Boston, August 21, 2025
News Summary
This weekend, Boston will come alive with a variety of community events, including a watercolor workshop, dance parties, and social dinners aimed at fostering connections. Families can enjoy a Kids Day at the Boston Triathlon, while music lovers can attend a jazz festival in Medford and a French film festival at the Museum of Fine Arts. The events are designed to be inclusive, encouraging participation from all age groups and providing opportunities for social interaction, creativity, and cultural enrichment across neighborhoods.
Boston
Boston will host a wide-ranging slate of community events this weekend, offering arts, music, family activities and social dinners across neighborhoods. Highlights include a beginner watercolor workshop inspired by Boston Harbor, an outdoor dance party on City Hall Plaza, social dinners aimed at reducing loneliness, a traditional jazz festival in nearby Medford, a French film festival at the Museum of Fine Arts, a kids’ day at the Boston Triathlon, and several pop-up markets and cultural performances.
Key events and practical details
Watercolor by the Water (Beginner workshop)
A beginner-friendly watercolor workshop led by Boston-based artist Lisa Goren invites participants to create work inspired by Boston Harbor. Supplies are limited and will be provided on a first-come, first-served basis. The workshop is presented in conjunction with the Stanley Whitney: How High the Moon exhibition to provide additional inspiration for attendees. The session is designed for people of all experience levels.
Dance Party Series — City Hall Plaza
The Office of Tourism, Sports, and Entertainment is staging a three-part dance party series on City Hall Plaza. Programming is family-friendly with throwback music curated by a resident DJ to encourage a welcoming atmosphere for a range of ages and abilities.
100 Cities Project: Fighting Loneliness — Social Dinners
The 100 Cities Project is organizing group dinners at local restaurants to foster new connections. Participants complete a short questionnaire used to place diners in small groups with the goal of encouraging genuine conversation rather than creating a singles environment. As part of the program, organizers will allocate 25% of monthly dinner sales to charity or designated GoFundMe pages.
Bay State Hot Jazz Festival
The Bay State Hot Jazz Festival runs August 23–24 at the Condon Band Shell in Medford and features traditional jazz bands from around the country. Programming centers on historical styles of jazz and live ensemble performances.
Boston French Film Festival
The Boston French Film Festival continues at the Museum of Fine Arts through August 24, presenting a selection of critically recognized French films across genres, including dramas, comedies and select premiere screenings.
Family and community activities
DCR Carson Beach will host the 11th annual Kids Day during the Boston Triathlon on Saturday, offering races for children in multiple age groups. A Southie Thrift Market Pop-up invites residents to shop for second-hand clothing on August 23 from 1:00–4:00 PM. Additional weekend programming includes a bike community celebration, outdoor jazz events and symphonic and cultural performances across the city.
Ongoing and upcoming series
Boston’s Summer in the City Entertainment Series is offering free concerts through August 28, featuring a range of musical genres. The Boston Arts Festival is scheduled for September 7–8, showcasing more than 50 local artists and in-person opportunities to meet and purchase directly from creators.
How events support community goals
Organizers emphasize community building and social connection across events. Activities are designed to be inclusive, combining arts engagement, public performances and structured social experiences to encourage participation across age groups and neighborhoods. Several events incorporate charitable giving or community partnerships, such as the monthly donation program tied to the 100 Cities Project dinners.
Logistics and attendee guidance
Specific times, ticketing, registration requirements and accessibility accommodations vary by event. Some events are free to attend, such as elements of the Summer in the City series, while others may require advance registration or tickets. Workshop supplies are limited in certain cases and will be distributed on a first-come, first-served basis. Attendees should plan for travel time and check event notices for weather-related changes for outdoor programming.
Background context
These weekend activities reflect seasonal programming that combines cultural festivals, neighborhood markets, outdoor concerts and community-building initiatives. The slate of events aligns with typical late-summer offerings intended to engage residents and visitors with accessible arts and recreation opportunities across Boston and nearby communities.
Frequently Asked Questions
What are the dates and locations for the major events this weekend?
Major events include the Bay State Hot Jazz Festival on August 23–24 at the Condon Band Shell in Medford; the Southie Thrift Market Pop-up on August 23 from 1:00–4:00 PM; the Boston French Film Festival at the Museum of Fine Arts through August 24; and ongoing Summer in the City concerts through August 28. The watercolor workshop and City Hall Plaza dance parties are scheduled across the weekend at their respective venues.
Do I need to register or buy tickets?
Registration and ticket requirements vary by event. Some activities, such as portions of the Summer in the City series, are free, while others may require advance registration or tickets. Check the event listings for each activity for specific admission and registration guidance.
Is the watercolor workshop suitable for beginners?
Yes. The Watercolor by the Water workshop is described as beginner-friendly and open to participants of all experience levels. Supplies for the session are limited and provided on a first-come, first-served basis.
What is the purpose of the 100 Cities Project dinners?
The dinners aim to connect strangers and reduce loneliness through small-group shared meals. Participants are grouped using a questionnaire to promote real conversation. A portion of sales each month—25%—is donated to charity or designated GoFundMe pages.
Are there family-friendly activities this weekend?
Yes. Family-oriented options include a dance party series on City Hall Plaza with throwback music in a family-friendly format, Kids Day at the Boston Triathlon at DCR Carson Beach, and outdoor concerts and festivals appropriate for a wide range of ages.
Quick reference table
| Event | Date / Time | Location | Notes |
|---|---|---|---|
| Watercolor by the Water (workshop) | This weekend | Boston Harbor area (workshop venue) | Beginner-friendly; supplies limited, first-come, first-served; led by Lisa Goren |
| Dance Party Series | Series across the weekend | City Hall Plaza | Three-part celebration; family-friendly music by resident DJ |
| 100 Cities Project: Social Dinners | Various dates (monthly donations) | Local restaurants | Participants grouped by questionnaire; 25% of monthly dinner sales donated |
| Bay State Hot Jazz Festival | August 23–24 | Condon Band Shell, Medford | Traditional jazz bands from across the country |
| Boston French Film Festival | Through August 24 | Museum of Fine Arts | Selection of French films including premieres |
| Southie Thrift Market Pop-up | August 23, 1:00–4:00 PM | South Boston | Second-hand clothing market |
| Kids Day — Boston Triathlon | Saturday (weekend) | DCR Carson Beach | Races for children across age groups |
| Summer in the City Entertainment Series | Through August 28 | Various outdoor venues | Free concerts across genres |
| Boston Arts Festival | September 7–8 | City venues | More than 50 local artists; in-person sales and performances |
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Additional Resources
- Time Out Boston: Things to Do This Weekend
- Wikipedia: Boston
- Boston Globe: Canine Conversation
- Google Search: Boston Arts Events
- Bay State Banner: Boston Arts Festival
- Google Scholar: Boston Music Festivals
- Boston.com: Irish Music Festival
- Encyclopedia Britannica: Boston Events
- Boston.com: Boston Calling 2025 Information
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.
