Summer’s unofficial end comes with an extra day off for many of us. If you’re looking for ways to send off the season in style, we’ve gathered six fun activities and adventures from across the region.
1. Schooner Festival, Gloucester
September 3 to 6
From Thursday, September 3, through Sunday, September 6, Gloucester Harbor will come alive with the sight of magnificent schooners under sail. This Labor Day tradition draws vessels from near and far for parades, sails, deck tours, and the Mayor’s Cup Races. Hosted by Maritime Gloucester, the festival is your chance to get up close to these historic ships and be part of a celebration that has captivated thousands for over 40 years. On September 5 there will be fireworks over the harbor at 9:15pm.
Before and after the festival, local schooners like the Ardelle, Adventure, and the Thomas E. Lannon offer regular public sails.
For more information: maritimegloucester.org/schooner-festival
2. School of Rock, Firehouse Center for the Arts, Newburyport
August 21 to September 6
Andrew Lloyd Webber’s School of Rock – The Musical is a two-hour, two-act show (plus intermission), based on the hit movie. The tuner follows Dewey Finn, a failed, wannabe rock star who decides to earn an extra bit of cash by posing as a substitute teacher at a prestigious prep school. There he turns a class of straight–A pupils into a guitar-shredding, bass-slapping, mind-blowing rock band. But can he get them to the Battle of the Bands without their parents and the school’s headmistress finding out?
Learn more and buy tickets at firehouse.org/event/school-of-rock/2026-08-21
3. The Castle Hill Hike, Crane Estate, Ipswich
September 6
Explore the lesser-visited corners of Castle Hill and its surroundings. This hike brings you through historical built landscapes, past sweeping views of Castle Neck and the Great Marsh, and through quiet woodland trails. It runs from 1:00pm to 3:30pm.
Register at thetrustees.org/event/449233
4. Country Fair, Cider Hill Farm, Amesbury
September 5 to 7
Pick apples and berries, cut flowers, pet rabbits, compete at old-timey games, snack on kettlecorn and caramel apples, slurp a cider slushie, dance to live music, bounce around the farm on a hayride, and so much more at this celebration of the season’s abundance.
See the full schedule at ciderhill.com/country-fair
5. Yonder Mountain String Band, Shalin Liu, Rockport
September 5
Travel to the stunning Shalin Liu Performance Center to hear Grammy-nominated Yonder Mountain String Band. Good As True (2026), the band’s 12th studio album, released March 2026 captures Yonder in full stride. “Brand New Heartache,” the album’s lead single, lives in that fragile moment after a breakup when heartbreak and forward motion exist at the same time.
Buy tickets at rockportmusic.org/upcoming-shows/yonder-mountain-string-band
6. Bread and Roses Heritage Festival, Lawrence
September 7
Honoring the spirit of Labor Day, by recognizing the importance and contributions of the labor movement, this festival marks Lawrence’s “Bread and Roses” Strike of 1912. The festival includes musical performances, children’s entertainers, face painting, protest sign making, and walking and trolley tours, as well as lots of local food vendors.
Full schedule available at breadandrosesheritage.org.