What we recommend quite literally defines who we are. It’s one of the most basic forms of self-expression and identity. Our recommendations cement our taste, style. Our sense of humor and values. They say something about our level of discernment.

When someone asks me for a recommendation, it’s an honor. You want to know my favorite no-frills sushi restaurant within a 10 mile radius? (Hashi). My favorite podcast? (Culture Study). Where to send your creative kid after school? (Make Modern 100%).

I tailor every recommendation to who I’m talking to: What I know about them, what they love & loathe.

I take this work seriously, and I tend to gravitate towards people who do, too.

Here at The Plan, I’m kind of just a curator with lots of opinions. Sure, I try as many local spots & events as I can, but I am only one person. (And honestly, sometimes we just hibernate in the house on the weekend.)

Meanwhile, all of you are out there in the field, week after week, trying the things, going to the events, making the plans. You are collecting SO much data on what to do (and what NOT to do), and I want to shine a light on all of it.

I know you all have so much to say, and I feel like I haven’t provided a proper forum for you to be able to do that in a natural way.

SO: In the spirit of The Plan’s mantra – helping you find great things to do with your family on the weekends – I wanted to enter year 3 with a new focus.

This year, we’re going to do this work together. We’re going to share great advice, recs and tips in one place – and fight valiantly for the hills we’ll die on.

Introducing: The Plan Club

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Why isn’t The Plan free? | About Me

Happy Tuesday and welcome to the weekend roundup.

Two bits of news from The Plan:

• Free subscribers: You can now choose to unlock 1 free post (max) per month. I thought you might know what you were missing once in a while. 😉

• Paid All subscribers: I’m launching “The Plan Club” on Zoom. Because planning together is better than planning alone. Join us for the first one Nov 10 at 8PM. Free or paid subs can join!

JUMP TO: FRI / SAT / SUN

Lots of fun roundups coming your way soon. Thanks to everyone who has submitted their expert advice so far. I LOVE reading your recs. I have only one request: Don’t submit marketing fluff or AI slop. Be real. Please and thank you.

Are you local business who wants info on upcoming sponsorship & collab opportunities? Here’s what to do:

1. Click on Account Settings. (open in a new browser if it asks you to login)

2. Toggle on Sponsors.

3. Sit tight. You’ll get an email from me very soon.

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I am having SO much fun hosting these Fall workshops on Zoom on how to use tech to plan better weekends for your family. This past Tuesday, Johna and I co-hosted together and had a grand ‘ol time. (Thanks for doing this with me, friend.)

Everyone can watch the replay above, which I snagged from John C. Hart Memorial Library’s YouTube channel. Then, download the 15-page PDF companion guide I prepared for you. (To learn more about the guide, scroll to the end of this post.)

🔐 Premium subscribers: There’s a 25% off code waiting for you below.

🔓 Free subscribers: Upgrade to Premium if you want the code.

Give me the guide

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Welcome to “The Friday 5,” my weekly newsletter for free subscribers.

This is my weekly rundown of 5 hand-picked events you should know about from my big, fat list of all the best family-friendly weekend events I could find.

Every week, I curate all the best things to do in Lewisboro, Ridgefield, Katonah, North Salem, Pound Ridge, Bedford, Redding, New Canaan, Wilton, Somers, and every town in between.

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Why isn’t The Plan free? | About Me

Happy Tuesday and welcome to the weekend roundup.

Don’t forget about my free library workshop happening today at 1PM. All live participants will get the recording and 50% off the companion guide. Come.

JUMP TO: FRI / SAT / SUN

It’s Halloween weekend, and that means all of us kinkeepers are diving head-first into the busiest planning season of the year. It’s Q4 guys. May the odds be ever in your favor.

I’ve got big plans to beef up The Plan’s “Ask an Expert” archive. If you’ve got a moment this week, please click the links below to give me your expert advice.

And please, for the love of all that is holy, don’t submit marketing fluff or AI slop.

Be real about your reviews & feedback. You know: like how you’d text a friend about it. And if you’re a vendor, just say so. Or better yet: convince a happy parent customer to submit a review for you.

Are you local business who wants info on upcoming sponsorship & collab opportunities? Here’s what to do:

1. Click on Account Settings.

2. Toggle on Sponsors.

3. Sit tight. You’ll get an email from me very soon.

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November 17 workshop

Sending a quick reminder: My free library “lunch n’ learn” Zoom workshop is on Tuesday, October 27.

A bunch of you have already registered, which makes me so happy. It starts at 1PM and is about 45 mins, so bring a sandwich or salad if you like.

North Salem mom of 2 and fellow digital organization aficionado Johna Rae Barrow is joining me to tackle a few things to get your digital parenting life in order.

