# Festivals in Monterey, VA 2026 | Culture & Street Fairs

- **Subtitle**: Your guide to festivals in Monterey, Virginia 2026 — cultural celebrations, street fairs and food festivals. Find dates, locations and what to expect.
- **Category**: Festivals
- **Type**: category

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## About

The best things to do in the world include attending top-notch festivals in [CITY]. Be it a rocking music festival or scrumptious food festival in [CITY], you will have a gala time of your life with a few of your close friends or your family. With the best of fun, entertainment, and food, the experience in festivals lets the enthusiasts immerse in the local culture and vibe. Ranging from the biggest outdoor beach parties to crazy music festivals, the festivals fall under various categories to suit everybody’s tastes. If you are looking for the best events and festivals in [CITY] listed on one platform - we have you covered.

Immerse yourself in the mega dance festivals, electrifying music festivals, theatre & film festivals, quirky local festivals and more with us!

## Festivals Events in Monterey

- **Event Name**: 75th Annual Highland County Fair Kickoff Event
  - **Description**: 🎉 75th Annual Highland County Fair Kickoff Event  
📍 386 Myers‑Moon Road, Monterey, VA 24465
📅 Saturday, August 29, 2026  
💲 FREE ADMISSION
Join us as we kick off the 75th Annual Highland County Fair with a full day of events, exhibits, food, and fun for
  - **Interested Audience**:
    - Count: 63
  - **Date**: Sat Aug 29 2026 at 09:00 am (-04:00)
  - **Event URL**: https://allevents.in/monterey/75th-annual-highland-county-fair-kickoff-event/200030403171616
  - **Venue**: 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy85YWZhNjgxODM1MDA2MzlkZjg2OGViODYyYzVjNDZmMmFmNTg2MjI1YWRjYzYyZGI0NGU0MDM2YzUzN2UxZWFhLXJpbWctdzEyMDAtaDE1NTMtZGNmOGY4ZTgtZ21pcj92PTE3ODU3ODg1OTk.avif
  - **Categories**: festivals, dog, dog-shows, workshops, art, calendar, parades, bingo
- **Event Name**: 2026 Hands & Harvest Festival
  - **Description**: Visit www.highlandcounty.org/hands-harvest-festival frequently until the event begins to stay updated on the full list of activities, addresses, and hours!

Celebrate the beauty and bounty of fall at the 34th Hands & Harvest Festival in beautiful High
  - **Interested Audience**:
    - Count: 227
  - **Date**: Fri Oct 09 2026 at 06:00 am – Sun Oct 11 2026 at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/monterey/2026-hands-and-harvest-festival/200030245882230
  - **Venue**: 165 W Main St, Monterey, VA 24465-2754, United States
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy82NTgyYzBiNTg5M2U5MjVkZDY1YmRiY2I2ZDgyMjhjN2ViMTdiZjVjZGY2NDZiMWExNTA4NzVlZWU4MmE2MWZjLXJpbWctdzEyMDAtaDYyOC1kY2Y4ZThkOC1nbWlyP3Y9MTc4NjEyMzI2NQ.avif
  - **Categories**: festivals, harvest-festival, art, trips-adventures, oktoberfest
- **Event Name**: Highland Co. Fair, VA Demolition Derby & Power Wheels Derby
  - **Description**: Thomas Motorsport, LLC  Presents:
Highland County Fair, VA
Demolition Derby & Power Wheels Derby
FRIDAY, September 4th, 2026

Registration begins @ 2pm
Kids Power Wheels Derby starts @ 6pm
Demolition Derby starts @7pm

DRIVER ENTRY FEE: $30; CASH ONLY
  - **Interested Audience**:
    - Count: 957
  - **Date**: Fri Sep 04 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/monterey/highland-co-fair-va-demolition-derby-and-power-wheels-derby/200029771630736
  - **Venue**: 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy8yMmJjYzBlZGRkZDlkMjdhZDA3OWZmYjA1MmVhNTc3N2VlZDNiNTk1NTYzZGI3NDI2ZjYzNTgyNjE0ZTVmMGZmLXJpbWctdzEwODAtaDE3MzMtZGNmMmYzZjctZ21pcj92PTE3ODUxNzc5NTU.avif
  - **Categories**: sports, kids
- **Event Name**: Truck & Tractor Pull @ Highland Co. Fair, VA w/ Dragon Motorsports
  - **Description**: Dragon Motorsports Presents the Highland County Fair Truck & Tractor Pull
September 5, 2026 at 5pm
Registration begins around 2pm and will end around 4:30pm

