What's The Plan: MAY 30-JUNE 1
Merry Month of May in New Canaan, Fine Day Fair in South Salem, Mount Kisco's 150th, a Pound Ridge Color Run, Wilton & Ridgefield celebrate Pride, and more!
Welcome to the weekend roundup. It’s officially June on Sunday. Crazy, right? Just a few notes on the upcoming weekend and then we’ll get into it.
Some quick hits: Don’t plan on going to the Ridgefield Library on Saturday as they will be closed for their 11th Annual Great Expectations Gala. Honeybee Grove Flowers farmers market kicks off on Sunday and if their events are as dreamy as their Instagram videos, I think you’re all in for a big treat. Speaking of treats, I just read that every participant gets a free ice cream at the Pound Ridge Color Run on Sunday. Register by Friday so you don’t miss out.
May be worth the drive: We went to the Field + Supply’s Spring Market in Kingston years ago and I remember loving it. If your kid is a Laurie Berkner fan (sadly, we are past the “We Are the Dinosaurs” phase), she’s putting on a show at Paramount Hudson Valley Theater in Peekskill on Sunday. Kudos to her publicist for tying this show to National Dinosaur Day.
I can’t stop thinking about this beautiful essay about male friendships I read last weekend in NYT Magazine: “Where Have All My Deep Male Friendships Gone?” Read it and let’s discuss over on Notes.
Each week, I’ll pick an event that may not have a huge promotion budget but I think is worth highlighting. This week, the Plan of the Week goes to “Rock the Halls” at John Jay Middle School on Friday night.
My daughter and I went to the 2022 show and we couldn’t get over the level of talent these kids brought to the stage. My favorites that year: Asher Barnett singing We Are the Champions in his best Freddie Mercury impersonation, and Amanda Altholtz’s version of Valerie by Amy Winehouse. Tix $12 online, and cash only at the door. Go, but bring noise cancelling headphones just in case the music gets too loud for your little ones. »
Thanks to all the subscribers who signed up last week, including Mara G., Trish N., Barbara A., Chrissy L., Jennifer D., Jordan S., Nicole F., Erin F., Meredith B., Amanda C., Joan Y., Laurelle G., Amy F., Jackie G., Megan S., Kathryn L., Julia S., Cristina H., Dana M., Katherine R., Ana, Katy B., Kris M., Maria R., Alexandra H., Stefanie S., Jenn J., Caroline B., Nicole S., and Kim G. I really appreciate your support. 🫶
xo,
K
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PPS: Did you catch my post this week on 3 Local Things I’m Loving Right Now? Check it out if you haven’t already. There’s a code in there for 15% off a BIG summer wall calendar we’ve loved for years.
FRIDAY, MAY 30
International Hug Your Cat Day »
🍿 Karate Kid: Legends (PG-13) opening weekend »
1:00 PM-5:00 PM — 🫖 Afternoon Tea (Caramoor, Katonah)
Tea is served in the Music Room and includes a variety of tea sandwiches, scones with créme fraiche and preserves, desserts. Have some tea and then go on a self-guided tour of the Rosen House. $54/adults, $30/kids. »
4:00 PM-6:00 PM — 🖼️ Art in the Windows kickoff (New Canaan, CT)
There’s an art stroll tonight sponsored by the Carriage Barn and the New Canaan Chamber of Commerce. Lots of events and receptions in 70 downtown store and business windows. Strolling down Elm St is absolutely a great night out with the kids. »
5:00 PM-6:30 PM — 🧑🧑🧒🧒 Community Craft Nights with Rewilding School (Marsh Sanctuary, Mt Kisco)
The Rewilding School hosts free monthly Community Craft Nights on the last Friday of every month. Perfect for families. Free, but you must register online! They’re doing archery at this one, how cool. »
6:00 PM-11:00 PM — 🇬🇷 The Greek Fair & Carnival (1230 Newfield Ave, Stamford)
Rides, Greek food, and lots more. Running through Sunday night. If you go, read my carnival parenting strategy post; you'll thank me later. Opa! »
7:00 PM — 💃 Ridgefield High School Senior Prom (The Loading Dock, Stamford)
When I was a kid, my mom would take us to see all the dressed-up teenagers walk into their senior prom. I thought it was like what The Oscars would be like. May be a fun outing with littles! »
7:00 PM-9:00 PM — 🎤 The Wedding Singer: New Canaan High School Theatre (New Canaan High School)
