Explore Fairfield County :: New Canaan


“Explore Fairfield County” is an informational series that provides a glimpse into the wonderful towns and cities in Fairfield County. Fairfield County is diverse in that it includes big cities, small suburbs, beaches, farms, and busy highways. It covers a large geographic area and, because of this, it has a lot to offer families! To help you get the most out of Fairfield County, our contributors have shared the top 10 things they love about each local area. To read more in this series, click here.New Canaan

New Canaan started in 1731 as Canaan Parish, formed by residents of Norwalk and Stamford. It was primarily an agricultural town until after the Revolutionary War, when its primary industry became shoe-making. The shoe-making industry had the town settle into different districts (Ponus Ridge, Talmadge Hill, Silvermine) rather than have a central downtown. The downtown we see today came in the 1800s with the addition of the railroad. Once the railroad made its way to New Canaan, more New York City families started to settle for the weekends and summer. 

As New Canaan became a popular destination, it has continued to be a well-established and family-friendly town. Its rich history has also supported family-owned businesses that span generations like Karl Chevrolet and Walter Stewart’s grocery. Those are two of the many great businesses that call New Canaan home, and many of them you can find downtown.  

1. Walkable Downtown 

New Canaan has the most walkable downtown around. Street parking can get tricky at times, but several parking lots are just two blocks away from the stores to park and walk all around. You can easily park in one spot and walk around to the fun shops on Elm and Main Streets, coffee shops, dessert shops, restaurants, wine shops, library (a HUGE family favorite), post office, nail salons, and farmer’s market.

2. Santa Helicopters Into Mead Park 

One Saturday morning in December, Santa and Mrs. Claus fly into Mead Park via helicopter. Upon arrival, they naturally take a ride on the antique firetruck “Old Faithful” and visit with children at Weed & Duryea, the local hardware store. 

New Canaan3. Kiwanis Park 

New Canaan is landlocked and has no coastal shore. No worries! The town created the cute little Kiwanis Park, a small spring pond just outside downtown. The park has a fantastic and recently renovated playground, so kids of various ages can have a good time doing something. 

4. Kid-Friendly Restaurants

Some local favorites (in no particular order) are GatesTequila Mockingbird, New Canaan Diner, Le Pain Quotidien, and Rosie. There is also Patisserie Salzburg and the Adirondack Store to grab a quick treat too!

New Canaan5. Waveny Park & Irwin Park 

Waveny Park is one of New Canaan’s most well-known landmarks, and there’s so much to love about it. From the well-groomed walking and running paths to the serene gardens, the wide-open green spaces, and the gorgeous mansion (where the Parks and Rec department is), Waveny Park is an amazing town resource for all seasons.

A local Fliers Club meets there on Sunday mornings if you want to learn more about model airplanes, or sit back and let the kids revel in the model planes flying overhead.

Waveny House is the setting for a town-sponsored summer camp, which will even wear out the kid with the most energy. Waveny Park is also where you can find the town pool. In addition to the big family pool with diving boards, they have a baby pool with gradual entry, so it is safe for newly sitting and newly walking. Regarding the winter, Waveny Park boasts one of the best sledding hills around. 

Irwin Park is a 36-acre park with several trails for walking, jogging, and biking. There is also a “Great Lawn” and athletic field. In the spring, you’ll find thousands of daffodils and goats who help keep invasive species at bay. Also, The Gores Pavilion, which was the original pool house on the property and was designed by Landis Gores. Gores was one of the “Harvard 5” who made a huge impact on the architectural landscape in the 1940s.

6. New Canaan Nature Center  

New Canaan Nature Center is a hidden gem. It offers a variety of programs: Mommy & Me Classes, preschool, summer camp, and even adult programs!

Their hiking paths are all stroller accessible, and the kids can check out a backpack in the Visitors Center that is packed full of necessary exploratory materials. The NCNC also has seasonal programming to keep any family happy – from the Fall Fair to the Easter Egg Hunt and so much in between!

New Canaan7. The Downtown Holiday Stroll  

Another December delight is the downtown Holiday Stroll. The first Friday night in December, Elm Street becomes pedestrian traffic only as residents revel in the annual downtown tree lighting and the arrival of Santa Claus. Choirs from all the local schools provide the Holiday Stroll with beautiful carols. St. Aloysius (in the heart of downtown) provides a live nativity scene complete with animals and carols. The Holiday Stroll fun continues into Saturday with live ice sculpture carving and visits with Santa at a downtown real estate office. 

8. The Apple Cart at Mead Park

Do you like to have an easy and delicious al fresco lunch at the park with your children? Then The Apple Cart is your destination! Their Mead Park location among the playground, baseball fields, tennis courts, duck pond, and visibility of Metro-North train tracks is simply perfect. The menu is quite diverse and appealing to many audiences for a park cafe. 

9. Grace Farms

Grace Farms is fairly new to New Canaan, opening its River Building and property within ten years. The location provides huge wide open green spaces for children to run safely and numerous walking trails.

The facilities are simply breathtaking in their beauty and simplicity. They do loads of programming for families and have a cafe on the property. Admission is free at the gate, so stop by and feel inspired and peaceful in the Grace Farms surroundings.  

10. The “Harvard 5” & The Glass House

New Canaan became a new hub of modern architecture starting in the 1940s. A group of students and teachers from the Harvard Graduate School of Design had come to New Canaan and created homes opposite of a traditionally built home. The group consisted of Philip JohnsonMarcel BreuerLandis GoresJohn M. Johansen, and Eliot Noyes.

While many original homes have been torn down and rebuilt, two still stand and can be visited: Philip Johnson’s Glass House and Gores Pavillion (located at Irwin Park). You can tour the Glass House or even rent it for an event! Gores Pavillion can be visited during the week. They are some of New Canaan’s treasures.

Have you visited New Canaan? Do you live here? What do you love about it?

Be sure to read all the posts in our Explore Fairfield County Series by clicking here.


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