Full class rules at https://www.dragonpull.com/

Classes:
11,000 Altered Farm
Hot Street Dies
  - **Interested Audience**:
    - Count: 121
  - **Date**: Sat Sep 05 2026 at 05:00 pm (-04:00)
  - **Event URL**: https://allevents.in/monterey/truck-and-tractor-pull-highland-co-fair-va-w-dragon-motorsports/200030032418908
  - **Venue**: 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy85OTU5NjY3ZDJlZjFlYzAwMGQ2NjE1YTgwM2I5ZDQ3NzljNWY5NGVkMDhkYjEzYTljNzgwZDNmNDRkY2NmMDkxLXJpbWctdzEyMDAtaDY3NS1kYzA4MDgwOC1nbWlyP3Y9MTc4NTU1MzQ0Mg.avif
  - **Categories**: workshops
- **Event Name**: Bluegrass Music at The Highland Co. Fair, VA
  - **Description**: The Highland County Fair Presents:
Bluegrass Music
Saturday, September 5, 2026 at 11:00am
Caleb Bailey & Paines Run & The Conner Family

Caleb Bailey & Paine’s Run formed in 2021 after the success of Bailey’s debut album Poplar & Pine. Bas
  - **Interested Audience**:
    - Count: 21
  - **Date**: Sat Sep 05 2026 at 11:00 am (-04:00)
  - **Event URL**: https://allevents.in/monterey/bluegrass-music-at-the-highland-co-fair-va/200030056405542
  - **Venue**: 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy85NDllYzI2ODNiYTg4MTRlZTgzMDczODA0MGM1MGYxNTc1ZDJhMTAwZTc5OTY3ZDRjN2JmMjIwZmMwZGIwOWMyLXJpbWctdzEyMDAtaDY3NS1kY2Y4ZjhlOC1nbWlyP3Y9MTc4NTczNDM0Mg.avif
  - **Categories**: music, entertainment, festivals, concerts, art, live-music
- **Event Name**: The Gospel Harmony Boys at the Highland County Fair, VA
  - **Description**: Highland County Fair Presents:
The Gospel Harmony Boys
Thursday, Sept. 3rd 2026 at 3pm & 5pm
Under the big tent

The Gospel Harmony Boys are one of America’s longest‑running Southern Gospel quartets, sharing their signature harmonies since 1952. Known
  - **Interested Audience**:
    - Count: 11
  - **Date**: Thu Sep 03 2026 at 03:00 pm (-04:00)
  - **Event URL**: https://allevents.in/monterey/the-gospel-harmony-boys-at-the-highland-county-fair-va/200030209247750
  - **Venue**: 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy82Y2YxMGIxMTY2YWM5OGEwYmRlMWE5M2Y1ZGVhMTk3MGM5ZjlhMTlhZDI2ZTc3NmJlYjQ5OGM5ZDI4ZDcxYzYyLXJpbWctdzEyMDAtaDY3NS1kYzk4OTg4OC1nbWlyP3Y9MTc4NjEzMDY2Mw.avif
  - **Categories**: festivals, concerts, music, entertainment
- **Event Name**: Highland County Fair, VA Kiddie Show
  - **Description**: Highland County Fair, VA Kiddie Show
Chairperson: Susie Moyers
Friday, September 4, 2026 at 10:00am

Outside Under Big Tent

General Rules
Entry fee is $1.00 for each class.  Classes 8 and 9 are limited to Highland County residents.  This residency should
  - **Interested Audience**:
    - Count: 31
  - **Date**: Fri Sep 04 2026 at 10:00 am (-04:00)
  - **Event URL**: https://allevents.in/monterey/highland-county-fair-va-kiddie-show/200029771482206
  - **Venue**: 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9hNjZlZDRkMTVmNjdkYWM3MDhiOGExMGFmNmYzYTMzNThlMmQ1Y2MyOTk1M2RjMmFkNGFjMjExZmEzNzA3NzZmLXJpbWctdzEyMDAtaDYyOC1kY2Y4ZjhmOC1nbWlyP3Y9MTc4NjEzMDY3MA.avif
  - **Categories**: workshops, contests, health-wellness, art, theatre
- **Event Name**: Little Switzerland Cloggers at the Highland Co. Fair, VA
  - **Description**: Friday, September 4, 2025
6 pm
High School Gym
 

