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Boston’s Arts and Entertainment Weekend Events

Families enjoying Boston's Arts Festival with various art displays and fashion shows.

Boston, September 4, 2025

News Summary

This weekend, Boston will celebrate creativity with several free family-friendly events including Fashion in the Park, the Boston Arts Festival, and the ICA’s Play Date for International Dot Day. These events showcase local talent through fashion, fine arts, and interactive art activities, promoting community engagement and pride.

Boston — Boston will host a series of arts, fashion, and entertainment events across the city this weekend, highlighted by Fashion in the Park in Roslindale, the long-running Boston Arts Festival on the waterfront, and the Institute of Contemporary Art’s Play Date celebrating International Dot Day.

What’s happening (top-line)

All three headline events are free and family-friendly. Fashion in the Park returns for its 3rd annual edition as a community-focused celebration of style and creativity. The Boston Arts Festival continues its tradition of showcasing fine arts and live music in a historic waterfront park. The Institute of Contemporary Art (ICA) will host a Play Date on September 7 centered on International Dot Day, offering hands-on art activities and family programming.

Details on major events

Fashion in the Park — Roslindale

Presented by Save Our Streets-Boston, Fashion in the Park is billed as a free, family-focused event designed to spotlight local design and community creativity. The program includes a live runway show featuring local designers and models, performances by local musicians and artists, art installations, vendor booths, and music. The event aims to create a celebratory atmosphere while highlighting neighborhood talent and fostering community pride.

Boston Arts Festival — Waterfront

The Boston Arts Festival showcases the city’s creative community with fine arts displays and live musical performances. Running since 2003, the festival takes place in a historic waterfront park and presents work by local artists alongside on-site performances. The festival is scheduled to proceed rain or shine, offering a wide range of visual and performing arts for all ages.

ICA Play Date — Institute of Contemporary Art (September 7)

The ICA’s September Play Date celebrates International Dot Day, an event inspired by the children’s book “The Dot” by Peter Reynolds. Programming will include hands-on art-making activities in the Bank of America Art Lab and the State Street Corporation Lobby, screenings of animated short films based on Reynolds’ stories, and gallery-based picture book readings. The ICA’s Play Date also features a book signing and a question-and-answer session with the author, along with interactive activities designed to promote creativity for visitors of all ages.

Additional arts and entertainment offerings

Beyond these headline events, the city’s arts and entertainment scene this weekend includes a diverse schedule of music and comedy events across venues large and small. Programming ranges from headline artists to community-driven showcases and neighborhood performances. Organizers and event listings advise attendees to check local schedules for specific start times and locations.

Practical information

  • Cost: Major events noted here are free to attend.
  • Family-friendly: All three highlighted events are designed to welcome families and children.
  • Weather: The Boston Arts Festival is set to run rain or shine; other events may have specific weather policies.
  • Accessibility: Venues and outdoor parks typically provide accessible routes; attendees should consult individual event information for details on accessibility services.
  • Transport and parking: Public transit is recommended for waterfront and neighborhood events; street parking and event-specific lots vary by neighborhood.
  • Digital access: Attendees are encouraged to download available event apps where provided to listen to live events, browse schedules, and connect with community programming.

Background

The Boston Arts Festival has been an annual fixture since 2003, contributing to the city’s cultural calendar by offering a platform for local visual and performing artists. Community-driven fashion events such as Fashion in the Park have grown in recent years as neighborhood organizations and cultural groups seek to create public programs that combine design, performance, and local commerce. The ICA’s family programming aligns with broader efforts by cultural institutions to engage young audiences through participatory art-making and literature-based activities.

How to prepare

Attendees should verify event times and specific site locations before traveling. Layers and rain gear are advisable given variable New England weather. Families may want to arrive early for hands-on activities and limited-capacity performances. Where possible, use public transportation to reduce parking challenges around waterfront and neighborhood parks.

Frequently Asked Questions

Are these events free to attend?

Yes. The highlighted events — Fashion in the Park, the Boston Arts Festival, and the ICA Play Date — are described as free and family-friendly.

When is the ICA Play Date?

The ICA Play Date is scheduled for September 7 and focuses on International Dot Day programming for families and children.

Will the Boston Arts Festival be canceled in bad weather?

The Boston Arts Festival is planned to continue rain or shine. Other events may have different weather policies, so check event-specific information for changes due to severe weather.

Is Fashion in the Park suitable for children?

Yes. Fashion in the Park is presented as a family-friendly event with programming suitable for children, including performances and art installations.

How can I find specific schedules and artist lineups?

Event schedules, artist lineups, and exact locations are typically provided by event organizers and may be available through official event listings or apps when provided. Attendees should consult those resources for up-to-date details.

Are there accessibility accommodations?

Venues generally provide accessible routes and services, but availability varies. Check event-specific information or contact organizers directly to confirm accommodations.

Is there an app to follow live events?

Some events and organizers recommend downloading an app to listen to live events, view schedules, and connect with community programming. Availability and features vary by event.

Quick reference table

Event Date/Time Location Cost Highlights
Fashion in the Park This weekend (check local schedule) Roslindale Free Runway show, local designers, performances, vendors
Boston Arts Festival This weekend (running since 2003) Waterfront park Free Fine arts exhibits, live music; rain or shine
ICA Play Date September 7 Institute of Contemporary Art Free International Dot Day activities, art-making, films, readings

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STAFF HERE BOSTON WRITER
Author: STAFF HERE BOSTON WRITER

BOSTON STAFF WRITER The BOSTON STAFF WRITER represents the experienced team at HEREBoston.com, your go-to source for actionable local news and information in Boston, Suffolk County, and beyond. Specializing in "news you can use," we cover essential topics like product reviews for personal and business needs, local business directories, politics, real estate trends, neighborhood insights, and state news affecting the area—with deep expertise drawn from years of dedicated reporting and strong community input, including local press releases and business updates. We deliver top reporting on high-value events such as Boston Marathon, Head of the Charles Regatta, and Boston Harborfest. Our coverage extends to key organizations like the Greater Boston Chamber of Commerce and Associated Industries of Massachusetts, plus leading businesses in finance, biotech, and insurance that power the local economy such as Fidelity Investments, Biogen, and Liberty Mutual Insurance. As part of the broader HERE network, we provide comprehensive, credible insights into Massachusetts's dynamic landscape.

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