08/25/2026
☀️🎶 We’re wrapping up August and heading into September with live music, waterfront fun, local favorites, and plenty of ways to get out around Annapolis!
🪕🍻 Bay Grass Blues | Ashling Kitchen & Bar, Crofton
📅 Aug. 27 | ⏰ 6:00pm
Kick off the Baygrass spirit with free live bluegrass, drink specials, ticket giveaways, and festival fun.
🏓🍹 Drink & Dink | The HALL at Live! Casino & Hotel, Hanover
📅 Aug. 28 | ⏰ 1:00pm
Mix networking with pickleball, a DJ, food, drinks, prizes, and a little friendly competition.
⚽⚓ Navy Women’s Soccer vs. Maryland | Navy-Marine Corps Memorial Stadium, Annapolis
📅 Aug. 27 | ⏰ 7:00pm
Cheer on the Mids as they take on in-state rival Maryland under the lights.
🌊🐟 Kids on the Creek | Truxton Park Boat Ramp, Annapolis
📅 Aug. 29 | ⏰ 11:00am
A free family day with boat rides, paddleboarding, creek exploration, activities, and lunch.
🪕🌼 BloomHaven: Road to Baygrass | Maryland Hall, Annapolis
📅 Aug. 29 | ⏰ 3:00pm
Enjoy an afternoon of bluegrass, dancing, jam circles, and laid-back lawn party vibes.
🦀🎉 PDG Crab Feast | Kurtz’s Beach, Pasadena
📅 Aug. 29 | ⏰ 12:00pm
Dig into all-you-can-eat crabs, BBQ, drinks, music, games, and more while supporting a great cause.
🏃♀️🏅 51st Annual Annapolis Ten Mile Run | Navy-Marine Corps Memorial Stadium, Annapolis
📅 Aug. 30 | ⏰ 7:00am
One of Annapolis’ most iconic races returns for 10 scenic miles through the city and across the Naval Academy Bridge.
🥂💐 Mom’s Day Out Lunch | Leo, Annapolis
📅 Sept. 1 | ⏰ 11:00am
Celebrate back-to-school with lunch, spritzes, DJ Crawdads, a flower bar, shopping, and some well-deserved mom time.
🎶🌅 Tunesday featuring Higher Hands | Back Creek, Eastport
📅 Sept. 1 | ⏰ 6:00pm
Ease into September with free live music from a floating stage as the sun sets over Back Creek.
✨ Which event are you adding to your plans?
