Milford’s fall calendar is packed — Oktoberfest at Fowler Field, Apple Festival in West Haven, Restaurant Week menus all over town — and Gulf Street has its own classic this weekend: the beloved St. Mary’s Carnival at Saint Mary School, 72 Gulf Street.
According to the City of Milford community calendar and Saint Mary School’s 2026 carnival listing, the carnival runs Friday, Sept. 25 through Sunday, Sept. 27, 2026, with rides, games, food trucks, and family fun that directly support the school’s Home and School Association (HSA).
Hours (city calendar / school flyer):
Friday, Sept. 25 — 5–10 p.m.
Saturday, Sept. 26 — 1–10 p.m.; fireworks at 9:30 p.m.
Sunday, Sept. 27 — 1–5 p.m.
Rides, food trucks, and that Saturday sky
Organizers pitch the weekend as a community staple: exciting rides and games, delicious food trucks, and time together on the school grounds. The Saturday night fireworks at 9:30 p.m. are the signature finish — a longtime tradition for families who make Gulf Street their September hangout.
In the school’s Winter 2026 SMS Today newsletter, longtime carnival-goer Mrs. Adler put the feeling simply after a Saturday night visit with her husband, Ken, and daughters Erin and Tanya (SMS Class of 2012): “So many fun memories made at the carnival, no matter how old they get!”
Where it happens
Everything unfolds at Saint Mary School, the Catholic PK–8 campus at 72 Gulf Street in Milford’s Fort Trumbull neighborhood — the same grounds that host parish and school life year-round. The carnival is one of the school’s major HSA fundraisers, helping keep quality education accessible for SMS families.
Sponsors making the weekend possible
The city calendar listing offers a special thank-you to Big Top Sponsor Milford Junior Major League Baseball, and gratefully recognizes additional sponsors: Hyatt Place Milford, ACTIVE HEALTH, Montano Distributors, Shoreline Dental Care, NATURAL LIVING, LLC, Milford Pharmacy, Concierge Physicians of Westport, Sacred Heart University, and Frosty Twist.
Why it matters locally
Between Devon Rotary’s Oktoberfest, the West Haven Apple Festival, and Regional Restaurant Week, this is one of those Shoreline weekends where you can barely choose a lane. St. Mary’s Carnival is the neighborhood counterweight — a school fundraiser with lights, popcorn, and fireworks that has drawn Milford families for years. Proceeds support SMS’s HSA; the night supports the kids who call Gulf Street home.
PLAN YOUR VISIT — ST. MARY’S CARNIVAL 2026
St. Mary’s Carnival
Saint Mary School, 72 Gulf Street, Milford, CT 06460
When
- Friday, Sept. 25, 2026: 5–10 p.m.
- Saturday, Sept. 26, 2026: 1–10 p.m.; fireworks at 9:30 p.m.
- Sunday, Sept. 27, 2026: 1–5 p.m.
What to expect: Rides, games, food trucks, family activities, and Saturday fireworks. Event supports Saint Mary School’s HSA.
Admission / ride wristbands: Pricing for 2026 was not listed on the city calendar or school carnival page at press time — check at the gate or with the school for current wristband and ticket details.
Details: City calendar: milfordct.us/Calendar.aspx?EID=2047 · School: saintmaryschoolmilford.org · School phone: 203-878-6539
Getting there: Gulf Street is off the downtown / Fort Trumbull area. Parking is typically on and around the school grounds during carnival hours; arrive early on Saturday evening if you’re staying for fireworks.
Catch a favorite ride, spot the fireworks from the midway, or have a tip from the snack tent? Write us at news@milfordvoice.com.