SATURDAY
31
OCTOBER
Boston Neighborhood Festivals & Open Markets
The best family weekends in Boston are the free ones: a neighborhood shuts a street, opens its studios or puts bands on its porches. SoWa's Sunday market runs from spring to late autumn and needs no booking at all. The autumn circuit and Head of the Charles fill October.
Season: May–Nov · Updated October 21, 2026 · refreshed weekly
- SoWa Open Market: Sundays, May 3 – November 15, 11am–5pm, free — 500 Harrison Ave, South End
- Somerville PorchFest: The 2026 edition has already happened; no 2027 date is published.
- Head of the Charles: October 16–18, 2026 — Friday to Sunday on the river
- North End feasts: An August tradition. The 2026 season is over and no 2027 dates are published.
- Open studios: Roxbury, Jamaica Plain and Fort Point run theirs in September and October, free
SoWa: the one that runs every Sunday
SoWa's Open Market is the dependable thing on this page — free, weekly, and in the South End from spring to late autumn. When the stalls run out of interest the resident studios are right there, and open.
SoWa Open Market — South End, BostonVisit official site →
“One of the largest open-air farmer and artist markets in Boston” — regional and local vendors, food and beverage trucks, all of it among working artist studios, galleries and shops.
Dates
- Sundays, May 3 – November 15
- 11am–5pm
Tickets
Free
Know before you go
- The farmers' market runs alongside the artist market, so it doubles as the week's grocery trip
- No dog or stroller policy is published — a double buggy on a warm Sunday is your own call
Who it's for
Families who want a plan that never needs checking first
PorchFest: how it works, and when it next runs
Somerville PorchFest is “a community-powered music festival where neighbors host musicians on porches across the city” — hundreds of them, one afternoon, free, with no stage and no gate. The 2026 edition has already taken place and no 2027 date is published.
- West Zone, west of Willow Ave: noon–2pm
- Central Zone, Willow Ave to Central Street: 2–4pm
- East Zone, east of Central Street: 4–6pm
- Pick one zone and walk it — two hours in one zone is a complete afternoon for a small child
- Watch somervilleartscouncil.org in the spring; the date surfaces with the musician application
- Cambridge, Jamaica Plain and other neighborhoods run their own versions on their own weekends
The autumn circuit: open studios and Opening Our Doors
September and October are when Boston's neighborhoods open their doors, and all of it is free to walk into. A working artist showing a seven-year-old how the thing on the wall was made holds attention far longer than a gallery does.
Open studios: Roxbury, Jamaica Plain, Fort Point — Boston
Three neighborhoods of working artists opening their studios, each on its own weekend, with the makers there to explain what you are looking at.
Dates
- September and October — each neighborhood picks its own weekend
Tickets
Free to walk in
Who it's for
School-age children who like making things
Skip if
You need a fixed time — the weekends are announced neighborhood by neighborhood
Opening Our Doors — Boston
“Boston's Largest Day of FREE Cultural Experiences” — a long list of institutions dropping admission on the same day, which is a different proposition from any one museum's free day.
Dates
- Indigenous Peoples' Day, Monday, October 12, 2026
Tickets
Free
Know before you go
- The MFA's Massachusetts-resident Open House falls on the same Monday, so a state zip code has two free routes into the day
Who it's for
Any family, and especially one that has been putting off the pricier museums
Head of the Charles: a walking event, not a sitting one
The regatta turns three miles of riverbank into the busiest weekend of the Boston autumn, Friday to Sunday in October. Crews come past in a long procession rather than one race, so you walk the bank rather than take a seat.
- Bridges are the good vantage points and also the crowded ones
- The Cambridge side is generally the easier one with a pushchair
- Ticketed seating: the Eliot Bridge Enclosure and the Directors' Lounge
- The race schedule lives on hocr.org
Festivals & street markets coming up
Live from our catalog — 16 upcoming, refreshed weekly.
