# Events & Things To Do in Leonardtown in May 2026 | AllEvents - **Subtitle**: Find events and things to do in May 2026 in Leonardtown. Discover parties, concerts, meets, shows, sports, club, reunion, Performance happening in May 2026 in Leonardtown. - **Category**: May - **Display Name**: Events in May - **Type**: time_filter ## Audience - **Followers**: 1.1k+ - **Recent Followers**: - **Avatar 1**: https://cdn2.allevents.in/thumbs/attendeethumb689b208d2a182.png - **Avatar 2**: https://cdn2.allevents.in/transup/fe/dd6c34afa04838afcc0e34e7154a39/user-14.png - **Avatar 3**: https://cdn2.allevents.in/transup/37/ead652edca48399666fefbbee25262/user-50.png ## Featured Events - **Event Name**: 15th Annual Southern Maryland Hiring Event - JobSeeker Registration - **Description**: Exciting Opportunity Ahead! Join us at the 15th Annual Southern Maryland Hiring Event on May 21 2026 at the prestigious College of Southern Maryland in La Plata! ?Event D - **Date**: Thu, 21 May at 10:00 am – Thu, 21 May at 04:00 pm (-05:00) - **Event URL**: https://allevents.in/la-plata/15th-annual-southern-maryland-hiring-event-jobseeker-registration-tickets/80001809499502 - **Venue**: College of Southern Maryland - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4yLmFsbGV2ZW50cy5pbi90aHVtYnMvdGh1bWI2OTg2Mzg1MTkwZjY0LmpwZw.avif - **Price**: min: 0, max: 0, currency: USD - **Categories**: exhibitions, calendar, job-fairs - **Event Name**: 15th Annual Southern Maryland Hiring Event! - Business Registration - **Description**: **15th Annual Southern MD Hiring Event #TCCSMDGetHired** ?**Date:** May 21 2026**Time:** 10:00 AM**Venue:** College of Southern Maryland 8730 Mitchell Rd La Plata MD 20646 United States La Plata - **Date**: Thu, 21 May at 08:00 am – Thu, 21 May at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/la-plata/15th-annual-southern-maryland-hiring-event-business-registration-tickets/80001475785128 - **Venue**: College of Southern Maryland, Mitchell Road, La Plata, MD, USA - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4yLmFsbGV2ZW50cy5pbi90aHVtYnMvdGh1bWI2OTgzOGM4ZjcxYzQ3LmpwZw.avif - **Price**: min: 0, max: 1500, currency: USD - **Categories**: business, meet-and-greet, job-fairs ## About Wondering what to do on the weekend or on a not-so-fun night? We have all you need, discover all the happening events in May [YEAR] in [CITY] and find the best picks of yourself. Be it a theatre workshop, meditation class or an entertaining concert, there are a bunch of curated events in [CITY] in May [YEAR] for you. ## May 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**: 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 - **Interested Audience**: - Count: 1 - **Date**: Sat May 23 2026 at 10:00 am – Sun May 24 2026 at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/renfest-southern-maryland/100001981749677633 - **Venue**: Brüdergarten (Brü) - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy80MjVjOGRjNjg3ODMxNzcyOTE4NzA1NzE3MDZlOTQ4MjNiN2I4YTE5ODM0MDM2YTM0MjM5MjE5NzQ3NWU1ZWEwLXJpbWctdzEyMDAtaDgwMC1kY2Q5ZGZlYS1nbWlyLmpwZz92PTE3NzA4NjQ0ODc.avif - **Price**: USD 18 to 50 - **Categories**: music, entertainment, festivals, live-music, trips-adventures, music-festivals - **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**: 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 - **Interested Audience**: - Count: 4 - **Date**: Sat May 09 2026 at 08:00 am (-04:00) - **Event URL**: https://allevents.in/leonardtown/the-2026-smfca-smac-football-showcase/200029971737156 - **Venue**: Leonardtown High School - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9kMzg3YTY5Yzc3YjBjNjI0ZmEzNmJjMjZiZmM1NDY2MzkzY2JlMGMxYmYwYTliYWRkN2JiMzMxZWE4MzRkNWYwLXJpbWctdzEwODAtaDEzNTAtZGNhOGExOGYtZ21pcj92PTE3NzY4NDkyOTU.avif - **Categories**: sports, football, workshops, entertainment, business, conferences - **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* - **Interested Audience**: - Count: 2 - **Date**: Sun May 24 2026 at 10:00 am – Sun May 24 2026 at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/spin-it-again-at-renfest-southern-md/200029889793724 - **Venue**: Brudergarten Beer Garden at Shepherd’s Old Field Market - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8yOGMzMTRhNjM3YTA2YjEwOGQ3MDU3OTg4NjI4NzExZDU5NDg5YjEyMzk3OTc5MWRiZDI5ZTgxNTg4ZDVlYzcxLXJpbWctdzg2OS1oNDI1LWRjNTZiYmJkLWdtaXI_dj0xNzc1OTIxMTQ5.avif - **Categories**: music, entertainment, festivals, live-music, music-festivals, food-drinks, food-truck-festivals - **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 - **Date**: Mon May 11 2026 at 06:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/rabies-clinic-with-smawl-st-marys-fair-grounds/200029684902610 - **Venue**: St. Mary's County Fairgrounds - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy83OGJlMmQxMWFhZTUzODRlNTJmYjQ4ZGQ1YmRkZDI3MTdjZDRkYmJmMTIyN2ZlODYzYTcxNGZlYzAzMmExMDYzLXJpbWctdzEyMDAtaDYyOC1kY2ZmZmZmZi1nbWlyP3Y9MTc3NTIwMjE5MA.avif - **Categories**: health-wellness, dog - **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**: Momchella: Disco Cowgirl Day Party - **Description**: Okay but… Momchella?! 🪩💖🐄 The ultimate daytime party for the girls who deserve a BREAK 💅✨ Think: disco balls, pink cow print, cocktails, and main character energy 🗓 Saturday, May 16th ⏰ 12–4 PM @ The Rex More info coming soon 👀 Tag a friend! - **Interested Audience**: - Count: 201 - **Date**: Sat May 16 2026 at 12:00 pm – Sat May 16 2026 at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/momchella-disco-cowgirl-day-party/200029834720648 - **Venue**: 22695 Washington St, Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9iMDRiZmFjYWUyZjU4YmYyNjg2NmI2YmI2YWNiZDYwYjU1N2JkNTI0ZmJhOTY1Mjg3ZmFjNTgyODg1MjYzZDE1LXJpbWctdzEwMjQtaDE1MzYtZGNmMTc5YTQtZ21pcj92PTE3NzY3Mzc0NzQ.avif - **Categories**: parties, entertainment - **Event Name**: 2026 Fundraiser Event - Uncorked & Unveiled: Island Edition - **Description**: Purchase your ticket soon for our fundraiser event Uncorked & Unveiled: Island Edition, in benefit of our community programs, public art projects, scholarships, and more. A limited number of tickets are available for a donation of $100 each. This is - **Interested Audience**: - Count: 21 - **Date**: Thu May 21 2026 at 06:00 pm – Thu May 21 2026 at 09:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/2026-fundraiser-event-uncorked-and-unveiled-island-edition/200029971733836 - **Venue**: Port of Leonardtown Winery - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy81MmM0ZDBkZjhmMjI4MTZlM2NkOTVmNDRlMTg0NzdjZjUyYzE3OWY3NTQwNTFmNGJmOThiOTQxMjIwYTY5ZDkxLXJpbWctdzEyMDAtaDYyOC1kY2M1ZTdmOS1nbWlyP3Y9MTc3Njg0OTI3NQ.avif - **Categories**: nonprofit, contests, art, fine-arts - **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: 15 - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8wNjEyZjA0NDUwOGE4NDM3ZjQzOTE2MzNjYmY2YmUxNWViYWVhYWM5MzlhM2Q2Zjg4Mzg0MzFkYWIzNjg0NWY0LXJpbWctdzEwODAtaDEzNTAtZGNkOGQ5ZGEtZ21pcj92PTE3NzY0Mzc5MTc.avif - **Categories**: health-wellness, parties, entertainment - **Event Name**: Leonardtown Wharf Coastal Arts Market - **Description**: The Coastal Arts Market is an open-air market where local crafters, artists, and makers come to sell their products. All items are handcrafted. - **Interested Audience**: - Count: 61 - **Date**: Sat May 09 2026 at 09:00 am – Sat May 09 2026 at 03:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/leonardtown-wharf-coastal-arts-market/200029971734943 - **Venue**: 25500 Washington St. , Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy8wMDllZjM1N2I2MjBjMjNhOTdhOTAzMDgwZTA2ZDk5ZDViN2RiMDhkNTMxNzU0ZjVmNzRiZTFlNjUxYWZhN2Q0LXJpbWctdzEwMjQtaDEwMjQtZGNmMGYwZWYtZ21pcj92PTE3NzY4NDkyODM.avif - **Categories**: art - **Event Name**: MARYLAND - St. Mary's County Morning Meetup - **Description**: Join us at Wieck Community Playground for a morning meetup to connect moms in St. Mary’s County!About this EventHey MARYLAND MOMS — Join the Maryland Chamber of Mothers for a casual meet-up designed to bring together moms - **Date**: Sun May 17 2026 at 08:30 am – Sun May 17 2026 at 10:30 am (-04:00) - **Event URL**: https://allevents.in/leonardtown/maryland-st-marys-county-morning-meetup/100001987151308055 - **Venue**: Wieck Community