The Steve Morse Band
Reunited and performing together for the first time in over 10 years, the Steve Morse Band returns with a long-awaited live set including fan favorites from the band’s illustrious career. …
Live Music from Guava Jelly
Don’t miss live music from Guava Jelly at O’Loughlin’s Restaurant on September 27, 2025 starting at 7:00 pm!
Live Music from Kevin Pollock
Don’t miss live music from Kevin Pollock at O’Loughlin’s Restaurant on September 20, 2025 starting at 7:00 pm!
Live Music from Alex Peters
Don’t miss live music from Alex Peters at O’Loughlin’s Restaurant on September 13, 2025 starting at 7:00 pm!
Live Music from SRB Duo
Don’t miss live music from the SRB Duo at O’Loughlin’s Restaurant on September 6, 2025 starting at 7:00 pm!
Live Music from Kristi Allen
Don’t miss live music from Kristi Allen at O’Loughlin’s Restaurant on August 30, 2025 starting at 7:00 pm!
The Garden Ramble w/ the Black-Eyed Suzies
Wander through our 10-acre gardens, enjoy delicious drinks, and revel in live music stations scattered throughout the grounds. Take in the beautiful fall colors while sipping on tasty beverages. From …
Kunta Kinte Heritage Festival
Join us for our free family friendly festival as we celebrate afrofuturism! There will be live music, food, art, culture, and community education! The Kunta Kinte Heritage Festival will take …
Baygrass Kickoff Party
Start your Baygrass weekend with a high-energy night of live music in downtown Annapolis! Featuring soulful grooves from Fitzkee Brothers and the vibrant, “grassalicious” sound of Wicked Sycamore—Baygrass alumni and crowd favorites. The Baygrass …
Annapolis Vintage Market
Don’t miss the Annapolis Vintage Market on September 14, 2025 from 11:00 am – 5:00 pm in the parking lot of Vintage Vibe Finds and Artfully Acquired. There will be …