# All Events in Leonardtown - **City**: Leonardtown - **State**: Maryland - **Country**: United States - **Continent**: North America - **Timezone**: -05:00 - **Currency**: USD - **Banner**: https://cdn2.allevents.in/transup/4a/3eb947ce48417e9f724bc0a3c8a200/USA-default.webp ## Featured Events in Leonardtown - **Event Name**: St. Mary's County Job Fair 2026- Jobseeker Registration - **Description**: Looking for your next career move? Don't miss out on the upcoming St. Mary's County, Maryland, Job Fair, taking place on Wednesday, September 2nd, from 9:30 AM to 1 PM. Over 50 BusinessesVariety of Job Opportunities - **Date**: Wed, 02 Sep at 09:30 am – Wed, 02 Sep at 01:00 pm (-05:00) - **Event URL**: https://allevents.in/california/st-marys-county-job-fair-2026-jobseeker-registration-tickets/80003103346473 - **Venue**: USMSM Smart Builing - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4yLmFsbGV2ZW50cy5pbi90aHVtYnMvdGh1bWI2YTU5M2RlZWJlNzZhLmpwZw.avif - **Price**: min: 0, max: 0, currency: USD - **Categories**: job-fairs - **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, 08 Sep at 09:00 am – Fri, 11 Sep 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:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8xZGIwMDBhYTEyNmZlYTA1MTg0MDI1OWY2YTY0YmJiNDcwODBmZjhlMjcwZjU0MTg3NTZiMmUzYTM2ZDRmNjI2LXJpbWctdzEyMDAtaDU1NC1kYzVjNjI0Ni1nbWlyLmpwZz92PTE3NjkxMTU3Mjk.avif - **Price**: min: 1591.59, max: 1800, currency: USD - **Categories**: fitness, trips-adventures ## Leonardtown's Most-Loved ### Events Categories - [Music (9 events)](https://allevents.in/leonardtown/music) - [Parties (26 events)](https://allevents.in/leonardtown/parties) - [Food & Drinks (12 events)](https://allevents.in/leonardtown/food-drinks) - [Crafts (8 events)](https://allevents.in/leonardtown/crafts) - [Festivals (14 events)](https://allevents.in/leonardtown/festivals) - [Health & Wellness (15 events)](https://allevents.in/leonardtown/health-wellness) - [Kids (22 events)](https://allevents.in/leonardtown/kids) - [Performances (12 events)](https://allevents.in/leonardtown/performances) - [Sports (7 events)](https://allevents.in/leonardtown/sports) - [Theatre (5 events)](https://allevents.in/leonardtown/theatre) - [Fine Arts (4 events)](https://allevents.in/leonardtown/fine-arts) - [Trips & Adventure (4 events)](https://allevents.in/leonardtown/trips-adventures) - [Dance (2 events)](https://allevents.in/leonardtown/dance) ## Popular 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, 04 Sep at 05:00 pm – Fri, 04 Sep 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, 04 Sep at 05:00 pm – Fri, 04 Sep 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, 24 Sep at 04:00 pm – Sun, 27 Sep 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**: 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 - **Interested Audience**: - Count: 28 - **Date**: Sat, 29 Aug at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/the-joe-cox-band-live-the-rex-theatre/200030384428756 - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9mNmM0NzQxNTIzMWViNjAxNTgzZWEyNDQ4ZGQ4NTdmOGMwMTljYjhkOTAxNDYyNTQ5NmE1NjAyMjM3NzI4YjJmLXJpbWctdzEyMDAtaDE1NzgtZGMwODA4MDgtZ21pcj92PTE3ODcxODUxNjg.avif - **Categories**: music, art, theatre, entertainment, country-music-festivals - **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, 08 Sep at 09:00 am – Fri, 11 Sep 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**: fitness, trips-adventures - **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: 286 - **Date**: Sat, 19 Sep at 03:00 pm – Sat, 19 Sep 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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9jNzRjZTU3ZTQ3MTkzYzNlYTI0ZDllN2NkNTAzMjYxMzI4NTZlNjIxODE5Yjg1NjAzZDAwYjEwYjJmYTg2MzY5LXJpbWctdzEyMDAtaDY3NS1kY2Y4ZjhmOC1nbWlyP3Y9MTc4NzQ1ODA5Ng.avif - **Categories**: entertainment, art - **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, 03 Oct 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**: 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 - **Date**: Sat, 19 Sep at 12:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/ellachella-day-party/200030495130345 - **Venue**: 22695 Washington St, Leonardtown, MD - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy8wNjlhZmQ0OTU3MmY1ODE5NjRlYjQ3YTBhMDU0M2JmOWUyOGU5ZmYzNjUwMmVkMDVmZGJkOTQxYjM4ZjgyNWQ0LXJpbWctdzEwNTQtaDE0OTItZGMwODA4MDgtZ21pcj92PTE3ODU2NDc1NjU.avif - **Categories**: Art, Theatre, Music - **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: 261 - **Date**: Sat, 12 Sep at 11:00 am – Sat, 12 Sep 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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy84YmEyMTE5Y2U0ODE1MTI0YzI5NWEzYTE1ZDM1MDg1YmI3YzEyZWIwMDBkM2I1NmY2ZDMwOGMyZTg0YWNkMzNhLXJpbWctdzczNS1oNDkwLWRjZThlOGY4LWdtaXI_dj0xNzg3MzI1MjA1.avif - **Categories**: sports, kids, workshops, dance, entertainment, dog, contests - **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 - **Date**: Mon, 31 Aug (-04:00) - **Event URL**: https://allevents.in/leonardtown/weekly-sound-reset/100001993298682016 - **Venue**: 22660 Washington St - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy84ODQ4YjVhMWM1Y2MzNGM5YWRjYThjZWQzMDdkZDQxMDJjZjRlNjVhZjU3NTE3YTgwNzk2MjNkOTBlYTI5YjgyLXJpbWctdzEyMDAtaDEzNjItZGMwNTA0MDQtZ21pci5qcGc_dj0xNzgzMzYxNzM1.avif - **Price**: USD 25 to 45 - **Categories**: meetups, art - **Event Name**: Senator Jack Bailey’s 5th Annual Bull Roast - **Description**: I am excited to announce my 5th Annual Bull Roast is honoring Cruisin’ Southern Maryland. Since 2012, they have raised over $255,000 for the Charlotte Hall Veterans Home and $65,000 to other local charities for the benefit of veterans. Their events span 1 - **Interested Audience**: - Count: 16 - **Date**: Thu, 10 Sep at 05:00 pm – Thu, 10 Sep at 09:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/senator-jack-baileys-5th-annual-bull-roast/200030552859556 - **Venue**: Olde Breton Inn and Bailey's Catering - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy8wZTBmMDcwY2U0MDE0ZWU2YWZjN2FmNWZjMzRjMzRmYWQyNmI4ODAwYTJiNWRlZGFiMjYwN2RjNTFmYzhjNmJkLXJpbWctdzk0Mi1oMjA0OC1kYzA4MDgwOC1nbWlyP3Y9MTc4NzQ1NjE3OA.avif - **Categories**: nonprofit, charities - **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, 04 Sep at 10:00 am – Fri, 04 Sep 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**: One Million Oysters for Breton Bay - **Description**: Show your support for a cleaner, more vibrant, and healthier Breton Bay by joining us on September 12th! Saturday, September 12, 2026, at 10 am, join the St. Mary’s River Watershed Association and Friends of St. Clements Bay at Abell’s Wharf to plant a m - **Interested Audience**: - Count: 32 - **Date**: Sat, 12 Sep at 10:00 am (-04:00) - **Event URL**: https://allevents.in/leonardtown/one-million-oysters-for-breton-bay/200030122442221 - **Venue**: Abells Wharf Rd, Leonardtown, MD 20650, United States - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy8wYjQ4N2Q0OTViMzIzYjQ4M2M3Y2VkYWJlNjdjODg2NThiM2U4NTRkOGZmODM3YWRlNGMwYzVkNjE2NTk0MzY5LXJpbWctdzEyMDAtaDkwMC1kYzM4NzhjOC1nbWlyP3Y9MTc4NzMyNTE5OQ.avif - **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 - **Interested Audience**: - Count: 19 - **Date**: Mon, 12 Oct at 06:00 pm – Mon, 12 Oct at 08:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/rabies-clinic-with-smawl-st-marys-fair-grounds/200030494481946 - **Venue**: St. Mary's County Fairgrounds - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy84ODU1ZThhZWE2OWNhMzU4ODJiZWQ1MzZlNzI3MmE2Y2QzYjcxZjcwMWM5YjVlMjk2NmMzNmVhODVlNDhmY2U1LXJpbWctdzEyMDAtaDYyOC1kY2Y4ZjhmOC1nbWlyP3Y9MTc4Nzc0NjM0NA.avif - **Categories**: dog, health-wellness - **Event Name**: End of Summer Bash - **Description**: More details coming soon - **Interested Audience**: - Count: 3442 - **Date**: Sat, 05 Sep at 05:00 pm – Sat, 05 Sep 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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy81MGU0NzE5MTYxMGZjN2FlZDliNDY1YTg1ZGEwODBhMTVjZDc3MWZkM2I3YWU3MmJjYTc2ZDc1NTAzYjQwZGRmLXJpbWctdzEyMDAtaDE1NTMtZGMwODI4NTgtZ21pcj92PTE3ODc0NjIxOTM.avif - **Event Name**: Senator Jack Bailey’s Golf Tournament - **Description**: Please join me at my annual Golf Tournament! Tickets are available at the link above and senatorbailey.com - **Interested Audience**: - Count: 16 - **Date**: Thu, 10 Sep at 09:30 am (-04:00) - **Event URL**: https://allevents.in/leonardtown/senator-jack-baileys-golf-tournament/200030552850928 - **Venue**: Breton Bay Golf & Country Club - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy84NTM3ZGY3OGM5NWYzYTQ3NjkwNTQxNWNkMTMyZGIyZTZjYjA1MWU1NjliNTFiYTljYWRiMzJlZGUwNTAzOTdkLXJpbWctdzExNzEtaDE1MjktZGNmOGY4ZjgtZ21pcj92PTE3ODc0NTIwOTA.avif - **Categories**: Sports - **Event Name**: Kitten And Cantrips - **Description**: Kittens & Cantrips is a whimsical Level 3 Obojima one-shot where cozy adventure meets magical mischief—all in support of a great cause! Join us at the cat café for an unforgettable afternoon of charming characters, curious critters, and heartwarming h - **Interested Audience**: - Count: 68 - **Date**: Sun, 06 Sep at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/kitten-and-cantrips/200030548086027 - **Venue**: Meow Dyer Cat Cafe, LLC - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy9lNGRkMWI5MDY4ZWE0YzIzYTU5NTZiYTljNDRiMDI3NDYwMTVkNDA4YzFmYWI3Njg1Y2U1MjkyMzc2YTU5MjVjLXJpbWctdzEwODAtaDEzNTAtZGNlOGU4ZTgtZ21pcj92PTE3ODczOTI0NzQ.avif - **Categories**: Nonprofit, trips-adventures - **Event Name**: Cars & Coffee Car Show - **Description**: Come out and see some amazing cars. Enjoy the day out with some friends. 50/50 Raffle Door Prizes Corn Hole Music Please direct message us to become a vendor and spaces are 10x10 Attending: Sweet Tea & 3D Prints - **Interested Audience**: - Count: 15 - **Date**: Sun, 06 Sep at 10:00 am – Sun, 06 Sep at 02:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/cars-and-coffee-car-show/200030211798058 - **Venue**: 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9iM2U3ZjY0MTA3MGQwNDJkYjIzMmZhMTU3NjRkM2E5OWM3MDhkZTFhZmU0ODJlOTA2YzAxYTM2YTE3MWJiYjA4LXJpbWctdzEyMDAtaDE1NzEtZGNmOGU4ZDgtZ21pcj92PTE3ODczMTgxNjQ.avif - **Categories**: car-shows ## Parties in Leonardtown - **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 - **Date**: Sat, 19 Sep at 12:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/ellachella-day-party/200030495130345 - **Venue**: 22695 Washington St, Leonardtown, MD - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy8wNjlhZmQ0OTU3MmY1ODE5NjRlYjQ3YTBhMDU0M2JmOWUyOGU5ZmYzNjUwMmVkMDVmZGJkOTQxYjM4ZjgyNWQ0LXJpbWctdzEwNTQtaDE0OTItZGMwODA4MDgtZ21pcj92PTE3ODU2NDc1NjU.avif - **Categories**: Art, Theatre, Music - **Event Name**: Senator Jack Bailey’s 5th Annual Bull Roast - **Description**: I am excited to announce my 5th Annual Bull Roast is honoring Cruisin’ Southern Maryland. Since 2012, they have raised over $255,000 for the Charlotte Hall Veterans Home and $65,000 to other local charities for the benefit of veterans. Their events span 1 - **Interested Audience**: - Count: 16 - **Date**: Thu, 10 Sep at 05:00 pm – Thu, 10 Sep at 09:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/senator-jack-baileys-5th-annual-bull-roast/200030552859556 - **Venue**: Olde Breton Inn and Bailey's Catering - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy8wZTBmMDcwY2U0MDE0ZWU2YWZjN2FmNWZjMzRjMzRmYWQyNmI4ODAwYTJiNWRlZGFiMjYwN2RjNTFmYzhjNmJkLXJpbWctdzk0Mi1oMjA0OC1kYzA4MDgwOC1nbWlyP3Y9MTc4NzQ1NjE3OA.avif - **Categories**: nonprofit, charities - **Event Name**: End of Summer Bash - **Description**: More details coming soon - **Interested Audience**: - Count: 3442 - **Date**: Sat, 05 Sep at 05:00 pm – Sat, 05 Sep 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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy81MGU0NzE5MTYxMGZjN2FlZDliNDY1YTg1ZGEwODBhMTVjZDc3MWZkM2I3YWU3MmJjYTc2ZDc1NTAzYjQwZGRmLXJpbWctdzEyMDAtaDE1NTMtZGMwODI4NTgtZ21pcj92PTE3ODc0NjIxOTM.avif - **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 - **Interested Audience**: - Count: 2322 - **Date**: Sat, 24 Oct at 01:00 pm – Sat, 24 Oct at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/monster-mash-bash/200029807526150 - **Venue**: Leonardtown Wharf - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy83N2I4MWRhMDE4ZDhjOWEzOWJlMTQ1MDRkMjg4YjVkMDQxOGViYzhkMjNlNTY5MzcwYThjZjQ4OTUwMmE1Y2EyLXJpbWctdzEyMDAtaDY3NS1kY2Y4ZjhmOC1nbWlyP3Y9MTc4NzQ2MjE5Mg.avif - **Categories**: halloween - **Event Name**: Trunk or Treat & Vendor Show - **Description**: Come on over for Trunk or Treat starting at 12 Noon. We will have the classic cars all set up and ready to give out candy to all the little ghouls, goblins and monsters. Crafters and Food vendor will be onsite beginning at 9am. Vendors Attending: Po - **Interested Audience**: - Count: 88 - **Date**: Sat, 24 Oct at 12:00 pm – Sat, 24 Oct at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/trunk-or-treat-and-vendor-show/200029527918023 - **Venue**: Town Market LLC - **Banner**: https://dyn-image.allevents.in/generate-image?v=4&title=Trunk+or+Treat+%26+Vendor+Show&date=Sat%2C+24+Oct+at+12%3A00+pm&bg=4 - **Categories**: trunk-or-treat, halloween, trick-or-treat - **Event Name**: Stab & Gab - August 2026 - **Description**: Stab & Gab end of summer edition. Come cool down with the coolest cats around! - **Interested Audience**: - Count: 21 - **Date**: Sat, 29 Aug at 09:00 am – Sat, 29 Aug at 12:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/stab-and-gab-august-2026/200030170653611 - **Venue**: Leonardtown Library - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9lZTAyOWRkMTQ2N2RhOGM1YTkxNzBlMjZhNTE1Y2E0ZjZiYTQ0NTYzODFiZmZiMmVmODcxMGE5MGVlNGFiZjhiLXJpbWctdzEyMDAtaDY3NS1kYzM4MzgzOC1nbWlyP3Y9MTc4Nzg5MjYzMQ.avif - [View all Parties in Leonardtown](https://allevents.in/leonardtown/parties) ## Artists & Performers on Tour in Leonardtown - **Artist**: Gorillaz - **Artist Page**: https://allevents.in/performer/gorillaz - **Artist**: Kany García - **Artist Page**: https://allevents.in/performer/kany-garc-a - **Artist**: Rahat Fateh Ali Khan - **Artist Page**: https://allevents.in/performer/rahat-fateh-ali-khan - **Artist**: Air Supply - **Artist Page**: https://allevents.in/performer/air-supply - **Artist**: Beck - **Artist Page**: https://allevents.in/performer/beck - **Artist**: Rush - **Artist Page**: https://allevents.in/performer/rush - **Artist**: Flex - **Artist Page**: https://allevents.in/performer/flex - **Artist**: Beartooth - **Artist Page**: https://allevents.in/performer/beartooth - **Artist**: Cooper Alan - **Artist Page**: https://allevents.in/performer/cooper-alan - **Artist**: Struggle Jennings - **Artist Page**: https://allevents.in/performer/struggle-jennings - **Artist**: The Spinners - **Artist Page**: https://allevents.in/performer/the-spinners - **Artist**: Arlo Parks - **Artist Page**: https://allevents.in/performer/arlo-parks - **Artist**: Tasha Cobbs Leonard - **Artist Page**: https://allevents.in/performer/tasha-cobbs-leonard - **Artist**: Colt Ford - **Artist Page**: https://allevents.in/performer/colt-ford - **Artist**: The Roots - **Artist Page**: https://allevents.in/performer/the-roots - **Artist**: Yaya Bey - **Artist Page**: https://allevents.in/performer/yaya-bey - **Artist**: Colin Hay - **Artist Page**: https://allevents.in/performer/colin-hay - **Artist**: Epik High - **Artist Page**: https://allevents.in/performer/epik-high - **Artist**: Inayah - **Artist Page**: https://allevents.in/performer/inayah - **Artist**: Scarface - **Artist Page**: https://allevents.in/performer/scarface - **Artist**: Athena - **Artist Page**: https://allevents.in/performer/athena - **Artist**: MARO - **Artist Page**: https://allevents.in/performer/maro - **Artist**: Cortex - **Artist Page**: https://allevents.in/performer/cortex - **Artist**: William Black - **Artist Page**: https://allevents.in/performer/william-black - **Artist**: Michael Ray - **Artist Page**: https://allevents.in/performer/michael-ray - (more artists omitted) ## Browse Events in Leonardtown by Date - [Events Today in Leonardtown](https://allevents.in/leonardtown/today) - [Events This Weekend in Leonardtown](https://allevents.in/leonardtown/this-weekend) - [Events in August 2026 in Leonardtown](https://allevents.in/leonardtown/august) - [Events in September 2026 in Leonardtown](https://allevents.in/leonardtown/september) ## Moments from Events in Leonardtown - **Review**: "Thank you all that came out" - **Rating**: 5/5 - **By**: Macathure Vixama - **Event**: Fullyfocusedmgnt & burna brothers presents RUBEE stone at Wavy lounge - **Date**: 2026-08-28 12:03:13 - **Photo**: https://cdn2.allevents.in/transup/ce/12c5952fd14d03adb7957118609576/images/FullSizeRender.webp - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocLM4056PcRumUhtT4O2WuXuT3ELJsbRI4CSOlscTzQr-FL7nqc=s96-c?sz=200 - **Review**: "Great band ; very talented" - **Rating**: 5/5 - **By**: Doug Goerss - **Event**: LEVITT AMP SCANDIA MUSIC SERIES by OMC--Pert Near Sandstone (bluegrass) at Scandia Community Center - **Date**: 2026-08-27 14:54:42 - **Photo**: https://cdn2.allevents.in/transup/72/6fbe166eb943f9a5798777a8cba9f6/images/IMG_1781.webp - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocJBIy8HXaUAQag1X9pKrC6X-cgzVCInDDMIN5NxJZMBk5_r1pk=s96-c?sz=200 - **Review**: "Didn't attend this event" - **Rating**: 5/5 - **By**: Rose Benja - **Event**: Rickey Smiley at Rivers Casino Portsmouth at Rivers Casino Portsmouth - **Date**: 2026-08-27 15:08:11 - **User Avatar**: https://lh3.googleusercontent.com/a/AGNmyxbPGLLvr1d1x7vhoLDXkWhuIqE-Gh3fNrkT38Qw=s96-c?sz=200 - **Review**: "it was very nice" - **Rating**: 5/5 - **By**: Jacqueline Clark - **Event**: The Encore