Things like:

• Our current tech stack (apps, calendar hacks & systems) we use to capture “what-to-do” suggestions from everywhere;

• 3 easy ways to auto-add perfectly-formatted event listings into your own calendar (a flyer, a road sign, etc.);

• The email and calendar settings that completely changed how we plan weekends with our families;

• Strategies on how to turn saved ideas from “let’s do that someday” to actually making plans with friends & family.

sign me up

Each Zoom participant will get a video recording and a free PDF companion guide after the call.

Thanks to fan of The Plan Courtney Akin (over at John C. Hart Memorial Library in Yorktown) for pitching me on hosting a workshop series for local parents. So far, so good.

Other participating WLS libraries are: Lewisboro Library and Pound Ridge Library.

Hope to see ya there!

Welcome to “The Friday 5,” my weekly newsletter for free subscribers.

This is my weekly rundown of 5 hand-picked events you should know about from my big, fat list of all the best family-friendly weekend events I could find.

Every week, I curate all the best things to do in Lewisboro, Ridgefield, Katonah, North Salem, Pound Ridge, Bedford, Redding, New Canaan, Wilton, Somers, and every town in between.

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Why isn’t The Plan free? | About Me

Happy Tuesday and welcome to the weekend roundup. This Fall weather is so insanely beautiful, isn’t it?

JUMP TO: FRI / SAT / SUN

This morning, a friend and I did the Pound Ridge Town Park walking path with her 4-month-old and I was reminded how great of a stroller walk this is. Go if you’ve never tried it. Park at the village green (near Breads n’ Bakes) and go as far as you can; we’ve never actually made it to the town park but it IS possible.

Speaking of, here are 3 things coming up for The Plan this week and next:

• Stroller walks – I’m updating this post from July 2025 (“Scenic Stroller Walks”) and need your help. Click here to add your $.02 in the chat:

• Library workshop #2 – Coming up on Tuesday, October 27 at 1PM. Come nerd out with me and Johna Rae Barrow on how to use tech & AI to plan better weekends with the fam. It’s free! 🤓

• What’s the plan for Halloween? – A really great roundup of kid-friendly Halloween events coming your way later this week. Stay tuned…

Are you a business owner who wants info on sponsorship or collab opportunities? Click this button. 👇

Click meHide

1. Click on Account Settings.

2. Toggle on Sponsors.

3. Sit tight. You’ll get an email from me very soon.

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🚨 Several events on Sunday have been canceled or postponed because of the weather. Make sure to check the event pages before you head out.

Welcome to “The Friday 5,” my weekly newsletter for free subscribers.

This is my weekly rundown of 5 hand-picked events you should know about from my big, fat list of all the best family-friendly weekend events I could find.

Every week, I curate all the best things to do in Lewisboro, Ridgefield, Katonah, North Salem, Pound Ridge, Bedford, Redding, New Canaan, Wilton, Somers, and every town in between.

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Why isn’t The Plan free? | About Me

Happy Tuesday and welcome to the weekend roundup. I found 80+ great events, so buckle up.

JUMP TO: FRI / SAT / SUN

Last weekend we tried two new places and it felt like we were on a mini-vacation: The Fall Festival at New Canaan Nature Center (very small, but cute fundraiser), and then brunch at Arden’s in Rowayton. Highly recommend both.

At Arden’s, I split the yogurt parfait & chicken tacos with my youngest. And my soup-loving 9yo ate an entire bowl of the chicken & chickpea soup. People watching was great (lots of too-cool-for-school Rowayton teenagers in boat shoes + fancy moms in barrel jeans and yellow-tinted aviators).

Did your fam try something new last weekend? Leave a comment and tell us about it.

Read more

Welcome to “The Friday 5,” my weekly newsletter for free subscribers.

This is my weekly rundown of 5 hand-picked events you should know about from my big, fat list of all the best family-friendly weekend events I could find.

Every week, I curate all the best things to do in Lewisboro, Ridgefield, Katonah, North Salem, Pound Ridge, Bedford, Redding, New Canaan, Wilton, Somers, and every town in between.

Read more

When someone asks me what I do, I cringe when I blurt out: “I write a local event newsletter.”

Because The Plan isn’t just a list of local events; it’s a system that helps you plan better weekends with your family. It has a point of view. It shines a light on the hard, under-appreciated work of kin-keeping.

The bread and butter is the weekend event letter I send every Tuesday + the real-time calendar that lets you plan weekends with friends & family weeks ahead or on the fly.

But the icing on top is the original reporting I publish each month to help keep us tuned in to all the great places to discover around here.

I consider The Plan an essential service that’s well worth a $50 line item on your family’s annual budget.

