# Events & Things To Do In Leonardtown This Weekend | May 1-3, 2026| AllEvents

- **Subtitle**: Leonardtown is a city full of experiences, activities and events. Explore some of the best things to do in Leonardtown this weekend and make your Friday, Saturday and Sunday full of fun and excitement.
- **Category**: Weekend
- **Display Name**: Events this weekend
- **Type**: time_filter

## Audience

- **Followers**: 20.7k+
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## About

Weekends become special if you know how to make the most out of it. There are a lot of fun things to do and events in [CITY] this weekend for you to explore.

Make your weekends memorable. Check out all upcoming weekend events in [CITY].

## Weekend Events in Leonardtown

- **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
  - **Date**: Sat May 02 2026 at 07:00 pm – Sat May 02 2026 at 11:30 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/yung-joc-live-at-the-rex-—-its-goin-down-in-leonardtown/100001985166701042
  - **Venue**: The Rex
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvNmVlOWI0NTZiMGE4NTFlZDg4NDMwNTU1YzBhNzZjMjA0NTgyNzEyZmU5OGIxMTlmYjBkOTA1YjVhM2M2MGU3NC1yaW1nLXcxMjAwLWgxNDY2LWRjMDIwMTAxLWdtaXIuanBnP3Y9MTc3Mzc0OTgzOA.avif
  - **Price**: USD 98 to 535
  - **Categories**: music, entertainment, live-music, art, theatre, concerts, parties, performances, workshops, dance
- **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
  - **Interested Audience**:
    - Count: 12
  - **Date**: Fri May 01 2026 at 05:00 pm – Sun May 03 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/somd-spring-festival/200029971733736
  - **Venue**: St. Mary's County Fairgrounds
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy8xZDEwNzJhZWRkNDJlNWQzZDIwZGMzMzhiMGMxMGQ0NzRkMzUyY2ZiZDEyMzZhNTQ2ZDk5YjRiMjBkMTk1NDdkLXJpbWctdzEyMDAtaDE1MDAtZGNmOGY2ZjEtZ21pcj92PTE3NzY4NDkyNzU.avif
  - **Categories**: festivals, spring-break
- **Event Name**: May First Friday - Butterfly Trail
  - **Description**: Kick off the magic of May First Friday with the relaunch of Leonardtown's Butterfly Trail! In Ltown Alley Parkette, explore nature and plant-themed vendors and exhibitors (Wild Ones Chesapeake Bay, St Mary's County Garden Club, and EcoBay Landscape), enjo
  - **Interested Audience**:
    - Count: 177
  - **Date**: Fri May 01 2026 at 05:00 pm – Fri May 01 2026 at 08:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/may-first-friday-butterfly-trail/200029968013908
  - **Venue**: 22698 Washington St, Leonardtown, MD 20650-3882, United States
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvMzUzMjc2YjZlZmM1MjE5ZWM4MmQyYTkxMzdiMTQ2ZTZhZmJlZTdhM2Y5ODhkODA2YjA2NjY4NGVjMjBiMzQ2NC1yaW1nLXcxMjAwLWgxNTUzLWRjZjBmNGYyLWdtaXI_dj0xNzc2NzM3NDY4.avif
  - **Categories**: first-friday, trips-adventures, music, live-music, entertainment
- **Event Name**: Rainbow Rollout
  - **Description**: 🛼 Join us Saturday, May 2nd, from 2:00–4:00 PM at Leonard Hall Recreation Center (Leonardtown, MD) for our Rainbow Rollout Roller Skating Party! This is a family-friendly event—bring your friends and roll with us!

