Watch the full video on YouTube | A Beautiful Fall Day in Cheshire, Connecticut

With Fall approaching, I’ve been reminiscing on some of my favorite memories of Connecticut during the fall. One of which happens to be in Cheshire Connecticut.

Cheshire, Connecticut, truly shines in the fall. The town is filled with vibrant foliage, crisp autumn air, and a welcoming community spirit that makes it a perfect place for a seasonal stroll. One of my favorite traditions is walking along South Main Street, where local businesses, families, and organizations create festive decorated scarecrows that line the sidewalks.

Each scarecrow has its own unique personality—some are whimsical, some are clever, and others are just plain fun! They add such charm to the historic street and make you smile as you walk past.

Cheshire itself is rich with New England history. Founded in 1780, the town was once known as the “Bedding Plant Capital of Connecticut,” thanks to its many family-owned farms and greenhouses. Even today, Cheshire maintains its small-town charm with scenic trails, historic churches, and cozy cafes that invite you to slow down and enjoy.

Fun fact: Cheshire is also home to parts of the Farmington Canal Heritage Trail, a popular route for walking and biking that’s especially breathtaking when lined with colorful fall leaves. Pair that with the festive scarecrows downtown, and you have the perfect recipe for a true autumn escape.

If you’re looking for small-town beauty, Cheshire in the fall is the perfect stop. Between the brilliant leaves, cozy local spots, and these festive scarecrows, it feels like stepping into a New England postcard.