Subscribe now

Because knowing what’s going on and where to go around here isn’t just about helping you entertain your kids on the weekends. It's about feeling more rooted in your chosen town, meeting your neighbors, and widening your circle.

Making another event listing site felt boring to me. I wanted The Plan to be a tool for building and maintaining friendships. That's how I use it, and it’s still the whole point of this.

Today, I’m taking a quick look back at what it’s been like to build The Plan in the last 2 years, and a preview of what’s coming in year 3.

What I set out to build.

I suppose when I started this thing 2 years ago, I didn’t really know what I was building. I just knew it had to exist.

At the time, our own weekend planning system was a mess. We were stuck in a “let’s just go to the diner and then the playground” rut every Saturday. I was only sort-of aware of what was happening around town, and what was nearby.

Every season, I had the same questions about the local spots or events I’d heard about from other parents, or saw on a flyer in a coffee shop somewhere. Things like:

• Wait, when is the town tree lighting? Isn’t there a menorah lighting too?

• What is that Ghosts of Ridgefield thing? Is it for little kids?

• Wait, WHAT is Caramoor again?

• What was that bike trail that preschool mom recommended?

I kept hearing these things from other parents I knew IRL and online. We all were sort of existing in this state of only half-knowing what was going on at all times. (Which is also, I suppose, parenthood in a nutshell.)

So I duct-taped together a weekend planning solution for us using Google Calendar, Apple Shortcuts/Automations, Google Gemini AI, and Substack. I was diligent about it. When it was ready, I started sharing it around. I committed to a publishing schedule and kept showing up, week after week.

Then I bugged every parent “tastemaker” I knew to give me their honest opinion of great local things to do with the kids. (My favorite part.) Skiing, bike trails, beer gardens, flower gardens, day trips, stroller walks, fishing spots, best thrift shops, best places to buy kids gifts, best places to volunteer with kids, etc. I was relentless.

Two years and 256 posts later, I’ve got: 1,230 newsletter subscribers (314 of them paying), a ~70% average email open rate, and 2,160 people following along on Instagram. And Substack just told me I’m the #10 rising parenting publication on the Substack leaderboard (whatever that means?)

OK, but are you making any money?

When I started, I told a friend I’d do it just for fun. “I don’t need to make any money off of this. I’m doing it anyway for my own family.” (Hi, Shantala 👋).

In the back of my mind, I figured it’d be a nice resume-builder for relaunching my ghostwriting and PR consulting work on a local level.**

Looking back, I’d tell that version of me to knock it off already. This is a business, and it takes real work. (Shoutout to the first friend I made through this newsletter – – for literally telling me one evening to knock it off.)

For the first 16 months, I published everything for free. A “build it and they will come” strategy. Then last March, I put up a paywall on my Tuesday letters. And wouldn’t you know: that was my biggest month ever for new paid subscribers.

That realization clarified something for me: You either need The Plan or you don’t. If you need it, you’ll pay for it. If you don’t, you won’t. And that’s fine.

My free-to-paid conversion rate hovers at around 25%. The Substack average is 2%. So that is pretty cool and validating.

But this still isn’t really about the money yet; I believe that will come in time. Right now, it’s about building something genuinely good for all of us.

No matter how this thing will evolve, know that I’ll never turn The Plan into something I wouldn’t use personally. (Or into something I’d side-eye from the sidelines).

** I realized pretty early that I don’t actually want to ghostwrite or do PR anymore. That career is behind me, and it feels great that I don’t have to keep doing something just because I’m good at it.

A few things I’ve learned in year two.

1. Events are the new front porch.

This year, I found a mantra as our family’s designated kin-keeper. No one’s hosting at home as much, and so local events have become our front porch: the places where neighbors gather.

This mindset shift was huge for me this year. I started inviting friends much more regularly to meet up at local events, and showing up at the ones where I thought I might bump into people I knew. And this intentionality is working.

This realization is a big reason why I love what I do. It’s given my family community, and I hope it’s starting to change how you see your weekends, too.

2. The PDF guides weren’t worth it.

I made a summer guide and a fall guide in 2025 and I’m not sure I’ll do these again. It made a little money, but took a ton of time. More important: I realized it's not how we actually live. Nobody's carrying a binder around with them. Recommendations need to live somewhere in context.

In fact: I ended up just putting every good rec from these projects into my own personal Wanderlog list, which told me a PDF wasn’t really the answer.

Instead of selling a bulky downloadable with pretty much the same info every year, I thought I’d try something useful:

Launch a workshop series where I teach you my own system of how to gather, store, save and act on the recommendations you collect from friends, neighbors, event flyers (and The Plan!) that pique your interest. It’s been fun so far and I hope you’ll join me for one this Fall.

