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  • Boo Fest by the Beach

    Naugatuck Avenue, Walnut Beach Naugatuck Avenue, Milford, CT, United States

    A full day of Halloween fun along Naugatuck Avenue, with trick-or-treat stops through the Walnut Beach business district, live entertainment, vendors and kids’ activities. Costumes are highly encouraged.

  • Great Pumpkin Festival at Boothe Memorial Park

    Boothe Memorial Park 5800 Main Street, Stratford, CT, United States

    Celebrate Stratford’s free fall festival fills Boothe Park with pumpkins, a costume parade, food, music and family activities, plus Public Safety Day with Touch-a-Truck. The rain date is Sunday, Oct. 18.

    Free

  • Hall-O-Weekend Fall Festival

    Milford Green 84 S Broad Street, Milford, CT, United States

    The DMBA’s family Halloween festival takes over the Milford Green with vendors, food trucks and fall fun.

  • Halloween on the Green

    West Haven Green West Haven, CT, United States

    West Haven United and the City of West Haven team up for a Halloween evening on the West Haven Green.

    Free

  • Falls Hollow Fest

    Milford Green 84 S Broad Street, Milford, CT, United States

    The DMBA hosts “a perfect fall day on the Milford Green,” with vendors and food trucks. Check the DMBA before you go for final hours.

  • Halloween Movie Night: Casper + Parsons Trick-or-Treat

    Parsons Government Center Auditorium 70 West River Street, Milford, CT, United States

    Pick up a trick-or-treat map at Parsons Auditorium and visit City departments for treats from 3:45 to 5 PM, then settle in for “Casper” (1995) at 5:15. Costumes encouraged; free and open to all.

    Free

  • West Haven Little League Trunk or Treat

    Morse Park West Haven, CT, United States

    WHLL’s first Trunk or Treat at Morse Park. Admission is free with a canned or non-perishable food donation for WHEAT of West Haven.

    Free with a food donation

  • 20th Annual Walnut Beach Halloween & Witch Parade

    Walnut Beach Creamery 17 Broadway, Milford, CT, United States

    Candy starts at 5, then the Walnut Beach Witches and Wizards lead the kids’ costume parade at 6, with a DJ and dancing. Anyone in costume gets free ice cream on the creamery’s last day of the season, while it lasts.

  • Halloween Dance Party at the MAC

    MAC Downtown (Milford Arts Council) 40 Railroad Ave South, Milford, CT, United States

    DJ Sonja spins at downtown Milford’s only Halloween dance party, with a swirling disco ball, snacks, a cash-bar Speakeasy and prizes for the best costumes. Tickets are sold at the […]

    $20

  • Orange Community Women Holiday Craft Fair

    High Plains Community Center 525 Orange Center Rd, Orange, CT, United States

    The Orange Community Women’s 4th annual holiday craft fair brings handmade gifts to the High Plains Community Center.

  • 3rd Annual Milford Holiday Market

    Ethan Allen 1620 Boston Post Rd, Milford, CT

    Kick off the holidays with one-of-a-kind gifts from local makers at the third annual Milford Holiday Market! Artisans, crafters and unique gift vendors are still wanted — email Maura.Gilson-ODonnell@ethanallen.com to […]

    Free

  • Homemade Holiday Fair (Friday Evening)

    First United Church of Christ Milford 34 West Main Street, Milford, CT, United States

    First UCC’s Homemade Holiday Fair opens with a Friday evening session in Fellowship Hall, perfect for early gift shopping.