From Mayflower Princess to Miss Southeastern Massachusetts: Meet Lily Jeswald
- Kelsey Garcia Witzgall
- Jun 16
- 2 min read
This weekend, Miss Southeastern Massachusetts, Lily Jeswald, takes the Miss Massachusetts stage with a story full of purpose, perseverance, and heart. Her journey began as a child in the Miss Massachusetts Mayflower Princess Program, where she was first inspired by a titleholder who came to visit her school. That early spark ignited a passion that has carried her all the way to the state competition.
Lily, a licensed educator and trained singer, has always been drawn to the professional development and scholarship opportunities that the Miss America Organization provides. “As an educator, it’s important to me that pageants focus on bettering young women in how they present themselves and how they speak to others,” she says. “I’ve been able to use the scholarship money I’ve earned to help pay back my student loans, and I encourage my students to explore this program.”
The Power of Interview and a Love for Talent
Lily's favorite area of competition is the interview. “A woman who can speak is a woman who can lead,” she explains. “It’s a chance to share who I am and why I’m here.” Talent is a close second for Lily, who has a background in musical theater and has performed across New England, including as a representative for the Kennedy Center American College Theater Festival. As a vocalist, she’s used her gift to bring joy to nursing homes, classrooms, and community events alike.
Living with Purpose: Type 1 Diabetes and Me
Lily’s Community Service Initiative focuses on raising awareness and support for those living with type 1 diabetes, something she knows firsthand. Diagnosed at just four years old, Lily grew up learning how to manage her health while also navigating a world that didn’t always understand her condition. Today, she proudly wears her insulin pump and CGM and is using her voice to educate others and break down stigma.
She has taken her initiative to the next level by:
Writing and illustrating her own children’s book, You Can’t Catch It! which helps kids understand type 1 diabetes
Creating a journal for newly diagnosed diabetics, Type 1 Diabetes and Me
Partnering with Breakthrough T1D to spread awareness on social media
Launching her own diabetic fashion line
Designing a purse collection inspired by her younger self, a little girl who carried her medical supplies in stylish bags to feel confident and prepared
Explore Lily’s work here:
📘 You Can’t Catch It!: Buy on Amazon
📓 Type 1 Diabetes and Me Journal: Buy on Amazon
A True Role Model
As Miss Southeastern Massachusetts, Lily has spoken to thousands of people across the state, hosted storytimes in libraries, and advocated for those with chronic illness. Her message is one of strength, education, and empowerment. “We can all relate to becoming our own advocate,” she says. “That’s what makes this work meaningful.”
Cheer Lily on at Miss Massachusetts
Lily will compete for the title of Miss Massachusetts this weekend at the Hanover Theatre in Worcester.
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