Make your life happening by enrolling to entertainment events in Leonardtown. Find a partner through a salsa night or take your partner to live in concerts by upcoming bands in your town. Get high while playing Beer Pong in a pub crawl or attending stand-up comedy events in Leonardtown. Shake your legs in the happy streets, zumba or dance workshops or go for a film screening in the nearby cafes or theaters.
Explore Entertainment Events in Leonardtown.
## Entertainment Events in Leonardtown - **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 Oct 24 2026 at 01:00 pm – Sat Oct 24 2026 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**: Meet & Greet with Hip-hop legend Judah Priest - **Description**: Come out and meet some of Hip-Hops all stars! Judah Priest The 144000 Chosen Few crew Supreme Da Rezarekta, E Supreme, Theotis Joe and Twist-Flava and more! we have 4 hours for you to come out and get a personal interaction with some of the old school gre - **Interested Audience**: - Count: 35 - **Date**: Sat Sep 26 2026 at 12:00 pm – Sat Sep 26 2026 at 04:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/meet-and-greet-with-hip-hop-legend-judah-priest/200030677239453 - **Venue**: 41665 Fenwick St. unit 15, Leonardtown, MD - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy84OWNmZDJkNzVlNDdkNjQxYjZkYTQ5NWFkN2ZkNDNhNWNhMDFmYjM0MzIzMGQ2ZjUwMzA3MDAyMjVjMmU4M2Y0LXJpbWctdzEwMjQtaDE1MzYtZGMwODA4MDgtZ21pcj92PTE3ODg5MTEyNzM.avif - **Categories**: dance, entertainment - **Event Name**: Christmas on the Square & Annual Tree Lighting - **Description**: The holiday season begins in Leonardtown when Santa arrives for the annual Christmas Tree Lighting in the Town Square. The festivities begin at 4:30 PM with holiday music, entertainment, horse and carriage rides, sleigh rides, train rides, hayrides, live - **Interested Audience**: - Count: 201 - **Date**: Fri Nov 27 2026 at 04:30 pm – Fri Nov 27 2026 at 08:30 pm (-05:00) - **Event URL**: https://allevents.in/leonardtown/christmas-on-the-square-and-annual-tree-lighting/200030733435447 - **Venue**: Town of Leonardtown - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9jODZhZjFkMzI4NzQyY2IxZTYyYjU4NmYxZmNmYjNmZTBhMjM2YWZlZjc3NjBjNGVkNTcyNWIxZmNiM2I0OTE1LXJpbWctdzY0MC1oOTU5LWRjMDgwODA4LWdtaXI_dj0xNzkwMjcxMzQ3.avif - **Categories**: holiday, art, fine-arts, christmas, christmas-lights, kids - **Event Name**: Foreign Company at The Rex - **Description**: Get ready for a night of pure rock nostalgia as Foreign Company returns to The Rex! We are bringing all the sing-along anthems from two legendary bands — Foreigner and Bad Company! “Feels Like the First Time” “Can’t Get Enough” “Cold as Ice” …and so many - **Interested Audience**: - Count: 46 - **Date**: Sat Jan 23 2027 at 08:00 pm (-05:00) - **Event URL**: https://allevents.in/leonardtown/foreign-company-at-the-rex/200030686985159 - **Venue**: The Rex Theatre - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvZTQwYjRiM2RlN2MwNzMyNjk1OWM4ZDEzOWU3MWM5YzJhZmViN2Q3MTg0NDZmYmJjODI0YmVmZGMyNzlmMjdjYi1yaW1nLXcxMjAwLWg2NjctZGMwODA4MDgtZ21pcj92PTE3ODkxNTE4Nzg.avif - **Categories**: music, entertainment ## Trending Events in Leonardtown - **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/events2/banners/8855e8aea69ca35882bed536e7272a6cd3b71f701c9b5e2966c36ea85e48fce5-rimg-w1200-h628-dcf8f8f8-gmir?v=1787746344 - **Event Name**: Blessing of the Fleet 2026 - **Description**: Celebration honoring Southern Maryland Watermen's heritage and community - a family-friendly day with fireworks at 8 pm! - **Venue**: Leonardtown Wharf - **Banner**: https://cdn-az.allevents.in/events1/banners/af584c06022b4d850b927b258e359dd39486abe7c8062f23da53ef0b538adbf3-rimg-w1200-h1200-dce8e8d8-gmir?v=1789151234 - **Event Name**: Faire Witch: Ladies Night Out - **Description**: Grab your favorite witches and join us for an enchanting evening of sipping, shopping & all the spooky fall vibes. Think unique vendors, spooky-chic finds, seasonal cocktails, photo worthy moments, and a little bit of magic. More details, vendors a - **Venue**: 22695 Washington St, Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-az.allevents.in/events7/banners/ea184d169e12ccb840141d5a56423fe5adf7b4714accb6c6f8d3ee4a11e52484-rimg-w1200-h500-dc080808-gmir?v=1787110447 - **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-dcf8f8f8-gmir?v=1787462192 - **Event Name**: Jackson Perkins Live at the Rex Theatre - **Description**: 🇺🇸🎶 From serving our country to chasing his country music dream... Join us at the Rex Theatre on Saturday, October 17 as rising country artist Jackson Perkins takes the stage! An active-duty U.S. Marine, Jackson is quickly making a name for himself with - **Venue**: 22695 Washington St, Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-az.allevents.in/events7/banners/c663a093134c4a93a18aaa6161f822af19d68908de4b0fdbd10f44931d09b816-rimg-w1200-h500-dc080808-gmir?v=1787325198 - **Event Name**: 250th Under the Oaks @ Tudor Hall - **Description**: The St. Mary’s County Historical Society invites the community to enjoy a FREE afternoon of local music, history, and fellowship at Under the Oaks at Historic Tudor Hall on Sunday, October 4, 2026, from 3:00 to 5:00 p.m.! The free outdoor event will fea - **Venue**: 41680 Tudor Pl, Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-az.allevents.in/events7/banners/2c77dee1f434442fcbd5bff9d6cbdcef0c62fce795499df133442dd7fabcfb84-rimg-w1200-h628-dcf8f8f8-gmir?v=1790272445 - **Event Name**: Falling for Local Weekend Sale - **Description**: Fall is upon us! Join us for the Falling for Local Weekend Sale, October 2-4, 2026, and enjoy savings at participating shops throughout the Market! Whether you’re looking for home decor, new Fall wardrobe pieces, or other items for your home or office, w - **Venue**: 22725 Duke St, Leonardtown, MD - **Banner**: https://cdn-az.allevents.in/events1/banners/b3d42c6aeac261d31c23630cc2a294fa326cee8f7864dd5e6adff8d86da5491f-rimg-w1200-h1200-dc080808-gmir?v=1790271985 - **Event Name**: Public Hearing on the Draft of the St. Mary's 2050 Plan - **Description**: The Commissioners of St. Mary’s County (CSMC) have scheduled a public hearing to consider public testimony on the draft of the St. Mary’s 2050 plan. The decision to move the draft plan to a public hearing was made following a briefing provided by the Dep - **Venue**: 41770 Baldridge Street, Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-az.allevents.in/events7/banners/720ac83054850c1f7943f0ee49280cf5fd45f7cc54a08def6cba858de0b6df45-rimg-w851-h315-dc685858-gmir?v=1790272855 - **Event Name**: Team Trivia at The Bay! - **Description**: Join us for fun filled night of trivia every other Thursdays. - **Venue**: 21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-az.allevents.in/events10/banners/a3e0841cf0f45c2cebe78d29b85513a35fd25a4363fdd7116d7e4eb59bd93bbf-rimg-w1054-h1492-dc082818-gmir?v=1790446717 ## Browse Entertainment Events by Date - [Entertainment Events Today in Leonardtown](https://allevents.in/leonardtown/entertainment--today) - [Entertainment Events This Weekend in Leonardtown](https://allevents.in/leonardtown/entertainment--this-weekend) - [Entertainment Events in September in Leonardtown](https://allevents.in/leonardtown/entertainment--september) - [Entertainment Events in October in Leonardtown](https://allevents.in/leonardtown/entertainment--october) ## FAQs - **Q**: What are the top Entertainment events in Leonardtown? - **A:** Monster Mash Bash (Sat Oct 24 2026 at 01:00 pm at Leonardtown Wharf), Meet & Greet with Hip-hop legend Judah Priest (Sat Sep 26 2026 at 12:00 pm at 41665 Fenwick St. unit 15, Leonardtown, MD), Christmas on the Square & Annual Tree Lighting (Fri Nov 27 2026 at 04:30 pm at Town of Leonardtown), Foreign Company at The Rex (Sat Jan 23 2027 at 08:00 pm at The Rex Theatre). - **Q**: What Entertainment events are happening in Leonardtown this weekend September 25–27, 2026? - **A:** Meet & Greet with Hip-hop legend Judah Priest (Sat Sep 26 2026 at 12:00 pm at 41665 Fenwick St. unit 15, Leonardtown, MD). - **Q**: What Entertainment events are happening in Leonardtown in September 2026? - **A:** Meet & Greet with Hip-hop legend Judah Priest (Sat Sep 26 2026 at 12:00 pm at 41665 Fenwick St. unit 15, Leonardtown, MD). - **Q**: How can I find Entertainment events in Leonardtown? - **A:** You can discover upcoming Entertainment 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 Entertainment 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 Entertainment events in Leonardtown? - **A:** Some popular venues hosting Entertainment events in Leonardtown include Leonardtown Wharf, 41665 Fenwick St. unit 15, Leonardtown, MD, Town of Leonardtown. - **Q**: Who are the top organizers for Entertainment events in Leonardtown? - **A:** Popular organizers hosting Entertainment events in Leonardtown include Town of Leonardtown, Velvet Razor Tattoo Company, Foreign Company. - **Q**: Are there any online Entertainment events available? - **A:** Yes, many Entertainment 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 Entertainment events in Leonardtown? - **A:** Follow the Entertainment category on AllEvents.in to get notified when new Entertainment events are listed in Leonardtown. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/58/5efbefdb8e438db5c829e697673309/Maskgroup-3-.webp ## Entertainment events from nearby cities - [Entertainment events in California](https://allevents.in/california-md/entertainment) - [Entertainment events in Lexington Park](https://allevents.in/lexington-park/entertainment)