Playground - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9hOTllN2Q5YjIzNDY2ODZmMDQ4NTcyZmI2YTNiNWEwZGYyOTYzOGY1ZmU1OWY3YjllM2QwZTNiMzY0Yjk5ZTFjLXJpbWctdzEyMDAtaDYwMC1kY2U3ZTZlMS1nbWlyLmpwZz92PTE3NzU4NjMwODU.avif - **Price**: Free - **Categories**: meetups, health-wellness - **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: 19 - **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_dj0xNzc1OTg1MTU3.avif - **Categories**: Festivals - **Event Name**: Mom's Day Out - **Description**: Bring your Mom's out for day of shopping!! We will have hanging baskets and assorted flower bouquets. There will be vendors there with crafts, apparel, desserts, jewelry and food. Accepting Vendors and 10x10 spaces are $40. Please message us for furth - **Interested Audience**: - Count: 78 - **Date**: Sat May 09 2026 at 09:30 am – Sat May 09 2026 at 04:30 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/moms-day-out/200028936341347 - **Venue**: Town Market LLC - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy85NDk0NDMxZDg4MDJmMzBkMjU0ZTgxZjBhN2RmNjFhNTFlNWNlZTcxMWMwNTIyOGE1NjQyMGI4NzY3MTA2ZTM0LXJpbWctdzEyMDAtaDY3NS1kYzc5NWQ0Ny1nbWlyP3Y9MTc3NTkzMjg1NQ.avif - **Categories**: shopping - **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 ## 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 May Events by Date - [May Events Today in Leonardtown](https://allevents.in/leonardtown/may--today) - [May Events This Weekend in Leonardtown](https://allevents.in/leonardtown/may--this-weekend) - [May Events in April in Leonardtown](https://allevents.in/leonardtown/may--april) - [May Events in May in Leonardtown](https://allevents.in/leonardtown/may--may) ## FAQs - **Q**: What are the top May 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), RenFest Southern Maryland (Sat May 23 2026 at 10:00 am at Brüdergarten (Brü)), SOMD SPRING FESTIVAL (Fri May 01 2026 at 05:00 pm at St. Mary's County Fairgrounds), The 2026 SMFCA - SMAC Football Showcase (Sat May 09 2026 at 08:00 am at Leonardtown High School), Spin It Again at RenFest Southern MD (Sun May 24 2026 at 10:00 am at Brudergarten Beer Garden at Shepherd’s Old Field Market). - **Q**: What are the top free May events in Leonardtown? - **A:** MARYLAND - St. Mary's County Morning Meetup (Sun May 17 2026 at 08:30 am at Wieck Community Playground), 15th Annual Southern Maryland Hiring Event - JobSeeker Registration (Thu, 21 May at 10:00 am at College of Southern Maryland). - **Q**: How can I find May events in Leonardtown? - **A:** You can discover upcoming May 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 May 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 May events in Leonardtown? - **A:** Some popular venues hosting May events in Leonardtown include The Rex, Brüdergarten (Brü), St. Mary's County Fairgrounds. - **Q**: What is the price range for May events in Leonardtown? - **A:** Prices for May events in Leonardtown range from USD 18 to USD 1,500. Many events also offer free entry. - **Q**: Who are the top organizers for May events in Leonardtown? - **A:** Popular organizers hosting May events in Leonardtown include The Rex | J&J Ent Group, Brudergarten Beer Garden, Epicurean Confections. - **Q**: Are there any online May events available? - **A:** Yes, many May 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 May events in Leonardtown? - **A:** Follow the May category on AllEvents.in to get notified when new May events are listed in Leonardtown. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/76/446ab5b8894647afc5dbe2e4aac27e/may.webp - **Mobile Banner**: https://cdn2.allevents.in/transup/90/8647e35ea145e785f95cbfaed96658/may.webp ## Events in May from nearby cities - [Events in May in Hollywood](https://allevents.in/hollywood-md/may) - [Events in May in California](https://allevents.in/california-md/may) - [Events in May in Callaway](https://allevents.in/callaway-md/may) - [Events in May in Great Mills](https://allevents.in/great-mills/may) - [Events in May in Lexington Park](https://allevents.in/lexington-park/may) - [Events in May in Solomons](https://allevents.in/solomons/may)