Women's Openweight Crew competes against the Head of the Fish Regatta on Fish Creek in Saratoga Springs, NY.
Silicon Valley AI Film Festival Screening Showcase at Ray & Maria Stata Center, 32 Vassar Street, Cambridge.
SUNDAY
1
NOVEMBER
Boston's largest open-air farmers and artist market offers regional farm stands, 100+ makers, food trucks, and artist studios on pedestrian‑only Thayer Street; free.
WEDNESDAY
4
NOVEMBER
Greek Festival at Saint Sophia Church in New London, CT.
FRIDAY
6
NOVEMBER
Greek Festival at Holy Apostles Saints Peter & Paul Greek Orthodox Church, 154‑156 Winter Street, Haverhill, MA.
TUESDAY
10
NOVEMBER
Boston Comedy Festival Contest Round 1 (The Comedy Studio) — 96 comedians compete over eight rounds for $7,000 prize, hosted by Rob Crean with guest Alex Giampapa, ages 18+.
Would you like a personalized local event newsletter?
Tell us what you like, and get a free weekly email of hand-picked local events from 300+ Boston venues:
Festivals · Kids' classes · Craft workshops · Live music
WEDNESDAY
11
NOVEMBER
96 comedians compete over eight rounds for $7,000 prize, hosted by Chris Zito with guest Kathe Farris, at The Comedy Studio; bar opens early for drinks, ages 18+.
96 comedians compete over eight rounds for 32 semifinal spots and $7,000 prize at The Comedy Studio, hosted by Kindra Lansburg, with Maurice Smith closing, for ages 18+.
THURSDAY
12
NOVEMBER
96 comedians compete in stand‑up competition at Upstairs at McCarthys, hosted by Jason Cordova with guest Karen Morgan, 12 comedians per show, 32 advance.
96 comedians compete over a week at Upstairs at McCarthys, with Jack Lynch hosting and Chris Post as special guest, battling for $7,000 prize and semifinal spots.
FRIDAY
13
NOVEMBER
Boston Comedy Festival Comedy Contest: Semifinal Round 1 at The Rockwell.
Festival Jazz Ensemble's Fall Concert — Building W18, 201 Amherst Street, Cambridge, MA.
Boston Comedy Festival Comedy Contest semifinal round 3 performed at The Rockwell in Somerville.
SATURDAY
14
NOVEMBER
Performances by Hound & Hander, Cardineau, and the Brighton Mountain Pals accompany specialty beers, Mimi's Chuka Diner waffles, and limited‑edition glassware at Aeronaut Brewing Company.
Emo Philips performs at The Rockwell as part of the Boston Comedy Festival, with Jay Leno providing a description.
Boston Comedy Festival Contest Finals (Somerville Theatre).
Would you like a personalized local event newsletter?
Tell us what you like, and get a free weekly email of hand-picked local events from 300+ Boston venues:
Festivals · Kids' classes · Craft workshops · Live music
- Personalized event feed based on your interests, city, and age groups.
- Weekly event picks delivered to your email inbox.
- Search and filter the full event catalog.
How it works
Create your free profile
About a minute. No payment required.
Tune your picks
Choose ages, interests, and nearby cities.
Get your weekly shortlist
Fifteen event picks for you.
Explore the full list
Browse the complete local catalog anytime.
FAQ
Is Head of the Charles free to watch?
Its own site sells seats in the Eliot Bridge Enclosure and the Directors' Lounge and publishes no price for general riverbank spectating. Check hocr.org before you plan around it. The 2026 dates are October 16–18, Friday to Sunday.
When is Somerville PorchFest 2027?
Not announced. The Arts Council's page reads “Thank you for a Great PorchFest, see you next year!” and its 2026 applications are closed. The date usually appears in spring alongside the musician sign-up.
When are the North End feasts?
August, by long tradition — the saints' feasts fill a run of weekends in the North End. The 2026 season is over and no 2027 dates are published. They are street events: free to walk into, and crowded after dark.