Family events in Gloucester, MA

This drop-in art session in Create Space Studios invites participants to craft a tiny decorative broom that captures the playful spirit of Halloween, using materials like twigs, dried grasses, and other seasonal natural elements. Admission covers the activity. It is part of the in-person Drop-in Art Making program. Friday sessions are recommended for ages 10 and up, while weekend and holiday offerings are designed for ages 4 and up. All activities are created and led by PEM art educators.

Ipswich Illumination returns with an expanded celebration that unfolds over two weekends at multiple spots around town. The first weekend centers on Top of Town Hill, the second highlights the Takeout Terrace, and everything culminates with closing ceremonies at Pavilion Beach. Expect a lively mix of lights, music, art, and strong community spirit. Local food trucks will be serving throughout the festivities, with area vendors offering beer, wine, and mead to complement the experience. Traffic and parking changes are planned around Town Hill during the first weekend. Some periods will feature soft closures that still allow residents within the area to access their homes under the guidance of public safety personnel and posted signs. One period is designated as a hard closure with no through traffic. Review maps that outline closure and no‑parking zones, follow on-site directions, and allow extra time for travel.

Families of creative students curious about crafting, science, drama, or robotics can explore Melrose Destination Imagination at an info session held at MMTV Studios. The session introduces the program for kids and parents in grades K through 12 and explains how teams are formed and how to participate. Attendees can try sample Instant Challenges and bring one home, play acting and improv games, preview this season’s challenges, meet other interested families, and speak with experienced DI team managers to get questions answered. For questions, contact di@melrosedi.com.

Sweet Sisters Boston will be on site at Connolly Center’s indoor yard sale with a table of baked treats. The selection includes glazed pumpkin loaves, macarons, cookies, and chocolate covered Oreos. It is a convenient chance to pick up something sweet while browsing the sale.

This family friendly Halloween craft fair and trick or treat event takes place at the American Legion in Beverly, Massachusetts. More than 15 local vendors will be on site along with raffles and giveaways, activities for children, character encounters, trick or treating, and food vendors, creating a festive experience for all ages. Prizes will be awarded for standout spooky costumes. Families must preregister by scanning the QR code on the event flyer and completing the form. Space is limited and once capacity is reached additional families cannot be accepted. Vendor opportunities are available.

Copley Square hosts the Boston Book Festival, a lively celebration of literature and ideas. A dozen local authors will be available for book signings, among them Ann Goltz in women's fiction, Susan Beach and Peter Clenott in historical fiction, Cynthia Kallai, also known as Irene Hagan, in cozy mystery, Kathleen Jeffrey and James Rebello, who also writes as George Bridge, in children's, Shawn McCarthy with a fantasy series, Pierce Press with epic fantasy and children's, Caleb Mason in mystery and thriller, Ann Wells, InSup Kim, John Gillooly focusing on sports and nonfiction, Lauren Brown, Lizzie Seibert, and Christopher Mirabile with mystery thrillers. Each year the festival draws thousands who come to find new books and connect with authors and publishers at Copley Square.

Designed for those preparing for parenthood, this expo blends inspiration, practical learning, and a sense of fun. Explore leading pregnancy, baby, and parenting brands through interactive product demonstrations, hear guidance from knowledgeable experts during supportive seminars, and take part in unique experiences. Throughout the event there are chances to win more than 50 grand prize giveaways, with items ranging from baby gear to wellness must haves. It brings together education and excitement so participants leave feeling confident, connected, and celebrated.

Explore the storied landscape of Dogtown on Cape Ann during a guided walk that traces the old roads of an early settlement once at the heart of Gloucester. Hear about the people who lived and worked here for nearly 150 years, how the place got its name, why residents moved on, and what has changed in the two centuries since the last house disappeared. Along the way, take in stone walls, cellar holes, and vistas that have long suggested witches and widows, an ill-fated bullfighter, pastures, picnics, blueberries, and a sea of rocks. Learn how writers and artists drew inspiration from this terrain, discover the reservoirs created here, and encounter several of the famed word-inscribed boulders that reflect the legacy of entrepreneur and philanthropist Roger Babson (1875-1967). The route covers nearly three miles in about two hours on generally easy but uneven trails with rocks, roots, and gentle hills. Wear trail-ready clothing and closed-toe shoes, and consider bringing walking poles. Bring water and insect repellent, as they are not provided. This experience is not recommended for those with mobility concerns. The tour takes place at Babson Boulder Parking. Tickets are $10 for CAM members and $20 for non-members, and advance registration is required.

Now in its 18th year, the ALS & MS Walk for Living features a 2-mile dog-friendly route followed by family activities that include baby farm animals, live entertainment, DJ music, a raffle, and a barbecue provided by Chili’s. Registration takes place before the walk begins, then the festivities continue after participants complete the course.

Experience Jewish campfire tales beside a cozy fire pit in a newly enclosed pergola. Families and friends can share stories, connect, and enjoy food and drinks. Admission is $10 per adult, $5 per child, with a $20 family maximum.

A local photographer offers a mini portrait experience in Boston’s North End, capturing you amid historic architecture and old world charm. The session includes 15 minutes of photography and one favorite image to download. After the shoot, a Zoom video call is scheduled to review your images and pick the top choice, which will be edited and delivered for download. If you want more than the included photo, additional digital files, boxed prints, wall art, albums, cards, and other upgrades are available for purchase. Longer portrait experiences and options that include additional locations are also offered for those who want extra time or variety.

Discover the seaside castle residence of 20th century inventor John Hays Hammond Jr., now a museum dedicated to sharing ancient architectural art with the Gloucester community. Through Gloucester Gratis Days, Gloucester residents receive complimentary self-guided admission during the regular tour season and during the museum-wide holiday exhibition, Deck the Halls. Proof of residency is required at check-in for each reservation. Advance registration is suggested but not required, and sign-ups can also be completed in the Museum Shop upon arrival.

Discover a potion making experience in Salem, Massachusetts where children and families mix, pour, and bottle a whimsical creation to take home. This interactive, self-paced activity is designed for families and typically lasts about 15 to 25 minutes. Hosted at The Good Witch of Salem Spell Studio near the historic Witch House, it offers a uniquely Salem outing that is welcoming to a wide range of ages and creates a memorable keepsake from your visit.

Family Movie Night features a PG-rated mystery inspired by Leonie Swann's novel Three Bags Full, centered on The Sheep Detectives. Hugh Jackman and Emma Thompson star, with voice roles from Patrick Stewart, Julia Louis-Dreyfus, and Regina Hall. The story follows George, a shepherd who reads detective novels to his flock, and after an unsettling incident on the farm the sheep take on the investigation, tracking clues and questioning human suspects to crack the case. The film runs 109 minutes and was released in 2026. Free snacks will be available. Showtime is approximate.

Experience a lively weekly market with an expanded lineup of more than 30 local vendors, including farms, small batch food makers, artisans, and community organizations. Browse seasonal fruits and vegetables, fresh bread, pasta, hummus, coffee, olive oil, and other everyday staples, plus a wide selection of specialty items and ready-to-enjoy dishes. The day features live music, cooking demonstrations, and activities for children. SNAP customers receive a $15 match, and three participating farms accept HIP benefits.

Set along Broadway at Salisbury Beach, Salisbury’s Trunk or Treat transforms the parking lot into a festive Halloween route for families. Community members, local businesses, and organizations decorate their vehicles and hand out candy and small goodies while kids trick or treat from car to car. The event is free, and those who are able may be asked to bring an item to be determined. It offers a friendly way for participants to showcase community spirit through creative trunk displays and treats.