Band at The Sanctuary Hotel 6pm at The Sanctuary at Kiawah Island Golf Resort - **Date**: 2026-08-27 14:18:17 - **Photo**: https://cdn2.allevents.in/transup/8e/5bbd77172a43418713582060285ebd/images/27f2f46b303c3a6a6e5d4ee39a7ac3d11ccc3f3848ad96dc815304d4b0232320_exif.webp - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocLCL-d8xX-YVltBe3H6aZoGkowcrTzH6ZUu3ghQ4QS1v9GkeJ1h=s96-c?sz=200 - **Review**: "Great class with an Awesome instructor. Thanks Tiffani" - **Rating**: 5/5 - **By**: Susan Ball - **Event**: Flower Brush Paint Party at 311 Howard Street Unit 2A, Petoskey, MI - **Date**: 2026-08-26 15:27:40 - **Photo**: https://cdn2.allevents.in/transup/04/fe787fd301443ebf145ce61b192f85/images/20260824_104805.webp - **User Avatar**: https://cdn-az.allevents.in/events1/banners/bb798f70-8359-11f1-8a8c-3fe57d70e589-rimg-w200-h200-dcbbc0c7-gmir - **Review**: "great time" - **Rating**: 5/5 - **By**: Kathleen Robinson - **Event**: Sip and Paint Moonlit Dragon Fly at The Farm Brewery at Broad Run - **Date**: 2026-08-26 09:32:23 - **Photo**: https://cdn2.allevents.in/transup/16/a92e663f1044c98d175d396604df13/images/20260813_064710.webp - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocLyDktBGPaQwwMdbW3I70FkXSYgnWtVA5gDXaPq1avx0p1WVgMqbA=s96-c?sz=200 - **Review**: "my nephews loved it all!!" - **Rating**: 4/5 - **By**: Jan O'Tuel - **Event**: Ultimate *National* Reptile Show: Myrtle Beach, South Carolina at Myrtle Beach Convention Center - **Date**: 2026-08-25 22:04:05 - **Photo**: https://cdn2.allevents.in/transup/23/54efd7020045eb92588354336056c2/images/b9f3b8cf5e827726364e8fda5d5a11e3_exif.webp - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocIP2xm92VIQ3JcAqkcV2-5KMUxWat77TtqVLP_WKItSko3ZaA=s96-c?sz=200 - **Review**: "It was nice to see the whole town involved in their community." - **Rating**: 4/5 - **By**: carrie perkins - **Event**: 20th Annual Wonderland Festival of the Imagination at 43 Main Street, Phillips, ME, United States, Maine 04966 - **Date**: 2026-08-27 00:08:43 - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocKm0mi4NoSpu3DCx-rQqmUsQxTDNzG5YdeMIiHrM5vlSj9kmdiT=s96-c?sz=200 - **Review**: "Valuable learning in a fun and relaxed environment" - **Rating**: 5/5 - **By**: Chet Kloss - **Event**: Ukulele Gent Workshop / NashUkes Meeting at Saturn Church - **Date**: 2026-08-25 17:15:15 - **Photo**: https://cdn2.allevents.in/transup/c8/ba4c55c13447f7ab0c7de049dd24ee/images/NashUkes.webp - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocJizrcU3tctenuyb8k1Upw_nSCiomnF5vzWzyhz7d45e-zA7Xs=s96-c?sz=200 - **Review**: "perfect summer morning for YOGA !" - **Rating**: 5/5 - **By**: Nadine Seemann - **Event**: Outdoor Yoga & U-pick Flowers at Gust Flower and Produce Farm - **Date**: 2026-08-25 15:13:28 - **Photo**: https://cdn2.allevents.in/transup/c9/3dcc4d377b41d5984fc587054f3615/images/a159058764305ca38507d959ec43062a_exif.webp - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocKn-EzJryIy8Qbs2ad5A0RDF0sFFSIV6UXNM3Jr04p0qjRLJBXkyg=s96-c?sz=200 - **Review**: "Awesome!!!" - **Rating**: 4/5 - **By**: Dr Daniel G. - **Event**: Cruces Car Show Fiesta at Sisbarro GMC - **Date**: 2026-08-25 01:05:48 - **Photo**: https://cdn2.allevents.in/transup/0c/b4a4ba4abe47dc89094dee029acbb0/images/1000004257.webp - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocKlYgAVWum4v6g-NGmoyJu79l8Yq-TCwLmwUiOvQCZKxYZug10e=s96-c?sz=200 - **Review**: "When the thunderstorm hit, it didn’t ruin the day. It actually made it better. Thunder cracked, rain came sideways, hail bounced off the