# Festivals in Leonardtown 2026 | Culture & Street Fairs

- **Subtitle**: Your guide to festivals in Leonardtown 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

## About

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

- **Event Name**: St. Mary's County Fair - 2026
  - **Description**: St. Mary's County Fair for 2026
Please submit your items on Wednesday, 23 September 2026, from 1p-8p. 

*Important Note*: There should be a virtual system in place to submit your list of items this year! Please be on the lookout for this new entry method!
  - **Interested Audience**:
    - Count: 148
  - **Date**: Thu Sep 24 2026 at 04:00 pm – Sun Sep 27 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/st-marys-county-fair-2026/200030332835247
  - **Venue**: St Marys County Fair
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy80N2Y0M2ZhNmU1MGI2ZDkxZDE5ZGExNzVmYjQxOWI3ZjMxZDY2NDAxNzIxN2MxMGZmM2NkYzM2OGE0MWI2OTQyLXJpbWctdzEyMDAtaDY3NS1kYzU4YThlOC1nbWlyP3Y9MTc4NzcxOTM2OQ.avif
- **Event Name**: Blessing of the Fleet 2026
  - **Description**: Celebration honoring Southern Maryland Watermen's heritage and community - a family-friendly day with fireworks at 8 pm!
  - **Interested Audience**:
    - Count: 68
  - **Date**: Sat Oct 03 2026 at 12:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/blessing-of-the-fleet-2026/200030686915614
  - **Venue**: Leonardtown Wharf
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9hZjU4NGMwNjAyMmI0ZDg1MGI5MjdiMjU4ZTM1OWRkMzk0ODZhYmU3YzgwNjJmMjNkYTUzZWYwYjUzOGFkYmYzLXJpbWctdzEyMDAtaDEyMDAtZGNlOGU4ZDgtZ21pcj92PTE3ODkxNTEyMzQ.avif
- **Event Name**: 2026 First Friday Audience Participation Drum Circle
  - **Description**: Join us on First Fridays for our Audience Participation Drum Circle from 5 to 6 PM for the months of April, June, July, August, and September 2026!

(May & October drum circle events are 5 - 5:30 PM followed by a drumline performance from 5:30 - 6 PM.
  - **Date**: Fri Oct 02 2026 at 05:00 pm – Fri Oct 02 2026 at 05:30 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/2026-first-friday-audience-participation-drum-circle/200030668577832
  - **Venue**: 22660 Washington St., Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy8wNmIyNjMxODNlMDVhNTZlYmU4Y2Q5YzZmMWFmMjIyODYxMmQxYTIzMTg1YzhlYjVlYTY0NGI2OWU2YjNlZTFmLXJpbWctdzEyMDAtaDYyOC1kYzA4MDgwOC1nbWlyP3Y9MTc4ODc1NTA3Mg.avif
  - **Categories**: Art
- **Event Name**: Harry Potter Mystic Market & First Saturday of the Month
  - **Description**: See Town Market transform into Hogwarts.  Take on the quest to find all the Horcruxes. Come out and see us as we will have all types of mums, pumpkins, crafters, apparel, tumblers and desserts to shop from.  

Prize for Best Harry Potter Character Costume
  - **Interested Audience**:
    - Count: 251
  - **Date**: Sat Nov 07 2026 at 09:30 am – Sat Nov 07 2026 at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/leonardtown/harry-potter-mystic-market-and-first-saturday-of-the-month/200029882573109
  - **Venue**: 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy81MDQ5YjRhNTNhMmU0MjgxNDRiZDc3NTU4OTAzY2ZlYjI0MzU3M2JjMGEyYjk5ZDM3MTIwMDYwYjBlNjUzYTE5LXJpbWctdzEyMDAtaDY3NS1kYzA4MDgwOC1nbWlyP3Y9MTc4NzY2OTE2MQ.avif
- **Event Name**: Monster Mash Bash
  - **Description**: Application is now open share this event with your family and friends!
This is going to be a great event and we look forward to seeing you!

