The Plan | Kayla Kaplowitz | Substack

START HERE: The Plan Resource Hub

If you're new here, this is a great place to start poking around to get answers to all your questions.

Jul 7, 2025 • Kayla Kaplowitz

What's The Plan: FEBRUARY 20-22

Maple Sugaring at Trailside, Fiddler on the Roof at St. Luke’s, Sybil’s Ride at Ridgefield Theater Barn, African drumming in Yorktown, Bark x Brine in…

Feb 17 • Kayla Kaplowitz

What's Coming Up in The Plan?

Today is February 13. Here are a handful of events coming up.

Feb 13 • Kayla Kaplowitz

What's The Plan: FEBRUARY 13-15

Valentine’s Day events, Frozen at ACT, anti-Valentine’s Day library parties, Olympics Skating Event in Stamford, a family dance class at Pivot in…

Feb 10 • Kayla Kaplowitz

What's Coming Up in The Plan?

Today is February 6. Here are a handful of events coming up.

Feb 6 • Kayla Kaplowitz

Weekend Roundups

What's The Plan: FEBRUARY 20-22

Maple Sugaring at Trailside, Fiddler on the Roof at St. Luke’s, Sybil’s Ride at Ridgefield Theater Barn, African drumming in Yorktown, Bark x Brine in…

Feb 17 • Kayla Kaplowitz

What's The Plan: FEBRUARY 13-15

Valentine’s Day events, Frozen at ACT, anti-Valentine’s Day library parties, Olympics Skating Event in Stamford, a family dance class at Pivot in…

Feb 10 • Kayla Kaplowitz

What's The Plan: FEBRUARY 6-8

An escape room in Bedford Hills, Project Cupid in Pound Ridge, Winter Fest at Muscoot, Curious George, Winter Wildlife at Ward Pound, Lunar New Year at…

Feb 3 • Kayla Kaplowitz

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What's Coming Up

What's Coming Up in The Plan?

Today is February 13. Here are a handful of events coming up.

Feb 13 • Kayla Kaplowitz

What's Coming Up in The Plan?

Today is February 6. Here are a handful of events coming up.

Feb 6 • Kayla Kaplowitz

What's Coming Up in The Plan?

Today is January 30. Here are a handful of events coming up.

Jan 30 • Kayla Kaplowitz

What's Coming Up in The Plan?

Today is January 23. Here are a handful of events coming up.

Jan 23 • Kayla Kaplowitz

Ask An Expert

Master The Plan Calendar Workshop is Happening Today at 12:30PM

Join us on Zoom!

Jan 30 • Kayla Kaplowitz

What Do You Want to See in The Plan in 2026?

Your suggestions are what makes The Plan great. Now's your chance to tell me what you want to see next year.

Dec 22, 2025 • Kayla Kaplowitz

Guest Post: A Holiday Boundaries Guide for Toddler Parents

Kat Sabath of The Family Well has some advice for all you toddler parents who are gearing up for the madness of the holidays.

Dec 15, 2025 • Kayla Kaplowitz and The Family Well | Kat Sabath

So You Want to Take Your Kid Skiing?

Read this first. Real advice from ski families in Westchester County on where to go, what to bring, and how to prepare the kids.

Dec 8, 2025 • Kayla Kaplowitz

Summer Camp 2026 Updates

Summer Camp Update #1

New Pond Farm, Westchester Parks Camps, Ambler Farm, and more!

Feb 10 • Kayla Kaplowitz

Introducing The Plan Summer Camp Database

This is a community effort here, guys. May the odds be ever in your favor.

Feb 9 • Kayla Kaplowitz

Seasonal Roundups

All The Best Family-Friendly Holiday Events Around Town 2025

Lewisboro, North Salem, Katonah, Bedford, Pound Ridge, Ridgefield, New Canaan, Wilton, Redding, Mount Kisco, Yorktown, Stamford, Somers and more!

Nov 17, 2025 • Kayla Kaplowitz

Happy First Day of Autumn

It's September 22. Here are 36 pieces of unsolicited local advice on the season from me.

Sep 22, 2025 • Kayla Kaplowitz

Your Fall Guide is Here

An 18-page printable with every family-friendly Fall event you need to know about. Plus great recommendations from locals with littles. Upgrade today…

Sep 17, 2025 • Kayla Kaplowitz

I Have Two Huge Wall Calendars to Give Away

We have ours hanging in our kitchen and love them. Perfect for making a Fall and Winter plan with the kids.

Aug 25, 2025 • Kayla Kaplowitz

Columns

5 Local Things I'm Loving Right Now

And an AI app I just think you need to know about.

Nov 10, 2025 • Kayla Kaplowitz

It's My Plan-iversary 🎉

The Plan just turned one. Today, I'm peeling back the curtain on how it's going, and giving you a sneak peek at the plan for year two. (See what I did…

Oct 8, 2025 • Kayla Kaplowitz

Buy a Classified Ad in The Plan

A new advertising section for business owners who want to reach local parents in Lewisboro, Katonah, Pound Ridge, Bedford, Ridgefield, New Canaan and…

Sep 29, 2025 • Kayla Kaplowitz

I Made a Mom Cry (With Joy)

"My friend is moving here and was so concerned this was a 'sleepy' area. I sent her your newsletter and she literally cried."

Jun 14, 2025 • Kayla Kaplowitz

Sell Me on This Event

17:25

Sell Me on This Event: Ghosts of Ridgefield

Is it really worth your time, money, and parenting energy? I put Keeler Tavern's Executive Director in the hot seat this morning to find out.

Oct 14, 2025 • Kayla Kaplowitz and Hildegard Grob

11:05

Sell Me on This Event: The Pound Ridge Harvest Festival

Is it worth your time, money, and parenting energy? I chatted live with volunteers Jen Saldutti and Jenn Tavolacci to find out. (Spoiler alert: It is.)

Oct 2, 2025 • Kayla Kaplowitz

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