Fall on Cape Ann brings more than colorful foliage and crisp days by the coast. Throughout October and November, Gloucester and the surrounding North Shore come alive with art events, open studios, Halloween celebrations, seasonal tours, hands-on workshops, and unique experiences you’ll only find here.
Whether you’re planning a fall getaway to Gloucester, adding a day on Cape Ann to an October trip to Salem, or looking for something new to do close to home, add these upcoming events to your calendar.
Spiritualism Tours by Candlelight at Hammond Castle Museum
Thursday Evenings Throughout October: Discover the more mysterious side of Hammond Castle Museum during its Spiritualism Tours by Candlelight. This 55-minute guided experience explores John Hays Hammond Jr.’s attempts to communicate with supernatural entities, Irene Fenton Hammond’s astrological writings, and other intriguing stories from the Castle’s history, all illuminated by handheld lanterns. Learn More >>
Painting Workshop: Color & Light with Water-Based Oils
Thursdays, October 1, 8, 15 & 22, 2:00–4:00 PM: Embrace the colors of fall with local artist Melody Phaneuf during this four-week painting workshop exploring color and light with water-based oils. Designed for beginners and experienced artists alike, the small-group classes offer a personalized introduction to this environmentally friendly alternative to traditional oil paints while exploring color relationships and the effects of light. Learn More >>
Halloween on the Hill at Long Hill
Wednesday-Sunday, October 1-30: Just a short drive from Gloucester, Halloween on the Hill transforms the grounds of Long Hill in Beverly with thousands of glowing, hand-carved jack-o’-lanterns. Follow the illuminated trail through an enchanting woodland filled with an eerie graveyard, haunted pirate ship, creative scarecrows, and larger-than-life seasonal displays designed for all ages. Learn More >>
Elizabeth Bish Artist Talk
October 2, 6:00 pm: Gloucester artist and 2026 Gloucester Invitational Artist Elizabeth Bish kicks off her residency with an intimate artist talk at the Cultural Center at Rocky Neck. Hear about her artistic journey, creative process, and plans to use her residency to explore new directions in her painting. Learn More >>
Cape Ann Plein Air
October 3–11: Cape Ann Plein Air brings 36 juried artists to Gloucester and communities across Cape Ann for a week of painting inspired by the region’s coastal landscapes. Watch artists at work and enjoy a full schedule of events including live demonstrations, a Quickdraw competition, opening reception, Gala & Art Sale, and more. Learn More>>
Cape Ann Artisans Fall Open Studios
October 10–11, 10:00 AM-5:00 PM: Explore Cape Ann’s creative community during the 43rd Annual Cape Ann Artisans Fall Open Studios. Visit artists in their studios throughout Gloucester and Rockport, see where their work is created, meet the artists, and purchase a new piece of art. Learn More >>
Rocky Neck Beaux Arts Ball Halloween Bash
October 24, 6:00–10:00 PM: Celebrate Halloween with a distinctly Rocky Neck twist at the third annual Beaux Arts Ball Halloween Bash. The evening brings together costumes, live music, dancing, passed hors d’oeuvres, a costume contest, prizes, and plenty of creative energy from Cape Ann’s arts community. This year’s celebration also includes an online silent auction featuring 12 one-of-a-kind experiences, with bidding open whether or not you attend the Ball. Learn More >>
Barebones Wood Carving Workshops
October 24–29 and November 7-12: Try your hand at traditional woodcarving during a multi-day Barebones Wood Carving Workshop with master woodcarver David Calvo. Workshops run from 9:00 AM–5:00 PM, offering an immersive opportunity to develop your carving skills. Learn More >>
Elizabeth Bish Open Studio
October 24, 2:00 PM-4:00 PM: Step inside Elizabeth Bish’s studio and get a closer look at the work of the 2026 Gloucester Invitational Artist. Bish works primarily in oils, with paintings spanning landscapes, still life, figurative work, and abstraction inspired in part by her longtime connection to Cape Ann. Learn More >>
Halloween Halibut Hoedown
October 28, doors at 7:00 PM: Schooner Adventure puts a Halloween spin on its beloved “anti-gala” as the historic schooner celebrates its 100th anniversary. Head to The Cut for live music, dancing, costumes, maritime mischief, a Pumpkin Cod-Fish Carving Contest, a Fish Market Full of Candy, and a celebration of Gloucester’s fishing heritage. Come as a 1920s flapper, salty fisherman, fabulous fish, or anything else you can dream up! Learn More >>
Boo-Port Spooktacular Halloween Cruise
October 31, 11:00 AM-12:30 PM: Halloween fun heads out onto Gloucester Harbor with Beauport Cruiselines’ family-friendly Boo-Port Spooktacular. Little ghosts and goblins can enjoy pumpkin decorating, crafts, Halloween treats, music from a live DJ, and more festive surprises aboard the cruise. Costumes are encouraged for kids and adults alike. Learn More >>
Halloween Spoon Carving Workshop
October 31, 9:00 AM–5:00 PM: Spend Halloween learning a new craft with a hands-on spoon carving workshop led by David Calvo. All tools are provided, and participants will leave with both a new skill and a beautiful and useful tool to take home. Learn More >>
Beauport Hotel Halloween Soirée
October 31, 8:00 PM-11:00 PM: Dress to impress for a Halloween celebration by the sea at Beauport Hotel Gloucester. This 21+ soirée features live DJ entertainment, late-night bites from 1606 Restaurant & Oyster Bar, a costume contest, and a few surprises along the way, all set against the backdrop of Gloucester Harbor. A portion of event proceeds will benefit the Mass General Brigham Cancer Institute. Learn More >>
From the Deep: A Downtown Gloucester Arts Party
November 7, 11:00 AM-5:00 PM: Dive into Gloucester’s creative side during From the Deep, a downtown arts and culture celebration presented by the Harbortown Cultural District. Spend the day exploring free art activities, live art making, gallery openings, poetry readings, and more throughout the city. Learn More >>
Hammond Castle Museum Renaissance Faire
November 7–8: Step back in time as Hammond Castle Museum transforms into a Renaissance Faire filled with knights, artisans, performers, music, fantasy, and family-friendly fun. The Castle’s medieval-inspired architecture provides a one-of-a-kind backdrop for armored combat demonstrations, entertainment, hands-on activities, and opportunities to explore portions of the museum. Cosplay is encouraged for all ages, and complimentary shuttles will run between Stage Fort Park and Hammond Castle Museum throughout the event. Learn More >>
Forge Your Own Woodcarving Tools Blacksmithing Workshop
November 13–16: Combine two traditional crafts during David Calvo’s four-day blacksmithing workshop focused on forging your own woodcarving tools. Sessions run from 9:00 AM–5:00 PM. Learn More >>
Make a weekend of it and discover even more things to do in Gloucester this fall, from exploring the working waterfront and local arts scene to dining on fresh seafood, getting out on the water, and taking in the season along the coast.