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Kid  & Family-Friendly Things To Do & Events  Labor Day Weekend on the South Shore Boston September 12th & 13th

Happy Labor Day   The calendar is super busy with events this weekend with a carnival, music and more   Discover the Best Things to Do in the South Shore this Summer  Weekend. Events with the kids and family Eating, Drinking, Events & more

   save the date 

October:

Oct 2: Comedy Giant Steve Sweeney, Greg Thomas, Brett Davey, and Stephanie Griffith White 6:30pm doors

Oct 3: Mimosa’s with the Medium Maureen Hancock 10:15am

October 3: Sip & Stroll Harvest Fest, Oct 3, 2026 Besse Park in Wareham 3-7pm

October 18th  Princesses & Villains Ball in Plymouth

October 17th  White Pine Vintage and Artisan Market Milton 

October 16-18: Lion King Jr directed by Stacy Dawson

Oct 24: Sip & Stroll Harvest Norton, Oct 24, 2026, 2-6pm

Oct 31. Mimosa’s with the Medium Maureen Hancock 10:15am

*Halloween programming to be announced

November:

Nov 6: Jacob Gervais honoring Veterans sponsored by Thrive. Completely free to the public. Not a ticketed event.

Nov 7: Sip & Stroll Holiday November 7 Middleborough Town Hall

Nov 12: The Junkyard Dogs. Sponsored by George Randall Randall Electric. Completely free to the public. Not a ticketed event.

Nov 14-15   2026 Holiday Shopping Expo at North Quincy High School 

North Quincy High School

Nov 15: Broadway in the Boro Masterclass with Victor Carrillo Tracey from The Original Broadway Cast of The Outsiders

Nov 28: Mimosa’s with the Medium Maureen Hancock 10:15am

December:

December 5: Sip & Stroll Winter December 5, 2026 Emerald Square Mall

December 5th Merry Milton Market   Fontbonne  · Milton

December 6: Jacob Gervais Blue Christmas sponsored by Monica Kavanaugh and Peter Pmk Glass Kavanaugh

December 11-13: Trolls Jr directed by Stacy Dawson

Dec 12: Mimosa’s with the Medium 10:15am doors open.

December 16: Recitals