Hello Charm City Kids—Deep Dive
Trust Your Gut, Even When It Feels Scary
Last week I sat across from my friend Kayon at Artifact Coffee in Hampden, both of us with steaming lattes and that French toast bread pudding everyone raves about. Between bites, she said something I can't stop thinking about: "No school is perfect, but when pink flag after pink flag piles up, you're looking at a saturated red flag."
She'd just pulled her son out of a school at the last minute. Her gut told her it wasn't right for her kid, even though on paper it looked fine.
Here's what I want you to hear: No one knows your child better than you do. Not the school counselor, not your neighbor whose kid thrives there, not the rankings on GreatSchools. What's a pink flag for one family might be a complete non-issue for another.
Your job isn't to find the perfect school; it's to find the right fit for your family, right now, in this season.
Sometimes we overlook things because we're desperate for something to work. I've done it. And sometimes those gambles pay off. But when they don't? That's when trusting yourself matters most.
Important School Dates/Reminders
October 2 (Thursday): Wellness Day - Schools closed for both students and staff in observance of district wellness initiatives.
October 16 (Thursday): Early Release & Parent-Teacher Conferences - Early dismissal for students; parent-teacher conferences in the afternoon.
October 21 (Tuesday): Board of School Commissioners Public Meeting - Parents and community members invited to participate.
October 18 (Saturday): Staff Professional Development Day - Schools closed to students for a district-wide staff professional development day.
Progress Report Distribution - Progress reports typically released in early October per district calendar; confirm exact distribution window with your child’s school.
Parent Conference Window - SLP/parent conference window often begins in mid-October—schools may send details about meeting times.
Parent Spotlight: Meet Dr. Kayon DePina
Literacy interventionist. Children's book author. Mom on a mission.
Dr. Kayon DePina doesn't just teach kids to read—she helps families fall in love with learning together. As a K-2 literacy interventionist and founder of LearnLink Consulting, she's bridging the gap between school and home with a two-generational approach that empowers both kids and their caregivers.
Her Heart of a Scholar book series brings social-emotional learning into daily reading time with simple stories designed for those critical 15 minutes families spend together. But Kayon's most ambitious project yet? The Scholar Experience—a mobile classroom (yes, a converted school bus!) bringing learning directly into Baltimore neighborhoods this summer.
What stuck with me most from our conversation:
"I use the word Scholar very intentionally. It tells every child, from the moment they sit with me, that they are already a learner of value—not someday, but right now."
This is the kind of educator Baltimore needs more of. Someone who sees potential where others see deficits. Someone who brings resources to families instead of expecting families to navigate impossible systems alone.
Kayon's also refreshingly real about the challenges facing Black and brown students in Baltimore's school system—and she's doing something about it.
Want to support her work?
Check out her books and resources at LearnLink Consulting and follow along as The Scholar Experience takes shape this year.
Neighborhood Spotlight: Hampden-Woodberry
If you haven't made it to Hampden yet, October is your month. The weather's perfect, the Avenue is buzzing, and there's something about this neighborhood that just feels like Baltimore—quirky, creative, unpretentious, and a little weird in the best way.
What makes Hampden special:
Once a working-class mill town, Hampden-Woodberry has transformed into one of Baltimore's most distinctive neighborhoods while holding onto its industrial roots. Artifact Coffee sits in the historic Union Mill building on Union Avenue—a gorgeous nod to the area's past as a textile hub.
The neighborhood is walkable, eclectic, and proudly independent. You'll find vintage shops next to boutiques, dive bars next to upscale restaurants, all within a few blocks on "The Avenue" (36th Street). It's the kind of place where you can grab a $4 coffee or a $40 dinner and feel equally at home.
Close to everything you love:
10 minutes from downtown Baltimore
Walking distance to Druid Hill Park and Wyman Park
Quick access to I-83
Near Johns Hopkins, Maryland Institute College of Art, and Loyola
Why families are moving here:
Hampden has that neighborhood feel—people know each other, kids ride bikes on side streets, and there's always something happening. It's also more affordable than neighborhoods like Federal Hill while still offering walkability and charm.
October Family Events:
October in Baltimore is chef's kiss. The weather's perfect—not too hot, not too cold—and most importantly, the lanternflies are finally dying off. (If you know, you know.) This is the month to get outside with your family and soak up everything Baltimore has to offer.
