Meet the Staff: Caitlin Ward

Almost every special event you’ve ever attended on campus has a conductor behind the scenes—a hidden hand guiding each moment. From Reunion to Commencement, Fall Family Weekend to the Bobcat Open, Special Events & Program Manager Caitlin Ward has been that conductor since joining Brewster in 2022. We caught her between events (the Board of Trustees Meeting/Dinner, an Admissions Open House, an alumni gathering at Maine Beer company in Freeport, and the upcoming Winni Classic) to get to know this Methuen, Massachusetts native who loves cats, travel, and a good rom-com.

Q. What first drew you into event planning as a career, and how did that path eventually lead you to Brewster?

A. I didn't actually plan to have a career as an event planner—I have a degree in psychology and worked in human services for a while after college, but I also always had a second job as a catering waitress for events. I really enjoyed watching all of the behind-the-scenes details come together at weddings. I was lucky enough to have a great boss at one of the hotels I worked for who saw how much I loved it and gave me a chance to try it out. When COVID-19 shut down events for a while, my husband and I relocated to Alton. That’s when I learned about Brewster from our neighbor, Kristy Kerin. A while later, I saw they were hiring an events manager, so I had to apply! I had never worked for an independent school before but it has been a great experience and a lot of fun.

Q. When you think “quintessential Brewster event,” what’s the first one that comes to mind—and why?

A. That would be Grandparents and Special Family Members Day. The first thing I always think about when planning an event is the “why.” What is the purpose of this event? Are we trying to teach a new group of people about Brewster? Are we trying to engage specific members of our community? Or is it about the experience and spending time together? To me, the most quintessential Brewster events are about members of our community and bringing them together. Our families love to be on campus and see what their students do every day—from joining in on classes to having lunch in the Estabrook, it brings them a lot of joy.

Q. What’s a behind-the-scenes detail about events that most people would be surprised to learn or never notice, but you obsess over?

A. There are so many behind-the-scenes details that most people don't notice but the one I spend the most time obsessing over is the weather! Some of our largest events of the year take place outside, so always having a backup plan and being able to pivot when the weather doesn't cooperate is super important.

Q. Can you share a favorite “wow” moment from an event—one of those times when you looked around and thought, “This is why I love my job”?

A. The first one that comes to mind is Commencement in 2022. It was my first year at Brewster and definitely the largest event I had planned. It was amazing to see it all come together and watch our students and families celebrate out on Brown Field.

Q. Events rarely go 100% according to plan. Without naming names, what’s a funny or memorable hiccup you’ve had to troubleshoot on the fly? 

A. This happened a while ago at one of the first weddings I had planned for a close friend. The ceremony and first half of the reception had gone off without a hitch, and it was almost time for the bride to change into her second dress. I went to the dressing room to get everything ready for her to change, but I realized her mom had packed an empty garment bag instead of the one with the dress. Thankfully, this was a local wedding, so we were able to quickly drive to her apartment and grab the dress before she even noticed it was missing! It was very stressful in the moment, but one of the great things about event planning is that even when things go wrong, you usually have the opportunity to fix them behind the scenes before anyone else notices.

Q. What’s your favorite Brewster tradition to help plan or support?

A. My favorite Brewster tradition to help plan is the Lifer Dinner. For most of the events I don't get a lot of input from our students, but for the Lifer Dinner, they get to pick the menu and some of the other details—it feels more special when they get to be involved!

Q. If you had an unlimited budget and no logistical constraints, what kind of “once-in-a-lifetime” event would you design for the Brewster community?

A. Oh this is a fun question! I think it would have to be some sort of “destination” Reunion Weekend. Our campus is beautiful and I love having alumni back for the weekend, but it would be a lot of fun to plan a huge trip at a fancy resort with all of our alumni and faculty.

Q. What tools, tricks, or rituals keep you organized when you’re juggling multiple events at different stages of planning?

A. The biggest hack or “trick” for event planning is that as soon as an event ends, I need to start planning for the next year. The first thing I do after every event is hold a debrief meeting to review what went well and identify any changes we want to make for next time. Even when we have multiple events in one week, it's important to get feedback and start planning early; otherwise, it’s easy to fall behind.

Q. When you’re not working, how do you like to spend your time?

A. When I’m not working, I spend a lot of time with my family in Maine and Massachusetts. I also love to bake and spend a lot of my weekends trying out new recipes. My niece Evelynn, who is 5, is also starting to get into baking, and it’s such a fun activity to do with her! Although I’m pretty sure she’s only interested because she knows I'll let her eat all the chocolate chips she wants.

Q. Ha! That is definitely an aunt’s prerogative! What’s something students or colleagues might be surprised to learn about you—an unexpected hobby, hidden talent, or past job?

A. I don't know if this qualifies as a hidden talent, but something most people may not know about me is that I did tap, ballet, and jazz dancing for about 15 years. It was something I really enjoyed when I was younger and I even won a few national competitions!

Q. Your much-loved cats sometimes make appearances in team Zoom calls. Can you tell us about your newest furry friend?

A. Milo! He joined our family in August and he is almost 3 years old. Milo is a sweet little guy who loves to cuddle but also enjoys a healthy dose of chaos. His favorite hobbies include watching squirrels from our living room window and chasing our other cat, Taz, around the house, trying to get him to play.

Q. You've had some terrific travel experiences…is there someplace you dream of going, or a place you'd love to return to for an even longer visit?

A. My husband and I have been lucky enough to travel to some amazing places together (Norway, Ireland, Scotland, and Lapland, to name a few) but the place I’d most like to go back to is Iceland! We went for a week a few years ago, but I'd love to go back for a longer trip one day. It is such a beautiful country, and nothing compares to the scenery.

Q. What's your go-to pump-up song before a big event?

A. It changes a lot, but right now it would have to be “Opalite” by Taylor Swift. You can’t listen to that song and not get hyped up!

Q. You have a lot of wedding planning experience. How many times have you seen the Jennifer Lopez movie, “The Wedding Planner”?

A. At least a dozen times. I love a good rom-com!

Feature Image: Caitlin Ward and her husband, Lucas, visiting Copenhagen in 2024.