Email tamaramort6@gmail.com

We Like Unique One of a Kind Vendors, Traditional Vendors, Snacks & Food Vendors,
  - **Date**: Sat Oct 24 2026 at 08:00 am – Sun Oct 25 2026 at 11:00 am (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/monster-mash-bash/200030460773513
  - **Venue**: 22510 MD-326, Leonardtown, MD 20650-3898, United States
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9hODcyNzZlODMwZDgyNzY0OWMwYWZlMTYzYWViZWQzYzM5NmVlYTFiNTc5MjIxN2E2MDdjMTliYTNkMzZmZGRkLXJpbWctdzEyMDAtaDY3NS1kY2ZmZmZmZi1nbWlyP3Y9MTc4NTA4NTE1Mg.avif
  - **Categories**: food-drinks, health-wellness, Kids

## Trending Events in Leonardtown

- **Event Name**: St. Mary's County Fair - 2026
  - **Description**: St. Mary's County Fair for 2026
Please submit your items on Wednesday, 23 September 2026, from 1p-8p. 

*Important Note*: There should be a virtual system in place to submit your list of items this year! Please be on the lookout for this new entry method!
  - **Venue**: St Marys County Fair
  - **Banner**: https://cdn-az.allevents.in/events3/banners/47f43fa6e50b6d91d19da175fb419b7f31d664017217c10ff3cdc368a41b6942-rimg-w1200-h675-dc58a8e8-gmir?v=1787719369
- **Event Name**: Rabies Clinic with SMAWL @ St. Mary's Fair Grounds
  - **Description**: Low-Cost Vaccination Clinics
     St. Mary’s Animal Welfare League, in partnership with St. Mary’s County Health Department, offers monthly low-cost rabies and distemper vaccinations, as well as microchipping to the public for their cats and dogs.

    Th
  - **Venue**: St. Mary's County Fairgrounds
  - **Banner**: https://cdn-az.allevents.in/events2/banners/8855e8aea69ca35882bed536e7272a6cd3b71f701c9b5e2966c36ea85e48fce5-rimg-w1200-h628-dcf8f8f8-gmir?v=1787746344
- **Event Name**: Faire Witch: Ladies Night Out
  - **Description**: Grab your favorite witches and join us for an enchanting evening of sipping, shopping & all the spooky fall vibes. 

Think unique vendors, spooky-chic finds, seasonal cocktails, photo worthy moments, and a little bit of magic.

More details, vendors a
  - **Venue**: 22695 Washington St, Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-az.allevents.in/events7/banners/ea184d169e12ccb840141d5a56423fe5adf7b4714accb6c6f8d3ee4a11e52484-rimg-w1200-h500-dc080808-gmir?v=1787110447
- **Event Name**: 🎯 CORK FOR CUTIES🎯
  - **Description**: 🎯CORK FOR CUTIES EVENT🎯

We are excited to announce we are CORKING FOR CUTIES! Saturday, Sept. 26, 2026 at Action Lounge and Billiards 

All proceeds for this event will be donated to Clements cuties. 😃

Please save the date and hope to see you there to s
  - **Venue**: 25470 Point Lookout Rd Leonardtown md 20650
  - **Banner**: https://cdn-az.allevents.in/events8/banners/04748a17302c33164b6a3aa025ef437b1c039b11b1f1fa457ae2b7483b6b71e7-rimg-w1024-h1536-dc080808-gmir?v=1788387650
- **Event Name**: Jackson Perkins Live at the Rex Theatre
  - **Description**: 🇺🇸🎶 From serving our country to chasing his country music dream...