pavement — and instead of running for our cars, we all tucked ourselves under vendor tents together. Neighbors who’d never spoken before were suddenly laughing, talking, and sharing the moment like we’d known each other for years. Some people even danced in the rain. It was a truly magical moment. The vendors were incredible. They stood tall through every minute of the storm, calm and steady, making sure everyone felt welcome and safe. Their commitment to the market and the community was obvious — even in the worst weather, they didn’t pack up or panic. What could’ve been a quick dash to the parking lot turned into one of those rare Arizona moments where people slow down, connect, and remember why local markets matter. By the time the storm passed, it felt less like an interruption and more like a shared story we all got to be part of. Five stars — not just for the marke" - **Rating**: 5/5 - **By**: Tammy Holden - **Event**: 🍦 Sundays with Soul Tagline: Chill Out – Connect – Discover at Prescott Valley Town Center 7210 E Pav Way, Prescott Valley, AZ, United States, Arizona 86314 - **Date**: 2026-08-24 16:09:02 - **Photo**: https://cdn2.allevents.in/transup/fb/025b1bca8c497ab901e9553299c047/images/Screenshot_23-8-2026_172732_www.facebook.com.webp - **User Avatar**: https://cdn-az.allevents.in/events1/banners/81a48e19983f80f37f93f6fb2a84459e7f9d616f0a98656e9e9be1e7dc6540af-rimg-w300-h300-dc080808-gmir?v=1787420404 - **Review**: "My kids & I loved it; very fun! It was exciting to make something of my own as a takeaway." - **Rating**: 5/5 - **By**: Rachel Pierce - **Event**: Yard Art (Level: Intro to Intermediate) at 1350 S 3rd Ave, 85364 - **Date**: 2026-08-26 18:00:27 - **User Avatar**: https://platform-lookaside.fbsbx.com/platform/profilepic/?asid=3361649174000689&height=100&width=100&ext=1769631895&hash=AT9ltvXV1qz9oIkLzGX0CrgY - **Review**: "great variety of local jazz musicians" - **Rating**: 5/5 - **By**: carlo piraino - **Event**: Jazz in Central Park at Central Park - **Date**: 2026-08-24 14:39:45 - **Photo**: https://cdn2.allevents.in/transup/8f/172b458c364a33ace0427e5d94a834/images/1c0238c8f3b9c75cdda8480e0584fed5_exif.webp - **User Avatar**: https://www.gravatar.com/avatar/8c38155a4fbb9bd5e72e239e24de2943?s=800&d=identicon&r=g?sz=200 - **Review**: "it was a lot of fun, however it was unreasonably hot and stuffy inside the venue. didn’t stay long." - **Rating**: 4/5 - **By**: Crystal Sutton - **Event**: Ultimate *National* Reptile Show: Myrtle Beach, South Carolina at Myrtle Beach Convention Center - **Date**: 2026-08-24 14:28:50 - **Photo**: https://cdn2.allevents.in/transup/12/25349b2e78471caeb8a597d6068f96/images/428f01074bf7de4a8909acaa20464fd2_exif.webp - **User Avatar**: https://lh3.googleusercontent.com/a/ACg8ocJ8zMYGy5ZeWY-RrE0VHrKu76oGBvJCxqz_mVSRjpoXeLX-0y0hlw=s96-c?sz=200 - (more moments omitted) ## Frequently Asked Questions - **Q**: What are the top events happening in Leonardtown? - **A:** Here are the top events in Leonardtown: Arts & Entertainment Celebration First Friday (Fri, 04 Sep at 05:00 pm, at Leonardtown Square), 2026 Leonardtown Art Walk - First Friday Launch (Fri, 04 Sep at 05:00 pm, at 22660 Washington St., Leonardtown, MD, United States, Maryland 20650), St. Mary's County Fair - 2026 (Thu, 24 Sep at 04:00 pm, at St Marys County Fair, Leonardtown), The Joe Cox Band LIVE @ The Rex Theatre (Sat, 29 Aug at 07:00 pm, at 22695 Washington St, Leonardtown, MD, United States, Maryland 20650), 2026 Sultana Adult Paddling Experience-St. Mary's, MD (Tue, 08 Sep at 09:00 