# 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+
- **Recent Followers**: 
  - **Avatar 1**: https://cdn-az.allevents.in/events4/banners/c7a3bd77620a92a1fee77ed0b46cc305d65fcaf166695040aabebd480d9323a4-rimg-w200-h200-dc7e887a-gmir?v=1749580804
  - **Avatar 2**: https://cdn-az.allevents.in/events2/banners/87514fe09e2e42afe6f2e6b5b9e483315429bdfa0a64d2af3268e7f6798e263a-rimg-w200-h200-dc182a60-gmir?v=1760132405
  - **Avatar 3**: https://cdn-az.allevents.in/events4/banners/4372fbe0-97b1-11f0-925d-a7ce5707d3d8-rimg-w200-h200-dc445c46-gmir

## Featured Events

- **Event Name**: CrimeStery Fest 2026
  - **Description**: CrimeStery-Fest 2026 — All Things Crime and MysteryThe Northeast's Coolest Crime Convention!Calling all true crime enthusiasts, CrimeStery-Fest returns for an immersive three-day celebration
  - **Date**: Fri, 09 Oct at 04:00 pm – Sun, 11 Oct at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/danvers/crimestery-fest-2026-tickets/80005231957486
  - **Venue**: DoubleTree by Hilton Hotel Boston North Shore, Ferncroft Road, Danvers, MA, USA
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4yLmFsbGV2ZW50cy5pbi90aHVtYnMvdGh1bWI2OWY4MmM1YjU5MDBmLmpwZw.avif
  - **Price**: min: 30, max: 90, currency: USD
  - **Categories**: exhibitions, conferences
- **Event Name**: Stand Up Comedy Night at Cahoots Taproom and Arcade
  - **Description**: Get ready to laugh your socks off with some killer stand-up sets and cold brews!About this EventBeer Run Comedy is a dynamic comedy group that brings the laughter and good times wherever
  - **Date**: Fri, 31 Jul at 07:00 pm – Fri, 31 Jul at 09:00 pm (-04:00)
  - **Event URL**: https://allevents.in/middletown/stand-up-comedy-night-at-cahoots-taproom-and-arcade/100001993499361253
  - **Venue**: CAHOOTS by YAH Brew & Cartel
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy84MGZiYTRjNzk3Nzg4NmYwMGUyNDVjZWEzM2MwY2Y3ZmNiNmIxZWJlODc3NGQ2ZmM1NmQxOWNmOWMxZmI2NDJjLXJpbWctdzEyMDAtaDYwMC1kYzAxMDEwMS1nbWlyLmpwZz92PTE3ODM1OTc1Njc.avif
  - **Price**: min: 17.85, max: 17.85, currency: USD
  - **Categories**: comedy, entertainment, performances, festivals

## 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 Middletown

- **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: 143
  - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9hMmUwODNkYjZiYzNlNDAyMGE5NmEwZWYzZmNmNmEwNjM4NTY5ZjJlMWUwODAzM2QxMmU2YThkZDBkYzNiMGI1LXJpbWctdzEyMDAtaDY3Ni1kY2Q3ZWFlZC1nbWlyP3Y9MTc4NDgxNDYyOQ.avif
  - **Categories**: festivals, parties, entertainment
- **Event Name**: 2026 Frederick Family Shopping Festival
  - **Description**: Join the 2026 Frederick Family Shopping Festival for fun deals, tasty eats, and good vibes with the whole crew!About this Event2026 Frederick Family Shopping FestivalExperience a Weekend of Shopping, Entertainment &
  - **Interested Audience**:
    - Count: 1
  - **Date**: Fri Aug 21 2026 at 10:00 am – Sun Aug 23 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/middletown/2026-frederick-family-shopping-festival/100001994002688719
  - **Venue**: Middletown Park
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9kZGUwNTUwYzEwZjJmYWZhYzk4MGJlYWQ0MjkxNGRhZGNlZGIyYWMyYWQwNTNiNmYzNjVjNmEzMDBjYTlmNjIxLXJpbWctdzk0MC1oNDcwLWRjNDYyZTFkLWdtaXIuanBnP3Y9MTc4NDE1MDEyNg.avif
  - **Price**: Free
  - **Categories**: shopping, festivals, business, food-drinks
- **Event Name**: 2026 Flower Festival at Summers Farm!
  - **Description**: Your favorite summer tradition is back, and it's blooming better than ever! Join us on the farm this August and September for fields of color, fresh air, and unforgettable memories during our 2026 Flower Festival!