Here's your list of what's happening this month:
Spooky Science at Maryland Science Center
Oct 11, 12–4 p.m.
Science-themed Halloween fun with monster engineering, bubbling chemical reactions, and glowing jack-o-lanterns.
Magical Moon Stroll at Waldorf School
Oct 11, 4–7 p.m.
An enchanted autumn walk for families—magical, cozy, and not too spooky.
Gabby’s Dollhouse Live at Lyric Baltimore
Oct 18, 1 p.m.
The hit kids’ show comes alive on stage! Advance tickets recommended.
Trunk or Treat at Maryland Zoo
Oct 24, 6–8 p.m.
Trick-or-treat stations, food trucks, and special animal appearances.
Great Baltimore Lantern Parade & Día de Los Muertos Festival (Patterson Park)
Oct 25, from 4 p.m.
Celebrate with lantern-making, costumes, performances, and a family-friendly parade.
Twilight Stroll: Spooky Edition at Maryland Zoo
Oct 25, 5:30–7:30 p.m.
Explore the zoo after dark in costume (optional) for a unique nighttime adventure.
Doors Open Baltimore
Oct 25, 10 a.m.–5 p.m.
Discover Baltimore’s architecture and hidden gems—free and open to all ages.
National Aquarium Read to Reef Book Club, Pratt Library (October 2025)
Free reading program for Baltimore City children (grades 5 and younger) with a Pratt Library card. Pick up a bookmark, read five aquatic-themed books, and earn up to four free tickets to the National Aquarium. Includes kickoff crafts and family activities at Pratt branches.
Resources & Tips: Parent-Teacher Conference Prep
Parent-teacher conferences are happening this month. Here's how to make the most of that 15-minute slot:
Questions that actually help:
"What does my child do well that I might not see at home?"
"Where is my child struggling, and what can I do to support them?"
"How does my child get along with other kids?"
"If my child is confused or struggling, do they ask for help or sit quietly?"
"What can we do at home to support what you're working on in the classroom?"
For Baltimore parents:
"If my child is GAL-identified, what differentiation actually happens in your classroom?"
"Does this school have summer programming? Can my child access Baltimore City's summer programs if we're at a charter?"
Before you go: Ask your child what they want you to know. Review recent work to spot patterns. Write down 2-3 specific questions.
After the conference: Share one positive thing the teacher said with your child, then create one actionable step based on what you learned.
Want the full conference survival guide? We've got a complete breakdown of what to ask, what to skip, and how to follow up. Read the full guide here →
Ask Me Anything
Q: We've been at the same school for three years but I'm not seeing the growth I want for my child. At what point do you make a change?
Trust your gut. If you've given a school 2-3 years and you're still not seeing the academic or social growth you want, it's time to explore options. I tell parents: your kid only gets one childhood. Don't waste years hoping things will magically improve. Look at the actual data: test scores, how engaged your child is, whether they're being challenged. Sometimes a fresh environment is exactly what a kid needs to thrive.
Now, I know leaving a school can kick you in the butt logistically. The new start time, the new schedule, figuring out a new travel route, and let's not even talk about managing multiple drop-offs if you've got more than one kid. Depending on your situation, changing schools can feel like it's turning your whole life upside down.
But here's the thing: if staying means your child continues struggling, you've got two real choices. You can switch schools and give them that fresh environment. Or you can stay put and continue to be proactive about finding activities and programs outside of school that challenge them academically and socially.
Either way, you're not just sitting there hoping things get better. You're doing something about it.
Let me know if you have specific areas where your child needs growth and I got you!
Q: "We're moving from the suburbs and I'm worried about my kids adjusting to city life. Any tips?"
Start with the positives they can see immediately—playgrounds within walking distance, the excitement of row houses, being able to bike to the library. Let them be part of exploring new neighborhoods and finding "their" spots.
Most kids adapt faster than parents. Give them time to find their rhythm, and don't project your suburban-to-city anxiety onto them.
Final Thoughts
October always makes me think about growth—how trees change, how kids learn new things, how we adapt to challenges we never saw coming. Baltimore isn't perfect, and neither is its school system. But there's something powerful about a city where parents like Kayon are turning buses into classrooms and neighborhoods are hosting lantern parades that bring 12,000 people together.
Trust yourself. Trust your kid. And when those pink flags start piling up? Trust that too.
Forward this to a parent who needs to hear they're doing great—even when it doesn't feel like it.