I’m not ruling out big fat printable guides in the future, but I’m reworking what that might look like.

3. The summer camp database was quite an undertaking.

This one’s a real love-hate. A lot of you loved it, but it doesn’t quite fit what I’m trying to build here. The Plan is about reconnecting with your family and your community, and a camp database is closer to “here’s where to drop the kids off.” I know it’s a huge part of life here, and I know a lot of you found it useful, so I may keep it around. If I bring it back, I want to rethink the format.

* Speaking of databases, I’ve been talking about a “Birthday Party Database” forever and perhaps year 3 is when I finally launch this puppy…

4. It feels good to say no to things that feel off.

Classified ads, for example. I was so grateful to the local businesses that supported me in this pilot program. I paused ad sales in March because the whole program just turned me into the kind of sales rep I didn’t want to be. I’m still on the fence about what comes next, but I am toying with the idea of launching an editorial partnership program.

Hear me out.

When done well, editorially-focused partner content can genuinely be useful, interesting, and irresistible to readers. When I see reader-supported newsletters I love doing smart collabs & partnerships, I appreciate it. (My favorite Substacks in this genre are , , , and ).

So I think there’s an opportunity to be really creative here. If you have a local business and are interested in potentially working together, do these 3 things while I sort some things out on my end:

1. Click on Account Settings.

2. Toggle on Sponsors.

3. Sit tight. You’ll get an email from me very soon.

5. More venues should invite my readers to things.

I launched Field Trips in May, and they’ve been a great way for us to meet up and discover things around town together (e.g., The Aldrich, Jacob Burns, Woodcock Nature Center, Caramoor, Ridgefield Farmers Market, etc.)

But here’s what I’m thinking: More event organizers should throw some perks our way in year 3. Don’t you agree?

Discounts on tickets, free popcorn/soda, early access to registration, a designated space for us to hang out at a great event together – it doesn’t matter; what matters is getting us in the door.

Because here’s what I know: You all are a super influential bunch in your own group chats. And if I were an in-house marketer at a local venue, I would be doing everything I could to entice The Plan readers to show up at my events. (HINT HINT.)

6. I’m a curator, not an influencer.

I decided on a title for what I do here. I’m a collector of great recommendations. That’s who I am. A collector. A curator. Not an influencer.

Here’s the difference: Many events & places I curate for The Plan aren’t really my cup of tea; but I know they’re perfect for another kind of family who happens to love things I don’t personally find engaging or interesting.

So I promise to keep adding reputable events & things to do if they happen to be standouts in their niche. If it’s a schlocky place or event (you know it when you see it), you probably won’t find it on The Plan.

However, I do hold strong opinions and I’ll keep sharing them with you because it’s fun. Here are some hills I’ll die on: Grace Farms is the best go-to for a first mom-date, Breads n’ Bakes plain croissant is bar none, Bedford Playhouse is the best movie theater, Farmer’s Grind should serve their Honeysuckle Latte year-round, Corner Cafe lunch in Ridgefield is the best, Wilton Town Forest is the prettiest hike, Mead Memorial Park and Lewisboro Town Park are tied for best playground, Lewisboro Library Fair is the must-go event of the Fall, Ridgefield Farmers Market & Rowayton Farmers Market are the best local farmers markets, Kawa Ni is the best restaurant in the area, and New Canaan Library is by far the best spot for getting work done.

7. Making merch is fun.

Just kind of makes this official, you know? So far, I’ve got a ball cap and a tote. Shoutout to Custom T’s & More in Ridgefield for being great to work with.

Where is this going?

Right now, The Plan lives as an organized Substack archive. All the good stuff is in there, but it’s not easily browsable.

In year 3, I want it to feel more like a Thrillist or an Eater. Remember those sites? Organized, searchable, and built for how people actually look things up.

I’d also love to bring in a few voices beyond my own. A correspondent for local finds, day trip recommendations, date night spots, moms-(or dads)-night-out ideas? A deuxmoi-like reporter covering local gossip for us? (I KID). But seriously: email me if this speaks to you.

ALSO: Christmastime is the biggest season for The Plan, and I’m already planning how to show up for it. Stay tuned for that.

Thanks, y’all.

Thank you for 2 years of reading, replying, recommending, showing up to Field Trips, and telling all your friends about this thing.

I’m glad you’re here for year 3. 🥂

Happy planning.

xo,
K

Get more from Kayla Kaplowitz in the Substack app

Available for iOS and Android

Get the app

1. Click on Account Settings.

2. Toggle on Sponsors.

3. Wait for an email from me in a few weeks.

Meantime, start thinking of some fun ways we can partner together on creative editorial content for Substack (+ Instagram!) that will be useful, interesting, and irresistible to my readers.

