If you are a food stylist, food blogger, gourmet chef, caffeine junkie or just a keen foodie, you definitely are more worried about your salad being finely chopped than your appearance. To keep up with your food cravings there are these street food fairs, wine tasting events and food festivals in Leonardtown. For all the foodies who are avid learners; there are cooking workshops, baking workshops, cake making classes in Leonardtown and a lot more. You can also explore various food truck festivals happening in the Leonardtown.
Content your taste buds with sumptuous food. Craving for food already? Explore some amazing food events in Leonardtown.
## Food & Drinks Events in Leonardtown - **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 - **Interested Audience**: - Count: 117 - **Date**: Thu Oct 08 2026 at 06:00 pm – Thu Oct 08 2026 at 09:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/faire-witch-ladies-night-out/200030453062245 - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9lYTE4NGQxNjllMTJjY2I4NDAxNDFkNWE1NjQyM2ZlNWFkZjdiNDcxNGFjY2I2YzZmOGQzZWU0YTExZTUyNDg0LXJpbWctdzEyMDAtaDUwMC1kYzA4MDgwOC1nbWlyP3Y9MTc4NzExMDQ0Nw.avif - **Categories**: shopping - **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 - **Date**: Sun Oct 04 2026 at 03:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/250th-under-the-oaks-tudor-hall/200030733560305 - **Venue**: 41680 Tudor Pl, Leonardtown, MD, United States, Maryland 20650 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy8yYzc3ZGVlMWY0MzQ0NDJmY2JkNWJmZjlkNmNiZGNlZjBjNjJmY2U3OTU0OTlkZjEzMzQ0MmRkN2ZhYmNmYjg0LXJpbWctdzEyMDAtaDYyOC1kY2Y4ZjhmOC1nbWlyP3Y9MTc5MDI3MjQ0NQ.avif - **Categories**: performances, Art, Entertainment - **Event Name**: U.S. Oyster Festival - **Description**: The iconic U.S. Oyster Festival returns to St. Mary’s County Fairgrounds on October 17 - 18, 2026, bringing together oyster lovers, top shuckers, and seafood enthusiasts from across the region. Tickets are on sale now at usoysterfestival.org. This year, - **Interested Audience**: - Count: 83 - **Date**: Sat Oct 17 2026 at 10:00 am – Sat Oct 17 2026 at 06:00 pm (-04:00) - **Event URL**: https://allevents.in/leonardtown/us-oyster-festival/200030724883454 - **Venue**: St. Mary's County Fairgrounds - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvNzIzZGJkNTc5MWZiNjI0ZDFiNmI4MTU5ODMxNjU2NjFjMzEzYzVjZjI0NDRhZTllZmM2MjE1Y2Y1YmViZDk2OC1yaW1nLXcxMjAwLWg2MjgtZGMwODU4NzgtZ21pcj92PTE3OTAwNTUwNTQ.avif - **Categories**: festivals, sports, music, live-music, entertainment, nonprofit, contests - **Event Name**: Ledo Pizza Spirit Night - Leonardtown - **Description**: 🍕🍕🍕🍕🍕🍕🍕🍕 Stop by Ledo Pizza in Leonardtown on Wednesday, November 11, 2026 for some great food and to help support The Auxiliary of the Leonardtown Volunteer Fire Department. Make sure you mention the flyer to your server between 4pm & 8pm when payin - **Date**: Wed Nov 11 2026 at 04:00 pm – Wed Nov 11 2026 at 08:00 pm (-05:00) - **Event URL**: https://allevents.in/leonardtown/ledo-pizza-spirit-night-leonardtown/200030724909108 - **Venue**: Ledo Pizza - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy81ZmMxYzc2ODFiNGJjOWVjM2UwMGQ2MGEzYWMyMjMyMDAwMWY2ZTg2NDUxMjI3MmNiZGIyNWZmZTYzMDA1MWNkLXJpbWctdzExMDQtaDE0MjQtZGNmOGY4ZjgtZ21pcj92PTE3OTAwNTUzNjg.avif ## 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**: Veterans Day Parade and Memorial Wreath Laying Ceremony - **Description**: The Commissioners of Leonardtown invite the public to salute America’s Veterans at the Annual Veterans Day Parade in Leonardtown! The parade steps off from St. Mary’s Ryken High School, proceeds through Town Square and is immediately followed by a Memoria - **Venue**: Town of Leonardtown - **Banner**: https://cdn-az.allevents.in/events1/banners/4a7dcd2b74f031c3ba15acac08cf1030c5e53b2ab3c8ac5a2df8afc94232a86a-rimg-w1200-h675-dcf8f8f8-gmir?v=1790271985 - **Event Name**: Latin Dance Night: Ferocity After Dark at Antoinette's Garden - **Description**: Looking for Saturday night plans? Join us Saturday, October 3rd at Antoinette’s Garden for FEROCITY AFTER DARK! 