From Discover Gloucester:
From seasonal events and spooky experiences to art, outdoor adventures, fresh seafood, and more, there are plenty of reasons to plan a visit this month.
Here’s what’s happening this month in America’s Oldest Seaport:
Credit: Apple TV
Love Widow’s Bay? You might recognize some familiar places! Much of the series was filmed right here on Cape Ann, with Gloucester and Rockport standing in for the fictional coastal town. Discover the real-life locations behind the show on our blog.
Spiritualism Tours by Candlelight | Thursday Evenings Throughout October
Explore the mysterious side of Hammond Castle Museum on a candlelit tour featuring stories of spiritualism, astrology, and the supernatural.
Color & Light with Water-Based Oils | October 1, 8, 15 & 22
Explore color and light with local artist Melody Phaneuf during this four-week, small-group painting workshop for all experience levels.
Halloween on the Hill | October 1–30, Wednesdays–Sundays
Thousands of glowing jack-o’-lanterns, an eerie graveyard, haunted pirate ship, and more family-friendly frights transform Long Hill in Beverly for the season.
Elizabeth Bish Artist Talk| October 2
Join 2026 Gloucester Invitational Artist Elizabeth Bish at the Cultural Center at Rocky Neck for an intimate conversation about her artistic journey, process, and residency.
Cape Ann Plein Air | October 3–11
Watch 36 juried artists capture Cape Ann’s coastal landscapes during a week of plein air painting, demonstrations, special events, the Gala & Art Sale, and more.
Cape Ann Artisans Fall Open Studios | October 10–11
Visit artists in their studios throughout Gloucester and Rockport, meet the makers, see where their work is created, and find a new piece to take home.
Rocky Neck Beaux Arts Ball Halloween Bash | October 24
Celebrate Halloween Rocky Neck-style with costumes, live music, dancing, a costume contest, prizes, and a silent auction of one-of-a-kind experiences.
Barebones Wood Carving Workshops | October 24–29 & November 7–12
Learn traditional woodcarving techniques during upcoming workshops with master woodcarver David Calvo.
Halloween Halibut Hoedown | October 28
Celebrate Schooner Adventure’s 100th anniversary at The Cut with live music, dancing, costumes, maritime mischief, and plenty of Halloween fun.
Boo-Port Spooktacular Halloween Cruise | October 31
Set sail on Gloucester Harbor for a family-friendly Halloween cruise featuring pumpkin decorating, crafts, treats, music, costumes, and more.
Beauport Hotel Halloween Soirée | October 31
Dress up for a 21+ Halloween celebration by the harbor featuring live DJ entertainment, late-night bites, a costume contest, and more.View the Full Event Calendar >>
