# Festivals in Middletown, MD 2026 | Culture & Street Fairs

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

## Audience

- **Followers**: 2.5M+
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## About

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

- **Event Name**: 2026 Fall Festival at Summers Farm!
  - **Description**: Join us for our annual Fall Festival at Summers Farm! 🎃 

Experience 45+ attractions, meet farm animals, enjoy delicious treats and drinks & so much more! 🍂

Here's what we have planned:

🎃 Pumpkin Train
📸 Photo Ops
🍦 Specialty Food & Drinks
🌽 Fam
  - **Interested Audience**:
    - Count: 90
  - **Date**: Sat Sep 26 2026 at 10:00 am – Sat Sep 26 2026 at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/middletown/2026-fall-festival-at-summers-farm/200030588567802
  - **Venue**: 7503 Hollow Road, Middletown, MD, United States, Maryland 21769
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  - **Categories**: festivals, fall-festivals
- **Event Name**: Middletown Heritage Festival 2026
  - **Description**: Middletown, MD's Middletown Heritage Festival, our town's cornerstone event and its biggest party of the year!
  - **Interested Audience**:
    - Count: 1121
  - **Date**: Sat Sep 26 2026 at 10:00 am – Sat Sep 26 2026 at 04:00 pm (-04:00)
  - **Event URL**: https://allevents.in/middletown/middletown-heritage-festival-2026/200030014952419
  - **Venue**: Middletown Heritage Festival
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9hMmUwODNkYjZiYzNlNDAyMGE5NmEwZWYzZmNmNmEwNjM4NTY5ZjJlMWUwODAzM2QxMmU2YThkZDBkYzNiMGI1LXJpbWctdzEyMDAtaDY3Ni1kY2Y4ZjhmOC1nbWlyP3Y9MTc4NzQ0NDk3Mw.avif
  - **Categories**: festivals, parties, entertainment
- **Event Name**: Fall Fest 2026 at South Mountain Creamery
  - **Description**: Mark your calendars:  Fall Fest is coming back to the farm!  🍂

Fall Fest is our free, family-friendly festival. We will have hayrides, a petting zoo, farm tours, cornhole, a costume contest (pets are encouraged to join), a farmers market, and live music
  - **Date**: Sat Oct 03 2026 at 12:00 pm (-04:00)
  - **Event URL**: https://allevents.in/middletown/fall-fest-2026-at-south-mountain-creamery/200030588444321
  - **Venue**: 8305 Bolivar Rd, Middletown, MD, United States, Maryland 21769
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  - **Categories**: Festivals, Music, Entertainment, Nonprofit, Kids, Contests
- **Event Name**: Sleepy Hollow Fall Festival
  - **Description**: Come out to Holy Family Catholic Community in Middletown, MD for our 3rd Annual Sleepy Hollow Fall Festival! We will have food trucks, bounce houses, children's activities, a live band, fairy hair, face paint, touch a truck, and MORE! Event is Free! We lo
  - **Interested Audience**:
    - Count: 61
  - **Date**: Sun Nov 08 2026 at 12:00 pm – Sun Nov 08 2026 at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/middletown/sleepy-hollow-fall-festival/200030669698805
  - **Venue**: 7321 Burkittsville Road, Middletown, MD, United States, Maryland 21769
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  - **Categories**: festivals, fall-festivals, music, food-drinks, entertainment, food-truck-festivals, live-music

## Trending Events in Middletown

- **Event Name**: The Gathering of the People pow wow and cook out
  - **Description**: Join us for an inter-tribal performance of song and dance hosted by the Southern Singers: 2:00-3:15Then enjoy a tour of the wolfdogs at our sanctuary before ending at our firepit picnic area for a campfire supper. Event ends at 6pm. Registration
  - **Venue**: Red Riding Hood Rescue Project, a wolfdog sanctuary
  - **Banner**: https://cdn2.allevents.in/thumbs/thumb6aa2b2821b8ef.jpg
- **Event Name**: The Power Palette: Women in Business Edition
  - **Description**: A curated evening for women in business to connect, discover local resources, plant seeds for collaboration, and unwind together.About this EventThe Power Palette: Women in Business Edition
  - **Venue**: Giuseppe's Place
  - **Banner**: https://cdn-az.allevents.in/events10/banners/04217bdb65df2363847ad576a7ae62764a221b0aa86c71e9424162b16e21f0b0-rimg-w1200-h600-dc080808-gmir.jpg?v=1786357207
- **Event Name**: Meditate in Middletown
  - **Description**: Meditate in Middletown, ongoing Mondays, 7-8:15pm beginning 10/19, at First Church, 190 Court Street (Memorial Room). Classes taught by Matthew Stein, Resident Teacher of Odiyana Buddhist Center, Glastonbury. This world needs more peace.
  - **Venue**: First Church in Middletown, UCC, Congregational
  - **Banner**: https://cdn2.allevents.in/thumbs/thumb6aa4b2656783d.jpg
- **Event Name**: 2026 Fall Festival at Summers Farm!
  - **Description**: Join us for our annual Fall Festival at Summers Farm! 🎃 

Experience 45+ attractions, meet farm animals, enjoy delicious treats and drinks & so much more! 🍂

Here's what we have planned:

