Your Ultimate Guide to Halloween in Fairfield County, CT (2024 Edition)

Halloween in Fairfield County

As Halloween approaches, Fairfield County transforms into a hub of festive activities and trick-or-treating fun. Whether you're searching for family-friendly events or the best neighborhoods to fill those candy bags, this guide covers some popular happenings in the community. 

Westport

Halloween Activities:
Westport’s Annual Halloween Parade on October 28, 2024, is perfect for families. The parade takes place on Main Street, followed by trick-or-treating along the route and entertainment at Veterans Green. Don’t miss the Halloween Window Painting Contest on the same day, where kids can showcase their creativity on downtown storefronts.

Trick-or-Treating Hotspots:
For trick-or-treating, head to the Compo Beach area and Gault Avenue. Both locations are known for their flat streets and festive decorations.

Greenwich

Halloween Activities:
In 2024, the Ghouls in the Garden event at the Greenwich Botanical Center is scheduled for October 26, offering spooky hikes, a costume parade, and Halloween-themed crafts. Another fun event is Greenwich Greet & Treat on October 31, where local businesses on Greenwich Avenue hand out candy.

Trick-or-Treating Hotspots:
Check out Maher Avenue and Orchard Street in Cos Cob. Both streets are well-known for their elaborately decorated homes.

New Canaan

Halloween Activities:
New Canaan’s Annual Halloween Block Party on Elm Street is scheduled for October 27, 2024. This event brings families together for music, a costume parade, and trick-or-treating. Another fun event is the Halloween Spooktacular at the New Canaan Nature Center on October 28, featuring a Jack-o-lantern walk, crafts, and campfire stories with marshmallow roasting.

Trick-or-Treating Hotspots:
Kimberly Place and the area around the New Canaan YMCA are among the best places to trick-or-treat, known for their welcoming atmosphere and festive decorations.

Fairfield

Halloween Activities:
The Halloween on the Green at the Fairfield Museum will take place on October 29, 2024, transforming the museum grounds into a Halloween village with trick-or-treating, bounce houses, and local vendors.

Trick-or-Treating Hotspots:
The Fairfield Beach area is always a top spot for trick-or-treating. Streets like Rowland Road, Penfield Road, Lalley Boulevard, and James Street are particularly popular for their festive decorations and community spirit​

Darien

Halloween Activities:
Darien’s Halloween Parade will be held on October 26, 2024, starting at the Darien Fire Station and winding through the downtown area. Local businesses participate, providing treats along the way. The Darien Lions Club Halloween Party on October 31, 2024, at the Darien Sportsplex is another great family-friendly event featuring games, prizes, and more.

Trick-or-Treating Hotspots:
For trick-or-treating, head to Lake Drive and Elm Street (off West Avenue), where streets are closed to traffic.

Wilton

Halloween Activities:
Wilton’s Pumpkin Parade returns on October 26, 2024, turning downtown into a trick-or-treating haven for kids. For those looking for something spookier, Fright Night at Ambler Farm (October 25-26, 2024) offers haunted hayrides and Halloween-themed games for kids.

Trick-or-Treating Hotspots:
Highfield Road is one of the most popular spots for trick-or-treating in Wilton.

Weston

Halloween Activities:
The Halloween Fun Fest at the Weston Historical Society is back for 2024, featuring pumpkin decorating, hayrides, and a haunted barn experience. Great event for families with younger children!

Trick-or-Treating Hotspots:
Weston Woods and Georgetown Road are known for their festive homes and family-friendly atmosphere.

Southport

Halloween Activities:
Southport’s Trick-or-Treat on Pequot Avenue will take place on October 31, 2024, offering a charming Halloween experience where local businesses hand out candy in a family-friendly environment.

Trick-or-Treating Hotspots:
For trick-or-treating, Old South Road and surrounding streets in Southport are well-known for their festively decorated homes and welcoming community vibe.

Celebrate Halloween 

We love staying on top of what's happening in Fairfield County. Our community has so many great ways to celebrate Halloween, whether you're exploring the local events or enjoying the best trick-or-treating spots. 

If you’re thinking about making Fairfield County your home or want to learn more about its neighborhoods, we'd be 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.