# 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

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## 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**: Arts & Entertainment Celebration First Friday
  - **Description**: Join us for a special First Friday in September, when we celebrate the anniversary of becoming the first Arts and Entertainment District in Southern Maryland. Enjoy live music, art activities & demonstrations, vendors and more! 
For more information,
  - **Interested Audience**:
    - Count: 69
  - **Date**: Fri Sep 04 2026 at 05:00 pm – Fri Sep 04 2026 at 08:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/arts-and-entertainment-celebration-first-friday/200030211797155
  - **Venue**: Leonardtown Square
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9mOWI0ZGJlZjdjMTBkMmJhNmNjZjBjYmFlYTQwYjFjOGNmY2JmM2JjZTFjMjFlMDhjYTExMjQ5MjliMDcyNDViLXJpbWctdzEyMDAtaDY3NS1kY2Y4ZjhmOC1nbWlyP3Y9MTc4NzE1Njk4OA.avif
  - **Categories**: Art, Music, Entertainment
- **Event Name**: 2026 Leonardtown Art Walk - First Friday Launch
  - **Description**: St. Mary’s County Arts Council and the Town of Leonardtown host an annual Art Walk every September. This event celebrates Leonardtown’s Arts & Entertainment District designation.

Local artists submit their work for display in businesses in the downt
  - **Date**: Fri Sep 04 2026 at 05:00 pm – Fri Sep 04 2026 at 08:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/2026-leonardtown-art-walk-first-friday-launch/200030578419750
  - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy84ZWI2YmMyNjliNjgwYjllY2IyNDQ3YmQ2ZGRiMTVlMmE5YTM5YmQzYzk3OWMwYWZlNzgyOWVhNDljODI4MzExLXJpbWctdzEyMDAtaDYyOC1kYzk4MThhOC1nbWlyP3Y9MTc4NzA2NzQ3MA.avif
  - **Categories**: Art, Contests
- **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: 147
  - **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: 196
  - **Date**: Sat Oct 03 2026 at 12:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/blessing-of-the-fleet-2026/200030429031706
  - **Venue**: Leonardtown Wharf
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy9kOGEzNWIwZmNkY2Q4MzNjYjlhNDg2NGI2ZDIxYmM2ZWM1N2YxYmI3OTg1Nzk2N2Q5YWZiYzIzNmMzZmMyN2UwLXJpbWctdzEyMDAtaDEyMDAtZGNlOGU4ZDgtZ21pcj92PTE3ODc4NDc3NjM.avif
- **Event Name**: The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours) (FREE)
  - **Description**: The Old Jail Museum, a popular landmark in the heart of Leonardtown, is open to the public during Leonardtown First Fridays for extended hours.

Come take a FREE tour of this unique and fascinating historic site while enjoying Leonardtown First Friday tha
  - **Interested Audience**:
    - Count: 13
  - **Date**: Fri Sep 04 2026 at 10:00 am – Fri Sep 04 2026 at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/the-old-jail-museum-open-for-leonardtown-first-fridays-extended-hours-free/200030332835349
  - **Venue**: 41625 Courthouse Dr, Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy81MzliYzI4MDRhMWU1OThiOWRlYzdlMzU1ODQyZmFlYWRiZDFlMGM5N2ZkZTc5OGFkNjMxZGI5ZWQyMmU0MTA0LXJpbWctdzEyMDAtaDYzNC1kY2M4ZDhmOC1nbWlyP3Y9MTc4NzI3MjExNQ.avif
  - **Categories**: art, literary-art, kids, first-friday
- **Event Name**: 5th Annual Walk for Recovery
  - **Description**: Join us for this free, family-friendly event to celebrate and support those in recovery!

Come walk, connect, and celebrate! This event will feature:
- Music & DJs
- Family Friendly Activities
- Lawn Games
- Face & Rock Painting
- FREE Naloxone/Na
  - **Interested Audience**:
    - Count: 27
  - **Date**: Sat Sep 19 2026 at 09:00 am – Sat Sep 19 2026 at 12:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/5th-annual-walk-for-recovery/200030554141223
  - **Venue**: Leonardtown Square
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy81ZmE5NmIxYmJjNmY1YzkzM2Q4MTIxM2E1NjIzYjI4N2Q2MWY3Njg2N2M5YzQyZjA3NzQ1ODY1ZDA4YTk1NTllLXJpbWctdzEyMDAtaDYwMC1kY2Y4ZjhmOC1nbWlyP3Y9MTc4NzYxNzc3MA.avif
  - **Categories**: workshops, health-wellness, art, fine-arts, virtual
- **Event Name**: 2026 First Friday Drumline Events
  - **Description**: Join us on May 1st and October 2nd from 5:30 to 6 PM for the 2026 First Friday youth drumline events!

Limited seating will be available. Bring a blanket or chair and join us for this FREE event!

