Gloucester’s Annual Festivals
Gloucester comes alive with festivals that celebrate its rich maritime heritage, creative spirit, and close-knit community. Signature events like St. Peter’s Fiesta, the Gloucester Schooner Festival, and Culture Splash highlight everything from waterfront traditions and historic vessels to art, music, and local culture. From lively parades to open studios and performances, there’s always something happening worth celebrating.
Gloucester's So Salty
JANUARY 24-25, 2026: Dazzling ice sculptures, winter festivities, live entertainment and coastal New England charm are highlights of this weekend downtown.
Cape Ann Pride Weekend
MAY 28-31, 2026: Cape Ann Pride Weekend celebrates inclusivity across Gloucester and Cape Ann with events, live music, flags, performances, and community gatherings.
Battle of Gloucester Reenactment
JUNE 20-21, 2026: Experience the pivotal early naval clash that helped spark the creation of the U.S. Navy, with immersive 18th-century experiences.
St. Peter's Fiesta
JUNE 24-28, 2026: St. Peter’s Fiesta in Gloucester celebrates Italian-American heritage with parades, processions, waterfront festivities, music, food, and the famous Greasy Pole competition.
Gloucester Independence Day Celebrations
JULY 3, 2026: Enjoy fireworks over the harbor, family activities, live music, parades, and classic coastal New England traditions.
Culture Splash
JULY-AUGUST: Visit Gloucester's Rocky Neck Cultural District on Thursday nights for art exhibitions and demonstrations, open studios, live music, community artmaking, and more.
Blackburn Brew Fest
JULY 18, 2026: Head to Stage Fort Park to sample dozens of beers, ciders, hard seltzers and meads brewed by over 20 local craft breweries, all in support of the Cape Ann Community Foundation.
Gloucester Schooner Festival
SEPTEMBER 4-6, 2026: his Labor Day tradition draws vessels from near and far for parades, sails, deck tours, the Mayor's Cup Race, and more.
Cape Ann Plein Air
OCTOBER 3-11, 2026: Cape Ann Plein Air week brings 36 juried artists to the coastal landscapes of Cape Ann, Massachusetts, where they paint through the week and compete for awards.
Gloucester's Holiday Celebrations
NOVEMBER-DECEMBER: Celebrate the holiday season in Gloucester with local shopping specials, tree lightings, parades, and more.
There’s always something special happening in America’s oldest seaport. In addition to annual festivals and events, Gloucester is home to live music, art exhibitions, theater and performing arts, specialty schooner sails, and so much more throughout the year.