🆓 Skate rentals are covered by PFLAG Sou
  - **Interested Audience**:
    - Count: 19
  - **Date**: Sat May 02 2026 at 02:00 pm – Sat May 02 2026 at 04:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/rainbow-rollout/200029889794426
  - **Venue**: Leonard Hall Rec Center
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8wNjEyZjA0NDUwOGE4NDM3ZjQzOTE2MzNjYmY2YmUxNWViYWVhYWM5MzlhM2Q2Zjg4Mzg0MzFkYWIzNjg0NWY0LXJpbWctdzEwODAtaDEzNTAtZGNkOGQ5ZGEtZ21pcj92PTE3NzcwOTk1MjY.avif
  - **Categories**: health-wellness, parties, entertainment
- **Event Name**: Southern MD Spring Festival Car Show
  - **Description**: Holy Face Church Annual Spring Festival Car Show, Awards, Music, Door Prizes with good food. May 2nd.  Rain Date Sunday May 3 2026
  - **Interested Audience**:
    - Count: 38
  - **Date**: Sat May 02 2026 at 10:30 am – Sat May 02 2026 at 04:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/southern-md-spring-festival-car-show/200029889896746
  - **Venue**: St. Mary's County Fairgrounds
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy83MjA4M2IxODVjNTdiMmIxNTRiYTAyYWU0Zjk1ZTBhZWU1ZGUyMjFkNjliMTAyZTY3MWM0MGUzMTZlZDJjNDZlLXJpbWctdzk2MC1oNzIwLWRjZmZmZmZmLWdtaXI_dj0xNzc3MTgwMTk3.avif
  - **Categories**: festivals, spring-break, car-shows, music-festivals
- **Event Name**: Vintage Yard Sale
  - **Description**: Vintage Yard Sale!!  If you are looking for some bargains and find some unique items stop by and see what we have.  

Perfect time to do some spring cleaning and make yourself some money.  We are accepting vendors as well as anyone that has yard sale item
  - **Interested Audience**:
    - Count: 168
  - **Date**: Sat May 02 2026 at 09:30 am (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/vintage-yard-sale/200029839119407
  - **Venue**: 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9lYjYzZWVkZWFhZmNhOGJiNDE1YzhjZDFkMGQ0YTljOWNmNTViYmMxNjA5NDE1Yjg1NWM2NzFmOTI5OWMzZTVlLXJpbWctdzQ3Mi1oNDIwLWRjNWI0NzJiLWdtaXI_dj0xNzc3MDkyMTUy.avif
- **Event Name**: The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours)
  - **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: 4
  - **Date**: Fri May 01 2026 at 10:00 am – Fri May 01 2026 at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/the-old-jail-museum-open-for-leonardtown-first-fridays-extended-hours/200029971734239
  - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9lOGRmZWI5YzEwY2ZjMzk5NmNlZDcyN2E4ZTFjMmJhMmU3ODM0NzQ2MDkwODYwNTkwYjk4OTQ0YTM4Y2Y4OWNkLXJpbWctdzEyMDAtaDkwMC1kYzM1NDYyOC1nbWlyP3Y9MTc3Njg0OTI3OQ.avif
  - **Categories**: art, literary-art, kids, first-friday
- **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 May 01 2026 at 05:30 pm – Fri May 01 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/2026-first-friday-drumline-events/200029889794930
  - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy81NmM0Mzk4ODQ2YTMyZWY2OGJhNzMwNGUzM2ZhMzhhYmQwNGViYzFiMDdiZGJhYTBjODVmNzdkNThkZDg1NzdiLXJpbWctdzEyMDAtaDYyOC1kYzE3MTgxNi1nbWlyP3Y9MTc3Njc1NzkzNg.avif
  - **Categories**: first-friday, art
- **Event Name**: La Casita the Narcisse Fashion Soft Opening.
  - **Description**: Welcome to La Casita De Narcisse Fashion, created to bring elegance, confidence, and modern style to Leonardtown and beyond.

I’m excited to invite you to our Soft Opening:

Feel free to stop by anytime between those hours—and please bring your family and
  - **Interested Audience**:
    - Count: 31
  - **Date**: Sat May 02 2026 at 11:00 am (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/la-casita-the-narcisse-fashion-soft-opening/200029971735347
  - **Venue**: 23432 Lindsay Dr, Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy8yODhiZTBjNTE2NWU0NmUxOGJlZWU5N2IyMjY5MjkyOWZhYzBlZTdjNDRjMGY3MDc1NGU1NTI4ZmFhZTdiNWMyLXJpbWctdzEyMDAtaDgwMC1kY2JmYWE5MC1nbWlyP3Y9MTc3Njg0OTI4Nw.avif
- **Event Name**: First Saturday of the Month Market Series
  - **Description**: First Saturday of the month we will have all types of crafters, apparel, tumblers and desserts to shop from.

Please message me us directly for further details to join.

