What's The Plan: MAY 9-11
A “May Fair" in New Canaan, Farmers Market opening days at North Salem & Muscoot, a family party at Westmoreland, the Old Salem Farm Horse Show, and more!
Any moms out there stressing about your BIG DAY on Sunday? I am. For weeks now, I’ve been bombarded on the Internet with really great advice from my favorite writers and podcasters, like this…
“Your family can’t read your mind. If you're someone who has felt a bit let down on Mother’s Day you need to tell them—specifically!—what would make your day great…” – Barbara Costello (Brunch with Babs)
“… no one can read your mind. Tell people what you want. If we don’t say what we want, we’re just setting ourselves up for disappointment and resentment.” – Jo Piazza (Over the Influence)
“The key to a nice Mother’s Day is setting expectations of what you want the day to look like, and then effectively communicating them.” – Caro Chambers (What to Cook When You Don’t Feel Like Cooking)
… and it’s left me in a state of complete decision paralysis.
Sunday will mark my 9th Mother’s Day, which is crazy. I’m basically a veteran mom—shouldn’t I know by now what will make me happy? Do I want lots of family time or lots of time alone? Do I want a nice brunch out or a home-cooked meal? Do I want to window shop with a mimosa buzz, or launch into a caffeine-fueled day of Swedish death cleaning? (Look it up.)
It’s okay if you don’t know what you want yet, either. Maybe the whole point of Mother’s Day Planning is that it’s supposed to feel a little uncomfortable for moms. For me, the act of spending time thinking about my needs and wants feels a little too luxurious. It stirs up feelings of guilt, because my natural state is to just think about what everyone else needs or wants.
But I know I’ll get over it; I always do. 😉
I’m thinking this week of all the moms who make it happen. The kinkeepers, the plan-makers, and the ultimate organizers. You deserve whatever you ask for on Sunday. And if this day is a tricky one for you, I’m sending you lots of love.
Thanks to all the subscribers who signed up last week, including Corey S., Haley R., Melinda V., Andrea O., Ali H., Anabel H., Coleen A., Anna C., Rebecca S., Carla P., Deena K., Chiara B., Emma C., Sue T., Georgina C., Lisa C., Alix T., Emily W., Beatrice C., Bree M., Luz O., Julia H., Liz H., Molly W., Susan G., Kelly S., and Eric D. I really appreciate your support. 🫶
Enjoy the weekend ahead, and be sure to send this roundup to a new parent friend. Remember: we hate gate-keeping around here. Sharing is caring.
xo,
K
PS: Follow The Plan on Instagram!
PPS: Did you catch my list of great local bike paths on Monday? Thanks to loyal reader Julie Haddix for the additional recco. I’ve already updated the post and gifted her a 3-mo Premium membership. Happy planning, Julie.
PPPS: New Canaan’s "May Fair” kicks off this week, and on tap for next week is the St. Patrick’s carnival in Bedford and the Lions Club Carnival in Somers. So I need your help: What are your best carnival season parenting tips? Click this Note to comment or drop me an email and I’ll include your tip in my “Ask an Expert” post on May 12. (Anyone who contributes gets a 3-month Premium membership.)
FRIDAY, MAY 9
National Child Care Provider Day »
1:30 PM-3:00 PM — 🌷 Preschool Spring Celebration with the LLT (Bedford Audubon Society, Katonah)
Preschoolers will celebrate spring with a hike along the storybook trail, plant flower seeds to help birds and butterflies, and read a spring-themed book in the garden at Bylane Farm. This free event is put on by the Lewisboro Land Trust, which organizes such great nature-based events to connect local families. »
4:45 PM-5:45 PM — ✌️ Mommy & Me Tie Dye Workshop (Pinecrest Manor Community Center, Mount Kisco)
A sweet event taught by friend of The Plan Katie Sheehan of Hippie Feet Tie Dyes. Create matching t-shirts with you & your kiddo. $50/pair and all materials are included. $25 per add'l child. »
5:00 PM-10:00 PM — 🎡 New Canaan “May Fair” carnival: Friday Night Lights (St. Mark's Episcopal Church, New Canaan)
This is such a great carnival; I hope there’s good weather. There’s a shuttle service, and strawberry shortcake & ice cream starting at 5PM. The Friday night food court goes from 5-8PM, and there’s face-painting too. Check the site for ride pricing. »