If you loved the Adam Sandler / Drew Barrymore classic, then why not give this show a try? Recommended for ages 10+. Shows will be May 30 at 7PM and May 31 at 1PM and 6PM. »
6:30 PM-9:00 PM — 🎸 John Jay Middle School "Rock the Halls" Concert (John Jay Middle School)
My daughter and I LOVED this show. These kids brought the house down. Bring protective ear coverings for your kiddos as this show can get loud. Tix $12 and cash only at the door! »
7:00 PM-9:00 PM — 🇺🇸 Mount Kisco Memorial Day Parade and Ceremony (Mount Kisco Public Library)
A nice evening event for the family. The parade will line up at the Green Street firehouse at 6:30PM and will head down Main Street to the memorial in front of the library at 7:00PM. Refreshments will be served at the American Legion immediately following. »
7:30 PM-8:30 PM — 🎼 The Merry Month of May concert (First Presbyterian Church of New Canaan)
This one promises to be a "celebration of madrigals old & new." Bring the family to hear Renaissance songs and "jaunty new works" at this gorgeous church lawn. Tix $25 in advance ($30 at the door, children/students free) »
SATURDAY, MAY 31
National Smile Day »
8:00 AM-9:00 AM — 🐦⬛ Last Saturday on the Trail: Bird Walking Event (Bristow Park, New Canaan)
Meet at The Apple Cart in Mead Park for a guided bird walking event led by New Canaan Land Trust board member Newell Cotton. Stay after for a morning at the playground. We love this park. Bring binoculars! »
9:00 AM-4:00 PM — 🛍️ Fine Day Fair Home and Garden Show (Onatru Farm, South Salem)
GORGEOUS local artisan fair under a big tent in one of South Salem's most beautiful parks. This one is a bit elevated. Tethered balloon rides are sold out, but still worth a trip here. Tix $25-$40. »
9:00 AM-5:00 PM — 🛍️ Sidewalk Sale Days in the Village (Bedford, NY)
A great day to stroll around town if you've never been. Go to oHHo for a pizza lunch for the kids and don't forget to stop by Bedford Books. Expect live music, food, and drinks. Go! »
10:00 AM-6:00 PM — ☀️ Field + Supply | Spring MRKT 2025 (Hutton Brickyards, Kingston)
Love this market. Shop hundreds of vendors, and enjoy live music, local eats, and activities for the entire family. Worth the drive! »
10:00 AM-5:00 PM — 🎨 White Plains Outdoor Art Festival (Tibbits Park, White Plains)
Here’s another good one! »
12:00 PM-11:00 PM — 🇬🇷 The Greek Fair & Carnival (1230 Newfield Ave, Stamford)
Runs through Sunday! »
1:00 AM-12:00 PM — 🐢 Meet the Animals with the Stamford Museum & Nature Center (Bedford Farms)
An interactive experience perfect for all ages. Expect hands-on encounters with friendly reptiles, mammals, and insects, educational talks, and photo ops. Tix $25 for adult/child pair. »
11:00 AM-2:00 PM — 🌳 Celebrate Nature at Baxter Preserve (Baxter Preserve, North Salem)
Baxter is one of my favorite area preserves. We went here much more often over the pandemic and this is a good reminder to go there again. Today, they'll have a guided birding hike, a pond-side discovery walk, a live falcon program, and a nature craft table. Expect "tasty bites" & refreshments, too. Free. »
11:00 AM-8:00 PM — 🎉 Mount Kisco Sesquicentennial Community Day (Village Hall, Mount Kisco)
Celebrate 150 years of this lovely town. Opening ceremony starts at 11AM, and there will be historic trolley tours all day (currently sold out but call to get on a wait list!). Plus, a Food Truck Festival from 4PM-8PM. »
11:00 AM-12:30 PM — 🤖 Ron's Gone Wrong: Movie screening (Jacob Burns Film Center, Pleasantville)
Kid-friendly screenings take place every weekend! Tix $5/non-member adults, and just $5/kid now. »
12:00 PM-6:00 PM — 🌏 Asian-American Heritage Festival (Kensico Dam Plaza, Valhalla)
Part of Westchester County Parks' summer’s series of heritage festivals. Bring blankets or folding chairs for sitting on the lawn, but no coolers are allowed. Free. »
1:00 PM-2:00 PM — 🌻 Introduction to Wildflower Identification (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. »
5:30 PM-9:30 PM — 🧺 KVIS Community Picnic (Katonah Memorial Park)
Bring a blanket, lawn chair and of course a picnic to this night of "fun, music, and neighborly cheer." Bands, food trucks, games, and an outdoor movie. Looks so fun. Postponed to September 6 because of weather.
