September brings plenty of ways to enjoy the changing season in Annapolis. 🍂 From art and live music to seafood, fairs, and community festivals, there's no shortage of things to do around town this month.

Funky Art Club

September 2

Get creative at Funky Art Club, a fun opportunity to explore your artistic side in a relaxed and welcoming setting. Whether you're an experienced artist or just looking to try something new, it's a great way to spend an afternoon getting crafty. 🎨

Make Something


Pops in the Park: Downs Park

September 5

Pack a blanket and head to Downs Park for an evening of live music in the great outdoors. Pops in the Park is a fun way to enjoy a concert with family and friends while taking in the beautiful park surroundings. 🎶

Listen to the Music


First Sunday Arts Festival

September 6

Spend the day exploring downtown Annapolis during the First Sunday Arts Festival. Browse work from local artists, enjoy live entertainment, and discover something new as the city's arts community fills the streets.

Support the Art

Annapolis Songwriters Festival

September 10-13

Enjoy four days of live music and original songwriting at the Annapolis Songwriters Festival. With talented songwriters performing throughout the city, it's a great chance to discover new music and experience Annapolis' vibrant music scene. 🎶

See Who's Playing


Maryland Seafood Festival

September 11-13

Celebrate Maryland's favorite flavors at the Maryland Seafood Festival! 🦀 Enjoy fresh seafood, live music, vendors, cooking demonstrations, and plenty of waterfront fun throughout the weekend.

Enjoy Seafood


Anne Arundel County Fair

September 16-20

Make some fall memories at the Anne Arundel County Fair! From carnival rides and fair food to animals, exhibits, entertainment, and family activities, this annual tradition has something for everyone to enjoy. 🎡

Have Fun at the Fair

West Annapolis Oktoberfest

September 27

Get into the fall spirit at West Annapolis Oktoberfest, a lively community celebration featuring food, drinks, music, and plenty of festive fun. Gather your friends and enjoy a day of local entertainment as the season gets underway. 🍻

Grab a Drink