🕯 Where to Trick-or-Treat in Fairfield County This Halloween

If you’re searching for the best neighborhoods for trick-or-treating in Fairfield County, Connecticut, you’ve come to the right place. Our team at Fowler Sakey Team – Coldwell Banker Realty lives and works right here in the community, and we’ve rounded up the can’t-miss streets and neighborhoods where Halloween spirit shines brightest.

From beachside homes in Fairfield to historic streets in Ridgefield, here’s where local families go for safe, fun, and candy-filled Halloween adventures.

🏠 Fairfield

🎃 Jackman Avenue
A local favorite known for walkable blocks, short driveways, and over-the-top decorations.

🌊 Rowland Road, Penfield Road & Lalley Boulevard
Down by Fairfield Beach, these streets deliver ocean breezes, glowing porches, and friendly faces.

👻 Jennings Road
Ideal for younger kids — plenty of light, easy parking, and a warm neighborhood vibe.

💡 Tip: Many Fairfield neighborhoods start early — plan to head out around 5:30 PM!

🌅 Westport

🏖 Gault Avenue & Compo Beach Area
Westport’s most famous Halloween destination! Expect big crowds, even bigger decorations, and full-size candy bars.

🎃 Soundview Drive & Compo Hill Avenue
A little quieter but equally festive — perfect for families with younger trick-or-treaters.

💡 Local vibe: Community spirit meets coastal charm.

🎃 Wilton

🕯 Highfield Road
A Wilton classic — lined with lights, pumpkins, and friendly homeowners who really get into the spirit.

🏡 Village Walk & Drum Hill Road
Family-oriented neighborhoods with sidewalks and safe crossing points.

💡 Insider tip: Wilton’s Pumpkin Parade downtown makes a perfect warm-up event before trick-or-treating.

🌲 Weston

🍁 Weston Woods & Georgetown Road
Beautiful tree-lined streets with that “New England Halloween” feel — plenty of friendly faces and well-decorated homes.

🏠 Old Mill Road / School Road Area
Close to Weston’s community events and easy to navigate with little ones.

💡 Best for: Families who prefer quiet, scenic routes.

🚗 Norwalk

👻 Ponus Avenue (West Norwalk)
A well-loved neighborhood with bright lights, lots of kids, and creative decorations.

🎃 Rowayton Area
Classic small-town charm and walkable streets, often paired with local Halloween parades.

💡 Best time: Between 5:30 PM–7:30 PM before the streets get busy.

🏙 Stamford

🍬 Glenbrook Road & Colonial Road
Fun, walkable streets with vibrant décor and lots of candy stops.

🌆 ZIP 06902 (Downtown & West Side)
Named one of Fairfield County’s top trick-or-treat zones — high participation and tons of energy.

💡 Bonus: Many downtown businesses also hand out treats during the early evening.

🏡 New Canaan

🎃 Kimberly Place & Maple Street (near YMCA)
Quaint, close-knit, and perfect for families.

🕯 Oenoke Ridge Road
Wide sidewalks and classic colonial architecture set the stage for an unforgettable Halloween night.

💡 Pro tip: Park near the center and walk — it’s part of the charm.

🌾 Easton

🍁 Sport Hill Road & Silver Hill Road
Spacious homes, open lawns, and friendly residents make this a hidden gem for trick-or-treating.

🎃 Easton Center / Town Green
Home to town-wide Halloween events and safe, community-focused routes.

💡 Vibe: Small-town spirit meets big Halloween fun.

🕸 Stratford

🏠 Academy Hill & Elm Street
Historic Stratford comes alive on Halloween with beautiful décor and classic charm.

🎃 Black Rock Turnpike / Cutspring Road Area
Lively, well-lit streets with welcoming homeowners and candy to spare.

💡 Local favorite: Many homes coordinate themes — worth a drive-through even after the big night.

🍂 Ridgefield

🏘 Main Street
One of the most picture-perfect Halloween destinations in Connecticut. Expect old-fashioned charm, glowing jack-o-lanterns, and costumed crowds.

🌾 Branchville Road & High Ridge Avenue
Walkable, well-lit streets known for creative decorations.

🎃 Farmingville Neighborhood
A quieter choice with friendly neighbors and easy walking — perfect for younger kids.

💡 Must see: Downtown Ridgefield’s shop windows decked out in Halloween displays.

🕯 Tips for a Great Halloween Night

• Go early — most neighborhoods start around 5:30 PM.

• Bring a flashlight or glow sticks for visibility.

• Always cross streets together and stick to sidewalks.

• Say thank you (and compliment the best decorations!).

• Share your local Halloween photos and tag @FowlerSakeyTeam — we love seeing our community celebrate!

💛 From Our Team to Yours

At Fowler Sakey Team, we believe “home” is more than a place — it’s a community.
That’s why we love sharing local traditions and family favorites across Fairfield, Westport, Wilton, Weston, Norwalk, Stamford, New Canaan, Easton, Stratford, and Ridgefield.

Wishing everyone a safe, sweet, and spooky Halloween! 🎃👻