1:00PM & 6:00PM — 🎤 The Wedding Singer: New Canaan High School Theatre (New Canaan High School)
May not be suitable for super young kiddos, but maybe bring your older ones! »
SUNDAY, JUNE 1
National Dinosaur Day »
8:40 AM-12:00 PM — 🎨 Pound Ridge Color Run - register by May 30! (Pound Ridge Elementary School)
This one's hosted by the Pound Ridge Partnership in collaboration with the Human Rights Advisory Committee. Celebrate Pride Month with a splash of Holi-inspired color. Kids can do the Fun Run! Free ice cream for all participants Tix $28-$34. »
9:00 AM-2:00 PM — 🌼 Farmer's Market - opening day! (Honeybee Grove Flower Farm, Somers)
Held rain or shine on the grounds of this gorgeous flower farm, right in the center of town. Runs every Sunday 9AM-2PM. I’ll move this one to the Ongoing Events section. »
9:00 AM-4:00 PM — 🛍️ Fine Day Fair Home and Garden Show (Onatru Farm, South Salem)
Last day! »
9:00 AM-5:00 PM — 🛍️ Sidewalk Sale Days in the Village (Bedford, NY)
Last day! »
9:30 AM-11:30 AM — 🧑🏻💻 Children's Business Fair (Boys & Girls Club of Ridgefield)
Go see some innovative middle school entrepreneurs showcase their business and raise funds for a great cause. Bring cash! »
10:00 AM-1:00 PM — 🍓 Strawberry Picking Season opens - SOLD OUT (Harvest Moon Farm & Orchard, North Salem)
These tickets go like Beyonce tickets, so act fast. This one sold out, but add'l ticket dates will be opened on a rolling basis. Check in at front counter of the Farm Store. A good check-off-the-summer-bucket-list activity. Tix $17, which includes admission plus 1 quart. Kids 5U and under pick free. »
10:00 AM-11:30 AM — 🦕 Celebrate National Dinosaur Day (Lasdon Park, Katonah)
Bring the kiddos to make a "paleo-pouch" at the Lasdon Studio, then go on a guided tour of the Dinosaur Trail. They'll get up close with real dinosaur fossils, and dino poo. Good for ages 6+. Tix $10. Also at 1PM. Love this park. »
10:00 AM-4:00 PM — 🥤 Tarrytown Street Festival (Tarrytown, NY)
This one is organized by the Sleepy Hollow Tarrytown Chamber, and has 75+ arts & crafts vendors, food, music, and entertainment. Go if you love this sort of thing. Stay home if you hate crowds. »
10:00 AM-4:00 PM — ⛲️ Garden Conservancy Open Days for New Canaan, Fairfield, Westport & Weston (Fairfield and Westchester Counties)
Go see why Ridgefield mom of 2 Sarah Kaplan recommends an Open Days garden tour for a family outing. If you're a garden voyeur, this is the event for you. Tix $10/adults, kids are free »
10:00 AM-12:00 PM — 🐭 Sensory Friendly Screening: Lilo & Stitch (Prospector Theater, Ridgefield)
Head to The Prospector for a 10AM sensory-friendly screening of the new Lilo & Stitch. Tix $15/adult, $13 kids U11. »
10:00 AM-5:00 PM — 🎨 White Plains Outdoor Art Festival (Tibbits Park, White Plains)
Last day! »
10:00 AM-6:00 PM — ☀️ Field + Supply | Spring MRKT 2025 (Hutton Brickyards, Kingston)
Last day! »
11:00 AM-1:00 PM — ☀️ First Sundays (Keeler Tavern Museum, Ridgefield)
A free monthly program for families to explore this historic landmark. Head to the Garden House for a craft. Just drop in any time between 11AM-1PM. No advance registration necessary. »
11:00 AM-4:00 PM — 🍔 Wilton Historical Society Food Truck Festival 2025 (Schenck’s Island, Wilton)
