New Canaan is where modern architecture quietly took root in the Connecticut woods. After the Second World War a small group of designers, known as the Harvard Five, built daringly plain houses of glass, steel and wood among the old stone walls here, and the most famous of all is the Glass House, designed by Philip Johnson and finished in 1949 as his own residence. It is a glass box in a meadow, and it is now open for guided tours that sell out, so booking ahead matters if it interests you. Other, newer buildings, such as the Grace Farms pavilion of 2015, carry on the tradition.
Away from the architecture, the town is a handsome New England suburb, with a small, well-kept center of brick buildings and flowering planters, good coffee, and enough restaurants to make lunch easy. Waveny Park, on the edge, is a pleasant open space with a big Tudor-style mansion. Fuel is available in the town, and you will not go hungry.
For the ride, New Canaan sits just off the Merritt Parkway, and the connecting lanes between the two are the interest. The back roads here are narrow, shaded and twisting, with stone walls close to the tarmac, steep little humps and the occasional blind bend. They are charming but demand care: oncoming drivers cut corners, cyclists are common, and in autumn wet leaves can make surfaces slick. Move slowly and enjoy the scenery rather than trying to make time. The woodland is mixed oak, maple and beech, and the light under the canopy in October is something special.
The Art Deco bridges of the parkway are the other reward. Not every overpass is a showpiece, but many carry ornamental railings and sculpted details from the thirties, and a few sit on short lengths of road that feel like private estate drives. Come in late spring, when the dogwoods are blooming, or in early fall. Midday on a summer weekend brings the heaviest traffic, but mornings are quiet and cool, and the parkway has a calm, almost old-fashioned feel that is quite unlike any other highway in the region.