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Why are there always five hats on a row of evergreens along Route 33 in North Wilton?
We moved to Wilton when my son was in 4th grade, and cars would go whizzing by while he waited for the bus. I wanted to do something to encourage people to drive more slowly. It was December so I decided to put five Santa hats on the trees in front of our house,” says Leslie Hines.. “People seemed to get a kick out of seeing them there so I started putting out a different series of hats every few weeks.” Past toppers include chef hats, Indian headdresses, Mexican sombreros, admirals’ hats, ski hats, police hats, even English Bobby hats.  Hines finds them online, in costume stores, and at stores like Marshall’s. “I did flowered bathing caps one year, but they were too floppy. I did construction hats during our house renovation. My kids ride and play ice hockey so I would love to do riding hats and hockey helmets, but they’re too heavy.” She occasionally gets mail addressed to “the house with the hats on the trees.” She also receives unexpected visitors. “A Wilton woman, someone I didn’t know, showed up at my door with five matching hats she’d brought back from India. I had no idea when I started that this would mean anything to anyone other than my family.” So does she wear hats herself? “No. I’m not a hat person,” admits Hines.

What is the dollhouse-like structure on Route 7 across from the bridge? 
The tiny structure was originally a corn crib from a local farm.  For the past 15 years, it has been home to cobbler Chris Kydes’ shoe-repair business. “No one seems to know when or why the crib was moved here. The sides were probably made of chicken wire for ventilation, but someone replaced them with wood and added a cellar and plumbing,” Kydes notes. Before he moved into the space, it housed a wide variety of businesses including an H&R Block and real estate agency. Today, customers toting everything from Manolos to penny loafers walk through Kydes’ door, hoping he can work his magic on their footwear. Most of the repair work he does involves sewing seams, replacing soles and repairing heels, particularly on designer shoes, which, according to Kydes, are particularly fragile.  He claims he’s never met a shoe he couldn’t fix. “Sometimes a woman comes in with her husband’s well-worn shoes, and she’ll say ‘I wish he’d just buy a new pair.’ I tell her a man who doesn’t throw out his shoes makes a great husband; he gets comfortable with something and sticks with it. Shoes say a lot about the person who wears them.” —Carolyn Rundle Field