Local StoriesMay 25, 2026

Hidden Gems: Meet Amanda Henning of The Comfy Cup

Local Stories

Today we’d like to introduce you to Amanda Henning.

Hi Amanda , we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
During COVID, like so many people, I began working remotely. At first it felt convenient — flexible hours, no commute — but over time something started to feel missing. My days began to blur together. Going to the gym in the mornings was often the only social interaction I had. I realized I wasn’t unmotivated — I was unfulfilled. I missed human connection, casual conversation, and having somewhere to go that felt alive.
At the same time, I was thinking about Essex, the place I call home. We didn’t have many spaces where people could work remotely, meet up, or simply exist together. I kept asking myself: why should connection only exist in big cities? Why can’t we create that right here in our own backyard?
So the idea of opening a coffee shop started brewing.
I began asking people in the community whether they would want a local coffee shop, and the response surprised me. Over and over I heard the same thing: we would love a place like that. Around that same time, an incredible grant opportunity through the Essex Community Development Corporation came to my attention. The process wasn’t easy. It required countless hours building a business plan, gathering financial data, networking, interviewing, and pushing myself far outside my comfort zone. There were moments I wanted to give up, but I kept reminding myself that if it were easy, everyone would do it.
When my business plan was finally selected, I had to decide whether I was ready to go all in on myself — and I chose to move forward.
I’ve been fortunate to travel around the world, and everywhere I went, coffee shops were more than places to grab a drink. They were community hubs — spaces where people worked, shared ideas, and felt like they belonged. I wanted to bring that feeling home. And in September of 2025, The Comfy Cup opened its doors.
But what I’ve learned is that this story isn’t just about me.
There are others in Essex doing the same thing in their own way. Nurse Chelsea is passionate about making wellness accessible and approachable for everyone. Tre’shawn, behind the barber chair, creates a space where his clients feel respected, secure, and confident when they walk out the door. Allison preserves creativity and craftsmanship through her fiber art in a world that often favors mass production. And Chrissy is helping lead the effort to revitalize Essex, reminding us that community development isn’t really about buildings — it’s about people.
What connects all of us is intention. We’re not just opening businesses. We’re creating spaces. We’re solving problems. And we’re choosing to invest in Essex with care.
The Comfy Cup is my piece of that story. It’s a place where neighbors run into each other, where students can study, where vendors can showcase their work, where we host adoption events, open mic nights, and community gatherings. It’s a space where people can work, dream, and connect over a cup of coffee.
But small businesses like this rely on something powerful: a community that chooses to show up. Every time someone chooses a local shop instead of a corporate chain, they’re doing more than buying coffee — they’re investing in the future of their town.
My hope is that The Comfy Cup becomes a place where Essex continues to gather, collaborate, and grow together.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Some challenges I’ve encountered include hiring and training staff, navigating the unpredictability of busy and slow days, and balancing a full-time job while running the coffee shop.

Alright, so let’s switch gears a bit and talk business. What should we know?
We are more than just a.place to buy coffee. Our emphasis is on community and connection and we hold space here for everyone. From open mic nights, to high school fundraisers, pet adoption events, book clubs, and game nights – there is literally something for everyone. That is in addition to our fully stocked bookshelf, with games and coloring books – we provide free of charge for our friends to use.
We also put a lot of thought into our signature drinks each season and offer hot and iced coffee flights, which allows someone to try different flavors in smaller sizes to determine which is their favorite!

Where we are in life is often partly because of others. Who/what else deserves credit for how your story turned out?
My mom, Betsey, helped me significantly prepare to open. We would spend 10-12 hour days at the shop cleaning, rearranging, decorating, stocking, etc.
My friend, Rob, owner of a local bar, spent a lot of time in the beginning stages walking me through the Health Department process. He also invited me to many networking events where I could begin to spread the word about the business while we prepared to open.
My friend, Bobby, also was a big cheerleader and also pushed me to network and start building a client base before opening.
The Essex CDC provided resources through the Project Restore 2.0 grant.

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