Vendors Attending:
Bee-You-Tiful Bakes
JC's Kitchen
The Glided Whisk
Morning Star Bak
  - **Date**: Sat May 02 2026 at 09:00 am (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/first-saturday-of-the-month-market-series/200029509863001
  - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy8zNjk1NjUxODMzMzllNTIyNmRiMGEwYzQ3Y2QwZjcwODMwOWZjYTEyYTJlMzIxMDBiZWNlYWE4NzhkOGZlMTFkLXJpbWctdzEyMDAtaDY3NS1kY2YyZGZiZi1nbWlyP3Y9MTc3NzIzMzYyNw.avif
- **Event Name**: Stab & Gab @ Social Coffee
  - **Description**: Our usual meet-up except at a different location!

0900-1200 and we have a couple of tables booked in the party room (up the two stairs to the right with good lighting!). Order coffee and bring your lights!
  - **Interested Audience**:
    - Count: 9
  - **Date**: Sat May 02 2026 at 09:00 am – Sat May 02 2026 at 12:00 pm (-04:00)
  - **Event URL**: https://allevents.in/leonardtown/stab-and-gab-social-coffee/200029771048432
  - **Venue**: Social Coffeehouse
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy80NDQ1OGI1YjRmYTNjMzM4ZTkwMGM2ZjUwYWJjN2Y1ZGQxOTY4MDJjMWMzMjM5M2Q0Njg0Y2ViOWQxODJiODljLXJpbWctdzEyMDAtaDg5OS1kYzVmNDczMi1nbWlyP3Y9MTc3NjI4MDAzNw.avif
  - **Categories**: parties, entertainment

## 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=1777296221
- **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=1777163898
- **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=1777121437
- **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 Weekend Events by Date

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

## FAQs

- **Q**: What are the top Weekend events in Leonardtown?
  - **A:** Yung Joc LIVE at The Rex — It's Goin' Down in Leonardtown (Sat May 02 2026 at 07:00 pm at The Rex), SOMD SPRING FESTIVAL (Fri May 01 2026 at 05:00 pm at St. Mary's County Fairgrounds), May First Friday - Butterfly Trail (Fri May 01 2026 at 05:00 pm at 22698 Washington St, Leonardtown, MD 20650-3882, United States), Rainbow Rollout (Sat May 02 2026 at 02:00 pm at Leonard Hall Rec Center), Southern MD Spring Festival Car Show (Sat May 02 2026 at 10:30 am at St. Mary's County Fairgrounds).
- **Q**: What Weekend events are happening in Leonardtown this weekend May 1–3, 2026?
  - **A:** Yung Joc LIVE at The Rex — It's Goin' Down in Leonardtown (Sat May 02 2026 at 07:00 pm at The Rex), SOMD SPRING FESTIVAL (Fri May 01 2026 at 05:00 pm at St. Mary's County Fairgrounds), May First Friday - Butterfly Trail (Fri May 01 2026 at 05:00 pm at 22698 Washington St, Leonardtown, MD 20650-3882, United States), Rainbow Rollout (Sat May 02 2026 at 02:00 pm at Leonard Hall Rec Center), Southern MD Spring Festival Car Show (Sat May 02 2026 at 10:30 am at St. Mary's County Fairgrounds).
- **Q**: How can I find Weekend events in Leonardtown?
  - **A:** You can discover upcoming Weekend 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 Weekend 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 Weekend events in Leonardtown?
  - **A:** Some popular venues hosting Weekend events in Leonardtown include The Rex, St. Mary's County Fairgrounds, 22698 Washington St, Leonardtown, MD 20650-3882, United States.
- **Q**: What is the price range for Weekend events in Leonardtown?
  - **A:** Prices for Weekend events in Leonardtown range from USD 98 to USD 535. Many events also offer free entry.
- **Q**: Who are the top organizers for Weekend events in Leonardtown?
  - **A:** Popular organizers hosting Weekend events in Leonardtown include The Rex | J&J Ent Group, Epicurean Confections, Town of Leonardtown.
- **Q**: Are there any online Weekend events available?
  - **A:** Yes, many Weekend 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 Weekend events in Leonardtown?
  - **A:** Follow the Weekend category on AllEvents.in to get notified when new Weekend events are listed in Leonardtown.

## Category Banner

- **Banner Image**: https://cdn2.allevents.in/transup/01/bac113436441a783feaca7074943a8/this-weekend.webp

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