Events & Happenings in Leonardtown

Events & Happenings in Leonardtown | #Leonardtown https://stayhappening.com/leonardtown Explore all events & things to do in Leonardtown. Explore various shows, cultural activities, festivals or concerts happening in Leonardtown. The full Events Calendar for the city. en Events & Happenings in Leonardtown | #Leonardtown https://stayhappening.com/assets/img/stay-happening.png https://stayhappening.com/leonardtown <![CDATA[St. Mary's County Fair - 2026]]>

]]> <![CDATA[Rabies Clinic with SMAWL @ St. Mary's Fair Grounds]]>

]]> <![CDATA[Faire Witch: Ladies Night Out]]>

]]> <![CDATA[Monster Mash Bash]]>

]]> <![CDATA[Jackson Perkins Live at the Rex Theatre ]]>

]]> <![CDATA[250th Under the Oaks @ Tudor Hall]]>

]]> <![CDATA[Falling for Local Weekend Sale]]>

]]> <![CDATA[Walk w/Brandon in the St. Mary's County Fair Parade]]>

]]> <![CDATA[Public Hearing on the Draft of the St. Mary's 2050 Plan]]>

]]> <![CDATA[TRX Pilates Strength & Stretch ]]>

]]> <![CDATA[U.S. Oyster Festival]]>

]]> <![CDATA[Kelly McGinn Clinic 27 September ]]>

]]> <![CDATA[�¯ CORK FOR CUTIES�¯]]>

]]> <![CDATA[The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours) (FREE)]]>

]]> <![CDATA[Blessing of the Fleet 2026]]>

]]> <![CDATA[Trunk or Treat & Vendor Show]]>

]]> <![CDATA[Fall Paw Crawl]]>

]]> <![CDATA[Open Water Diver – Scuba Certification Weekend Class]]>

]]> <![CDATA[Cars & Coffee Car Show]]>

]]> <![CDATA[Re-Activate – Scuba Refresher Program Weekend Course]]>

]]> <![CDATA[Discover Scuba Diving – Try Scuba Experience]]>

]]> <![CDATA[Cars & Coffee Car Show - Trunk or Treat]]>

]]> <![CDATA[2026 First Friday Audience Participation Drum Circle]]>

]]> <![CDATA[Pages in the Park]]>

]]> <![CDATA[Bedazzle night]]>

]]> <![CDATA[Coastal Arts Market]]>

]]> <![CDATA[Monday Madness]]>

]]> <![CDATA[LGBTQ+ Family Ice Cream Social]]>

]]> <![CDATA[FOLs Fall BOOK Sale - Bigger & Better!]]>

]]> <![CDATA[FREE 6 Week Cessation Class offered through the St. Mary's County Health Departmen]]>

]]> <![CDATA[Home for The Holidays - A New St. Mary's County Holiday Tradition]]>

]]> <![CDATA[Sins And Secrets After Dark]]>

]]> <![CDATA[Harry Potter Mystic Market & First Saturday of the Month ]]>

]]> <![CDATA[Meet & Greet with Hip-hop legend Judah Priest ]]> Meet & Greet with Hip-hop legend Judah Priest

]]> <![CDATA[Christmas on the Square & Annual Tree Lighting]]>

]]> <![CDATA[FREE Individual Cessation Classes available through The St. Mary's County Health Department]]>

]]> <![CDATA[Veterans Day Parade and Memorial Wreath Laying Ceremony]]>

]]> <![CDATA[Ledo Pizza Spirit Night - Leonardtown]]>

]]> <![CDATA[WITCHES OF SOUTHERN MD 2026]]>

]]> <![CDATA[Foreign Company at The Rex]]>

]]> <![CDATA[Pictures with Santa Clause ]]>

]]> <![CDATA[Mechanicsville Braves 6th Annual Golf Tournament]]>

]]> <![CDATA[Small Business Saturday with The Grinch & Cindy Lou Who]]>

]]> <![CDATA[Fur Babies with the Grinch and Holiday Market]]>

]]> <![CDATA[Team Trivia at The Bay!]]>

]]> <![CDATA[Holiday Market with The Grinch & Cindy Lou Who]]>

]]> <![CDATA[SKYBOX & THE BAAC MEDIA PRESENTS LANEPUSHERS IN MY OWN LANE (MARYLAND)]]> SKYBOX & THE BAAC MEDIA PRESENTS LANEPUSHERS IN MY OWN LANE (MARYLAND)