Halloween in Fairfield County
As Halloween approaches, Fairfield County once again becomes a center of festive fun and trick-or-treating excitement. 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 2025.
Westport
Halloween Activities:
This year, Westport’s Annual Halloween Parade is scheduled for Wednesday, October 29, 2025 (rain date: October 30). The parade starts at 3:30 PM, travels along Main Street through Avery Place, then onto Myrtle Avenue, and ends at Veterans Green. Children may trick-or-treat along Main Street and at Town Hall afterward.
Also, on Tuesday, October 28, 2025, Wakeman Town Farm will host a “Halloween Parade at the Farm” event from 2:00 to 3:00 PM for little ones (ages 0–5), complete with spooky costumes, songs, and mini pumpkins.
Trick-or-Treating Hotspots:
The Compo Beach area and Gault Avenue remain excellent options—flat, walkable streets, festive decorations, and ease of navigation for families.
Greenwich
Halloween Activities:
Greenwich’s “Halloween Happenings” event will take place on Friday, October 24, 2025, at the Bendheim Western Greenwich Civic Center. The event offers two sessions (5:30 PM & 7:00 PM) and includes a dance, games, costume contests, and treat bags.
Meanwhile, in the Botanical Center, look for Ghouls in the Garden on October 26, 2025. This evening event features spooky garden walks, costume parades, and Halloween-themed crafts.
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.
New Canaan
Halloween Activities:
The long-standing New Canaan Halloween Block Party returns on Sunday, October 26, 2025, from Noon to 2:00 PM on Elm Street. Families can enjoy music, treats, and a community vibe.
Meanwhile, the New Canaan Nature Center will present its Halloween Spooktacular again on October 25, 2025. Attendees should pre-register; this event features crafts, nature-themed Halloween fun, and stories.
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.
Fairfield
Halloween Activities:
The Fairfield Museum & History Center will host Halloween on the Green on Sunday, October 26, 2025, from 12:00 to 4:00 PM. The museum grounds will transform into a Halloween village with trick-or-treating stations, bounce houses, vendor booths, and historic building displays.
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.
Darien
Halloween Activities:
In 2025, Darien’s standout Halloween celebration is the Howl-O-Ween Pup Parade, a fun and free community event perfect for families and their furry friends. This year’s event takes place on Sunday, October 19, 2025, from 12 PM to 2 PM at Tilley Pond Park.
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.
Wilton
Halloween Activities:
The Wilton Chamber of Commerce, in partnership with ASML and the Town of Wilton, is bringing back one of the community’s favorite fall traditions, the Pumpkin Parade and Trick-or-Treating event! This family-friendly celebration will take place in Wilton Center on Saturday, October 25, 2025, from 2 PM to 4 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.
Weston
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.
Southport
Halloween Activities:
Southport’s most anticipated Halloween event in 2025 is the Halloween Goat Parade at the Pequot Library, located on Pequot Avenue. This family-friendly celebration takes place on Friday, October 31, 2025, at 5 PM, and is open to participants of all ages. In addition to the main event, the Pequot Library will also host a Halloween Magic Show and Jack-o'-Lantern Contest on Saturday, October 25, 2025, offering another chance for families to celebrate the season with creativity, laughter, and community spirit.
Trick-or-Treating Hotspots:
Streets around Old South Road and adjacent blocks are well-known for their festive displays and community vibe.
Celebrate Halloween
We’re excited to see Fairfield County come alive for Halloween 2025. 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.
