# Events & Things To Do In Leonardtown This Weekend | April 17-19, 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+ - **Recent Followers**: - **Avatar 1**: https://cdn-az.allevents.in/events7/banners/5a33e730-9bcc-11f0-bc74-031dd7b2de88-rimg-w200-h200-dcd3d6db-gmir - **Avatar 2**: https://cdn-az.allevents.in/events9/banners/a48338257a84812cd54e2388b406d5790a67c1cb82be520068ac8692eb1cbcd6-rimg-w200-h200-dcbcc2c0-gmir?v=1758994204 - **Avatar 3**: https://cdn-az.allevents.in/events4/banners/438a0b277edc9e50d8e9d12b0bbf7d8ffa3406978736b8debf3a589dfaee445c-rimg-w200-h200-gmir.jpg?v=1622243409 ## 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**: Paint and Sip - **Description**: 🌸🎨 Let’s Welcome Spring with a Cherry Blossom Paint & Sip! 🍷🌸 Join us on April 18 at 6 PM at beautiful Port of Leonardtown Vineyard for a magical evening of creativity, wine, and springtime vibes! We’ll be painting a stunning cherry blossom masterpi - **Interested Audience**: - Count: 38 - **Date**: Sat Apr 18 2026 at 06:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/paint-and-sip/200029889791915 - **Venue**: Port of Leonardtown Winery - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9lZTIzMzM5ZTBlNzk4Y2U3ZGZjMGQ0ZmI5ZjFkYzBmNjc4MjNhNzlhZDliYTg5OTlhMzgxMDczZmM1MDViODY5LXJpbWctdzEyMDAtaDE1OTItZGM2M2M1YjgtZ21pcj92PTE3NzU4MTk4MDA.avif - **Categories**: Art, fine-arts - **Event Name**: FREE! A "Good Earth" Day - **Description**: Come all tall and small Good Earthlings to celebrate A "Good Earth" Day! Join us in our side parking lot for vendors and hands-on fun. We will have tons of activities for kids and adults: Global Wines- Organic Wine Tasting (inside) Back Porch Coffee Co. - **Interested Audience**: - Count: 276 - **Date**: Sat Apr 18 2026 at 10:00 am (-04:00) - **Event URL**: https://allevents.in/leonardtown/free-a-good-earth-day/200029846518755 - **Venue**: 41675 Park Ave, Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy81ZWQyMzg4MzA1MGEyOTFkOWIzZGQ0ZDJkNzMzZjFmYmNiMDA2ZDIxMDYzMTQxYzU0YjdmYzBmYzNhNjVmNjAyLXJpbWctdzEyMDAtaDYzMC1kYzBhNzA0ZS1nbWlyP3Y9MTc3NTYxMTQ5Mw.avif - **Categories**: kids, art, food-drinks, fine-arts, wine-tasting - **Event Name**: SMOKE SIGNALS & DJ PAPERS @ THE REX (LTOWN BAR CRAWL) - **Description**: If you were at All Sinners Night… you already know 😎🔥 We’re running back again at the Leonardtown Spring Bar Crawl We’re the Final Boss you meet at the end of your journey!!! Smoke Signals × DJ Papers The Rex • April 17 Gonna be lit… Spread the word - **Interested Audience**: - Count: 241 - **Date**: Fri Apr 17 2026 at 09:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/smoke-signals-and-dj-papers-the-rex-ltown-bar-crawl/200029724392257 - **Venue**: The Rex - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy8yMTZkMzBiNzY4NWIxOTJjNDY0ZjhiYjRiYjQ5Njk5MTEwMDgzZTNhOGFkYTkwN2EzNjIwNmQ1NzM1NTY0MjNjLXJpbWctdzEwMjQtaDE1MzYtZGMxODEyMTQtZ21pcj92PTE3NzUyMDIxODI.avif - **Categories**: parties, bar-crawls - **Event Name**: BARmuda Triangle 2026 Spring Bar Crawl! - **Description**: Get Lost in the Barmuda Triangle! It’s not just a bar crawl — it’s a legendary quest for the bold and the thirsty! Join us at 12:00 on April 17th for the Barmuda Triangle Bar Crawl, where your adventure takes you through The Rex 🍺, Social 🍹, and The Olde - **Interested Audience**: - Count: 620 - **Date**: Fri Apr 17 2026 at 12:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/barmuda-triangle-2026-spring-bar-crawl/200029917652357 - **Venue**: 41655 Fenwick St, Leonardtown, MD - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvYmM0MDg0ZmYwOTRhMTkwNmNmNTU4NmM4ODI5ZDZiOWM3YzFlYzU5YTRjZTFlZDdkYzk4NzA0OWY3ODY2ODYwMS1yaW1nLXc5MzgtaDc1MC1kYzk5ZDBjZC1nbWlyP3Y9MTc3NTc5MjU3Nw.avif - **Categories**: parties, bar-crawls, trips-adventures - **Event Name**: April Showers☔️: Pet Wash Fundraiser 🐶🛁 - **Description**: April Showers – Pet Wash Fundraiser 🐶 Celebrating Pet Owners’ Day! 