This one looks different from the food truck fests I'm used to! You and the fam can explore "Wilton’s culinary and food-producing history, with re-enactments from colonial educators and fly-fishing demos on the Norwalk River." Live music, historically-inspired games, face painting, and more. All funds benefit the Wilton Historical Society. Tix $10/adult, $5/kid, $20 max per group of 4. Also available at the door. »
11:00 AM-4:00 PM — 🐶 New Canaan Dog Days 2025 (New Canaan Nature Center)
The dog puns in this event description is a work of art, honestly. Bring your pup to this free event at this gorgeous nature center and enjoy activities like an ice cream "pawlour," a "sniffari," and a "bone bar." They'll have food trucks and a splash park, too. Great annual fundraiser put on by Pet Pantry Warehouse benefitting the Nature Center and Adopt-a-Dog. »
11:00 AM-3:00 PM — 🏳️🌈 Wilton Pride’s "Be You" Festival (Town Green At Wilton Center)
Vendors, food, beverages and community! »
11:00 AM & 2:00 PM — 🕷️ Charlotte’s Web (Ridgefield Playhouse)
"After all, what's a life, anyway?" Love this book. This show is recommended for ages 4-10. Tix $15. »
11:00 AM & 3:00 PM — 🦕 Laurie Berkner LIVE (Paramount Hudson Valley Theater, Peekskill)
Go see why the NYT calls her “the Adele of the preschool crowd.” My kids have grown out of their Laurie phase, but if you’ve got a toddler, I’d go. Tix $35-$108. »
12:00 PM-8:00 PM — 🇬🇷 The Greek Fair & Carnival (1230 Newfield Ave, Stamford)
Last day! »
12:00 PM-3:00 PM — 🌈 Ridgefield Pride in the Park (Ballard Park, Ridgefield)
Expect live music, kids crafts & activities, and lots and lots of rainbows. Go out and support this awesome annual event. »
12:00 PM-4:00 PM — 🌳 Welcome Summer Open House! (Caramoor Center for Music and the Arts, Katonah)
Kick off Caramoor’s 80th Summer Season by stopping by to celebrate. You can enjoy the open grounds, stop by the Herb Society‘s annual plant sale, and step inside the Rosen House to sample a tour. Concessions available all afternoon. Love this place. Free! »
12:00 PM-2:00 PM — 🍦 Lewisboro New Neighbor Ice Cream Social – register by May 28! (Lewisboro Town Park)
Great opportunity for new families to get to know each other. Don't miss out if you're new to town. Free! »
12:00 PM-2:00 PM — 🫖 Spring Tea Party - sold out (Muscoot Farm, Katonah)
Put on your fanciest getup and head to the main house for "a delightful afternoon tea party." Tix $33/person. This one’s sold out, but I’ll let you know about the next one in my new “What’s Coming Up” emails every Friday. »
12:00 PM-6:00 PM — 🇦🇱 Albanian Heritage Festival (Kensico Dam Plaza, Valhalla)
Part of Westchester County Parks' summer’s series of heritage festivals. Bring blankets or folding chairs for sitting on the lawn, but no coolers are allowed. Free. »
12:00 PM-5:00 PM — 🌈 Westchester Pride (Downtown White Plains)
Expect a ton of performances, vendors and lots of family-friendly activities. »
12:00 PM-1:00 PM — 🖍️ Celebrate "The Day The Crayons Made Friends" book (Barnes & Noble, Mt Kisco)
