# Events & Things To Do in Leonardtown In September 2026 | AllEvents

- **Subtitle**: Find events and things to do in September 2026 in Leonardtown. Discover parties, concerts, meets, shows, sports, club, reunion, Performance happening in September 2026 in Leonardtown.
- **Category**: September
- **Display Name**: Events in September
- **Type**: time_filter

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- **Followers**: 2.4k+
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## About

Here’s your guide to all the happening concerts, festivals and events in September 2026 in [CITY]. Catch the best of everything that your city has to offer here. Right from the flea market events to all the festivals; the September [YEAR] events in [CITY] is all curated and sorted for you. Get going, buy your tickets and register to all the fun and exciting events already!

## September Events in Leonardtown

- **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
  - **Interested Audience**:
    - Count: 111
  - **Date**: Sat Sep 19 2026 at 03:00 pm – Sat Sep 19 2026 at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/outdoor-art-and-movie-night/200029807525640
  - **Venue**: Town Market LLC
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9jNzRjZTU3ZTQ3MTkzYzNlYTI0ZDllN2NkNTAzMjYxMzI4NTZlNjIxODE5Yjg1NjAzZDAwYjEwYjJmYTg2MzY5LXJpbWctdzEyMDAtaDY3NS1kY2ZmZmZmZi1nbWlyP3Y9MTc3NjI1MDc2OA.avif
  - **Categories**: entertainment, art
- **Event Name**: Vendors of Southern MD
  - **Description**: We are looking for vendors that want to come out and show off their best of crafts, glasswork, woodwork, antiques, jewelry, baked goods, salsa's, custom gifts and apparel.   We will have selections of Mums for sale to help you with your fall decorating.
  - **Interested Audience**:
    - Count: 56
  - **Date**: Sat Sep 12 2026 at 11:00 am – Sat Sep 12 2026 at 05:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/vendors-of-southern-md/200029083442159
  - **Venue**: Town Market LLC
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy84YmEyMTE5Y2U0ODE1MTI0YzI5NWEzYTE1ZDM1MDg1YmI3YzEyZWIwMDBkM2I1NmY2ZDMwOGMyZTg0YWNkMzNhLXJpbWctdzczNS1oNDkwLWRjZWRlZmY0LWdtaXI_dj0xNzc2MjgxMDU3.avif
  - **Categories**: sports, kids, contests, workshops, dance, entertainment, dog
- **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
  - **Date**: Tue Sep 08 2026 at 09:00 am – Fri Sep 11 2026 at 03:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/2026-sultana-adult-paddling-experience-st-marys-md/100001981367993004
  - **Venue**: The Inn at Leonardtown, Ascend Hotel Collection
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8xZGIwMDBhYTEyNmZlYTA1MTg0MDI1OWY2YTY0YmJiNDcwODBmZjhlMjcwZjU0MTg3NTZiMmUzYTM2ZDRmNjI2LXJpbWctdzEyMDAtaDU1NC1kYzVjNjI0Ni1nbWlyLmpwZz92PTE3NjkxMTU3Mjk.avif
  - **Price**: USD 1,592 to 1,800
  - **Categories**: trips-adventures
- **Event Name**: End of Summer Bash
  - **Description**: More details coming soon
  - **Interested Audience**:
    - Count: 1290
  - **Date**: Sat Sep 05 2026 at 05:00 pm – Sat Sep 05 2026 at 09:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/end-of-summer-bash/200029680477803
  - **Venue**: Leonardtown Wharf
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy81MGU0NzE5MTYxMGZjN2FlZDliNDY1YTg1ZGEwODBhMTVjZDc3MWZkM2I3YWU3MmJjYTc2ZDc1NTAzYjQwZGRmLXJpbWctdzEyMDAtaDE1NTMtZGM0NzhhZDgtZ21pcj92PTE3NzYxMzE3ODQ.avif
- **Event Name**: Fall Paw Crawl
  - **Description**: Fall Paw Crawl 2026
  - **Interested Audience**:
    - Count: 58
  - **Date**: Sun Sep 27 2026 at 12:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/fall-paw-crawl/200029526572044
  - **Venue**: 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650
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## Trending Events in Leonardtown

- **Event Name**: 40th Annual St Mary's County Crab and Music Festival
  - **Description**: Get ready to rock at the 40th Annual St. Mary's County Crab & Music Festival! 🦀🎶