🎃 Pumpkin Train
📸 Photo Ops
🍦 Specialty Food & Drinks
🌽 Fam
  - **Venue**: 7503 Hollow Road, Middletown, MD, United States, Maryland 21769
  - **Banner**: https://cdn-az.allevents.in/events10/banners/34acc2b1d05cec692819adbcd278c684467f451a9d19e7a4ed7f8522f0abd735-rimg-w1200-h628-dc88b8e8-gmir?v=1788494985
- **Event Name**: Weekend Fall Festival at Jumbo's
  - **Description**: 🎃🍂 Fall Fun Awaits at Jumbo’s Pumpkin Patch! 🍂🎃

Looking for the perfect autumn adventure? 🍁
Jumbo’s has it all:
✨ 20+ Activities Included with Admission
🚜 Hayrides 
🌽 Corn Maze
🎈 Jumping Pillow
🐮 Farm Animals
🌾 Big Slides
🎨 Face Painting*
🐴 Pony Rides*
🌽
  - **Venue**: 6521 Holter Rd, Middletown, MD, United States, Maryland 21769
  - **Banner**: https://cdn-az.allevents.in/events10/banners/b5a0f7274d5c9c5b37f79072aa893bc160cd64eee75ad43d088310c6f0bb443b-rimg-w1080-h1080-dc080808-gmir?v=1788231476
- **Event Name**: 2026 Opening Weekend at Jumbo's Pumpkin Patch!
  - **Description**: 🎉Kick off the 2026 Fall season at Jumbo's!!!!🎃

🎃🍂 Fall Fun Awaits at Jumbo’s Pumpkin Patch! 🍂🎃

Looking for the perfect autumn adventure? 🍁
Jumbo’s has it all:
✨ 20+ Activities Included with Admission
🚜 Hayrides 
🌽 Corn Maze
🎈 Jumping Pillow
🐮 Farm Anima
  - **Venue**: 6521 Holter Rd, Middletown, MD, United States, Maryland 21769
  - **Banner**: https://cdn-az.allevents.in/events2/banners/aba82eeff97f16e5f6abb471075c72fe14c1e4132fe0026de82e299fd3a67179-rimg-w1080-h1080-dc080808-gmir?v=1788231133
- **Event Name**: Comedian Tim Meadows
  - **Description**: The Paramount Theatre is pleased to presentComedian Tim MeadowsTaking place Saturday, September 19th, 2026 at 7:30 PMTim Meadows is an actor, writer comedian who was one of the longest-running cast members on Saturday
  - **Venue**: Paramount Theatre
  - **Banner**: https://cdn2.allevents.in/thumbs/thumb6a8f4bdae9a7b.jpg
- **Event Name**: Jack Daniel's Distillery Dinner
  - **Description**: A four-course Jack Daniel’s dinner with brand ambassador Jed Lirette, paired pours, mini cocktails, swag, stories & more.About this EventWe’re going big for this one.Join us for an unforgettable evening with Ja
  - **Venue**: Vault & Cellar
  - **Banner**: https://cdn-az.allevents.in/events10/banners/9edbdf554ee0e0b391a32196801e170d8865c0cddf4bb0b5f57b88a7cca09e8c-rimg-w1200-h628-dc984808-gmir.jpg?v=1787337981
- **Event Name**: Harvest Fest GFFM
  - **Description**: Your favorite fall festival is here!

We welcome you to the Garver Family Farm Market Annual Harvest Fest!

The same annual festival we all know and love, has grown, with more to offer than ever before!

We invite you to join us Saturday, October 3rd for
  - **Venue**: 6790 Hamilton Lebanon Rd, Monroe, OH
  - **Banner**: https://cdn-az.allevents.in/events2/banners/48125e9a3361d1d3c7b37deb8db4edd9d74aae2055fee37a9d7fd5cf05d82906-rimg-w940-h788-dcc8c8a8-gmir?v=1789052596

## Browse Festivals Events by Date

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

## FAQs

- **Q**: What are the top Festivals events in Middletown?
  - **A:** 2026 Fall Festival at Summers Farm! (Sat Sep 26 2026 at 10:00 am at 7503 Hollow Road, Middletown, MD, United States, Maryland 21769), Middletown Heritage Festival 2026 (Sat Sep 26 2026 at 10:00 am at Middletown Heritage Festival), Fall Fest 2026 at South Mountain Creamery (Sat Oct 03 2026 at 12:00 pm at 8305 Bolivar Rd, Middletown, MD, United States, Maryland 21769), Sleepy Hollow Fall Festival (Sun Nov 08 2026 at 12:00 pm at 7321 Burkittsville Road, Middletown, MD, United States, Maryland 21769).
- **Q**: What Festivals events are happening in Middletown in September 2026?
  - **A:** 2026 Fall Festival at Summers Farm! (Sat Sep 26 2026 at 10:00 am at 7503 Hollow Road, Middletown, MD, United States, Maryland 21769), Middletown Heritage Festival 2026 (Sat Sep 26 2026 at 10:00 am at Middletown Heritage Festival).
- **Q**: How can I find Festivals events in Middletown?
  - **A:** You can discover upcoming Festivals events in Middletown 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 Middletown?
  - **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 Middletown?
  - **A:** Some popular venues hosting Festivals events in Middletown include 7503 Hollow Road, Middletown, MD, United States, Maryland 21769, Middletown Heritage Festival, 8305 Bolivar Rd, Middletown, MD, United States, Maryland 21769.
- **Q**: Who are the top organizers for Festivals events in Middletown?
  - **A:** Popular organizers hosting Festivals events in Middletown include Summers Farm, Middletown Heritage Festival, South Mountain Creamery.
- **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 Middletown?
  - **A:** Follow the Festivals category on AllEvents.in to get notified when new Festivals events are listed in Middletown.

## Category Banner

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

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