Updated October 2026
As Halloween approaches, Fairfield County once again becomes a center of festive fun and trick-or-treating excitement. With October 31 falling on a Saturday this year, families have a full weekend of celebrations to plan around. Whether you're looking for family-friendly events or the best streets to fill those candy bags, this guide highlights some of the top happenings around the area for 2026.
Halloween Activities: Westport's Annual Halloween Parade for children is traditionally held in the days leading up to Halloween. It starts at 3:30 PM at Main Street and the Post Road, travels up Main Street through Avery Place and Myrtle Avenue, and ends at Veterans Green, where kids can trick-or-treat along Main Street and in front of Town Hall. The 2026 date had not been announced at the time of writing, so check with Westport Parks & Recreation at (203) 454-6106 for the official date and rain date. [CONFIRM 2026 DATE BEFORE PUBLISHING]
Trick-or-Treating Hotspots: The Compo Beach area and Gault Avenue remain excellent options: flat, walkable streets, festive decorations, and easy navigation for families.
Halloween Activities: Greenwich's "Halloween Happenings" takes place on Friday, October 23, 2026, from 5:30 to 7:30 PM at the Bendheim Western Greenwich Civic Center. Families can dance in Dracula's Den, play games, collect candy and prizes, and enter the family costume contest. Tickets are $12 per person (ages 3 and up) and are required for entry.
Then on Sunday, October 25, 2026, from 4:30 to 6:30 PM, the Greenwich Botanical Center hosts Ghouls in the Garden. The evening includes crafts and games, a costume parade at 5:30 PM, and a haunted hike through the Montgomery Pinetum woods at 5:45 PM. Tickets are required.
Trick-or-Treating Hotspots: Maher Avenue and Orchard Street in Cos Cob continue to be well known for elaborately decorated homes and a festive trick-or-treating atmosphere.
Halloween Activities: The long-standing New Canaan Halloween Block Party returns on Sunday, October 25, 2026, from noon to 2:00 PM on Elm Street. Put on your costume and come downtown for music, treats, and a community vibe.
Later in the week, the New Canaan Nature Center presents its Halloween Spooktacular on Friday, October 30, 2026, from 5:30 to 7:30 PM. Guests can meet Halloween-themed animals, make crafts, roast marshmallows around a campfire with spooky stories, and take a jack-o'-lantern walk. Tickets are $15 per person (children 2 and under are free), and pre-registration is strongly suggested because the event has sold out in the past.
Trick-or-Treating Hotspots: The neighborhoods around Kimberly Place and the area near the New Canaan YMCA remain popular and welcoming for trick-or-treaters.
Halloween Activities: The Fairfield Museum & History Center hosts the 10th annual Halloween on the Green on Sunday, October 25, 2026, from 12:00 to 4:00 PM. The Museum Commons becomes a Halloween village with trick-or-treating, giveaways, food vendors, a bounce house, and displays in the historic buildings. Admission is free.
Trick-or-Treating Hotspots: Fairfield Beach area streets are still among the favorites. Rowland Road, Penfield Road, Lalley Boulevard, and James Street are often among the most decorated and busiest with families.
Halloween Activities: Darien's Halloween calendar is typically anchored by family events at Tilley Pond Park and the Darien Library. Details for 2026 had not been confirmed at the time of writing, so check the Darien Parks & Recreation and Darien Library event calendars for current dates. [CONFIRM 2026 EVENTS BEFORE PUBLISHING; the 2025 Howl-O-Ween Pup Parade is not confirmed for 2026]
Trick-or-Treating Hotspots: Lake Drive and Elm Street (off West Avenue) remain well regarded for their festive ambiance and community spirit when traffic is limited.
Halloween Activities: The Wilton Chamber of Commerce, in partnership with ASML and the Town of Wilton, brings back the Pumpkin Parade and Trick-or-Treating in Wilton Center on Saturday, October 24, 2026, from 2:00 to 4:00 PM.
Trick-or-Treating Hotspots: Highfield Road (and surrounding neighborhoods) typically remain among the more decorated and popular streets for trick-or-treaters in Wilton.
Trick-or-Treating Hotspots: Weston Woods and Georgetown Road are typically among the best streets for family-friendly decorations and a comfortable trick-or-treating route.
Halloween Activities: Southport's Pequot Library, on Pequot Avenue, is the village's go-to spot for Halloween programming, including its popular Halloween Goat Parade and a Halloween magic show and jack-o'-lantern contest in past years. Check the library's events calendar for 2026 dates and registration. [CONFIRM 2026 DATES BEFORE PUBLISHING; Goat Parade and Magic Show are not yet confirmed for 2026]
Trick-or-Treating Hotspots: Streets around Old South Road and adjacent blocks are well known for their festive displays and community vibe.
We're excited to see Fairfield County come alive for Halloween 2026. From community parades to decorated streets, there's something for all ages to enjoy. As always, event details may shift, so it's a good idea to check municipal parks & recreation websites or local event listings as October approaches.
If you're thinking about making Fairfield County your home or want to learn more about its neighborhoods, Cindy Raney & Team are happy to help. Feel free to reach out. We're here to guide you through the home-buying (or selling) process and help you discover all the things that make this area a special place to live.
355 Riverside Avenue Westport, CT 06880
355 Riverside Avenue Westport, CT 06880