Experience your city like never before! Massachusetts residents can explore Boston with Old Town Trolley for FREE when accompanied by a full fare adult paid guest with Hometown Pass.
Dates: October 3, 10, 17, 24, 31. This vibrant open-air market features 50 local artists and small businesses, making it a must-visit destination for anyone who appreciates handcrafted goods and locally-made products.
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10:00 AM - 3:00 PM
Play Date: Free Family Art Day at ICA Boston
Institute of Contemporary Art, 25 Harbor Shore Dr.
Join us on the first Sunday of the month for a day of free family fun! Enjoy art-making, gallery activities, performances, and workshops designed to deepen kids’ and families’ connections with contemporary art. All activities are drop-in, first-come, first-served. Space is limited. Explore our Kids + Families page to help plan your visit!
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Boston Asian American Film Festival
Various times and locations.
Celebrate the 18th annual Boston Asian American Film Festival (BAAFF)! The BAAFF empowers Asian Americans through film by showcasing Asian American experiences and serving as a resource to filmmakers and the Greater Boston Community. The festival is here for YOU — to see and be seen, to hear and be heard — as individuals exploring the joys and challenges of a collective community.
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10:00 AM - 5:00 PM
Boston Book Festival 2026
In and around Copley Square in the Back Bay neighborhood of Boston.
Celebrating the power of words to stimulate, agitate, unite, delight, and inspire, the Boston Book Festival presents year-round events culminating in an annual festival that promotes a culture of reading and ideas and enhances the vibrancy of our city.
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11:00 AM - 1:00 PM
PruBoo 2026
Prudential Center, 800 Boylston St.
Parents, bring your children to trick-or-treat at 30+ participating stores and restaurants. Other activities include face painting, Halloween crafts, magic shows, and a musical performance! All activities are free and open to all.
