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The Saint Peter's Fiesta is an annual festival in Gloucester, Massachusetts celebrating the city's fishing heritage, close-knit families, community, and religious traditions.  The five-day celebration includes a carnival, live entertainment, and unique traditional events like the infamous 'Greasy Pole' contest and classic seine boat races. The festival is proudly sponsored by the Italian-American fishing community of Gloucester, and has all kinds of family-oriented activities and events, making it a great early Summer destination weekend event.

The Saint Peter's Fiesta is an annual festival in Gloucester, Massachusetts celebrating the city's fishing heritage, close-knit families, community, and religious traditions.  The five-day celebration includes a carnival, live entertainment, and unique traditional events like the infamous 'Greasy Pole' contest and classic seine boat races. The festival is proudly sponsored by the Italian-American fishing community of Gloucester, and has all kinds of family-oriented activities and events, making it a great early Summer destination weekend event.

Celebrate Juneteenth, the oldest nationally celebrated commemoration of the ending of slavery in the United States with Cape Ann Museum! The 4th Annual Gloucester Juneteenth Celebration, presented by the Cape Ann Museum in collaboration with community organizations across the city, began as a grassroots initiative by Gloucester resident Toni Waldron in 2021 and became part of the museum's annual events calendar in 2022. Learn about the Juneteenth Holiday and its connection to Cape Ann history while celebrating Black history through music, dance, and food.

"Dogtown" on Cape Ann offers families an intriguing blend of history and natural beauty. Known for its vast woodlands, trails, stone walls, and cellar holes, Dogtown is a place where proud people once lived and worked for nearly 150 years before it was abandoned. The area is rich with tales of witches, widows, and an ill-fated bullfighter, making it a captivating destination for children and adults alike. This two-hour, three-mile walking tour invites families to explore the main roads of this early settlement, meet some of its historical residents, and hear their stories. Visitors will learn how Dogtown got its name, why it was abandoned, and how it has evolved over the past 200 years.