Scarecrows on Main Street: New Canaan’s Fall Tradition That Captures the Spirit of Halloween

Scarecrows on Main Street: A Beloved Fall Festival in New Canaan, CT

A decorative scarecrow brightens Main Street during New Canaan’s annual fall Scarecrow Festival.

As the leaves turn and the air gets crisp, New Canaan comes alive with one of our favorite autumn traditions: Scarecrows on Main Street. Each October, our charming downtown transforms into a creative display of community spirit. Families, local businesses and organizations craft whimsical scarecrows that adorn lamp posts along Main Street, Elm Street and nearby corners. Organized by the New Canaan Chamber of Commerce and the Young Women’s League, this month-long festival celebrates small-town charm and Halloween fun. It’s a free, family-friendly event where locals and visitors alike can stroll, snap photos, and enjoy the festive fall atmosphere in our town.

Highlights of Scarecrows on Main Street

• Artistry and Fun: Discover dozens of creative scarecrow designs lining Main and Elm Streets. From classic hay-filled figures to playful pop-culture pairings, there’s something imaginative for everyone.
• Family-Friendly: Bring the kids and capture memories! Enjoy strolling the decorated sidewalks, grab a hot cider or latte, and make a fun autumn day of it.
• Support Local: Many downtown shops, cafes and restaurants join in the fun with their own themed scarecrows or seasonal promotions. It’s a great way to support New Canaan businesses while you explore.
• Community Contest: Participate by voting for your favorite scarecrow. The Young Women’s League often holds a friendly competition (with kits available in early fall), and winners are typically announced around Halloween during the town parade.

New Canaan’s vibrant community events like Scarecrows on Main Street are just one reason our town stands out. As a luxury real estate agent serving New Canaan and Connecticut, I see firsthand how these traditions add to our quality of life. Our beautiful neighborhoods, top-rated schools and scenic parks are complemented by the friendly, small-town vibe reflected in events like this.

• Top-Notch Schools & Community: New Canaan boasts highly ranked schools and a welcoming atmosphere for families and neighbors.
• Charming Downtown: Enjoy a walkable center with boutiques, galleries and restaurants. Seasonal events (like Scarecrow Fest, farmers markets and concerts) make Main Street a lively gathering place.
• Stunning Homes: Our real estate market features historic Colonial estates, modern luxury homes and charming cottages. There’s an ideal property for every buyer looking for Connecticut living.
• Easy Commuting: The New Canaan train station on the Metro-North New Haven Line provides quick access to Manhattan. Many residents balance quiet suburban life here with careers in NYC or Stamford.

If you’re considering buying or selling in the New Canaan area, I’d love to show you everything this community has to offer. Now is an especially delightful time to fall in love with our town’s charm.

Ready to Find Your Dream Home?

Contact me to learn more about New Canaan real estate. I’m here to help you discover the perfect property or get top value when you sell. You can reach me at:

• Phone: (475) 245-4205
• Email: [email protected]
• Website: ColdwellBankerLuxuryHome.com

Enjoy the Scarecrows on Main Street and the beautiful Connecticut fall season. I look forward to helping you make New Canaan your home!