Essex is about to get a whole lot cozier thanks to lifelong resident and first-time business owner Amanda Henning. A 2008 graduate of Kenwood High School, Amanda is bringing her dream of a welcoming, community-centered café to life with The Comfy Cup, opening this fall at 25 Eastern Blvd., Suite 98B—right between Ramos Latin Restaurant and Essex Community Development Corporation.
The Comfy Cup is more than just a café. It’s a space created to bring people together over coffee, smoothies, snacks, and shared experiences. Whether you’re looking for a quiet place to read, an inspiring environment to work remotely, or a new go-to for date night or community events, Amanda is building a one-of-a-kind gathering place in the heart of Essex.
A Hometown Dream, Fueled by Community Support
Amanda’s journey to business ownership was made possible, in part, through Project Restore 2.0, a State of Maryland Department of Housing and Community Development initiative aimed at reactivating vacant properties and strengthening commercial corridors. Essex Community Development Corporation was awarded this grant to help revitalize Eastern Boulevard and support entrepreneurs like Amanda in launching new businesses that bring vitality, jobs, and opportunities to the community.
“Essex really needed a small, mom-and-pop coffee shop,” Amanda says. “We have chain options, but there wasn’t anything that felt local and personal. I saw the need and wanted to fill that gap.” The central location on Eastern Boulevard—convenient for residents, commuters, and even the boating community—was the perfect fit.
What to Expect at The Comfy Cup
The Comfy Cup will offer a wide range of beverages and bites, from locally sourced coffee and teas to healthy smoothies, acai bowls, and even kava—a natural, caffeine-free mood booster Amanda hopes will be a hit with customers looking for something new. Her goal? “To create a relaxing, inviting atmosphere that encourages connection—whether it’s a casual meet-up, a book club gathering, or a work-from-café day.”
Amanda is also planning to host engaging events like:
- Coffee flight tastings
- A community book club with a well-stocked library
- A walking club that meets at the café and explores nearby parks like Cox’s Point
- Seasonal workshops, such as a holiday ornament decorating class
- Sunday Fun Day events with live music
- “Meet and Taste” sessions featuring local coffee producers
Plus, Amanda is building partnerships with local schools like Kenwood High to offer internship opportunities to students interested in business and the food/beverage industry.
A Personal Touch
What sets The Comfy Cup apart is Amanda’s heartfelt vision. She wants every visitor to feel welcome and unrushed. “I’m focused on creating a more personalized experience than what you get at chains. I want it to be a place where people can connect and feel at home.”
Amanda’s inspiration for The Comfy Cup also comes from her love of exploring other coffee shops with her constant companion—Toby, her two-year-old dachshund. When she’s not working on the café, you might find her enjoying trivia nights, staying active, or traveling.
Her go-to drink right now? A brown sugar shaken espresso—but you can expect an exciting lineup of creative beverages on the menu, including:
- Campfire Cold Brew: Cold brew with chocolate sauce, marshmallow cold foam, and graham cracker bits
- Cereal Chiller: Cold brew topped with sweet cold foam, cinnamon, and Cinnamon Toast Crunch
- The Comfy Chata: Cold brew with horchata syrup, vanilla, sweet cold foam, and a sprinkle of cinnamon
The Journey So Far
Like many first-time business owners, Amanda has encountered her share of learning curves. From lease negotiations and business registration to understanding permits and loans, she’s gained valuable experience with each new step.
Her advice for fellow new entrepreneurs?
“Stay organized and make time management a priority. Don’t be afraid to reach out for help. People are often more willing to help than you think. The worst they can say is ‘no.’”
Coming Fall 2025
Amanda plans to open The Comfy Cup in fall 2025, with weekday hours from 6:30 AM to 3:30 PM, and weekend hours from 7:00 AM to 2:00 PM.
Want to stay in the loop?
👉 Sign up for updates: The Comfy Cup Newsletter
👉 Follow along on social:Facebook Instagram
Amanda is also eager to hear from the community! Have an idea for an event or menu item you’d love to see? Drop her a message on social media or stop by once the café opens.Let’s raise our (coffee) cups to Amanda and the exciting new addition coming soon to Essex’s Eastern Boulevard. Welcome to The Comfy Cup—where comfort, connection, and community meet. ☕💛