Happy planning.

xo,
K

PS: I’m keeping sponsorships limited and category-exclusive.

Why isn’t The Plan free? | About Me

Happy Tuesday and welcome to the weekend roundup.

JUMP TO: FRI / SAT / SUN

There’s an interesting discussion bubbling up on my Instagram in response to Derek Thompson’s latest on the decline of the dinner party. The TLDR:

• People are hosting less in their homes:“The share of adults who say they regularly have friends over has declined 70% since 1975.” - D. Thompson

• My hot take: That tracks. But I couldn’t help but wonder… Are families with young kids choosing local events over hosting at home?

Consider this: I clocked 60 family-friendly local events happening around us this weekend. It’s nuts, and I’d posit that the massive uptick in community events may be a big reason why parents today are opting out of hosting at home.

In my super scientific research (i.e., I ask friends about this sometimes), I’ve come to this conclusion: Parents who work hard all week who would rather just show up at a fun thing in town with friends. Maybe because it’s easier and it feels just as good.

What do you think? Am I off-base? Sound off in the comments or on Insta.

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Welcome to “The Friday 5,” my weekly newsletter for free subscribers.

If you’re new here, this is my weekly rundown of 5 events you should know about from my big, fat list of all the best family-friendly weekend events I could find.

Every week, I curate all the best family-friendly things to do in Lewisboro, Ridgefield, Katonah, North Salem, Pound Ridge, Bedford, Redding, New Canaan, Wilton, Somers, and every town in between.

Only paid subscribers have access to the complete weekend roundup + the real-time calendar, which is perfect for making last-minute (or weeks-ahead) plans with friends.

Subscribe now

Thanks to the handful of you who came to my library workshop on Tuesday about how to use tech to plan better family weekends. We had a grand ‘ole time, didn’t we? If you missed my first session, I’m also hosting one on Oct 27 and Nov 17.

Stay tuned for a recap next week: I’ll be sharing the video and a downloadable PDF of what we learned + what apps and systems you can implement into your weekly planning routine right now.

As always, nothing here is sponsored. Happy planning.

xo,
K

PS: Follow me on Insta.

1

🥂 Fall Fête @ Katonah Museum of Art, Katonah

FRIDAY, OCTOBER 2 (5:00 PM–7:00 PM) — Looks like a festive evening in the sculpture garden with live music, light bites, and art-making. Enjoy after-hours gallery access and a docent-led tour. Tix $45/kid, $75/adult, (U2 free). FETE26 gets you 10% off tickets! Looks like a good option for a Family Friend Hang (FFH). >>

2

🍻 Cider Night: The Saints @ Hardscrabble Cider, North Salem

FRIDAY, OCTOBER 2 (6:00 PM–9:00 PM) — We love this place. Grab a pizza, a beer, and hang on the picnic tables while the kids run wild. Don’t forget to grab a bag full of cider donuts for dessert. >>

3

🎃 14th Annual Giant Pumpkin Weigh Off Festival @ Ballard Park, Ridgefield

SATURDAY, OCTOBER 3 (10:00 AM–3:00 PM) — A free, family-friendly event which packs the park with spectators and pumpkin growers from all over. Last year’s champion pumpkin weighed over 2,000 pounds! Expect live music, farm stands, vendors, food trucks, kids activities, and more. Plus: the “Fall in Love with Ridgefield” event will be going on downtown, so it’ll be great people-watching. >>

4

🐾 The Dick Button Animal Rescue Palooza Day @ D.I.G. Farm, North Salem

SATURDAY, OCTOBER 3 (10:00 AM–1:00 PM) — Celebrate the legacy of Dick Button with a heartwarming living tribute at D.I.G. Farm. You’ll meet adoptable animals, tour the beautiful farm, and enjoy a community gathering supporting animal rescue and the land he loved. If you feel it’s time to finally get your kids a pup, I’d swing by. >>

5

🎶 Sleepy Hollow Music Festival @ Kingsland Point Park, Sleepy Hollow

SATURDAY, OCTOBER 3 (10:00 AM–8:00 PM) — Two stages featuring ‘90s bands like Everclear (!), The Smithereens with Marshall Crenshaw, Fastball, and Sophie B. Hawkins, with youth rock sets from the Briarcliff School of Rock. When I saw this lineup, I was immediately taken back to my Dawson’s Creek-watching days and teared up a little. It's all overlooking the Hudson River, and you can enjoy food, drinks, and lots of entertainment for kids. I hear the Headless Horseman will be there, as well as a Halloween costume contest. Tix $62.50 and U12 free. >>

Free subscribers get:

• 5 event recommendations every Friday

• The occasional free resource, like 2026 Farmers Markets printable.