🌼 PICK YOUR OWN EXPERIENCE: Every admiss
  - **Interested Audience**:
    - Count: 54
  - **Date**: Sat Aug 22 2026 at 11:00 am – Sat Aug 22 2026 at 08:00 pm (-04:00)
  - **Event URL**: https://allevents.in/middletown/2026-flower-festival-at-summers-farm/200030215728521
  - **Venue**: 7503 Hollow Road, Middletown, MD, United States, Maryland 21769
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy9kYzkwM2Q0YTY0MGMwNDkxODNhMTI5ZjhmN2U3ZmI3OGRlMDRhMWY0MjQyZjgxNDY5OWI3MDk2NDY5Zjk1YzIyLXJpbWctdzEyMDAtaDYwMC1kY2VlZWZmNC1nbWlyP3Y9MTc4NTA1MjY3NQ.avif
  - **Categories**: festivals

## Trending Events in Middletown

- **Event Name**: 29th Annual Cruise Night on Main Street
  - **Description**: 🚗 Save the Date!

The 29th Annual Cruise Night on Main Street presented by NAPA AUTO PARTS returns to downtown Middletown on Wednesday, September 2, 2026 from 4:30–8:00 PM!

In collaboration with the City of Middletown, Connecticut Government, we’ve moved
  - **Venue**: Main Street, 06457
  - **Banner**: https://cdn-az.allevents.in/events1/banners/cc084287121fd21132fe7c0447e2db8a1913f5b4a80561da2adbbddad9a896ef-rimg-w1200-h675-dc95c1dc-gmir?v=1784666299
- **Event Name**: 20th Annual Marshall+Sterling Run 4 Downtown
  - **Description**: R4DT.org for details and to register!

The R4DT is a 4 mile run/walk that starts and ends in the heart of downtown Middletown, NY, but it is so much more than a race! Plenty of on course music and entertainment will keep you motivated during the run/walk,
  - **Venue**: 17 North St, Middletown, NY
  - **Banner**: https://cdn-az.allevents.in/events8/banners/d02603e5a6f47b99afae1c5e2d9bc54c5dd4b04b9090565c300ddf7078d2f5cc-rimg-w1200-h900-dc94bbd4-gmir?v=1784897020
- **Event Name**: Hops in the Hangar 2026- Tickets on Sale Now
  - **Description**: A Craft Beer Event that Really Takes Flight!

Gathering a blend of craft beer fans and aviation enthusiasts in an airplane hangar, 

Hops in the Hangar is the EPIC craft beer event in the tri-state area.

Talk about unique ambiance! A beer event at an ope
  - **Venue**: 1701 Run Way, Middletown, OH 45042-2300, United States
- **Event Name**: Decked Out Live with The Luv Gods at The Vineyard at Hershey
  - **Description**: The dance floor will be packed, so get here early!About this EventIt’s back and better than ever for our 14th Anniversary!! Decked-Out-Live comes back, with your favorite bands, some new ones, and never a repeat. Every Fr
  - **Venue**: The Vineyard at Hershey
  - **Banner**: https://cdn-az.allevents.in/events7/banners/82de715be6ce38ad4326d3ebd60f783a35e3399c3105b0c9aa23c3bb299b288d-rimg-w1170-h772-dc010103-gmir.jpg?v=1764617723
- **Event Name**: Airshow Tailgate
  - **Description**: ✈️ Experience the Thrill of the Skies! 🛩️

Join the City of Middletown and the Middletown Regional Airport for a family-friendly Airshow Tailgate! Enjoy front-row views of breathtaking loops, maneuvers, and aerial tricks.

🎟️ FREE Admission | Open to the
  - **Venue**: Middletown Regional Airport - MWO
  - **Banner**: https://cdn-az.allevents.in/events5/banners/4c59f2d3b82de033afd0e623aba985e655be42a65815123a8727d339539d5d4d-rimg-w1200-h675-dccacfc9-gmir?v=1784807090
- **Event Name**: NGHL Labor Day Challenge (AA)
  - **Description**: NGHL LABOR DAY CHALLENGE, Sept 4-6, 2026, Cromwell, CT Divisions: 12U, 14U, 16U, 19U AA. 
Predominantly CT, NJ, NY, MA teams. Est. 60-65 teams.
  - **Venue**: Connecticut
  - **Banner**: https://cdn-az.allevents.in/events7/banners/07a2eec352c8ca2eac82559ef3beb916b3c3cb748e655baab409c565ff854eb9-rimg-w1000-h1000-dcffffff-gmir?v=1785147820
- **Event Name**: AUSTRALIA’S THUNDER FROM DOWN UNDER
  - **Description**: Get ready for a night of high-energy entertainment as Australia’s Thunder From Down Under brings their Most Wanted 2026 Tour to town on Sunday, August 9.

