# Festivals in Middleburg, FL 2026 | Culture & Street Fairs

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

## Audience

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## About

The best things to do in the world include attending top-notch festivals in Middleburg. Be it a rocking music festival or scrumptious food festival in Middleburg, 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 Middleburg 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 Middleburg

- **Event Name**: Middleburg Chili Cook off
  - **Description**: 🌶️ Middleburg Fall Festival Chili Cook-Off 🌶️

Think your chili has what it takes?

Join us for the 2026 Middleburg Fall Festival Chili Cook-Off!

📅 Saturday, November 7, 2026
💲 Entry Fee: $10 per entry

Whether your recipe is mild, smoky, sweet, or so sp
  - **Interested Audience**:
    - Count: 19
  - **Date**: Sat Nov 07 2026 at 11:00 am – Sat Nov 07 2026 at 02:00 pm (-05:00)
  - **Event URL**: https://allevents.in/middleburg/middleburg-chili-cook-off/200030469775438
  - **Venue**: 2102 Palmetto Street, Middleburg, FL
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  - **Categories**: festivals, contests, fall-festivals
- **Event Name**: 2026 Middleburg Fall Fest & Car Show
  - **Description**: TBD
  - **Interested Audience**:
    - Count: 278
  - **Date**: Sat Nov 07 2026 at 11:00 am – Sat Nov 07 2026 at 03:00 pm (-05:00)
  - **Event URL**: https://allevents.in/middleburg/2026-middleburg-fall-fest-and-car-show/200030115958616
  - **Venue**: 2102 Palmetto Street, Middleburg, FL
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  - **Categories**: festivals, fall-festivals
- **Event Name**: Festivus 2026
  - **Description**: We are making history again with the first ever 100 mile trail run on the Jennings State Forest and in the North East Florida region, we want to welcome you to the 4th Annual Festivus: For the rest of us! Sombrero Running Events and their sponsors are sup
  - **Interested Audience**:
    - Count: 91
  - **Date**: Sat Dec 05 2026 at 07:00 am (-05:00)
  - **Event URL**: https://allevents.in/middleburg/festivus-2026/200029735136746
  - **Venue**: 2A Live Oak Lane
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  - **Categories**: trips-adventures, calendar

## Trending Events in Middleburg

- **Event Name**: Cowabunga Café | Hodges Hidden Highlands Farm | Florida
  - **Description**: Cowabunga Café by Havenfield| Saturdays 11-2 | $28  per hour ticket. Sip beverages and enjoy pastries with free-roaming,cuddly Highland CowsAbout this EventLooking for the cutest way to spend your Saturday
  - **Venue**: 1683 Long Horn Rd
  - **Banner**: https://cdn-az.allevents.in/events6/banners/abf0d533f85be935cdc6c877eca7b17c28c2d0c2901f80c0a30405ea655cbfc4-rimg-w1200-h1600-dc4a4134-gmir.jpg?v=1774661841
- **Event Name**: The Shaggy Cow Lounge & Cabanas w/ Fluffy Highland Cows! | Middleburg, FL
  - **Description**: Middleburg, FL! - Introducing The Shaggy Cow Lounge & The Cowabunga Cabanas! 🐮🍹☀️
••••••
Welcome to The Shaggy Cow Lounge & our Cowabunga Cabana rentals! It is the ultimate retro-fluffy hangout for your favorite shaggy cows, adorable sheep, donkey
  - **Venue**: Middleburg, Florida
  - **Banner**: https://cdn-az.allevents.in/events8/banners/85a04de7843e39e708497226e74f566010b0c54eb8613184916e6671427a3dd6-rimg-w1200-h666-dca85838-gmir?v=1788958030
- **Event Name**: Hidden Highlands Full Moon Wellness  Experieence 6-8pm
  - **Description**: Relaxing evening at  featuring gentle seated Pilates, guided meditation, a sound bath, farm animals, and a fresh fruit prosecco bar. 6-8pmAbout this Event🌿 The Hidden Highlands Full Moon Experience 6pm -8pmS
  - **Venue**: Hodges Hidden Highlands Farm
  - **Banner**: https://cdn-az.allevents.in/events2/banners/7ed01e28f84fbe3bd8f281ae6e59d0c41547eec3a5e1818b43843549b5b1183b-rimg-w1200-h1200-dc080808-gmir.jpg?v=1787943657
- **Event Name**: 504 -> 904 Louisiana Style Cook - Off
  - **Description**: Jacksonville’s first live Louisiana-style cook-off! Watch teams cook, taste the dishes, and vote for your favorite.About this Event504 → 904 Louisiana Style Cook-OffGet ready for a Louisiana-style showd
  - **Venue**: 3470 Royal Pines Dr
- **Event Name**: How Can I Help? An Evening with Douglas Tallamy
  - **Description**: Back by popular demand, the National Sporting Library & Museum is thrilled to welcome Douglas Tallamy — New York Times Best Selling author, wildlife ecologist, and one of the most inspiring voices in conservation today — for an unforgettable evening o
  - **Venue**: 102 The Plains Rd, Middleburg, VA, United States, Virginia 20117
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- **Event Name**: 6th Annual Sunset in the Field
  - **Description**: Looking for the perfect fall tradition? Gather your family and friends, pull on your boots, and join us for LTV’s 6th Annual Sunset in the Field at beautiful Farmer’s Delight.


