Eastport-a-Rockin' has great waterfront vibes.

Bands Along the Bay: Where to Hear Live Music on the Water

One of the benefits of living on the Chesapeake is the proximity to East Coast entertainment with a laidback, waterfront feel. Some of the region’s best outdoor music festivals happen along our shorelines and on our beaches.

We’ve pulled together a list of some waterfront music festivals you’ll want on your calendar. Many are free, and even better, several can be experienced from your boat or personal watercraft!

Annapolis, MD
June 22
It’s a one-day festival featuring four stages and over 30 bands. The Annapolis Maritime Museum transforms into festival central featuring original, local musicians.

ALX Jazz Fest @ Portside
Alexandria, VA
June 21-22
Live music, local craft beer, and fun for the whole family on the Alexandria waterfront. Come on Friday for evening jazz, and then on Saturday enjoy an eclectic lineup, great food vendors, and lots of fun art experiences for the kids.

3rd Annual Calvert County Bluegrass and Acoustic Music Festival
St. Leonard, MD
June 21-22
Multiple bluegrass and acoustic musicians land in Calvert County for this fun, family-friendly festival. This event benefits Calvert Hospice.

Hampton Jazz and Music Festival
Hampton Roads, VA
June 28-30
Three days of headliners. Check out Kem, Boyz II Men, and Jon Batiste, among so many other standouts.

Reggae Rise Up Maryland
Baltimore, MD
June 21-23
Steel Pulse, Shaggy, Xavier Rudd, the Roots, and many more are headed to the Baltimore Peninsula (formerly known as Port Covington) for a three-day festival that is a scene.

Each year, the Potomac Jazz Festival attracts thousands to Colton’s Point in St. Marys.

Potomac Jazz and Seafood Festival
Leonardtown, MD
July 12-14
Now in its 24th year, this festival features incredible local seafood delicacies as well as some of the area’s best jazz musicians. Grab your tickets now to receive discounted rates.

Norfolk Waterfront Jazz Festival
Norfolk, VA
August 16-17
Event organizers are brilliant and are catering to boaters for this waterfront event. You can dock at Town Point Park Promenade with a reservation, or you can raft up in the Elizabeth River for a beautiful night of soulful sounds.

Thursday Night Concerts
Friday Eve is a well-known precursor to the weekend, so it’s no surprise that there are so many great venues hosting Thursday night concert series throughout the summer. Up and down the Bay, you’ll find great music (usually free) helping you kick off the weekends.

Fort Monroe Music by the Bay Summer Concert Series
Fort Monroe
Thursdays through August 15, 7pm
From big band to jazz, the Fort Monroe concert series features the music that has made Americana so rich.

Tides and Tunes Summer Concert Series
The Annapolis Maritime Museum
Thursdays through August 29
Classic rock to Irish shenanigans, Eastport is the place to be on Thursdays. Food trucks are on site, but to remain waste-free they ask you bring a cup.

WTMD First Thursdays Festival
Boston St. waterfront in Canton, Baltimore
First Thursday of the month, June through September
Since Baltimore traffic isn’t the most fun to sit in, it’s a great idea to take your boat and raft up for this concert series.