Bonus Offer:
Every ticket includes $10 in Free Play valid on the day of the show.

Tickets here: htt
  - **Venue**: Twin Pine Casino & Hotel
  - **Banner**: https://cdn-az.allevents.in/events3/banners/8e4dac593ce1c4e3dc8e883fd3fb6b32ce7ee4075879f1e1d989440679ad1baa-rimg-w972-h834-dcc6a889-gmir?v=1785019170
- **Event Name**: NGHL Dawg Daze of Summer (AAA, AA)
  - **Description**: NGHL DAWG DAZE OF SUMMER, August 28-30, 2026 • Northford, CT • Divisions: 14U, 16U, 19U. 
Est. 70 teams from across the USA and eastern Canada.
  - **Venue**: Connecticut
  - **Banner**: https://cdn-az.allevents.in/events9/banners/91072d39166e759731b50d019acdc3ac71a44e46dbbd0522a3cb877894a83fdb-rimg-w1000-h1000-dcffffff-gmir?v=1785147832
- **Event Name**: Decked Out Live with Bump City at The Vineyard at Hershey
  - **Description**: The dance floor will be bumpin!About this EventIt’s back and better than ever for our 14th Anniversary!! Decked-Out-Live comes back, with your favorite bands, some new ones, and never a repeat. Every Friday evening, all s
  - **Venue**: The Vineyard at Hershey
  - **Banner**: https://cdn-az.allevents.in/events6/banners/63801df3be247b71439d4b8e74932dd856d626fb5657788c591bfa131e26b876-rimg-w1024-h611-dc040102-gmir.jpg?v=1764617658

## 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 July in Middletown](https://allevents.in/middletown/festivals--july)
- [Festivals Events in August in Middletown](https://allevents.in/middletown/festivals--august)

## FAQs

- **Q**: What are the top Festivals events in Middletown?
  - **A:** Middletown Heritage Festival 2026 (Sat Sep 26 2026 at 10:00 am at Middletown Heritage Festival), 2026 Frederick Family Shopping Festival (Fri Aug 21 2026 at 10:00 am at Middletown Park), 2026 Flower Festival at Summers Farm! (Sat Aug 22 2026 at 11:00 am at 7503 Hollow Road, Middletown, MD, United States, Maryland 21769), CrimeStery Fest 2026 (Fri, 09 Oct at 04:00 pm at DoubleTree by Hilton Hotel Boston North Shore, Ferncroft Road, Danvers, MA, USA), Stand Up Comedy Night at Cahoots Taproom and Arcade (Fri, 31 Jul at 07:00 pm at CAHOOTS by YAH Brew & Cartel).
- **Q**: What are the top free Festivals events in Middletown?
  - **A:** 2026 Frederick Family Shopping Festival (Fri Aug 21 2026 at 10:00 am at Middletown Park).
- **Q**: What Festivals events are happening in Middletown this weekend July 31–2, 2026?
  - **A:** Stand Up Comedy Night at Cahoots Taproom and Arcade (Fri, 31 Jul at 07:00 pm at CAHOOTS by YAH Brew & Cartel).
- **Q**: What Festivals events are happening in Middletown in July 2026?
  - **A:** Stand Up Comedy Night at Cahoots Taproom and Arcade (Fri, 31 Jul at 07:00 pm at CAHOOTS by YAH Brew & Cartel).
- **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 Middletown Heritage Festival, Middletown Park, 7503 Hollow Road, Middletown, MD, United States, Maryland 21769.
- **Q**: What is the price range for Festivals events in Middletown?
  - **A:** Prices for Festivals events in Middletown range from USD 18 to USD 90. Many events also offer free entry.
- **Q**: Who are the top organizers for Festivals events in Middletown?
  - **A:** Popular organizers hosting Festivals events in Middletown include Middletown Heritage Festival, Toronto Market Co., Summers Farm.
- **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

## Festivals from nearby cities

- [Festivals in Boonsboro](https://allevents.in/boonsboro/festivals)
- [Festivals in Frederick](https://allevents.in/frederick/festivals)
- [Festivals in Sharpsburg](https://allevents.in/sharpsburg-md/festivals)
- [Festivals in Fairplay](https://allevents.in/fairplay-md/festivals)
- [Festivals in Lovettsville](https://allevents.in/lovettsville/festivals)