6 Kid-Friendly Bike Trails and a Quick Ask
I wish I looked as cute as my kids do in a bike helmet.
For today’s Ask An Expert post, I set out to research and write the ultimate local resource for family-friendly bike trails. But after some consideration, I decided to just give you our go-to’s and call it a day. If there are additional trails (or trail sections) local parents should consider, just email me or comment below and I’ll update it.
Oh, and I have a quick ask for you at the end. I hope you stick around to hear it.
xo,
K
VROOM VROOM
We Love These 5 Bike Trails and You Should, Too.
Slather on the sunscreen, guys.
But first, you gotta get the gear. Here’s a quick rundown of what’s worked for us.
THE GEAR
Pedal bike — Woom. I know, it’s a bit of a splurge, but it’s super light and has really held up over the years. It’s the perfect bike for kids to learn on. My now 8-year-old is still using the 16”, but we’re definitely due for an upgrade as her baby giraffe legs have gotten much too long.
Balance bike: Banwood. I spied this bike on the Maisonette site years ago, and can confirm it’s the cutest. We bought it 5 years ago and now my 4yo has her sister’s hand-me-down. She loves it. Both my kids have no fear on this thing. Skip the training wheels and just get a good balance bike; you’ll be glad you did.
Helmets: Woom
Bike rack:
Thule.My husband texted me with a correction. Our hitch bike rack is from Küat. Apologies for the fake news.
THE TRAILS
Irwin Park (New Canaan) »
This is the perfect paved path to bring your biking beginners. We always head left out of the parking lot because the first incline is so much fun to zoom down. Take a break at the natural wood gazebo and then make your way towards the benches near the big daffodil field at the end. If you’ve got the energy for two loops, go for it. It’s just under a mile.
Click here to view the Irwin Park loop in AllTrails.

Ridgefield Parks & Rec Path »
Another great option for kiddos. We always park in the parking lot right off of Danbury Road, go over the little red bridge and turn left. You’ll see the 9/11 Memorial, quirky metal sculptures, and after a short ride through the woods, you’ll arrive at the playground. You can choose to stop, or just keep going and take another loop.
Click here to see where we park in Google Maps.
North County Rail Trail to Trailside Café (Yorktown Heights) »
When you park at the North County Rail Trail parking lot, most people will tell you to head towards the picturesque rail trestle bridge. We like to go north instead. From there, it’s about a 3-mile ride to Trailside Café, which is a great kid-friendly snack or lunch destination. If it’s nice, you can park your bike and sit out back on a picnic table.
There’s so much to see along the way. You’ve got the Croton River to your left, some graffitied archways as you get closer to Yorktown, and the skate park right before you get to the café. Plus, the return trip will always be easier thanks to the mostly downhill path.
Click here to open the trail in Google Maps.
Norwalk River Valley Trail – Wilton East section (Wilton, CT) »
We went here exactly one time a few years ago on a cold day and I remember really liking it. We parked at the Sharp Hill Road parking lot and went north. It’s a nice, flat, stone dust path that’s perfect for biking. After about a mile, we spotted this huge rock structure with tons of little painted rocks and other trinkets. The girls loved it. Bike a few miles up and back and you’ve got yourself a fun afternoon.
Click here to see where we parked in Google Maps.
Pound Ridge Town Park trail (Pound Ridge) »
My youngest and I biked here when she was off preschool one day and had the best time. Just park in the parking lot, head towards the pond, and follow the signs. It’s a well-maintained paved trail, and there’s a cute Storywalk along the way. We rode our bikes to the Pound Ridge Town House, turned back, said hello to the ducks in the pond, and headed home.
Click here to see where we parked in Google Maps.
North County Rail Trail – Empire State trail »
Friend of The Plan Julie Haddix of South Salem reached out with this recommendation. She said her oldest (7) learned to ride his pedal bike here, and they're looking forward to getting their youngest (4) out there this spring/summer to practice.
"It's a bit more of a drive," she told me, "but if you park at Castle Park in Brewster and then head north on the trail, there are no roads to cross for at least 5 miles!" Literally my dream.
She says the best part is that the parking lot is next to a playground, which is ideal for occupying kids while unloading/loading bikes. Plus, when you finish your ride, you can have a picnic lunch on one of the tables there. "The trail goes next to some beautiful lakes and is a section where the old railroad tracks are still visible – my kids love that!"
Click here to see where she parks in Google Maps.
THINGS I’M WORKING ON
I Hate Asking People for Money
But here goes.
It’s wild that I’m literally the child of a public high school art teacher and a life-long YMCA executive team employee, and yet I still feel weird asking people to donate money to a worthy cause.
This past school year, a friend convinced me to take on the Co-VP role on Meadow Pond Elementary’s PTO board here in South Salem. It’s a lot more work than I imagined, but it’s fulfilling and keeps me in-the-know. (My toxic trait.)
We are a proper 501(c)3 organization with a budget, bylaws, fundraising goals and a TON of parent volunteers who keep the train running year after year. Being a part of the PTO was a game-changer for me. Before, I didn’t pay much attention to how it all happened. Field trip permission slips just appeared in my kid’s backpack, as did calendar notices for Halloween events, book fairs, and P.A.R.P. celebrations. I didn’t fully appreciate how much time, effort (and money) went into all this stuff that makes our school such a special place.
All this to say: We’re working on something big right now, and need your help.
A small but mighty committee has been working on a “Party For the Pond”—our end-of-year benefit happening on June 12 at The Benjamin in Ridgefield. The funds we raise here will set the stage for what our PTO is able to do in the coming school year. Field trips, author visits, events, teacher appreciation funds; you name it.
If you’re a local business and want to reach a captive audience of local parents, this is a good one to support.

We’re actively looking for:
Auction items
Think: Products, goods, services, lessons, vacation home stays, cool experiences. We need it all. Oh, you own an art studio and do birthday parties? Our parents will bid like crazy on that one. You’re a sleep-training consultant who offers at-home sessions? I can rattle off 10 sleep-deprived MPES parents right now.
Sponsorships
Depending on your commitment level ($100, $250, $500), your business name/logo could be featured at the event, on our website, in our parent e-newsletters, on our social media pages, or mentioned live at the event by our emcee.


So if you’ve got something in mind, just reach out to our oh-so-capable auction chairs Val Cancro or Dina Carelli (of Lewisboro Town Playground fame), or Pia Dorson (who just ran a hugely successful fundraiser last month in Bedford), and they’ll help guide you.
And that’s it! If you gotten this far, thanks for reading. As always, I appreciate your support. Share this with a friend if you feel so inclined.