📅 Date: Saturday, June 13, 2026
📍 Location: St. Mary's County Fairgrounds

Join us for an unforgettable day packed with delicious seafood, family fun, and electrifying l
  - **Venue**: St. Mary's County Fairgrounds
  - **Banner**: https://cdn-az.allevents.in/events9/banners/b1dca218be17b5d41948cc89b33d4ce57ea8ba199922920d29b743b1a0584bec-rimg-w909-h1159-dcffffff-gmir?v=1775997687
- **Event Name**: St. Mary’s Freedom Fest
  - **Description**: St. Mary’s Freedom Fest will be held Friday, July 3, 2026, marking America’s 250th anniversary 🇺🇸
Free admission • Fireworks at dark
  - **Venue**: St. Mary’s Freedom Fest
  - **Banner**: https://cdn-az.allevents.in/events1/banners/63a8b8fa022ba524aa470fae6d90c380d6c730c082722d01829c4e97c4d6babe-rimg-w1200-h1189-dc0557ac-gmir?v=1776219646
- **Event Name**: Yung Joc LIVE at The Rex — It's Goin' Down in Leonardtown
  - **Description**: Grammy-nominated rap legend Yung Joc headlines a LIVE night at The Rex with The Future Band & DJ Papers. May 2 · Leonardtown, MD.About this EventSouthern Maryland, the wait is over.May 2, 2026, The Rex The
  - **Venue**: The Rex
  - **Banner**: https://cdn-az.allevents.in/events10/banners/6ee9b456b0a851ed88430555c0a76c204582712fe98b119fb0d905b5a3c60e74-rimg-w1200-h1466-dc020101-gmir.jpg?v=1773749838
- **Event Name**: RenFest Southern Maryland
  - **Description**: An enchanted celebration of fun and feasting, live music and merriment, welcoming  mystical creatures and noble characters to play along!About this EventStep Back in Time at RenFest Southern Maryland, vote
  - **Venue**: Brüdergarten (Brü)
  - **Banner**: https://cdn-az.allevents.in/events1/banners/425c8dc68783177291870571706e94823b7b8a19834036a342392197475e5ea0-rimg-w1200-h800-dcd9dfea-gmir.jpg?v=1770864487
- **Event Name**: SOMD SPRING FESTIVAL
  - **Description**: Back for round two 🩷🩷 and sweeter than ever.

Epicurean Confections is returning to the 31st Annual SOMD Spring Festival and we’re bringing all your favorites (plus a few new indulgences you won’t want to miss). If you caught us last time, you already kno
  - **Venue**: St. Mary's County Fairgrounds
  - **Banner**: https://cdn-az.allevents.in/events1/banners/1d1072aedd42e5d3d20dc338b0c10d474d352cfbd1236a546d99b4b20d19547d-rimg-w1200-h1500-dcf8f6f1-gmir?v=1776849275
- **Event Name**: The 2026 SMFCA - SMAC Football Showcase
  - **Description**: Registration is now open for the 2026 SMFCA Southern Maryland Athletic Conference Football Showcase. Early registration closes April 19, so be sure to secure your spot today.

In past showcases, we’ve hosted 20+ college coaches on-site and shared particip
  - **Venue**: Leonardtown High School
  - **Banner**: https://cdn-az.allevents.in/events9/banners/d387a69c77b0c624fa36bc26bfc5466393cbe0c1bf0a9badd7bb331ea834d5f0-rimg-w1080-h1350-dca8a18f-gmir?v=1776849295
- **Event Name**: Spin It Again at RenFest Southern MD
  - **Description**: **SPONSORED BY BRUDERGARTEN BEER GARDEN**
Medieval and Renaissance Life Festival:
Live Music, demonstrations, vendors, food, drinks, petting zoo
*THIS IS A TICKETED EVENT! Please visit www.renfestsomd.com FOR FURTHER INFORMATION*
  - **Venue**: Brudergarten Beer Garden at Shepherd’s Old Field Market
  - **Banner**: https://cdn-az.allevents.in/events2/banners/28c314a637a06b108d7057988628711d59489b123979791dbd29e81588d5ec71-rimg-w869-h425-dc56bbbd-gmir?v=1775921149
- **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/events9/banners/78be2d11aae5384e52fb48dd5bddd2717cd4dbbf1227fe863a714fec032a1063-rimg-w1200-h628-dcffffff-gmir?v=1775202190
- **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-dcffffff-gmir?v=1776701360

## Browse September Events by Date

- [September Events Today in Leonardtown](https://allevents.in/leonardtown/september--today)
- [September Events This Weekend in Leonardtown](https://allevents.in/leonardtown/september--this-weekend)
- [September Events in April in Leonardtown](https://allevents.in/leonardtown/september--april)
- [September Events in May in Leonardtown](https://allevents.in/leonardtown/september--may)

## FAQs

- **Q**: What are the top September events in Leonardtown?
  - **A:** Outdoor Art & Movie Night (Sat Sep 19 2026 at 03:00 pm at Town Market LLC), Vendors of Southern MD (Sat Sep 12 2026 at 11:00 am at Town Market LLC), 2026 Sultana Adult Paddling Experience-St. Mary's, MD (Tue Sep 08 2026 at 09:00 am at The Inn at Leonardtown, Ascend Hotel Collection), End of Summer Bash (Sat Sep 05 2026 at 05:00 pm at Leonardtown Wharf), Fall Paw Crawl (Sun Sep 27 2026 at 12:00 pm at 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650).
- **Q**: How can I find September events in Leonardtown?
  - **A:** You can discover upcoming September 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 September 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 September events in Leonardtown?
  - **A:** Some popular venues hosting September events in Leonardtown include Town Market LLC, The Inn at Leonardtown, Ascend Hotel Collection, Leonardtown Wharf.
- **Q**: What is the price range for September events in Leonardtown?
  - **A:** Prices for September events in Leonardtown range from USD 1,592 to USD 1,800. Many events also offer free entry.
- **Q**: Who are the top organizers for September events in Leonardtown?
  - **A:** Popular organizers hosting September events in Leonardtown include Town of Leonardtown, Town Market LLC, Sultana Education Foundation Public Paddles.
- **Q**: Are there any online September events available?
  - **A:** Yes, many September 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 September events in Leonardtown?
  - **A:** Follow the September category on AllEvents.in to get notified when new September events are listed in Leonardtown.

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