My kids love this book. Head to B&N for a special visit with Blue Crayon. If you know the book, this is the one who is Duncan’s fave color, and as a result of overuse has been reduced to a mere stump. ("I need a BREAK!" he says. I hear you, Blue.) This store does SO many cute kids events. »
1:00 PM-1:30 PM — 🦅 Winged Wonders (Earthplace, Westport)
Every first Sunday, families will get to see a bird-on-glove demo. This place is magical. My kids love the natural playground. Admission is $10/adult, $5/kid. »
1:00 PM-4:00 PM — ☀️ First Sunday (Keeler Tavern Museum, Ridgefield)
A free monthly program for families to explore this historic landmark. Head to the Garden House for a craft and quality family time. Just drop in any time between 1PM-4PM. No advance registration necessary. »
1:00 PM-2:30 PM — 🦕 Celebrate National Dinosaur Day (Lasdon Park, Katonah)
Bring the kiddos to make a "paleo-pouch" at the Lasdon Studio, then go on a guided tour of the Dinosaur Trail. They'll get up close with real dinosaur fossils, and dino poo. Good for ages 6+. Tix $10. Also at 1PM. Love this park. »
2:00 PM-6:00 PM — 🎉 Mount Kisco Sesquicentennial Community Day 2 (Village Hall, Mount Kisco)
Today is the Celebration Grand Parade, where you'll see marching bands and other community organizations riding from East Main Street (at Moore Ave.) through the downtown and along South Moger Ave. Anniversary party kicks off at 3PM, with food, fun games and entertainment, and music by the Reservoir Road Band. Go! »
ONGOING EVENTS
Every Friday & Saturday (5:00 PM-9:00 PM) — 🍻 Cider Nights 2025 (Hardscrabble Cider, North Salem)
Read my review here. We love this place. »
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. »
Every Saturday (8:30 AM-1:30 PM) — 🍅 Tarrytown Sleepy Hollow Farmers Market: TaSH (Patriots Park, Tarrytown)
A bit of a drive, but worth it. Make a day of it! Outdoor market runs from May 24-Nov 22. »
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. 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 (10:00 AM-2:00 PM) — 🥕 New Canaan Farmers Market (244 Elm St, New Canaan)
Right behind the train station. So many great vendors! »
Every Saturday (10:00 AM-12:00 PM) — 🛍️ Take it or Leave it Shed (Bedford Hills Train Station)
You never know what you’ll find at the Take It Or Leave It Shed. Great community initiative to reduce waste and inspire sustainability. Open through Oct. »
Every Saturday (10:30 AM-2:30 PM) — 🎨 Open Arts Studio (Grace Farms, New Canaan)
Held every Saturday at this magical place. It’s a 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. Think: eco-art, science experiments, miniature pond exploration. »
Every Sunday (9:00 AM-2:00 PM) — 🌼 Farmer's Market (Honeybee Grove Flower Farm, Somers)
Held rain or shine on the grounds of this gorgeous flower farm, right in the center of town. Runs June 1–Oct 26. »
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. »
Every Sunday (11:00 AM-3:00 PM) — 🌽 Mt. Kisco Farmer’s Market (South Moger Ave, Mt. Kisco)
Live music and fresh produce, every Sunday. This is a good one. Ends Nov. 16. »
PS: If anyone wants to contribute to a "Summer Bucket List" I'm working on, submit your recs here. If your rec is chosen, you get a 3-mo Premium membership, so you're set for the whole summer. 😎 https://forms.gle/gukdn2scpFh3dQHc7