Tool Museum, Glass House, Waveny Park: 25 Things to Do in New Canaan

6/12/17 - By Katie McKnight

New Canaan. Quintessentially New England. Classically Connecticut. Known for it's famed Harvard Five architecture, postcard perfect New England landscape and quaint downtown in Fairfield County, New Canaan offers plenty to see and do year round. With a Norman Rockwell inspired Holiday Stroll not to be missed, family-friendly outdoor summer theater performances and no shortage of green space, this small city nestled in the Southwest corner of the state is teeming with kid stuff. Here are our picks for kid friendly destinations and activities in New Canaan:


If you're heading downtown, the first place on your list should be the New Canaan Toy Store on Park Ave., just across from the Metro North station (very cute, btw). This is the original mom-and-pop toy store, claiming to be the oldest in New England, with the quality selection and complimentary gift wrapping you'd expect. After the damage is done there, head east on Elm, and you'll find Pain de Quotidien's northernmost outpost from NYC. You can nosh on European-influenced cafe cuisine with every other young family in town. Or, hit up Bruegger's Bagels for something straightforward and simple. It's around the corner to the south on South Ave. If it's lunch or dinner, continue all the way east along Elm until it hits Main Street. On the left look for  Pinocchio's Pizza. These guys won an international pizza competition IN ITALY five years ago. Order the one with arugula and figs. It's so good the kids won't even notice it's covered in salad. Once you roll out of there, you can backtrack on Elm to the cute little, New Canaan Playhouse for a movie. 

Also high on my kids’ list of favorite places to stop for a snack are Gelatissimo, a phenomenal, authentic gelato store. You've also got Swirl for top-your-own frozen yogurt and Baskin Robbins for the original. When your crew has had it with shopping, (and by this we mean the kids, because Mom and Dad could find PLENTY more to look at if their pockets are deep), pile in the car and head for the outdoors. It's abundant here. Mead Memorial Park is a gem with ample playgrounds, ball fields, tennis courts, and waterways where kids can feed the ducks. Even better, a gourmet cafe food stand that's open when the weather's nice. Or, if you want a slightly higher altitude head a little further south along South Ave., and up into Waveny Park.

The amenities are ample here with a great lawn for picnics and frisbee, and if it's summer, check on tickets to a production put on in the open air by the Summer Theatre of New Canaan. They even have performances for children with special needs. Just looking for a place to have the kids chase geese and run around on a playground -- katty corner from Waveny is Saxe Middle School grounds. If you need a toddler-size jungle gym, take a ride to Dixon Park (accessible from Summer or Hoyt Street - but parking on Hoyt). Want un-manicured nature? The Bristow Bird Sanctuary fits that bill. A bit smaller in size is Irwin Park, laced with a rubberized walking/running/biking trail, perfect for small wheels. Or, Kiwanis Park has a great playground that sits in sand – nice and comfortable for little feet.

And, if that's not enough nature for you, head to the New Canaan Nature Center. In addition to the trails, which take young explorers through woods and marshes, there is a Visitor Center, and animal care building and a greenhouse. Head down Oenoke Ridge Road to the New Canaan Historical Society offering many venues – 8! – for kids to explore local history.  My kids’ favorite has been the Little Red Schoolhouse, a restored 1868 schoolhouse where kids can get a glimpse into days of yore. Another big hit is the Tool Museum, which showcases tools from the 18th and 19th century.  For my kids, who consider an iPad archaic tool, this was illuminating! While not on the grounds of the historical society, the Philip Johnson Glass House, is a National Trust Historic Site celebrating famed architect Philip Johnson with tours of the groundbreaking house and grounds.

New Canaan offers a number of events throughout the year that reflect the best of small town living and celebrate the seasons.  The New Canaan Nature Center hosts a Fall Fair and the New Canaan Chamber of Commerce hosts an annual Halloween parade in October. Come December, watch for the annual Holiday Stroll on Elm Street, when the roads are only open to foot traffic and the New England Academy of Dance's production of the Nutcracker. And if it happens to be Christmas Eve when you visit, well, lucky you. The place to be is God's Acre. Residents show up, like they have since 1919, to sing around the town tree with the town band in the shadow of alabaster churches​.  The town’s Elm Street is bedecked in holiday lights, gingerbread houses grace the store windows, and Santa, elves and carolers help celebrate the season. 

Springtime is the season for the Young Women's League annual Touch-a-Truck fundraiser, in which fire trucks, ambulances, excavators, and other fun trucks gather so that kids can explore them.  New Canaan's Old Faithful, an antique fire truck, is always on hand for kids to see and even ride upon. In May, the Memorial Day parade features Girl Scout troops, high school bands, veterans groups, and active servicemen and women.  The roughly 1 mile parade route goes right through the town’s idyllic Main Street. Also in May, St. Mark's hosts a fair complete with arcades, rides and a Strawberry Social.  And finally, summertime. The summer brings weekly free concerts at Waveny Park so pack a picnic dinners and enjoying a beautiful evening.  Also held at Waveny Park is the town’s annual firework display. Another summer favorite of ours is the Farmer's Market.   Local farmers - many of them of with organic farms- and purveyors of food set up every Saturday morning from May through October.   And if you're in the area in summer, be sure to check out the Coffee and Carburetor's selective Sunday events, in which antique car owners bring their cars together for a morning of coffee, chatter, and checking out old cars.  

In short, there are LOTS of great things to do and see in New Canaan all year long. 

Photo courtesy of Ally

Originally published 1/12/14.