📅 April 18th ⏰ 12:00 PM – 3:00 PM 📍 Balanced Paws Pet Care 🚶‍♂️ Walk-Ins Only ⸻ 🫧 What’s Included: • Basic Shampoo Bath • Towel Dry • Ear Cleaning Quick refresh baths to get your pu - **Interested Audience**: - Count: 65 - **Date**: Sat Apr 18 2026 at 12:00 pm – Sat Apr 18 2026 at 03:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/april-showers-pet-wash-fundraiser/200029734179647 - **Venue**: 22725 Duke St, Leonardtown, MD 20650-4165, United States - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvMzgyMzJmYzJlN2I2MjExOGFiMTRhNjFmNzVhYzMwOGYyZTZkZWZmMzM1ZTkwNGMzNjMyYTlhODZjYTBkYzJhNy1yaW1nLXcxMDI0LWgxMDI0LWRjZjBmMGYzLWdtaXI_dj0xNzc1MTk4MTU0.avif - **Categories**: nonprofit, dog - **Event Name**: St. Mary's County History Day - **Description**: St. Mary's County History Day: Revolution, Reaction, Reform in HistoryAbout this EventSt. Mary's County History Day ContestTheme: Revolution, Reaction, Reform in HistoryApril 18, 2026, from - **Date**: Sat Apr 18 2026 at 09:00 am – Sat Apr 18 2026 at 03:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/st-marys-county-history-day/100001982542538100 - **Venue**: Leonardtown Library - St. Mary's County Library - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy81NGU2OGFmMzI0MjA5MmVkZjhjMDFiMzUwOGZjMjJkMjUzMTNjOTNhNGE2ZWFkNmQ2NTdkMzQ1Y2IzM2NhZGQ0LXJpbWctdzEyMDAtaDYyOC1kY2ZmZmZmZi1nbWlyLmpwZz92PTE3NzMyNzYzNjY.avif - **Price**: Free - **Categories**: contests - **Event Name**: Trivia Fundraiser 2026 - **Description**: Come learn more about the ministry of Young Life St. Mary’s and learn how you can partner with us! All the while playing some super fun space themed trivia! - **Date**: Fri Apr 17 2026 at 06:15 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/trivia-fundraiser-2026/200029889791312 - **Venue**: SouthPoint Church - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9jYmViODRmZTlhMDNkYTI1NWM5ODRiY2UyYTdlYmFkZGE5ODgxYmY4OGJmZTg5NGU2MjdlNTQ4NWU5M2YxYmE5LXJpbWctdzEyMDAtaDE1NTItZGMwMzAzMDItZ21pcj92PTE3NzUyMDIxOTE.avif - **Categories**: Nonprofit ## 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=1775343882 - **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**: Leprechaun Lilly's Kids Consignment Sale - 2026 Spring/Summer - **Description**: **Register NOW** **NO ENTRY FEE to shop** Leprechaun Lilly's 2026 Spring/Summer Kid's Consignment Sale April 16-18, 2026 St. Mary's County Fairgrounds Thu, Apr 16: 4PM-9PM – Presales (Helpers, Consignors, & Registered First Time Parents/Grandparents - **Venue**: 42455 Fairgrounds Rd, Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-az.allevents.in/events2/banners/81ba3ffbaf53b563bc316f07179baacc3971c29c2f45844c1510ddc6db0c1ea1-rimg-w1200-h628-dcffffff-gmir?v=1775670144 - **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**: Paint and Sip - **Description**: 🌸🎨 Let’s Welcome Spring with a Cherry Blossom Paint & Sip! 