• Invites to all Field Trips

Paid subscribers get:

• The FULL weekend roundup every Tuesday at 12PM.

• Subscriber access to The Plan calendar.

• Every paid-only newsletter, like 11 Great Fall Music Festivals to Consider

• Every upcoming seasonal event roundup. 🎄

• A 50% discount on all downloadable guides.

• Access to the entire idea archive, like best playgrounds, best soft-play spaces, kid-friendly beer gardens, how to spend a day in Bedford, Georgetown or Pleasantville, fun day trips, where to shop for kids gifts, and where to hang with your newborn.

• Invites to all Field Trips.

What is Premium? | About Me

Happy Tuesday and welcome to the weekend roundup.

Well, last weekend was a wash, but this weekend looks pretty good.

JUMP TO: FRI / SAT / SUN

Sending good vibes to anyone who has taken care of a sick kid so far this school year. Parenting is not for the weak.

My free Zoom lunch n’ learn workshop is today (TUES) @ 1PM. I’ll teach you all the apps, systems, tech hacks & tricks I use to plan weekends with my family. Basically: How I find things + my system for saving them so I can easily retrieve them in seconds.

BONUS: All attendees will receive a free downloadable PDF with what we learned + all the prompts & Apple Shortcut recipes. Only paid subscribers will have access to the PDF download when I send out the video recap next week.

SIGN ME UP, BABE

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Welcome to “The Friday 5,” my weekly newsletter for free subscribers.

The Nor’easter is forcing many events on Saturday & Sunday to cancel or postpone, so make sure to check event websites & Instagram pages before making any plans.

I did confirm that Sunday’s Lewisboro Music Festival is postponed to sometime in May, and Hawk Watch Fest is postponed until Oct. 3. And sadly, the Chappaqua Book Festival on Saturday has been cancelled.

I’m still waiting on responses from a bunch of others and will try to update the calendar and weekend roundup as quickly as I can for you.

If you’re new here, The Friday 5 is my weekly rundown of 5 events you should know about from my big, fat list of all the best family-friendly weekend events I could find. (Only paid subscribers have access to it.)

Every week, I curate all the best weekend family-friendly things to do in Lewisboro, Ridgefield, Katonah, North Salem, Pound Ridge, Bedford, Redding, New Canaan, Wilton, Somers, and every town in between.

Every single event lives in The Plan calendar, which is perfect for making plans with friends weeks (or an hour) ahead of time. (Which is, according to Caitlin of Big Time Adulting, the preferred method.)

One reminder before we get into it:

Come to my Zoom workshop series on Tuesday, Sept 29 at 1PM. It’s all about how to use tech to plan better family weekends.

🚨 Here’s one freebie: Wanderlog is my favorite web/mobile app to store all my where-to-go faves & ideas (e.g., playgrounds, ramen restaurants, favorite indoor play-spaces). It’s great, and the free version is all you need. It’s SO much better than Google Maps lists and I’ll tell you why in the workshop.

As always, nothing here is sponsored. Happy planning.

xo,
K

PS: Follow me on Insta.

1

🦞 New Canaan Rotary 41st Annual Lobsterfest @ Waveny House

FRIDAY and SATURDAY, SEPTEMBER 25 & 26 (4:00 PM–8:00 PM) — Avoid cooking tonight and go pick up a steamed lobster dinner or lobster roll at one of our favorite parks in the area. The grounds are huge and Waveny House is so beautiful. Meals are between $50-$85 (as it’s a fundraiser!) and you can dine-in or carry-out. It’s going on, rain or shine! >>

2

🎬 Outdoor Movie Night: Monster’s University @ Onatru Farm Park, South Salem

FRIDAY, SEPTEMBER 25 (5:30 PM–9:00 PM) — Bring your lawn chairs and blankets to sit on the grass, buy some food from a food truck, and have some popcorn, candy, and drinks while you enjoy the show. $20/car at entrance. $15/car pre-registering. >>

3

📚 Chappaqua Children’s Book Festival @ Chappaqua Train Station

SATURDAY, SEPTEMBER 26 (10:00 AM–4:00 PM) — The mecca for children’s book authors. So many great authors come in for this one. Click here to watch my interview with the Executive Director, and to view a list of all the visiting authors, story times and “Draw With Me” sessions with illustrators. You can easily spend the whole afternoon here. Free! Cancelled! >>

4

🎬 Annie (1982) @ Jacob Burns Film Center, Pleasantville

SATURDAY and SUNDAY, SEPTEMBER 26 & 27 (11:00 AM–1:00 PM) — I think you’re gonna like it here. Tix $5 >>

5

🎃 14th Annual Giant Pumpkin Weigh Off Festival @ Ballard Park, Ridgefield

SUNDAY, SEPTEMBER 27 (10:00 AM–3:00 PM) — A free, family-friendly event which packs the park with spectators and pumpkin growers from all over. Last year’s champion pumpkin weighed over 2,000 pounds! Expect live music, farm stands, vendors, food trucks, kids activities, and more. Cancelled! >>

Free subscribers get:

• 5 event recommendations every Friday

• The occasional free resource, like 2026 Farmers Markets printable.

