Meet Jessie Berkshires | Songwriter and Independent Artist

We had the good fortune of connecting with Jessie Berkshires and we’ve shared our conversation below.

Hi Jessie, where are your from? We’d love to hear about how your background has played a role in who you are today?
I’ve lived in Southeast Michigan for most of my life, although I was born on the East Coast and moved around the Midwest during my teenage years and for college. Despite the moving, I proudly identify as a Michigander.

Music has been a constant in my life from a very young age. I remember being fascinated by my grandmother’s old Yamaha keyboard, spending hours experimenting with it. My dad always encouraged my musical curiosity, regularly bringing home new instruments for me to try out. Once I was old enough to join the school music programs, my passion truly ignited. I played at every school talent show, was part of the band, and even pursued music education for several years in college. But midway through, I panicked about job prospects and shifted my focus to becoming a therapist, which I practiced professionally for 10 years.

After having my daughter, I felt the urge to pivot toward something more creative, which led me to study design at the University of Michigan. During this time, I also rekindled my love for music, taking lessons and joining a band as a keyboard player, gigging around Detroit. Eventually, I found myself working as a product designer for tech startups, but when COVID hit, I left my job to pursue personal and family goals. That’s when Moon Date was born—an exciting collaboration between friends, my husband, and myself, blending our diverse musical backgrounds to create something unique. At the same time, I began to focus on my solo work on the Jessie Berkshires project, where I can explore more vulnerable and artistic expressions.

My varied background has shaped who I am as an artist. My experience in design has given me a methodical and strategic approach to songwriting, band management, and music marketing. My work as a therapist has instilled a deep compassion for people and mental health, which often finds its way into my songwriting. And now, I’m reconnecting with my formal music training in a more personal, authentic way.

This journey has brought me to where I am today as an independent artist, and I’m excited to see where it takes me next.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
What sets me apart from many others is my deep love for the creative process itself. I don’t do this for fame or global recognition—I do it because it’s cathartic, and I genuinely love making things. Being an indie musician allows me to take a holistic approach to my craft, where I embrace wearing multiple hats and hustling to bring my ideas to life. It’s not easy—nothing truly meaningful ever is—but it’s incredibly fulfilling.

I’ve gotten to where I am today by following my natural instincts and passions. Ever since I was a kid, I’ve been drawn to songwriting and creating. Even though I’ve worked in a variety of fields over the years, music and art have always called me back. They’ve been my constant.

One of the most important lessons I’ve learned is to learn from real people, and to embrace every step of the creative process—because that’s the only way you’ll actually finish anything. For me, the best part of all this is the ability to create something that truly moves people. That’s what drives me, and it’s what keeps me going.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
If my best friend were visiting Metro Detroit for a week, I’d make sure they experienced the best this area has to offer, from Detroit’s vibrant energy to Ann Arbor’s artistic charm. Here’s the ultimate itinerary:

Day 1: Exploring Belle Isle and Downtown Detroit
Morning: We’d kick off the trip with a bike ride around Belle Isle, stopping at the Belle Isle Aquarium (America’s oldest!) and the Anna Scripps Whitcomb Conservatory for some nature and gorgeous plant life.
Afternoon: Head downtown to Campus Martius Park—a bustling area with plenty of shops and restaurants. If it’s winter, we could go ice skating; if it’s summer, we’d grab a bite and relax by the beach-themed seating area.
Evening: Catch dinner at one of Detroit’s famous spots like Selden Standard or Grey Ghost. Both offer a farm-to-table experience with creative dishes.
Day 2: Arts and Culture Day
Morning: We’d start with a visit to the Detroit Institute of Arts (DIA)—one of my absolute favorite places. We could spend hours wandering through the galleries, and if we’re lucky, catch one of their live music events.
Afternoon: After soaking in art, we’d grab lunch at Wright & Company for some upscale small plates, then head to Cranbrook Gardens and Science Center to enjoy beautiful architecture, gardens, and some hands-on learning.
Evening: For dinner, Detroit Foundation Hotel’s Apparatus Room is a must for a chic, urban dining experience.
Day 3: Ferndale Fun
Morning: Start the day with brunch at One-Eyed Betty’s in Downtown Ferndale, then spend time exploring all the unique local shops and boutiques.
Afternoon: Ferndale has a great vibe, so we’d stroll through, grab a coffee at The Red Hook, and maybe check out Detroit Fleat for an outdoor bar experience with a rotation of food trucks.
Evening: We’d hit up some of the bars like The Oakland (known for its craft cocktails) or Loving Touch if we’re in the mood for a dive bar feel with live music or pool tables.
Day 4: Ann Arbor Adventure
Morning: We’d head to Ann Arbor, starting with breakfast at Zingerman’s Deli, a local legend known for its incredible sandwiches.
Afternoon: Stroll around Main Street for shopping and people-watching. Then we’d visit The Ark, a renowned music venue, or catch some live jazz at the Blue LLama Jazz Club.
Evening: For dinner, Pacific Rim or Sava’s is always a great choice, offering a mix of modern cuisine in an eclectic atmosphere.
Day 5: Nature and Metropark Day
Morning: Start the day with some outdoor fun at Kensington Metropark. Whether it’s hiking, paddle boating, or just enjoying the scenery, it’s a peaceful break from the city’s hustle.
Afternoon: We’d pack a picnic or stop at a nearby diner before heading back to Detroit for some downtime.
Evening: Check out a show at one of my favorite venues—either the historic Fox Theatre, the intimate St. Andrew’s Hall, or the iconic Majestic Theatre.
Day 6: Music and Nightlife
Morning/Afternoon: Spend the morning relaxing or visiting some of Detroit’s cool neighborhoods like Eastern Market for street art and fresh produce.
Evening: After a laid-back day, we’d hit the town for live music. If we’re feeling edgy, Magic Stick or PJ’s Lager House would be perfect for catching an indie band or local artists.
Day 7: Relax and Reflect
Morning: A chill breakfast at Avalon Bakery in Midtown Detroit followed by a lazy stroll through The Dequindre Cut—a greenway that’s perfect for some peaceful urban exploration.
Afternoon: Maybe one last visit to a museum or some shopping, then finish off the trip with dinner at Lady of the House for a modern dining experience with a farm-to-table flair.
Evening: If we still have energy, one last stop at a cool local bar like The Sugar House for craft cocktails.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I’d like to dedicate my shoutout to my husband. Long before we became a couple, we shared a deep passion for music, especially electronic music, which was one of the things that brought us together. He’s always been passionate about music, experimenting with it over the years, but when we got together, his musical abilities truly took off.

Balancing his responsibilities as a business owner and raising a family took a lot of his time, but as life settled and we found more time together, it felt so natural to start writing music and creating a band. He’s an absolute wizard when it comes to computers and anything engineering-related, which means he can make almost any of my creative dreams come true with technology. His passion and talent are remarkable—he’s fearless about making mistakes and embraces the entire creative process.

Though there have been challenges and growing pains along the way, I’m so grateful to be working side by side with him on both of our music projects. Watching him grow as an artist and collaborating together has been one of the most rewarding parts of my journey.

Website: https://www.jessieberkshires.com

Instagram: https://www.instagram.com/jessieberkshiresmusic

Youtube: https://www.youtube.com/@jessieberkshiresmusic

Image Credits
Derek Cookson Photography