🍿 Juliet & Romeo (PG-13) opening weekend
This one retells greatest love story of all time as an original pop musical. I'm hesitant as the Leonardo DiCaprio / Claire Danes version from 1996 is CINEMA PERFECTION, but I will give this one a whirl. Directed by Timothy Scott Bogart. Find a showing at your fave local theater this weekend. »
SATURDAY, MAY 10
National Clean Your Room Day »
8:00 AM-4:00 PM — 🐎 Spring Horse Show (Old Salem Farm, North Salem)
A gorgeous farm that will remind you how lucky you are to live here. Go and enjoy the competition, walk around the grounds, bring a blanket. Today they've got pony rides, face painting, SPCA Westchester dog adoptions, and a free ice cream party with Pegasus Therapeutic Riding. Free to park! »
8:30 AM-4:30 PM — 🌻 Gossett Brothers Nursery Fundraiser (Gossett Brothers Nursery)
Hosted by the Lewisboro Garden Club. Members will help you select plants for your garden and shop for delicious homemade baked goods; perfect for Mother’s Day. »
9:00 AM-6:00 PM — 🎡 New Canaan “May Fair” carnival (St. Mark's Episcopal Church, New Canaan)
This is such a great carnival. Today they've got New Canaan’s Town Band at 11:30AM, Pivot Ministries Choir at 12:30PM and the May Fair Dog Show at 1:30PM. Check the site for ride pricing. »
9:00 AM-1:00 PM — 🧺 North Salem Farmers Market (opening day!) (Back Street, Croton Falls)
Second Saturday of every month. Never been but looks very cute! Live music, great local goods, and a beautiful setting. Ends in Oct. »
10:00 AM-11:30 AM — 🌳 Trees and Their Frenemies (Weil Preserve, North Salem)
Arborist Taro Ietaka is great with kids. Join him for a guided walk to explore "how trees interact with insects, fungi, animals, and other trees in the ecosystem" and enjoy the natural beauty of this gorgeous preserve. Hosted by The North Salem Open Land Foundation (NSOLF). »
11:00 AM-12:00 PM — 📚 Book Buddies (Muscoot Farm, Katonah)
Sign up for a 30-min time slot for a storytime in an animal enclosure. Good for kids ages 7+. TIx $10. »
11:00 AM-12:30 PM — 🤖 Wall-E: Movie screening (Jacob Burns Film Center, Pleasantville)
Kid-friendly screenings take place every weekend. Tix $5/non-member adults, and just $5/kid now. »
11:00 AM-11:30 PM — 📚 Storytime with Mrs. Crummy (Rochambeau Farm, Mt Kisco)
Storytime at this beautiful farm. Bring the whole fam and enjoy the animals afterwards. Pizza available for purchase! Also held June 7. »
1:00 PM-2:30 PM — 🔥 Campfire: Spring Equinox (Earthplace, Westport)
Bring the family to roast marshmallows and make s'mores around a fire at this beautiful preserve. You'll also meet an animal ambassador and participate in a guided activity. $40 for non-member families. Also happening on June 14. »
1:00 PM-2:00 PM — 💕 Homemade Love for Mom (Lasdon Park, Katonah)
Bring your kids to make a homemade gift with you at this beautiful park. Great for ages 5 and up. Tix $10. »
1:00 PM-2:00 PM — 🌸 Wildflower Garden Tour (Trailside Nature Museum, Cross River)
Head over to Trailside Nature Museum in Ward Pound Ridge Reservation for a free nature program with the kiddos. The park entry fee is $5/car w/ Park Pass, $10/car without a Park Pass. »
2:00 PM-3:00 PM — ♥️ Mother’s Day Nature Walk (New Pond Farm Education Center, Redding)
Perfect for moms or grandmas who wish to spend some quality time with their kids while enjoying the beauty of nature. I've never been but I hear this farm is gorg. Tix $15 per non-member family and registration is required. »
3:30 PM-4:30 PM — 🥁 Reading and Rhythm with Orchestra Lumos and Music Together (New Canaan Library)
A collab between Orchestra Lumos and Music Together of Fairfield County. Great for infants, toddlers and preschool-age children and their families. This looks like a fun one! »
4:00 PM-7:00 PM — 🎉 Family Party (Westmoreland Sanctuary, Mt Kisco)
Food, drinks, crafts, games, animal programs, pond exploration, and more. This sanctuary has been on my bucket list forever; I hear it's beautiful. Tix for 1 adult & 1 kid $100, whole family $175. »
SUNDAY, MAY 11
Mother’s Day »
8:00 AM-4:00 PM — 🐎 Spring Horse Show (Old Salem Farm, North Salem)
Today they've got face painting, pony rides, a miniature horse meet and greet with Pegasus Therapeutic Riding and the $135,000 Old Salem Farm Grand Prix. Free to park. »