• Invites to all Field Trips

Paid subscribers get:

• The FULL weekend roundup every Tuesday at 12PM.

• Subscriber access to The Plan calendar.

• Every paid-only newsletter, like 11 Great Fall Music Festivals to Consider

• Every upcoming seasonal event roundup. Christmas is around the corner; just saying…

• A 50% discount on all downloadable guides.

• Access to the entire idea archive, like best playgrounds, best soft-play spaces, kid-friendly beer gardens, how to spend a day in Bedford, Georgetown or Pleasantville, fun day trips, where to shop for kids gifts, and where to hang with your newborn.

• Invites to all Field Trips.

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The first Google Image search result served me a snapshot of Liz in a T-shirt with the phrase “Read More. Ban Less” emblazoned on the front. It made me smile.

“Oh right! Yes, that t-shirt was designed by author and illustrator Jarrett Lerner,” Liz told me when we first spoke on the phone. “I love the message.”

Here she is in year 2 heading up one of the biggest children’s books festivals in the U.S., and isn’t afraid to mince words about what she believes in when it comes to child literacy.

Earlier this month, she joined me for a Substack Live conversation to go over all the nitty-gritty details for first-time festival-goers (parking situation, food, author lineup, mapping our your day, etc.). But my favorite part of our convo was hearing directly from her about what makes this event so magical.

After we hung up, I left feeling a lot less overwhelmed at the thought of navigating an event that draws 10K+ people every year to the Chappaqua Train Station lot. I also felt inspired.

“All you see in the news is literacy rates dropping, and tech taking over and ‘nobody reads anymore.’ But when you see all these kids and families come out for books, it’s just great,” says Liz. “I mean, sure. Are there a handful of people that just come for food trucks? Probably, right? But that’s okay. Maybe they’ll find a book on their way out.”

The details:

WHAT: Chappaqua Children’s Book Festival

WHEN: Saturday, September 26 from 10:00AM–4:00PM

WHERE: 11 Allen Place, Chappaqua (the train station!)

The author lineup this year is insane (170+ children’s book authors and illustrators);

Vendors look great (Camp Kiwi inflatables, sensory chill-out area);

Food trucks look delish (Poppin’ Pancake, Scotty’s Egg Rolls, Mobile Pie, etc.)

Below the paywall, Premium subscribers have access to:

• Our full 30-minute video interview;

• The official list of authors, organized by which tent they’re in. Print this, highlight it, and make sure you have a plan to visit all your kids’ faves.

• The official “Draw With Us” schedule, so you can map out which illustrator you want to draw with (my 6yo is going to love Stephen Shaskan of the Pizza and Taco series at 1:45PM!)

• The official Storytime Reading schedule for the day. All readings take place in the cozy Kiwi area. (Don’t miss Maggie Edkins Willis reading Little Ghost Makes a Friend at 11AM. Perfect for the start of spooky season.)

Hope to see you out there on Saturday. I’ll be going with my kids for the first time and can’t wait.

And if you happen to see Liz, say hi!

xo,
K

PS: Remember, nothing here is sponsored. I just love finding out fun things to do around town and sharing them with my readers. Enjoy.

PPS: Do you have an idea for an upcoming local event I might cover for my “Sell Me on This Event” series? Something you’ve been curious about forever? Email me at kaylakaplowitz@substack.com or leave me a text or voice-note at ‪(203) 594-6844‬.

Waiting for you below the paywall is the full list of 170+ authors coming to the festival (organized by tent). PLUS: the Draw With Us and Storytime lineup for the day. To unlock this and all future newsletters from The Plan, upgrade your subscription today. It’s only $50/yr and worth every penny; I promise.

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Upgrade | Ideas | About Me

Almost ALL outdoor events this weekend are cancelled or postponed because of the Nor’easter, so please check the event websites & Instagram pages for announcements.

Happy Tuesday and welcome to the weekend roundup.

Last weekend, a few readers came up to me at the library fair and said: “Thank you guys for doing what you do!”

