Upcoming Event

Leonardtown Summer Music Festival

Aug 22 recurring event

  • Location: Downtown Leonardtown

Come enjoy free concerts this Summer in Downtown Leonardtown. Listen to local favorites in Leonardtown Square, Port of Leonardtown Winery, and throughout the Town! See the line up below.

  • August 22nd, 2021 - Sam Grow (Acoustic Performance) in Leonardtown Square Born in Southern Maryland, and now based in Tennessee, Country singer/songwriter/musician, Sam Grow, grew up on "old school" music and lists Sam Cooke, Otis Redding, Eric Clapton, and Gavin DeGraw as some of his influences. Come see Sam perform in Leonardtown Square for the first time.
  • August 29th, 2021 - Phillip Michael Parsons from 2 p.m. - 5 p.m. at Port of Leonardtown Winery Country singer/songwriter from Southern Maryland returns to Leonardtown on Sunday, August 29th. Phillip has been making music and traveling the Country. He'll be performing some favorite Country and Rock hits as well as some of his own music.
  • September 3rd, 2021 - Higher Standards from 5:30 p.m. - 7:30 p.m. in Leonardtown Square Higher Standards returns to Leonardtown for Arts & Entertainment First Friday on Friday, September 3rd. Enjoy smooth jazz stylings during this popular annual event that celebrates Leonardtown's anniversary of becoming the only Arts & Entertainment District in Southern Maryland.
  • September 18th, 2021 - Robbie Boothe from 3 p.m. - 6 p.m. at Port of Leonardtown Winery Country singer/songwriter/musician and hometown favorite, Robbie Boothe, returns to Leonardtown on Saturday, September 18th. Robbie has been honing his songwriting skills since performing an original song in high school.
  • October 9th, 2021 - Latrice Carr from 2 p.m. - 5 p.m. at Port of Leonardtown Winery Southern Maryland singer/song writer, Latrice Carr, performs sophisticated stylings of favorite adult R&B, gospel, jazz, pop, rock and more.
  • October 16th, 2021 - Amish Outlaws in Leonardtown Square An exciting cover band from Amish Country that performs any and all music styles plays Leonardtown Square for the first time.

Upcoming Dates For This Event:

  • Sunday, August 29
  • Friday, September 3
  • Saturday, September 18
  • Saturday, October 9
  • Saturday, October 16

Leonardtown Summer Music Festival