🍷🌸 Join us on April 18 at 6 PM at beautiful Port of Leonardtown Vineyard for a magical evening of creativity, wine, and springtime vibes! We’ll be painting a stunning cherry blossom masterpi - **Venue**: Port of Leonardtown Winery - **Banner**: https://cdn-az.allevents.in/events2/banners/ee23339e0e798ce7dfc0d4fb9f1dc0f67823a79ad9ba8999a381073fc505b869-rimg-w1200-h1592-dc63c5b8-gmir?v=1775819800 - **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**: 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**: 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=1774908171 ## 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:** Paint and Sip (Sat Apr 18 2026 at 06:00 pm at Port of Leonardtown Winery), FREE! A "Good Earth" Day (Sat Apr 18 2026 at 10:00 am at 41675 Park Ave, Leonardtown, MD, United States, Maryland 20650), SMOKE SIGNALS & DJ PAPERS @ THE REX (LTOWN BAR CRAWL) (Fri Apr 17 2026 at 09:00 pm at The Rex), BARmuda Triangle 2026 Spring Bar Crawl! (Fri Apr 17 2026 at 12:00 pm at 41655 Fenwick St, Leonardtown, MD), April Showers☔️: Pet Wash Fundraiser 🐶🛁 (Sat Apr 18 2026 at 12:00 pm at 22725 Duke St, Leonardtown, MD 20650-4165, United States). - **Q**: What are the top free Weekend events in Leonardtown? - **A:** St. Mary's County History Day (Sat Apr 18 2026 at 09:00 am at Leonardtown Library - St. Mary's County Library). - **Q**: What Weekend events are happening in Leonardtown this weekend April 17–19, 2026? - **A:** Paint and Sip (Sat Apr 18 2026 at 06:00 pm at Port of Leonardtown Winery), FREE! A "Good Earth" Day (Sat Apr 18 2026 at 10:00 am at 41675 Park Ave, Leonardtown, MD, United States, Maryland 20650), SMOKE SIGNALS & DJ PAPERS @ THE REX (LTOWN BAR CRAWL) (Fri Apr 17 2026 at 09:00 pm at The Rex), April Showers☔️: Pet Wash Fundraiser 🐶🛁 (Sat Apr 18 2026 at 12:00 pm at 22725 Duke St, Leonardtown, MD 20650-4165, United States), St. Mary's County History Day (Sat Apr 18 2026 at 09:00 am at Leonardtown Library - St. Mary's County Library). - **Q**: What Weekend events are happening in Leonardtown in April 2026? - **A:** Paint and Sip (Sat Apr 18 2026 at 06:00 pm at Port of Leonardtown Winery), FREE! A "Good Earth" Day (Sat Apr 18 2026 at 10:00 am at 41675 Park Ave, Leonardtown, MD, United States, Maryland 20650), SMOKE SIGNALS & DJ PAPERS @ THE REX (LTOWN BAR CRAWL) (Fri Apr 17 2026 at 09:00 pm at The Rex), BARmuda Triangle 2026 Spring Bar Crawl! (Fri Apr 17 2026 at 12:00 pm at 41655 Fenwick St, Leonardtown, MD), April Showers☔️: Pet Wash Fundraiser 🐶🛁 (Sat Apr 18 2026 at 12:00 pm at 22725 Duke St, Leonardtown, MD 20650-4165, United States). - **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 Port of Leonardtown Winery, 41675 Park Ave, Leonardtown, MD, United States, Maryland 20650, The Rex. - **Q**: Who are the top organizers for Weekend events in Leonardtown? - **A:** Popular organizers hosting Weekend events in Leonardtown include The Red Apron Artist, The Good Earth Natural Foods Company, Smoke Signals. - **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 ## Events this weekend from nearby cities - [Events this weekend in Hollywood](https://allevents.in/hollywood-md/this-weekend) - [Events this weekend in California](https://allevents.in/california-md/this-weekend) - [Events this weekend in Callaway](https://allevents.in/callaway-md/this-weekend) - [Events this weekend in Great Mills](https://allevents.in/great-mills/this-weekend) - [Events this weekend in Coltons Point](https://allevents.in/coltons-point/this-weekend) - [Events this weekend in Chaptico](https://allevents.in/chaptico/this-weekend) - [Events this weekend in Lexington Park](https://allevents.in/lexington-park/this-weekend) - [Events this weekend in Solomons](https://allevents.in/solomons/this-weekend)