Cape Ann Pride

Cape Ann Pride is a community celebration run by the Cape Ann Pride Coalition, a nonprofit, across Gloucester and nearby towns. The main weekend opens with a Progress Pride flag raising at Gloucester City Hall and includes concerts, a dance party, a family bowling event, and Pride services at local houses of worship. Smaller events, including a families picnic and a teen sail, continue into the summer.

The Cape Ann Pride Coalition is led by a board of local residents with backgrounds in nonprofit work, activism, publishing and the arts. The Greater Cape Ann Chamber of Commerce was a co-founding and co-organizing partner of the first Cape Ann Pride Weekend and continues to help with business outreach, community engagement and event planning.

Board members describe the coalition's aims as advocating for, celebrating, educating about and supporting LGBTQIA+ people across Greater Cape Ann, and making queer community spaces available year-round rather than only in June.

Beyond the Pride weekend, the coalition has hosted a Masquerade Ball at the Great House at Castle Hill on the Crane Estate in Ipswich. Guests were encouraged to wear masks and formal or semi-formal attire, and the evening offered a cash bar, catered hors d'oeuvres and a live string quartet. The first floor of the main hall and the grounds are wheelchair accessible, and a tent covers the patio in case of rain.

Pride events celebrate LGBTQ+ people and mark the Stonewall uprising of June 1969. Most combine a parade or march with a festival of performers, community groups, vendors and food.

Cape Ann Pride has included flag raising, concert, dance party, family picnic, youth events and interfaith service.

The organizer has not announced dates for 2027 yet. In 2026 it was held May 28 to June 1, 2026. It usually falls main weekend around Memorial Day into early June, with events through the summer.