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Holidays, Seasonal & Lifestyle

Winter on the Annapolis
Romeo Santos III  |  December 21, 2025

August is one of those months when Annapolis is at its best summer is still going strong, the waterfront is buzzing, and there’s plenty happening around town. From live music and outdoor dining downtown to the return of a Maryland tradition celebrating its 50th season, there are still plenty of reasons to get out and enjoy these final weeks of summer. Here are a few local happenings worth putting on your calendar.

Dates and times can change. It is always worth confirming details with each venue before you head out.

The Maryland Renaissance Festival Turns 50 | Opening Weekend • Saturday, August 29


photo credits to Visit Annapolis & Anne Arundel County

One of Maryland's great traditions returns for its 50th season. Revel Grove opens its gates in nearby Crownsville on Saturday, August 29, and runs weekends plus Labor Day Monday through October 25. Expect jousting, more than 200 performers across ten stages, artisan crafts, feasting, and a brand new anniversary storyline.

Opening weekend, August 29 and 30, is Children's Weekend, with one child (ages 7 to 15) admitted free with each adult ticket. Tickets are date specific and online only, and popular dates sell out, so it pays to plan ahead.

Tides & Tunes Summer Concert Series | Thursdays (through Aug. 20)


Photo credits to Tides & Tunes at Annapolis Maritime Museum

Free live music continues on Thursday evenings on the water at the Annapolis Maritime Museum and Park in Eastport. Only a few weeks of the season are left, so catch it while you can.


Dining Under the Stars | Wednesdays


Photo credits to John R Lee. Visit Annapolis

West Street closes to traffic on Wednesday nights for open air dining under the lights, with extended hours and live entertainment through the end of summer.


Rams Head On Stage


Photo credits to Rams Head on Stage

The downtown stage stays busy all month with a rotating lineup of touring and local acts, just steps from City Dock.

  • August 9 – Bonnie Stewart & Maddie Lenhart (matinee)
  • August 9 – Disciple of The Garden: The Legacy of Chris Cornell
  • August 11 – Matt Schofield
  • August 12 – Southern Avenue
  • August 13 – Supernova – A Tribute to Oasis
  • August 14 – In Gratitude: A Tribute to Earth, Wind & Fire
  • August 15 – Jimmy Charles
  • August 17 – The Record Company: Give It Back To You 10th Anniversary Tour
  • August 20 – Donavon Frankenreiter: Ask Me Anything Tour w/ Iris And The Shade
  • August 21 – CusCampbell
  • August 22 – LIVE AT THE FILLMORE: The Midterm Tour!
  • August 23 – All You Need w/ Skribe
  • August 25 – Ghalia Volt w. Kent Burnside
  • August 26 – 7 Bridges: The Ultimate Eagles Experience
  • August 28 – Adam Hawley
  • August 29 – The Verve Pipe
  • August 30 – Mike Phillips


Looking ahead to fall. Navy football season and the famous Annapolis boat shows are right around the corner in September and October, when the city shifts into its lively autumn rhythm.

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