Spend the evening enjoying live bluegrass, delicious barbecue, local libation
  - **Venue**: Farmer's Delight
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- **Event Name**: Boxwood Portrait Experience
  - **Description**: Capture the magic of fall at Boxwood Estate Winery with an intimate golden-hour portrait experience among the vines.About this EventGather your favorite people and let a professional photograp
  - **Venue**: Boxwood Estate Winery
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- **Event Name**: Bovine & Crime | The Fall Farm Tour | Florida
  - **Description**: Join CSI Investigator and Expert Sheryl McCollum for an immersive live "who dunnit" mystery experience where YOU help solve the case.About this EventBovine & CrimeHoste
  - **Venue**: 1683 Long Horn Rd
  - **Banner**: https://img.evbuc.com/https%3A%2F%2Fcdn.evbuc.com%2Fimages%2F1189652739%2F2994601274467%2F1%2Foriginal.20260726-185855?auto=format%2Ccompress&q=75&sharp=10&s=71ef9f9ff4d37922852a891faaf0d7ab
- **Event Name**: Petals & Poses
  - **Description**: Join us for a cozy morning of stretch, wine, and flower arranging as we celebrate the fall season at Petals and Poses!About this EventHelp us celebrate Virginia Wine Month at the winery with a relaxing morning of yoga, fl
  - **Venue**: Cana Vineyards and Winery of Middleburg
  - **Banner**: https://cdn-az.allevents.in/events6/banners/6c7063882ce0d3e038dcf49f2aec4fb6721a867903104d649acb9e583f7a08df-rimg-w940-h470-dc637a43-gmir.jpg?v=1785032175

## Browse Festivals Events by Date

- [Festivals Events Today in Middleburg](https://allevents.in/middleburg/festivals--today)
- [Festivals Events This Weekend in Middleburg](https://allevents.in/middleburg/festivals--this-weekend)
- [Festivals Events in September in Middleburg](https://allevents.in/middleburg/festivals--september)
- [Festivals Events in October in Middleburg](https://allevents.in/middleburg/festivals--october)

## FAQs

- **Q**: What are the top Festivals events in Middleburg?
  - **A:** Middleburg Chili Cook off (Sat Nov 07 2026 at 11:00 am at 2102 Palmetto Street, Middleburg, FL), 2026 Middleburg Fall Fest & Car Show (Sat Nov 07 2026 at 11:00 am at 2102 Palmetto Street, Middleburg, FL), Festivus 2026 (Sat Dec 05 2026 at 07:00 am at 2A Live Oak Lane).
- **Q**: How can I find Festivals events in Middleburg?
  - **A:** You can discover upcoming Festivals events in Middleburg 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 Middleburg?
  - **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 Middleburg?
  - **A:** Some popular venues hosting Festivals events in Middleburg include 2102 Palmetto Street, Middleburg, FL, 2A Live Oak Lane.
- **Q**: Who are the top organizers for Festivals events in Middleburg?
  - **A:** Popular organizers hosting Festivals events in Middleburg include Middleburg Civic Assoc, Mike Martinez.
- **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 Middleburg?
  - **A:** Follow the Festivals category on AllEvents.in to get notified when new Festivals events are listed in Middleburg.

## Category Banner

- **Banner Image**: https://cdn2.allevents.in/transup/6e/5415e403f74b77938c0695ac11464e/Festival.jpg

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