🐆🔥 Kick off the night with a Bachata lesson led by our special guest, Kat Arias, then stay for Latin social dancing, special performances by t - **Venue**: Antoinette's Garden - **Banner**: https://cdn-az.allevents.in/events8/banners/974ac3769f3a17bd0da12d95c3040a6f7d813d491160a02dd60a96df1472ee68-rimg-w1200-h447-dc080808-gmir?v=1790524429 - **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**: 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 - **Venue**: Town of Leonardtown - **Banner**: https://cdn-az.allevents.in/events9/banners/c86af1d328742cb1e62b586f1fcfb3fe0a236afef7760c4ed5725b1fcb3b4915-rimg-w640-h959-dc080808-gmir?v=1790271347 - **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**: 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 - **Venue**: Town Market LLC ## Browse Food & Drinks Events by Date - [Food & Drinks Events Today in Leonardtown](https://allevents.in/leonardtown/food-drinks--today) - [Food & Drinks Events This Weekend in Leonardtown](https://allevents.in/leonardtown/food-drinks--this-weekend) - [Food & Drinks Events in September in Leonardtown](https://allevents.in/leonardtown/food-drinks--september) - [Food & Drinks Events in October in Leonardtown](https://allevents.in/leonardtown/food-drinks--october) ## FAQs - **Q**: What are the top Food & Drinks events in Leonardtown? - **A:** Faire Witch: Ladies Night Out (Thu Oct 08 2026 at 06:00 pm at 22695 Washington St, Leonardtown, MD, United States, Maryland 20650), 250th Under the Oaks @ Tudor Hall (Sun Oct 04 2026 at 03:00 pm at 41680 Tudor Pl, Leonardtown, MD, United States, Maryland 20650), U.S. Oyster Festival (Sat Oct 17 2026 at 10:00 am at St. Mary's County Fairgrounds), Ledo Pizza Spirit Night - Leonardtown (Wed Nov 11 2026 at 04:00 pm at Ledo Pizza). - **Q**: What Food & Drinks events are happening in Leonardtown this weekend October 2–4, 2026? - **A:** 250th Under the Oaks @ Tudor Hall (Sun Oct 04 2026 at 03:00 pm at 41680 Tudor Pl, Leonardtown, MD, United States, Maryland 20650). - **Q**: How can I find Food & Drinks events in Leonardtown? - **A:** You can discover upcoming Food & Drinks 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 Food & Drinks 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 Food & Drinks events in Leonardtown? - **A:** Some popular venues hosting Food & Drinks events in Leonardtown include 22695 Washington St, Leonardtown, MD, United States, Maryland 20650, 41680 Tudor Pl, Leonardtown, MD, United States, Maryland 20650, St. Mary's County Fairgrounds. - **Q**: Who are the top organizers for Food & Drinks events in Leonardtown? - **A:** Popular organizers hosting Food & Drinks events in Leonardtown include The Rex, St. Mary's County Historical Society, U.S. Oyster Festival. - **Q**: Are there any online Food & Drinks events available? - **A:** Yes, many Food & Drinks 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 Food & Drinks events in Leonardtown? - **A:** Follow the Food & Drinks category on AllEvents.in to get notified when new Food & Drinks events are listed in Leonardtown. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/7d/3b7eda185942c291f6c4d1b664725c/music.png ## Food & Drink events from nearby cities - [Food & Drink events in Hollywood](https://allevents.in/hollywood-md/food-drinks) - [Food & Drink events in California](https://allevents.in/california-md/food-drinks) - [Food & Drink events in Great Mills](https://allevents.in/great-mills/food-drinks) - [Food & Drink events in Lexington Park](https://allevents.in/lexington-park/food-drinks) - [Food & Drink events in Solomons](https://allevents.in/solomons/food-drinks)