Milford's Halloween season stays in one place for no more than a weekend at a time this October. It opens on Naugatuck Avenue at Walnut Beach on October 17. On October 23 it moves downtown to the Milford Green for three days. On October 29 it stops for a weekday afternoon inside Parsons. On October 31, a Saturday this year, it goes back to the shore for the Witch Parade at Walnut Beach Creamery. If you want the whole season, you'll be moving around town all month.
The Month, In Order
- Wednesday, Oct. 7: "Wicked Strange New England with Jeff Berlanger," a program on ghosts, monsters and regional lore at the Milford Public Library, 6:30 to 7:30 p.m.
- Saturday, Oct. 10: Happy Haunt at the Fannie Beach Neighborhood Center, hosted by Milford Adaptive Programs and Camp Happiness. The Downtown Milford Business Association's 17th Annual Wine Trail runs the same evening.
- Friday, Oct. 16: Trunk or Treat at the United Presbyterian Church of Milford.
- Saturday, Oct. 17: Boo Fest by the Beach on Naugatuck Avenue. The Milford Artisan Market opens on the Milford Green.
- Sunday, Oct. 18: Second day of the Artisan Market, plus the Walnut Beach Halloween Puppy Costume Contest at 2 p.m.
- Friday and Saturday, Oct. 23 and 24: Hall-O-Weekend on the Milford Green and downtown.
- Sunday, Oct. 25: Falls Hallow Fest on the Milford Green.
- Thursday, Oct. 29: Parsons Trick-or-Treat and a screening of Casper at Parsons Auditorium.
- Saturday, Oct. 31: The Walnut Beach Witch Parade and Halloween Celebration at Walnut Beach Creamery, followed by the Milford Arts Council's Halloween Dance Party.
Walnut Beach Goes First, On the Same Day as the Green's Biggest Market
The season's first big costume day happens near the water. Boo Fest by the Beach runs Saturday, October 17, from 10 a.m. to 3 p.m. on Naugatuck Avenue. The Giggling Pig Milford presents it, with trick-or-treat stops throughout the Walnut Beach Arts & Business District, live entertainment, vendors and children's activities. The organizers encourage costumes and don't list an admission price.
That same Saturday, the 10th Annual Milford Artisan Market sets up on the Milford Green at 168–176 Broad Street from 10 a.m. to 4 p.m. It runs again Sunday with the same hours, and admission is free. Artisan Events by Ally organizes the market, and owner Alison Kosakowski brings in 170 local crafters and makers selling pottery, paintings, jewelry, woodworking and gourmet foods. Live music comes from Seth Adam, Elana Zabari, Sean O'Reilly and Adelaide Punkin. Both days also include a free hour of yoga at 10 a.m., kids' craft activities, food vendors and a dance exhibition. To mark its tenth year, the market is giving the first 100 attendees each day a free phone wallet and stand. The market runs every October and May, and it was voted 2026 Best Community Event or Festival in the Milford Region.
Both events run all day on Saturday. Sunday's schedule leaves more room. The Artisan Market reopens at 10 a.m., and the Walnut Beach Halloween Puppy Costume Contest starts at 2 p.m. Entry is free, there's no preregistration, and a "Picture your Pup" photo station is set up for the occasion. A family can do Boo Fest Saturday, then spend Sunday morning on the Green and get back to the shore by mid-afternoon with the dog in costume.
The Green Holds the Middle Weekend for Three Straight Days
Downtown's turn comes a week later. The Downtown Milford Business Association runs Hall-O-Weekend on Friday and Saturday, October 23 and 24. It starts Friday at 6 p.m. with an outdoor showing of Hocus Pocus at the gazebo on the Green. Saturday's Fall Fest runs from 10 a.m. to 3 p.m. with a costume parade, pumpkin patch, hay maze, vendors, children's activities and entertainment. A downtown trick-or-treat trail runs from 11 a.m. to 2 p.m. The annual Trick or Trot, which benefits the Beth-El Center, is also part of Saturday.
