Issue 72: It's playtime

With Chessa Kenney from At Play

Genevieve Gearity, Ashley Matthews, Maddie Meehan, and Chessa Kenney

Apr 09, 2026

Two groups will always have our unwavering respect — 1. astronauts and 2. people who see a community need and work to address it themselves. Chessa Kenney is the latter (though we think she’d be pretty fearless on the moon, too.) The non-profit community playspace that she’s created with At Play brings adults and children such joy, and we’re so glad she’s joining us this week to share more about it. Welcome, Chessa!

Community and play have quietly been at the center of a lot of my life decisions — the two things my community playspace At Play is built on. Add in good coffee and the best chocolate chip cookie in town and there you have it.

Arriving from Brooklyn to Rhinebeck in 2019 with baby Ted and toddler Addie felt right immediately. Upstate felt slower, greener, and we found ourselves surrounded by people who were becoming real friends. But something was missing: places that felt as much for children as for adults, that you could actually stay in for a while, that felt well-designed and supportive. The kind of place where you might walk in as a stranger and leave with a plan for next week.

Paying attention to that absence meant a lot of conversations with other parents, especially those of older kids, and the same themes kept surfacing. Meeting a friend at a baby group who became essential to surviving early parenthood. That one coffee shop with enough space that it felt like an exhale. These weren’t luxuries people were describing. They were essentials that had held them together.

Something similar was happening in schools. My years of teaching made it clear what children are actually like when given time and space to play freely — how they light up, how they problem-solve, how they figure out who they are. And that time was shrinking, squeezed out by schedules and standards and the acceleration of life.

So began a long season of planning coffees and more conversations — surveying families, sitting with the data, trying to understand what was actually needed versus what was assumed. The picture got clearer, and a series of connections clicked into place in a way that felt less like coincidence and more like direction. In early 2024, feeling more certain of the real unmet need, less like a newcomer, I made the leap!

Building something from nothing requires a tolerance for the unknown. That’s uncomfortable, and also, unsurprisingly, exactly where things get interesting.

At Play opened September 6th as the area’s first nonprofit indoor playspace. We host open play, a café, on-site pediatric therapy, classes, and programming for newborns on up. The space itself is the work of Lindsay Bazos, a designer and friend who understands people and space in equal measure. What she created is warm, calming, and engaging. For any other non-designers reading, it’s like a warm hug from a great friend with a splash of the exact right shade of blue that’s both refreshing and cool.

Library pass programs through Starr Library and now Red Hook Library make access possible for families who need it, with expansion to other libraries in Dutchess, Ulster, and Columbia Counties underway. Play shouldn’t be a privilege.

What’s been most surprising since opening is how quickly At Play became part of people’s routines. Families return weekly. Friendships form. Kids ask to come back. Just like play itself, it’s not a destination — it’s a living, changing, responsive place that becomes part of how families grow, learn, and connect face to face.

The name is partly after Addie and Ted: the reasons all of this started making sense in the first place. They’re a daily reminder that play isn’t passive. It’s active, present, and necessary. For all of us.

General 3 — AT PLAY: A Community Playspace

Chessa Kenney is an educator and community advocate with a Master’s Degree in Education from Bank Street College of Education, whose career spans NYC public and private schools and the education technology sector. As Founder and Executive Director of At Play, she has built a nonprofit community playspace and family resource center in Rhinebeck combining play, pediatric therapy, early childhood programming, and a family-friendly café. At Play is designed to support connection, belonging, and joyful development. Chessa lives in Rhinebeck with her husband Mike, their two kids Ted and Addie, and their dog, Wolfie.

Thank you to Chessa for offering a special for our subscribers! Mention The Soft Spot at the At Play café and your first coffee or tea is on the house. Sit down, take a breath, and actually enjoy the place you just brought your kid to. That’s the whole point.

One For Us

In this section, we’ll share what we’re enjoying for ourselves these days.

The stunning Dassai Blue sake brewery in Hyde Park (*Photo: Pelli Clarke & Partners*)

[Chessa] - There’s a good chance you and I have something in common: not enough time during this stage of life to fit it all in. Travel in particular — the culture, the energy, the feeling of being somewhere entirely new — feels distant. A tour of the Dassai Blue sake brewery in Hyde Park unintentionally fulfilled that recently. Walking through the production process, seeing the beautiful machinery and systems, learning about rice polishing ratios, tasting the difference between grades — it scratched that itch for discovery that usually requires a plane ticket. We have such extraordinary things in our own backyard.

[Genevieve] - The new season of the adult animated show Rick and Morty finally has a premiere date of Sunday, May 24th. I needed to spread the word. ✌️

[Ashley] - A friendly reminder for our upstate folks: tick season is coming! My functional medicine doctor (who’s very cautious about any hint of toxicity) was adamant about two things: DEET-based insect spray and professional yard treatment for ticks. Tick-borne illnesses are serious, testing for them is unreliable, and the natural repellents aren’t effective. Stock up and get your yards treated for your whole family's health.

[Maddie] - I’m not quite sure how this term entered our familect, but I’m working hard to make the acronym EANABs happen outside of my household. Equally Attractive Non-Alcoholic Beverages is more fun and comprehensive than “mocktails”, no? Some recent favorites are the Salt and Lime Ghia, the Kolsch from Best Day, and Kimino’s yuzu juice. And I’m ready for Tart Vinegar’s newest batch of releases tomorrow – a splash of any of their offbeat flavors livens up seltzer so well.

One For Them

In this section, we’ll share what’s making parenting small children more enjoyable these days.

Our plans for a rainy spring afternoon (Photos: Nicolette's Couture; FAO Schwartz; eeboo)

[Chessa] - My kids are now 7 and 9 and they like some games that I also like! Lately it’s been Monopoly, Life, and a rotating cast of card games, and I’ve been transported back to the days of summer camp playing Spit. It’s consistently surprising how much is happening under the surface — negotiating, strategizing, handling a bad roll or a run on Pennsylvania through Boardwalk. There’s something about a game that doesn’t happen anywhere else: everyone’s focused on the same thing, the stakes are just high enough, and someone always surprises you.

[Genevieve] - As a Christmas gift, I gave my daughter a ceramic tea set as a test to see if she could manage not to shatter it immediately (this was, of course, before Wine Chat revealed she’s trustworthy with the breakables). It’s a great set that she loves to use, with or without real tea. I’ve also noticed this same set at friends’ houses with older kids, which tells me it withstands the tests of time and play.

[Ashley] - For Easter, we had a low-key brunch with friends whose daughter is equally obsessed with ballerinas, sparkles, and princesses. We couldn't resist buying the girls the most epic springtime twirly dresses for the egg hunt — and now we're ready for any excuse to wear them again, including the Hudson Valley Faerie Festival in May.

[Maddie] - Inspired by Chessa, my preschooler and I broke out this Go Fish deck (20% off with the code PICKLEFRIEND) and we had a delight of a time. He got to practice counting and sportsmanship, and I got to laugh each time he yelled, “Go Fish” with the gusto of a sports announcer calling the championship game.

Working Together

At Play is a not-for-profit playspace supported by the community. Consider contributing toward their mission and continued growth here.

We’d also like to shout out Perfect Ten and its mission to empower girls in the Hudson Valley. They have a Curated Closet Sale fundraiser on Saturday, April 18 that you can learn more about here.

In the Neighborhood

We live in the Mid-Hudson Valley and we’re keeping tabs on these (mostly family-friendly) events near us. If there’s another event you’d like us to share, please send it our way!