The Little Switzerland Cloggers, one of the oldest clogging groups in the state, have been captivating audiences at fairs, festivals, events, parties, and corporate gatherings throughout Virginia and West
  - **Interested Audience**:
    - Count: 26
  - **Date**: Fri Sep 04 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/monterey/little-switzerland-cloggers-at-the-highland-co-fair-va/200030201529415
  - **Venue**: 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy8xMzVkYmEyMDFmMGI1NDlhOWY5YTBlMDAyMjU1MmY5NGMzOWM0ZjMyY2Y5MGJlMGZjNmI3OTQ5ZTViNDJhYzU3LXJpbWctdzEyMDAtaDE1NjAtZGNmOGU4ZTgtZ21pcj92PTE3ODU5NzI1NTY.avif
  - **Categories**: festivals, sports, parties, entertainment, country-music-festivals
- **Event Name**: Highland Co. Fair, VA Rodeo
  - **Description**: Begoon Brothers Bucking Bulls, LLC Presents:
Highland County Fair, VA
Mutton Bustin, Jr Rodeo, Barrel Racing, & Rodeo

September 3, 2026
7:00pm
386 Myers-Moon Road, Monterey, VA 24465
www.highlandcountyfairva.com

4B, LLC is a family owned youth focus
  - **Interested Audience**:
    - Count: 889
  - **Date**: Thu Sep 03 2026 at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/monterey/highland-co-fair-va-rodeo/200029770369109
  - **Venue**: 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9lMTIzOGI0OWIyYTY3ZjVkYjA2NDdlOGZjNzFmNWE0MzIyOWQxYzEyM2U3Y2JkMGNlOWI1YjA4YjcxNjM3NTdkLXJpbWctdzEyMDAtaDYyOC1kYzQ4NDgzOC1nbWlyP3Y9MTc4NTg3MzkzMQ.avif
  - **Categories**: rodeo, trips-adventures, sports

## Trending Events in Monterey

- **Event Name**: Ancestral Healing Retreat | August 28th-30th
  - **Description**: Return to Great Waters: A Lunar Eclipse JourneyThe Celestial AlignmentThis retreat is intentionally timed with a rare and potent cosmic event. On the night of August 27–28, 2026, a Deep Partial Lunar Eclipse will sweep ac
  - **Venue**: Monterey
  - **Banner**: https://cdn2.allevents.in/thumbs/thumb6a5e8d579e0a6.jpg
- **Event Name**: Santa Barbara LOVE Scavenger Hunt for Couples Date Night!!
  - **Description**: CITY LOVE SCAVENGER HUNT Date For Couples (Self-Guided) Enjoy your city scavenger hunt with fun digital activities along the way!About this Eventhttps://youtu.be/-2gjHn9I0_cCITY L
  - **Venue**: Recommended scavenger starting point or other city spot of your choice! (YOU MUST USE PDF TICKETS EMAILED FOR EVENT- NO MOBILE APP OR QR CODES ACCEPTED)
  - **Banner**: https://cdn-az.allevents.in/events7/banners/3a7a6e92ca35d234cd42ed01dc2c1c28ec0fad47938fd1156e720ad0a15aa404-rimg-w1200-h660-dc171816-gmir.jpg?v=1758324199
- **Event Name**: Monterey Jazz Festival - 3 Day Pass at Monterey Fairgrounds
  - **Venue**: Monterey Fairgrounds
  - **Banner**: https://cdn-az.allevents.in/events7/banners/ca906f50-8fb2-11f1-a33a-f7150662a5aa-rimg-w940-h940-dc080808-gmir.jpg?v=1785813349
- **Event Name**: Monterey Jazz Festival (3 Day Pass)
  - **Description**: 📍 Venue: Monterey Fairgrounds
🏠 Address: 2004 Fairground Road, Monterey, CA 93940
🌆 City: Monterey
📍 Location: 36.5947, -121.864✨ Embark on an extraordinary journey at Monterey Jazz Festival (3 Day Pass), where every moment promises to b
  - **Venue**: Monterey Fairgrounds
- **Event Name**: Monterey Jazz Festival - Saturday at Monterey Fairgrounds
  - **Venue**: Monterey Fairgrounds
  - **Banner**: https://cdn-az.allevents.in/events10/banners/cc67ee70-8fb2-11f1-88dc-e3856eb2568f-rimg-w1200-h675-dc180808-gmir.jpg?v=1785813352
- **Event Name**: Monterey Jazz Festival - Sunday at Monterey Fairgrounds
  - **Venue**: Monterey Fairgrounds
  - **Banner**: https://cdn-az.allevents.in/events8/banners/cd1e4620-8fb2-11f1-af5a-17ce4ea54341-rimg-w1200-h675-dc180808-gmir.jpg?v=1785813353
- **Event Name**: AT&T Pebble Beach National Pro-Am - Thursday
  - **Venue**: Pebble Beach Golf Links
  - **Banner**: https://cdn-az.allevents.in/events1/banners/13c841f0-916d-11f1-a33a-f7150662a5aa-rimg-w1200-h675-dc282828-gmir.jpg?v=1786003309
- **Event Name**: The 69th Monterey Jazz Festival 2026 in Monterey
  - **Description**: 🎶 Get Ready for Herbie Hancock Live at Monterey Fairgrounds on Sunday, September 27, 2026! 🎶
This is not just a concert—it's a moment you'll talk about for years. Herbie Hancock is set to light up Monterey Fairgroun
  - **Venue**: Monterey Fairgrounds
  - **Banner**: https://cdn-az.allevents.in/events5/banners/d7055c80-6d9a-11f1-980e-39e44e9692a8-rimg-w1147-h645-dc020202-gmir.webp?v=1782064722
- **Event Name**: Monterey Jazz Festival (Friday Pass)
  - **Description**: 📍 Venue: Monterey Fairgrounds
🏠 Address: 2004 Fairground Road, Monterey, CA 93940
🌆 City: Monterey
📍 Location: 36.5947, -121.864✨ Experience the magic of Monterey Jazz Festival (Friday Pass), where moments become memories that last a lif
  - **Venue**: Monterey Fairgrounds

