Halloween Pumpkins

Best Streets for Trick or Treating in Fairfield County 2025 (according to locals)

Halloween is just around the corner—are you ready? Don’t let your kids end up trick-or-treating on a street with no decorations and no candy!

The good news? Most towns in Connecticut have streets that are famous for being Halloween hotspots. We turned to our Suburbs 101 insiders—local moms who know the best spots—to find out where the trick or treating really happens.

Here’s their list of the best streets for trick-or-treating in Fairfield County, CT—so your kids can have a night to remember!

Halloween Pumpkins
Halloween Pumpkins

Where to Go Trick or Treating in Fairfield County (CT)

Best Streets for Trick or Treating in Darien, CT

There are a few good streets in Darien for trick or treating. Go to Birch Road, Red Rose Circle and Sunset Road. Thomasina and Fitch Avenue are also great spots for trick or treating in Darien, CT.

Halloween Decorations Outdoor

Best Streets for Trick or Treating in Fairfield, CT

For the best trick or treating in Fairfield, go to the Fairfield beach area- (Rowland Rd, Penfield) and streets by Sasco Beach off of Oldfield Road.

Halloween Decorations Outdoor

Best Streets for Trick or Treating in Greenwich, CT

Definitely, the best streets for trick or treating in Greenwich are Maher Avenue and Park Avenue. We’ve heard from residents of Maher Avenue that they spend hundreds of dollars on candy every year!

If you are trick or treating at Maher Avenue, park at the Greenwich Bank Trust parking lot.

Halloween Decorations Outdoor

Best Streets for Trick or Treating in New Canaan, CT

Trick or treating is a lot of fun in New Canaan. There are a lot of good spots for trick or treating in New Canaan. Go to the neighborhood behind New Canaan YMCA.

Kimberley Place is also a good spot for trick or treating. You can park at the Acme grocery store shopping center and walk across to Kimberly Place.

Another area for trick or treating in New Canaan is Gower Road and South Avenue. Park at South School Elementary, there’s a secret passageway that leads directly to Gower Rd. from the South School parking lot.

Halloween Decorations Outdoor

Best Streets for Trick or Treating in Stamford, CT

There are a lot of good streets for trick or treating in Stamford. Go to the area of Amherst Place, Woodbridge Dr. South, Elaine Drive for good trick or treating.

Minivale Road in the Springdale section of Stamford is also a good trick or treating spot. Malvern Road and Club Road in Stamford are also other options for trick or treating.

Halloween Decorations Outdoor

Best Streets for Trick or Treating in Westport, CT

In Westport, Gault Avenue is a good street for trick or treating. The Compo Beach Area is also popular for trick or treating in Westport, CT.

Halloween Decorations Outdoor

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