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Events for August 16, 2026

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45th Annual Gloucester Waterfront Festival

45th Annual Gloucester Waterfront Festival
Stage Fort Park 24 Hough Ave, Gloucester

The historic Stage Fort Park along Gloucester Harbor will blossom into color and flavor for the 45th Annual Gloucester Waterfront Festival on Saturday, August 15th and Sunday, August 16th, 2026. This event features over 150 Booths of American made arts, crafts, foods and live music. Admission is free, handicap accessible, held rain or shine and...

There is no entry fee for the Fair. There is a parking fee at the beach parking lot. Make online parking reservations here: https://gloucester.blinkay.app/login

Marblehead Art Crawl & Open Studios

Marblehead Arts Association 8 Hooper Street, Marblehead

Enjoy a scenic, summer stroll around beautiful Marblehead visiting many of our artist studios on Sunday August 16th between 11am-4pm. Just download the map of participating artists and take your self-guided tour around town, stopping off to visit local art studios, meet the artists and learn more about their craft. With 25 Marblehead art studios...

Free

Gloucester Stage Company presents DALLOWAY: FIRST LOVE by Lindsay Joelle

Gloucester Stage Company presents DALLOWAY: FIRST LOVE by Lindsay Joelle
Gloucester Stage Company East Main Street 267, Gloucester

From the playwright behind last season’s The Garbologists comes an unlikely world premiere of feminine proportions. Clarissa Perry is a tree climbing, combat boot wearing goth with no interest in entertaining the slew of suitors found by her money-strapped father. The pressure is on Clarissa to find a husband and save her family’s estate when...

$18 – $74