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

Have you found yourself in sea of gray and black Chevy Suburbans recently? You might be in New Canaan. My family has lived in New Canaan for only three years, but we are completely in love with all that the town has to offer. From the family-owned businesses that span generations like Karl Chevrolet and Walter Stewart’s grocery to the fantastic Parks & Recreation Department, this town screams “family-friendly.” Just give us a gazebo and let us fancy ourselves to be the setting of Gilmore Girls.

1. School Pride  

We have three public elementary schools in town, and regardless of which district you live in, we are immensely proud to display school spirit on our cars. People in this town LOVE car magnets. And, yes, I’m in the magnet club. You will see either a blue paw print, a green whale, or a green eagle on nearly every car in town to indicate your elementary school.

It can also help you meet new friends in the parking lot, HA! We only have one middle school, but it seems that people still enjoy displaying Saxe school pride in this town! Once kids get to New Canaan High School, the car pride evolves into displaying the sport or other activity in which the kids participate.   

New Canaan 2. Walkable Downtown 

New Canaan has the most walkable downtown around. Street parking can get tough at times, but there are several parking lots just two blocks away from the stores to park and walk all around. The sidewalks have all been tested and (mostly) passed inspection with my double-wide stroller. You can easily park in one spot and walk around to the fun shops on Elm & Main Streets, coffee shops, dessert shops, restaurants, wine shops, library (HUGE family favorite), post office, nail salons, farmer’s market and even our hometown grocery store, Walter Stewart’s. I can literally “run” my errands in New Canaan and I love it.

3. Santa Helicopters Into Mead Park 

Yes, 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, our hometown hardware store. It is AMAZING. The kids love it, and I don’t think it’s too shabby either. 

New Canaan4. Kiwanis Park 

New Canaan is landlocked and has no coastal shore. No worries! The town created our cute little Kiwanis Park, a small spring pond just outside of downtown. Sure, it lacks the picturesque view of the Sound, but my kids truly don’t care what sand they are digging in and absolutely love Kiwanis. The park has a fantastic and recently renovated playground as well, so kids of various ages can have a good time doing something. We like to pack a picnic dinner and head over around 4 p.m. when the sun and sand aren’t so hot.

5. Kid-Friendly Restaurants

I’m the first to admit it….we don’t go out to eat very often. I know, I know, it’s silly! We are your classic lazy homebody parents. We are much more inclined to take the kids out to lunch than actual dinnertime when little people are likely to lose it; but whatever meal we are looking for, New Canaan has so many fun places that treat kids/tolerate them well.

Some of our local favorites (in no particular order) are GatesTequila Mockingbird, New Canaan Diner, Le Pain Quotidien, Rosie and Gingerbitz. My 3-year-old loves lunch at Gingerbitz because the Metro North station is in plain view from their front patio (which conveniently keeps him contained) and it’s just so exciting!  I like that the owner is friendly and a local mom; she is so accommodating and has done custom cupcakes for several of my kids’ birthdays!    

New Canaan6. Waveny 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/running paths to the serene gardens, the wide-open green spaces, and the gorgeous mansion (that happens to house our town’s Parks and Rec department), Waveny Park is an amazing town resource for all seasons.

I utilize the paths frequently for picturesque time outside with my stroller. My husband uses the wide-open green space to set off model rockets with the kids. A local fliers club meets there on Sunday mornings if you want to learn more about model airplanes, or just sit back and let the kids revel in the model planes flying overhead. Waveny House is the setting for our town-sponsored summer camp, which will even wear out the kid with the most energy.

Waveny Park is also where you can find our town pool, which is a huge family favorite here. In addition to the big family pool with diving boards, they have a baby pool with gradual entry, so it is safe for those who are newly sitting and newly walking…as well as my 6-year-old who could dump and scoop water all day long. Regarding the winter, Waveny Park boasts one of the most favorite sledding hills around. 

7. New Canaan Nature Center  

I think that the New Canaan Nature Center is one of our most perfect hidden gems. I did not even know about this place until a few months after I moved here and it is now one of our most utilized resources in town. Their summer camp is a family favorite, the kids absolutely love it. I have loved doing the Mommy & Me Nature Class with Miss Anna; it is hands down our favorite morning of the week!

I also hear only rave reviews for their Preschool program. Apparently it’s one of the best around if you are raising a little explorer or budding naturalist. 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, our family has taken full advantage.

They even do programming for adults! Last year, I attended Prosecco and Planters with some lady friends…we were given Prosecco and learned all about creating stylish planters from an expert who works with Terrain in Westport. I like to be modest, but my front porch planters looked AH-mazing last summer after that workshop.

New Canaan8. 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 (we seem to love welcoming Santa!). Choirs from all the local schools provide the Holiday Stroll with beautiful carols while we stuff our faces with toasted s’mores. St. Aloysius (in the heart of downtown) provides a living nativity scene complete with animals and carols that is not to be missed, my kids love watching it every year. The Holiday Stroll fun continues into Saturday with live ice sculpture carving and visits with Santa at a downtown real estate office. Maybe you’ll pick out a new house while the kids see Santa?  

9. 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. I will find any excuse to have a meal there. In the summer months when I can’t stand to cook, it’s not unheard of for me to take the kids to have dinner there rather frequently. For a park cafe, I find the menu to be quite diverse and appealing to many audiences. And they can do gluten-free!

10. Grace Farms

Grace Farms is a recent addition to New Canaan and my family absolutely loves visiting. It is so hard to describe exactly what Grace Farms is, other than a tranquil place to explore. The location provides huge wide open green spaces for the children to safely run as well as numerous walking trails. My kids love to attend the children’s Artist Studio offerings on Saturdays and we always do lunch at the cafe afterward. The facilities are simply breathtaking in their beauty and simplicity. They do loads of programming for families. There is so much that we haven’t even sampled it all. Admission is free at the gate, so stop by sometime and I promise that you will feel inspired and peaceful in the Grace Farms surroundings.  

Sneaky #11

Can I sneak in an 11th thing that I love about New Canaan? Because I feel that I must mention the MayFair at St. Mark’s. They have suffered terrible weather for the past two years, but my goodness they put on a fantastic fair. It will forever count as my kids’ first roller coaster ride. I still have little kids, so we have not fully embraced the MayFair as a rite of spring passage, but I know that this carnival is really important to most local families with older kids. And I trust that in the years to come, it will be a really big thing for my family as well.

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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