE
April
20
10:30 AM - 12:00 PM

Third Tuesday Bingo Location: Highland Public Library Play begins at 10:30 and ends at 12:15 Pm Free to play Open to community members over 60 years old Call 540-468-2178 for more information

TUE
May
18
10:30 AM - 12:00 PM

Third Tuesday Bingo Location: Highland Public Library Play begins at 10:30 and ends at 12:15 Pm Free to play Open to community members over 60 years old Call 540-468-2178 for more information

TUE
June
15
10:30 AM - 12:00 PM

Third Tuesday Bingo Location: Highland Public Library Play begins at 10:30 and ends at 12:15 Pm Free to play Open to community members over 60 years old Call 540-468-2178 for more information

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