Meet Kelly: Fitness Pro, Running Coach, and Barry's Favorite

This month we’re spotlighting a fitness leader who brings grit, heart, and curated coaching to every mile and every class: Kelly Whittaker-Cummings. As a longtime Barry’s Boston instructor and certified running coach, Kelly is known for her smart programming, welcoming energy, and unwavering dedication to helping others chase big goals.

We caught up with Kelly to talk about her fitness journey, what makes Boston’s running scene so special, and how to find joy in the process—whether you’re walking into your first Barry’s class or training for your next marathon. (BONUS keep reading for a JULY 2025 Barry's promo!)

Q&A with Kelly

How did you get started in fitness, and what drew you to the Red Room specifically?

I was an athlete in high school and started distance running in college, so was searching for something that combined fitness and community when I moved to Boston in 2012. Boutique fitness was still pretty new back then, so I started teaching spin classes at a local studio and was introduced to Barry's when it opened in Boston. I was hooked immediately. I left my corporate job in 2014 to help manage and coach at Barry's Boston, and I’ve never looked back!

How would you describe your classes in three words?

Challenging. Intentional. FUN.

Nothing makes me happier than seeing people working hard and having fun.

You’re also a certified running coach, what would you tell someone who’s new to it?

For beginners, I say: start small. Run five minutes straight or aim for one mile. Then build from there — maybe a 5K, maybe a marathon! Celebrate every bit of progress. I’ve been coaching runners for almost seven years now, and I learn from them just as much as they learn from me. It’s a collaboration.

What makes Boston’s fitness and running community so special?

Boston is a true running city. The sense of pride and support here is unreal. From organized run clubs to solo runners taking advantage of the first sunny spring day — the energy is infectious. And of course, there’s nothing like the vibe around Marathon Monday.

What’s one passion of yours outside of fitness?

I love spending time with my family — including my two golden retrievers who are basically oversized teddy bears. We love long walks and weekends at our beach house in Maine. I’m also a big reader (send recs!) and love trying new restaurants, cooking, and napping. Priorities!

How do you care for your mental health — especially when you give so much energy to others?

It’s taken me almost 39 years to really learn how to give that energy back to myself. Running is usually my moving meditation. I love getting lost in my thoughts or a good playlist on a long run. I also work with amazing therapists who’ve taught me how to set boundaries — like staying off Instagram and email in the evenings, scrolling less, and reading more to recharge.

What’s a long-term goal you’re working on?

This year I’ve pushed myself with both endurance and strength — I completed an ultra marathon in June and did my first powerlifting meet in May! Coming up: another marathon in Maine this fall and another lifting comp.

Long-term, I want to keep building my run coaching business, push my clients in the Red Room, explore partnerships and brand collaborations, and help more athletes chase their goals.

Anything else you’d like to share with the Fit Scene Boston community?

Boston is packed with talent — in every studio and on every street. I encourage you to step out of your comfort zone. Try a new instructor. Join a new run club. Take the big, scary leap you’ve been thinking about. I’ve been a part of this scene for 13 years, and watching it evolve has been incredible. I can’t wait to see where it goes next.

Ready to Train with Kelly?

Whether she’s leading a packed Red Room class or helping runners chase their next finish line, Kelly shows up with purpose, passion, and a whole lot of heart. Her approach to fitness is about more than just movement — it’s about building confidence, staying consistent, and finding joy in the process. Catch her on the mic at Barry’s Boston, or follow along on instagram as she supports runners and builds community one mile at a time.

If you’re new to the Red Room, now’s the perfect time to try it!

We’re teaming up with Barry’s to offer two free classes for new clients, July 14–27, 2025. Don’t miss your chance to experience the magic for yourself.

And keep an eye on @fitscenebos for future events, features, and ways to get moving with some of the best in the city.