Iconic Downtown New Canaan, CT by Colleen Rock.
Waveny Mansion is part of Waveny Park which includes an art gallery, pool, tennis, walking paths and theater. Public Domain photo

New Canaan has picturesque New England small-town ambience with plenty to do and enjoy which is why it was voted “one of CT’s Favorite Shopping Towns” by the Connecticut Office of Tourism. Filled with three unique streets of shopping, 30 restaurants, multiple ice cream shops and cafes, the arts, parks and recreations, it also has some of the top rated schools in the state. It is also almost a quick straight line drive to HAYVN for our members plus less than an hour by train to Manhattan.

Come for a day trip and explore art at the Waveny Carriage Barn or Silvermine Arts Center, the 300-acre Waveny Park trails, the Carriage Barn theatre productions, or the contemporary Philip Johnson Glass House. Grace Farms, completed in 2015, is worth more than a stop to explore nature, enjoy some tea, and walk under the canopy of steel called “The River” designed by Pritzker Prize-winning Japanese architecture firm SANAA before exploring their amphitheater. Come for some fun annual events such as Memorial Day parade, or the Halloween parade on the Sunday before Halloween, or Christmas Caroling on God’s acre. Also check out the Special Events below.

We’ve curated some listings we think will make it easy to explore New Canaan. We hope you will also explore other HAYVN HUB HOT SPOTS guides for Darien, Fairfield, Greenwich, Norwalk, Stamford, and Westport.

Moving from New York to Fairfield County? Learn more about what makes being here great!