Upcoming Events › Live Music

Soul Rebel Project – The Halloween Show

The Cut 177 Main Street, Gloucester

Show at 9:00pm / Doors at 8:00pm Costumes Encouraged! Soul Rebel Project were considered for a Grammy with their 2018 release of “Inspiration” are also two time winners of the Boston Music Awards international artist…

Brooks Williams – Matt Rich & Gil Clark Open

Old Sloop Presents 12 School St, Rockport, MA
$15

Statesboro, Georgia-born, Cambridge, England-based guitarist singer and songwriter Brooks Williams will return to the Old Sloop Presents performing arts series Saturday, November 1. Local rising stars Matt Rich and Gil Clark will open the show.…

Motor Booty Affair at The Cut

The Cut 177 Main Street, Gloucester
$20 – $35

Motor Booty Affair has been lighting up stages across America with their 70’s extravaganza for several years, continually improving on the show that has been dubbed “The Ultimate Disco Party Band”. The music is infectious…

Ryan Flynn Acoustic Mondays

Minglewood Harborside 25 Rogers Street, Gloucester, MA

Enjoy live acoustic music every Monday at Minglewood Harborside rom 6:00 to 8:00 PM with Ryan Flynn.

Wednesdays With Alex Anthony!

Minglewood Harborside 25 Rogers Street, Gloucester, MA

Join us every Wednesday at Minglewood Harborside for a bite to eat, a tasty cocktail and the lovely sounds of Alex Anthony!

Renaissance Faire Day at Hammond Castle Museum

Hammond Castle Museum 80 Hesperus Ave, Gloucester, MA
$4 – $12

Rain or Shine! Step back in time at our Renaissance Faire Day! Step into the world of medieval and Renaissance culture at Hammond Castle Museum, where the castle itself provides a uniquely dramatic backdrop for…

Fast Times

The Cut 177 Main Street, Gloucester
$15

11/8/25 Reserved Seating $25 GA Standing $15 7:00pm Doors / 8:00pm Show 21+ Positive I.D. Required Boasting wild hair, keytars, and all the stick twirls you can handle, their visual appeal can only be matched…

Ryan Flynn Acoustic Mondays

Minglewood Harborside 25 Rogers Street, Gloucester, MA

Enjoy live acoustic music every Monday at Minglewood Harborside rom 6:00 to 8:00 PM with Ryan Flynn.

Wednesdays With Alex Anthony!

Minglewood Harborside 25 Rogers Street, Gloucester, MA

Join us every Wednesday at Minglewood Harborside for a bite to eat, a tasty cocktail and the lovely sounds of Alex Anthony!