## Browse Festivals Events by Date

- [Festivals Events Today in Monterey](https://allevents.in/monterey/festivals--today)
- [Festivals Events This Weekend in Monterey](https://allevents.in/monterey/festivals--this-weekend)
- [Festivals Events in August in Monterey](https://allevents.in/monterey/festivals--august)
- [Festivals Events in September in Monterey](https://allevents.in/monterey/festivals--september)

## FAQs

- **Q**: What are the top Festivals events in Monterey?
  - **A:** 75th Annual Highland County Fair Kickoff Event (Sat Aug 29 2026 at 09:00 am at 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465), 2026 Hands & Harvest Festival (Fri Oct 09 2026 at 06:00 am at 165 W Main St, Monterey, VA 24465-2754, United States), Highland Co. Fair, VA Demolition Derby & Power Wheels Derby (Fri Sep 04 2026 at 06:00 pm at 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465), Truck & Tractor Pull @ Highland Co. Fair, VA w/ Dragon Motorsports (Sat Sep 05 2026 at 05:00 pm at 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465), Bluegrass Music at The Highland Co. Fair, VA (Sat Sep 05 2026 at 11:00 am at 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465).
- **Q**: What Festivals events are happening in Monterey in August 2026?
  - **A:** 75th Annual Highland County Fair Kickoff Event (Sat Aug 29 2026 at 09:00 am at 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465).
- **Q**: How can I find Festivals events in Monterey?
  - **A:** You can discover upcoming Festivals events in Monterey on AllEvents.in. Browse by date, venue, or price to find events that match your interests.
- **Q**: How do I buy tickets for Festivals events in Monterey?
  - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets.
- **Q**: What are the popular venues for Festivals events in Monterey?
  - **A:** Some popular venues hosting Festivals events in Monterey include 386 Myers-Moon Road, Monterey, VA, United States, Virginia 24465, 165 W Main St, Monterey, VA 24465-2754, United States.
- **Q**: Who are the top organizers for Festivals events in Monterey?
  - **A:** Popular organizers hosting Festivals events in Monterey include Highland County Fair, Virginia, Highland County VA.
- **Q**: Are there any online Festivals events available?
  - **A:** Yes, many Festivals events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere.
- **Q**: How can I get notified about new Festivals events in Monterey?
  - **A:** Follow the Festivals category on AllEvents.in to get notified when new Festivals events are listed in Monterey.

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