That's two days, and the DMBA has added a third. On Sunday, October 25, it hosts Falls Hallow Fest, a "Gilmore Girls" themed festival on the Milford Green. Milford Public Schools listed the Sunday event in its October 2 community newsletter. So the Green is booked Friday through Sunday that weekend.
Last year's Hall-O-Weekend coverage still turns up in search results with October 24–25 dates. Those were the 2025 dates. This year's event moves up a day, to Friday and Saturday.
A Weekday Afternoon Inside City Hall's Neighbor
Between the Green weekend and Halloween, Milford Recreation adds a Thursday option, October 29, at Parsons Auditorium, 70 West River Street. Starting at 3:45 p.m., families pick up a trick-or-treat map at the auditorium and walk the halls of Parsons, stopping at participating City departments for treats until 5 p.m. Casper, the 1995 film, starts at 5:15 p.m.
It's free and open to everyone. The city encourages costumes, and you don't need to RSVP, though families can register to get email reminders. The department says it will share the list of participating City departments soon. Because it runs indoors at 3:45 on a weekday, it fits the school calendar better than anything else this month.
Halloween on a Saturday Sends the Season Back to the Shore
October 31, 2026, falls on a Saturday, and the year's oldest Halloween tradition near the water is at Walnut Beach Creamery, 17 Broadway. The Walnut Beach Association lists this year's edition as the 20th Annual Walnut Beach Halloween Parade, with candy, costumes, a DJ, dancing, and free ice cream for anyone in costume while supplies last. The costume parade, led by the Witches and Wizards, steps off at 6 p.m.
The Walnut Beach Arts & Business Association's description fills in the route. It says the witch-led parade stops at participating businesses and some households along a short route for treats. Afterward everyone heads back to the creamery for music, dancing and a flash mob witch dance, with candy tossed from above. The two groups list different end times. The Walnut Beach Association says 5 to 7 p.m., and the Arts & Business Association says 5 to 8 p.m. Both list a 5 p.m. start, and the Walnut Beach Association puts the parade at 6 p.m.
Once the parade wraps up, the adult part of the night begins downtown. The Milford Arts Council's Halloween Dance Party at the MAC runs from 8 p.m. to midnight. A Saturday Halloween means both the parade and the dance party fall on a weekend night.
The Smaller Dates That Fill In the Gaps
A few earlier events lead into the big weekends. The DMBA Wine Trail on Saturday, October 10, from 5 to 9 p.m., takes guests through downtown boutiques and businesses. Each stop pours a featured wine from Marginetti Distributors, and local restaurants serve tastings. Tickets are $55, registration starts at 4:45 p.m. in front of Milford Bank at 33 Broad Street, and proceeds go to the Junior Major League of Milford. The ticket page showed the event as sold out when last checked, and the list of participating businesses was still marked "tbd."
The Milford Public Library opens the month with "Wicked Strange New England with Jeff Berlanger" on Wednesday, October 7. It's an adult program on ghosts, monsters, unexplained stories and lore. The Trunk or Treat at the United Presbyterian Church of Milford on October 16 falls the night before Boo Fest.
The shoreline stays open on days with nothing scheduled. Silver Sands State Park is open from 8 a.m. to sunset and has a three-quarter-mile boardwalk. The state says more than 200 bird species migrate through the park. Parking is free for vehicles registered in Connecticut. Farther along the shore, the Connecticut Audubon Coastal Center at Milford Point, 1 Milford Point Road, is free and open Tuesday through Sunday, and the sanctuary is open from dawn to dusk year-round.
Knowing which corner of Milford is busy on which weekend is part of knowing the town, and that local knowledge shapes how a home here gets priced and presented. If you're curious what your house near Walnut Beach, downtown or anywhere else in Milford is worth this fall, Scott Wright and the RE/MAX Right Choice team can give you a clear, local answer. Get your free home valuation.