I’m here to tell you that it’s just me behind this thing. I write every issue (often at my daughter’s bedroom desk, the Ridgefield Library, or Katonah Reading Room) and am constantly adding events to the calendar (often in the grocery line, or lying in bed on my phone at 6AM) every week, all in the margins of my life.

One day that may change, but for now: it’s just me, baby.

JUMP TO: FRI / SAT / SUN

PS: Click here for a video preview of a “Fall Bucket List” post I’m working on for paid subscribers. Someone commented it’s like a “who’s who” in Lewisboro. (It’s true.)

Buy a ball cap

Buy a tote bag

If you want to learn my calendaring and digital organization wizardry, then sign up for my Zoom workshop series on Sept 29 @ 1PM. I’ll help you manage the onslaught of recommendations you get from everywhere: Group chat texts, preschool pickup line, local influencers on Instagram, everything.

It’ll be simple; I promise. Bring your questions to the group and I’ll do my best to answer them. I’m also hosting one on Oct 27 and Nov 17.

Read more

Welcome to “The Friday 5,” my weekly newsletter for free subscribers.

In each issue, I’ll give you a rundown of 5 events you should know about from my big, fat weekend roundup of 70+ family-friendly weekend events I published on Tuesday.

I curate all the best weekend family-friendly things to do across Lewisboro, Ridgefield, Katonah, North Salem, Pound Ridge, Bedford, Redding, New Canaan, Wilton, Somers, and every town in between. Every single event lives in The Plan calendar, which is perfect for making plans with friends weeks (or an hour) ahead of time.

One reminder before we get into it: Would love to see you at 2 things in the next 2 weeks:

1. my library booth tomorrow at the Lewisboro Library Fair at Onatru Farm Park in South Salem.

2. my Zoom workshop series with the library on Sept 29. I’m going to be teaching you all my favorite apps, systems, shortcuts to plan better family weekends.

As always, nothing here is sponsored. Happy planning.

xo,
K

PS: Follow me on Insta.

1

🍁 The Lewisboro Library Fair @ Onatru Farm Park, South Salem

SATURDAY, SEPTEMBER 19 (10:00 AM–4:00 PM) — Love this annual fundraiser. Vendors, food trucks, a dunk tank, live music, a book sale, a bake sale, and more. Kids Zone bracelets are $10, or you can do a fairy garden craft AND the Kid’s Zone for just $20. My daughter saves up her money all summer to buy something at the Attic Treasures barn. Go! I’ll have a booth this year. >>

2

🎉 SeptemberFest @ Downtown Mount Kisco

SEPTEMBER 18-20 — Carnival rides, a street fair, food trucks, and live music all weekend long. This is a big one. >>

3

🇮🇹 Yorktown San Gennaro Festival @ Commerce St & Railroad Park, Yorktown Heights

SEPTEMBER 16-20 — An iconic 5-night Italian Heritage Festival. Expect food, carnival rides, games and live music. On Friday night at 6PM there will be a ceremonial procession of San Gennaro, the Patron Saint of Naples. Runs through Sunday night. >>

4

🌕 Mystic Moon opening night @ Harvest Moon Farm & Orchard, North Salem

FRIDAY, SEPTEMBER 18 (6:00 PM–9:00 PM) — This is a moonlit walk through the woods with glowing oak trees and pirate-themed fun. The twilight slots are perfect if you have little kids who might need a softly-lit experience. Bring a tough stroller and wear sturdy shoes for the trail. Costumes encouraged! Runs through Nov 1. Tix $23-$80, free U3. >>

5

🎡 Wilton Rotary Carnival @ School Rd and Danbury Rd, Wilton

SEPTEMBER 18-20 — Rides, games, food trucks and vendors. 100% of the proceeds will be reinvested into the Wilton community, how great is that? Runs through Sunday night. $35/wristbands. >>

Free subscribers get:

• 5 event recommendations every Friday

• The occasional free resource, like 2026 Farmers Markets printable.

• Invites to all Field Trips

Paid subscribers get:

• The FULL weekend roundup every Tuesday at 12PM.

• Subscriber access to The Plan calendar.

• Every paid-only newsletter, like 11 Great Fall Music Festivals to Consider

• Every upcoming seasonal event roundup. Christmas is around the corner; just saying…

• A 50% discount on all downloadable guides.

• Access to the entire idea archive, like best playgrounds, best soft-play spaces, kid-friendly beer gardens, how to spend a day in Bedford, Georgetown or Pleasantville, fun day trips, where to shop for kids gifts, and where to hang with your newborn.

• Invites to all Field Trips.

Get more from Kayla Kaplowitz in the Substack app

Available for iOS and Android

Get the app