am, at The Inn at Leonardtown, Ascend Hotel Collection). - **Q**: Which kind of events are trending in Leonardtown? - **A:** The top trending event categories in Leonardtown include Festivals, Fall Festivals, Car Shows, Live Music. - **Q**: How can I find events happening in Leonardtown? - **A:** You can discover upcoming events in Leonardtown on AllEvents.in. Browse by category, date, or venue to find events that match your interests. - **Q**: How do I buy tickets for 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 event venues in Leonardtown? - **A:** Some popular venues hosting events in Leonardtown include Leonardtown Square, 22660 Washington St., Leonardtown, MD, United States, Maryland 20650, St Marys County Fair, 22695 Washington St, Leonardtown, MD, United States, Maryland 20650, The Inn at Leonardtown, Ascend Hotel Collection. - **Q**: How can I get notified about new events in Leonardtown? - **A:** Follow Leonardtown on AllEvents.in to receive notifications when new events are listed in your city. ## Leonardtown at a Glance - **Total Upcoming Events**: 98 - **Featured Events**: 2 - **Followers**: 851 - **Trending Now**: This Weekend: 8, Live Music: 3 ## Trending Categories in Leonardtown - [Festivals (9 events)](https://allevents.in/leonardtown/festivals) - [This Weekend (8 events)](https://allevents.in/leonardtown/this-weekend) - [Car Shows (6 events)](https://allevents.in/leonardtown/car-shows) - [Fall Festivals (3 events)](https://allevents.in/leonardtown/fall-festivals) - [Live Music (3 events)](https://allevents.in/leonardtown/live-music) - [Back To School (1 events)](https://allevents.in/leonardtown/back-to-school) ## Seasonal & Special Events in Leonardtown - [Thanksgiving Weekend In Leonardtown 2026](https://allevents.in/leonardtown/thanksgiving) - [Back To School Events in Leonardtown](https://allevents.in/leonardtown/back-to-school) - [Labor Day Events in Leonardtown](https://allevents.in/leonardtown/labor-day) - [Best Pumpkin Patches Near Leonardtown](https://allevents.in/leonardtown/pumpkin-patch) - [Navratri Events In Leonardtown](https://allevents.in/leonardtown/navratri) ## Explore Leonardtown - [Car Shows 2026 In United States](https://allevents.in/events/car-shows-in-usa) - [Back To School 2026 Events & Giveaways In The USA](https://allevents.in/events/back-to-school-events-in-usa) - [Halloween 2026 Events & Celebrations In The USA](https://allevents.in/events/halloween-events-celebrations-in-usa) - [Labor Day 2026 Events & Celebrations In The USA](https://allevents.in/events/labor-day-celebrations-in-usa) - [Leonardtown Festival Guide 2026](https://allevents.in/leonardtown/festivals) - [Events & Things To Do In Leonardtown This Weekend](https://allevents.in/leonardtown/this-weekend) - [Fall Festivals Events Near Leonardtown](https://allevents.in/leonardtown/fall-festivals) - [Car Shows in Leonardtown](https://allevents.in/leonardtown/car-shows) - [Live Music Events Near Leonardtown](https://allevents.in/leonardtown/live-music) ## Events in Nearby Cities - [Events in Hollywood, Maryland, United States](https://allevents.in/hollywood-md) - [Events in California, Maryland, United States](https://allevents.in/california-md) - [Events in Great Mills, Maryland, United States](https://allevents.in/great mills) - [Events in Coltons Point, Maryland, United States](https://allevents.in/coltons point) - [Events in Lexington Park, Maryland, United States](https://allevents.in/lexington park) - [Events in Solomons, Maryland, United States](https://allevents.in/solomons)