9:30 AM-2:30 PM — 🐑 First Farmer's Market + Sheep Shearing (Muscoot Farm, Katonah)
Because what else would you rather do on Mother's Day? This hands-on, educational event will teach you about the journey from fleece to fiber. No experience is necessary. Enjoy hayrides (tix required), live music, and wool crafts all afternoon. The sheep shearing event begins at 12PM. Plus, it’s opening day for their weekly Farmer’s Market. »
11:00 AM-12:30 PM — 🥾 Ladies Only Mother's Day Hike (Marian Yarrow Preserve, Katonah)
Ditch the fam and join some local women for a social hike at this gorgeous preserve. Hosted by the Lewisboro Land Trust (LLT). »
1:00 PM-3:00 PM — 🌊 Coastal Cleanup with SoundWaters - Volunteer opp (Cummings Park, Stamford)
This charity hosts seasonal clean-up days year-round, where they give you all the tools you need to walk the public shoreline and pick up debris. Great for friends and families with kids of all ages. Sign up on their website. »
2:00 PM & 7:00 PM — 💄 Mean Girls (Play Group Theatre, White Plains)
The Play Group Theatre (PGT) is great for kids. Take your Mean Girls fan to this one. It's fetch. Tix $22/adult, $18/kids U12. »
ONGOING EVENTS
APRIL 19-MAY 18 — 👸 Sleeping Beauty (Downtown Cabaret Theatre, Bridgeport)
Friend of The Plan Lauren Mika says the Downtown Cabaret Theatre in Bridgeport is a children’s theater that “brings such talent, joy and passion to each production.” She said it’s absolutely worth the drive. Tix $35-$41. Go see it! »
Every Friday & Saturday (5:00 PM-9:00 PM) — 🍻 Cider Nights 2025 (Hardscrabble Cider, North Salem)
Every Saturday (9:00 AM-2:00 PM) — 🫛 John Jay Homestead Farmers Market (Lot No. 2, Downtown Katonah)
Friends of John Jay Homestead in partnership with Katonah Chamber of Commerce, have relocated the Farm Market to Lot No. 2 in downtown Katonah for the 2025 season while John Jay Homestead State Historic Site is closed for major site improvements. Genius! Runs every Saturday from May 3-Oct 25. »
Every Saturday (9:00 AM-1:00 PM) — 👩🌾 Gossett Brothers Farmers Market (Gossett Brothers Nursery, South Salem)
Shop for some yummy local treats and produce in the warmth of their newly-renovated greenhouse. Great selection, every Saturday morning. »
Every Saturday (8:30 AM-1:00 PM) — 🥕 Pleasantville Farmers Market (10 Memorial Plaza, Pleasantville)
60+ vendors and held outdoors, year-round. Located just off Bedford Road, right in a historic walking village. Longer hours now in effect! »
Every Saturday (10:30 AM-2:30 PM) — 🎨 Open Arts Studio (Grace Farms, New Canaan)
Held every Saturday at this magical place. We've done everything from paper art to cookie decorating. Great way to spend an afternoon. Recommended ages 4-12 (w/ adult). Non-member $5, register online. »
Every Saturday (12:00 PM-1:00 PM) — 🌍 Saturdays at Earthplace (Earthplace, Westport)
Pay the admission price ($10/adult, $5/kid) and drop in for a nature-based activity with your kiddo every Saturday. Think: eco-art, science experiments, miniature pond exploration. »
Every Sunday (9:30 AM-2:30 PM) — 🍅 Farmers Market (Muscoot Farm, Katonah)
Browse the vendors, visit the animals, grab a snack at the concession stand. It's a great afternoon. Goes until Nov. 17. »
WHAT’S COMING UP
Here’s a handful of events coming up that you’ll want to plan for now. Upgrade for just $5/mo so you can view all the details & ticket/registration URLs in your own calendar.
May 13-18 – 🎢 St. Patrick’s Carnival (Bedford)
May 13 – 📚 Bedford Books story-time with Melissa Toole (Bedford) »
May 14-18 – 🎡 Somers Lions Club Carnival (Somers)
May 15 – 📝 Tricky Trivia Night (South Salem)
May 15 – 💃 Our Swap Shoppe event at Plank Ridgefield (my other side hustle) 😉
May 16 – 🍕 Food Truck Friday - first one! (Scott’s Corners, Pound Ridge)
May 17 – ⛲️ Sleepy Cat Farm: Garden Conservancy Open Days (Greenwich)
May 18 – 🏃🏻♀️ Muscoot Farm “Run The Farm” race (Katonah)
May 18 – 🌟 "RARE": A Fundraiser benefiting STAR (South Salem)
May 23 – 🍕 Food Truck Friday (Lewisboro Town Park)
May 26 – 🏃 South Salem Memorial Day Race (South Salem)
June 1 – 🎨 Pound Ridge Color Run (Pound Ridge)
June 4-7 – 🎢 Katonah Fire Department Carnival (Katonah)
June 8 – 🌸 Ridgefield Garden Tour (Ridgefield)
I can't wait to get back to the farmer's market at Muscoot!