The location is the grassy area adjacent to our office (by
  - **Interested Audience**:
    - Count: 2
  - **Date**: Fri Oct 02 2026 at 05:30 pm – Fri Oct 02 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/2026-first-friday-drumline-events/200030360864036
  - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy83OGI1YzY0NTllYTRmNmMwMWUxYzIyMmFkZTZiODdlMjY5OTI0MmEzNzYxMTMyYjU1MTJjOWI3ZDg2MDlkY2U5LXJpbWctdzEyMDAtaDYyOC1kY2Y4ZjhmOC1nbWlyP3Y9MTc4NzUzMDAyMA.avif
  - **Categories**: first-friday, 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**: Arts & Entertainment Celebration First Friday
  - **Description**: Join us for a special First Friday in September, when we celebrate the anniversary of becoming the first Arts and Entertainment District in Southern Maryland. Enjoy live music, art activities & demonstrations, vendors and more! 
For more information,
  - **Venue**: Leonardtown Square
  - **Banner**: https://cdn-az.allevents.in/events7/banners/f9b4dbef7c10d2ba6ccf0cbaea40b1c8cfcbf3bce1c21e08ca1124929b07245b-rimg-w1200-h675-dcf8f8f8-gmir?v=1787156988
- **Event Name**: 2026 Leonardtown Art Walk - First Friday Launch
  - **Description**: St. Mary’s County Arts Council and the Town of Leonardtown host an annual Art Walk every September. This event celebrates Leonardtown’s Arts & Entertainment District designation.

Local artists submit their work for display in businesses in the downt
  - **Venue**: 22660 Washington St., Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-az.allevents.in/events6/banners/8eb6bc269b680b9ecb2447bd6ddb15e2a9a39bd3c979c0afe7829ea49c828311-rimg-w1200-h628-dc9818a8-gmir?v=1787067470
- **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**: The Joe Cox Band LIVE @ The Rex Theatre
  - **Description**: One Night. One Stage. All Country. 🎶

Country music is coming to The Rex, and you won’t want to miss it.
Join the Joe Cox Band on Saturday, August 29 from 7:00–10:00 PM for three hours of live country music 🤠, southern rock 🎸, and crowd-favorite singalong
  - **Venue**: 22695 Washington St, Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-az.allevents.in/events2/banners/f6c47415231eb601583ea2448dd857f8c019cb8d9014625496a5602237728b2f-rimg-w1200-h1578-dc080808-gmir?v=1787185168
- **Event Name**: 2026 Sultana Adult Paddling Experience-St. Mary's, MD
  - **Description**: Join the experienced staff of the Sultana Education Foundation for this four day kayaking expedition based from the Inn at Leonardtown.About this EventJoin the experienced staff of the Sultana Education Foundation for thi
  - **Venue**: The Inn at Leonardtown, Ascend Hotel Collection
  - **Banner**: https://cdn-az.allevents.in/events2/banners/1db000aa126fea051840259f6a64bbb47080ff8e270f5418756b2e3a36d4f626-rimg-w1200-h554-dc5c6246-gmir.jpg?v=1769115729
- **Event Name**: Outdoor Art & Movie Night
  - **Description**: Enjoy a magical evening under the stars with a free outdoor movie at the Town Market! Plus, we’ll have sidewalk chalk and art activities to participate in before the move starts! Grab your blanket or lawn chair, relax, and watch a family-friendly film (TB
  - **Venue**: Town Market LLC
  - **Banner**: https://cdn-az.allevents.in/events7/banners/c74ce57e47193c3ea24d9e7cd50326132856e621819b85603d00b10b2fa86369-rimg-w1200-h675-dcf8f8f8-gmir?v=1787458096
- **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/events5/banners/d8a35b0fcdcd833cb9a4864b6d21bc6ec57f1bb79857967d9afbc236c3fc27e0-rimg-w1200-h1200-dce8e8d8-gmir?v=1787847763
- **Event Name**: Weekly Sound Reset
  - **Description**: A weekly Crystal Bowl Sound bath every Monday evening. Let your stress melt away while laying in a hammock or special lounge.About this EventJoin us for a transformative sound bath each week, where no two sessions are the
  - **Venue**: 22660 Washington St
  - **Banner**: https://cdn-az.allevents.in/events4/banners/8848b5a1c5cc34c9adca8ced307dd4102cf4e65af57517a8079623d90ea29b82-rimg-w1200-h1362-dc050404-gmir.jpg?v=1783361735
- **Event Name**: EllaChella Day Party!
  - **Description**: 🌼 ELLACHELLA 🌼

Calling all Ella Fellas & Ella Bella’s — this one’s for YOU. 🤠💋

We’re turning The Rex Theatre into an all-out Ella Langley day party for ELLA CHELLA on Saturday, September 19th from 12–4 PM!

And the timing couldn’t be better… 🍺🌼 We’r
  - **Venue**: 22695 Washington St, Leonardtown, MD
  - **Banner**: https://cdn-az.allevents.in/events4/banners/069afd49572f581964eb47a0a0543bf9e28e9ff36502ed05fdbd941b38f825d4-rimg-w1054-h1492-dc080808-gmir?v=1785647565

## 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 August in Leonardtown](https://allevents.in/leonardtown/festivals--august)
- [Festivals Events in September in Leonardtown](https://allevents.in/leonardtown/festivals--september)

## FAQs

- **Q**: What are the top Festivals events in Leonardtown?
  - **A:** Arts & Entertainment Celebration First Friday (Fri Sep 04 2026 at 05:00 pm at Leonardtown Square), 2026 Leonardtown Art Walk - First Friday Launch (Fri Sep 04 2026 at 05:00 pm at 22660 Washington St., Leonardtown, MD, United States, Maryland 20650), 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), The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours) (FREE) (Fri Sep 04 2026 at 10:00 am at 41625 Courthouse Dr, Leonardtown, MD, United States, Maryland 20650).
- **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 Leonardtown Square, 22660 Washington St., Leonardtown, MD, United States, Maryland 20650, St Marys County Fair.
- **Q**: Who are the top organizers for Festivals events in Leonardtown?
  - **A:** Popular organizers hosting Festivals events in Leonardtown include Town of Leonardtown, St. Mary's County Arts Council, Blessing of the Fleet - Southern Maryland.
- **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

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