September is a wonderful time to explore Annapolis and Anne Arundel County. As summer begins to transition into fall, the calendar is filled with outdoor dining, live music, arts, seafood, cultural celebrations, and community events.

Whether you already call the area home or you're planning a visit, here are some events worth adding to your September calendar.

🍽️ Dinner Under the Stars

Dates: September 2, 9, 16, 23 & 30, 2026
Time: 5:00 PM–10:00 PM
Location: West Street, from Church Circle to Calvert Street

One of my favorite ways to experience downtown Annapolis is Dinner Under the Stars. West Street transforms into an outdoor dining destination where you can enjoy dinner outside while taking in the atmosphere of downtown.

It's a perfect excuse to try a local restaurant, meet up with friends, and enjoy a September evening in Annapolis.

Event Information:
https://calendar.annapolis.gov/annapolismd/260131419

🎶 September Sunsets Concert Series

Dates: September 3, 10, 17 & 24, 2026
Time: 5:30 PM–8:00 PM
Location: Annapolis

Thursday evenings in September bring live music to Annapolis with the September Sunsets Concert Series.

It's an easy way to get outside, enjoy the early fall weather, and experience another side of the local community.

Event Information:
https://www.annapolis.gov/calendar.aspx?CID=0&month=9&view=month&year=2026

🎨 First Sunday Arts Festival

Date: September 6, 2026
Time: 11:00 AM–5:00 PM
Location: Downtown Annapolis

Spend your Sunday exploring local art, handmade goods, creative vendors, and downtown Annapolis.

The First Sunday Arts Festival is a great opportunity to support local artists and businesses while spending an afternoon walking around the city.

Event Information:
https://www.annapolis.gov/calendar.aspx?CID=0&month=9&view=month&year=2026

🎸 Annapolis Songwriters Festival

Dates: September 10–13, 2026
Location: Multiple venues throughout Downtown Annapolis

Music takes over downtown during the Annapolis Songwriters Festival, a multi-day celebration featuring national and emerging songwriters performing at venues throughout the city.

The 2026 lineup includes artists such as Young the Giant, Maggie Rose, Josiah and the Bonnevilles, and Valerie June.

Whether you're a dedicated music fan or simply looking for something different to do downtown, this is one of September's standout Annapolis events.

Festival Information:
https://www.visitannapolis.org/blog/stories/post/september-music-festivals-in-anne-arundel-county/

💙 Annapolis Out of the Darkness Walk

Date: September 12, 2026
Time: 9:00 AM–12:00 PM
Location: Navy-Marine Corps Memorial Stadium and locations throughout Annapolis

This meaningful community walk brings people together for connection, remembrance, and support.

Event Information:
https://www.annapolis.gov/calendar.aspx?CID=0&month=9&view=month&year=2026

🏃 9/11 Heroes Run

Date: September 13, 2026
Time: 11:00 AM–12:30 PM
Location: Navy-Marine Corps Memorial Stadium & Admiral Heights

The 9/11 Heroes Run brings the community together to honor those who served and sacrificed.

It's another opportunity to participate in a meaningful local event while connecting with neighbors throughout Annapolis.

Event Information:
https://www.annapolis.gov/calendar.aspx?CID=0&month=9&view=month&year=2026

🛍️ Maryland Avenue Flea Market

Date: September 13, 2026
Time: 10:00 AM–3:00 PM
Location: Maryland Avenue, State Circle to Cumberland Court

Love searching for interesting finds?

Spend Sunday browsing the Maryland Avenue Flea Market while enjoying one of Annapolis' historic downtown areas.

Event Information:
https://www.annapolis.gov/calendar.aspx?CID=0&day=14&month=9&view=week&year=2026

🎶 Boatyard Beach Bash

Date: September 19, 2026
Time: 4:00 PM–10:00 PM
Location: Annapolis

The Boatyard Beach Bash brings another evening of entertainment and community fun to Annapolis.

Event Information:
https://www.annapolis.gov/calendar.aspx?CID=0&month=9&view=month&year=2026

🌾 Annapolis Baygrass Music Festival

Dates: September 19–20, 2026
Location: Sandy Point State Park, Annapolis

Music and Chesapeake Bay views come together at the Annapolis Baygrass Music Festival.

The waterfront festival combines jam, bluegrass, and Americana music, with the 2026 lineup featuring artists including Little Feat and Yonder Mountain String Band.

If live music by the water sounds like your perfect September weekend, this one deserves a spot on your calendar.

Festival Information:
https://www.visitannapolis.org/blog/stories/post/september-music-festivals-in-anne-arundel-county/

🕊️ Kunta Kinte Heritage Festival

Date: September 26, 2026
Location: City Dock, Annapolis

The Kunta Kinte Heritage Festival is a celebration of African heritage and resilience featuring music, culture, food, family activities, and community fellowship.

Held at City Dock, it's a meaningful opportunity to experience and celebrate the history and cultural heritage connected to Annapolis.

Festival Information:
https://www.visitannapolis.org/blog/stories/post/september-music-festivals-in-anne-arundel-county/

🤝 Old 4th Ward Unity Day

Date: September 26, 2026
Time: 12:00 PM–8:00 PM
Location: People's Park, Annapolis

Old 4th Ward Unity Day is another local community gathering taking place in Annapolis this September.

Event Information:
https://www.annapolis.gov/calendar.aspx?CID=0&month=9&view=month&year=2026

🍂 West Annapolis Oktoberfest

Date: September 27, 2026
Time: 11:00 AM–4:00 PM
Location: Annapolis Street

Welcome the beginning of fall with West Annapolis Oktoberfest.

Spend the day exploring West Annapolis while enjoying the neighborhood atmosphere and celebrating the changing season.

Event Information:
https://www.annapolis.gov/calendar.aspx?CID=0&month=9&view=month&year=2026

There's Always Something Happening in Annapolis

One of the things I love about Annapolis and Anne Arundel County is the strong sense of community.

From evenings dining outside on West Street to waterfront music festivals, arts events, cultural celebrations, and neighborhood gatherings, September gives us plenty of reasons to get out and enjoy where we live.

As a local REALTOR®, I love sharing not only homes and real estate updates, but also the places, events, and experiences that make our communities feel like home.

I'll continue sharing local favorites and upcoming events throughout Anne Arundel County, so be sure to follow along!

Heather Taylor, REALTOR®
RE/MAX One

Event dates, times, locations, schedules, and availability may change. Please check the official event links before attending.