Join us at the Rex Theatre on Saturday, October 17 as rising country artist Jackson Perkins takes the stage! An active-duty U.S. Marine, Jackson is quickly making a name for himself with
  - **Venue**: 22695 Washington St, Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-az.allevents.in/events7/banners/c663a093134c4a93a18aaa6161f822af19d68908de4b0fdbd10f44931d09b816-rimg-w1200-h500-dc080808-gmir?v=1787325198
- **Event Name**: Monster Mash Bash
  - **Description**: Get ready for a fang-tastic night of Halloween fun at the Monster Mash Bash, where ghosts, goblins, and ghouls of all ages are invited to join the festivities! This Halloween extravaganza is packed with activities, treats, and entertainment that will make
  - **Venue**: Leonardtown Wharf
  - **Banner**: https://cdn-az.allevents.in/events6/banners/77b81da018d8c9a39be14504d288b5d0418ebc8d23e569370a8cf489502a5ca2-rimg-w1200-h675-dcf8f8f8-gmir?v=1787462192
- **Event Name**: The book fair
  - **Description**: Remember the excitement of walking into the elementary school book fair and carefully deciding which book to take home?About this EventJoin us for a nostalgic evening at The Book Fair Bash
  - **Venue**: Antoinette’s Garden
  - **Banner**: https://cdn-az.allevents.in/events4/banners/e73c4265bee166eeac12b2404f4066a1038d9969bccfbccd857350f642e7cfcc-rimg-w1024-h1536-dcf8e8d8-gmir.jpg?v=1787337915
- **Event Name**: Sins And Secrets After Dark
  - **Description**: Come dressed SEXY. Come dressed DIFFERENT. Come dressed to make somebody question their decisions…AFTER DARKAbout this EventSins And Secrets After DarkGet ready for a night full of mystery and excitement at
  - **Venue**: The Rex
  - **Banner**: https://cdn-az.allevents.in/events5/banners/8dd0c52d832749de26bad9b753a75b6013119cf8e7fcb5ba7134289c09064c2b-rimg-w1055-h1491-dc080808-gmir.jpg?v=1789688774
- **Event Name**: Blessing of the Fleet 2026
  - **Description**: Celebration honoring Southern Maryland Watermen's heritage and community - a family-friendly day with fireworks at 8 pm!
  - **Venue**: Leonardtown Wharf
  - **Banner**: https://cdn-az.allevents.in/events1/banners/af584c06022b4d850b927b258e359dd39486abe7c8062f23da53ef0b538adbf3-rimg-w1200-h1200-dce8e8d8-gmir?v=1789151234

## Browse Festivals Events by Date

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

## FAQs

- **Q**: What are the top Festivals events in Leonardtown?
  - **A:** St. Mary's County Fair - 2026 (Thu Sep 24 2026 at 04:00 pm at St Marys County Fair), Blessing of the Fleet 2026 (Sat Oct 03 2026 at 12:00 pm at Leonardtown Wharf), 2026 First Friday Audience Participation Drum Circle (Fri Oct 02 2026 at 05:00 pm at 22660 Washington St., Leonardtown, MD, United States, Maryland 20650), Harry Potter Mystic Market & First Saturday of the Month (Sat Nov 07 2026 at 09:30 am at 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD), Monster Mash Bash (Sat Oct 24 2026 at 08:00 am at 22510 MD-326, Leonardtown, MD 20650-3898, United States).
- **Q**: What Festivals events are happening in Leonardtown in September 2026?
  - **A:** St. Mary's County Fair - 2026 (Thu Sep 24 2026 at 04:00 pm at St Marys County Fair).
- **Q**: How can I find Festivals events in Leonardtown?
  - **A:** You can discover upcoming Festivals events in Leonardtown 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 Leonardtown?
  - **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 Leonardtown?
  - **A:** Some popular venues hosting Festivals events in Leonardtown include St Marys County Fair, Leonardtown Wharf, 22660 Washington St., Leonardtown, MD, United States, Maryland 20650.
- **Q**: Who are the top organizers for Festivals events in Leonardtown?
  - **A:** Popular organizers hosting Festivals events in Leonardtown include Blessing of the Fleet - Southern Maryland, St. Mary's County Arts Council, Town Market LLC.
- **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 Leonardtown?
  - **A:** Follow the Festivals category on AllEvents.in to get notified when new Festivals events are listed in Leonardtown.

## Category Banner

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

## Festivals from nearby cities

- [Festivals in Great Mills](https://allevents.in/great-mills/festivals)
- [Festivals in Lexington Park](https://allevents.in/lexington-park/festivals)
- [Festivals in Solomons](https://allevents.in/solomons/festivals)