Sometimes, the most unexpected opportunities lead to life-changing endeavors. For the President of Bedford & New Canaan Magazine, stepping into this role was a serendipitous mix of timing, family collaboration, and a shared vision. What began as a dinner-table discussion during the height of the COVID-19 pandemic transformed into a creative venture that reimagined a beloved local publication. This week, we talk to Casey Kaplan about her journey to taking the helm of Bedford & New Canaan Magazine, working alongside her father, and how they’ve turned a small-town magazine into a sophisticated celebration of their community.
From its relaunch in September 2020, Bedford & New Canaan Magazine has grown into a vibrant platform that connects readers across its carefully chosen circulation area. With engaging stories, stunning photography, and a dedication to showcasing what makes their community special, the magazine has become a staple in the lives of its audience. This partnership, rooted in a shared passion for storytelling and community, demonstrates how a thoughtful approach to local media can create something truly extraordinary.
LEG: How and when did you first become involved with Bedford & New Canaan Magazine, and what inspired you to take on this role as President?
A little bit of luck and right place, right time... and some vision - from me, and from my Dad, who is my business partner. My Dad, Michael, had been writing for what was previously known as Bedford Magazine in his semi-retirement as a hobby, and had received a call only a few weeks into COVID asking if he'd be interested in buying the publication. We knew people were really reading the magazine because he’d regularly get approached around town - even by people he didn’t know - who would tell him how much they loved the feature articles he was writing. When he brought Bedford Magazine readers into Ralph Lauren’s private car museum in the 2017 Holiday Issue for a rare glimpse at the jaw-dropping collection and an interview with Ralph, it truly was all anybody in the area was talking about.
We were all busy doing COVID things like trying to procure toilet paper and sanitizing our groceries. I’d fled from my Manhattan apartment to my childhood home in Pound Ridge to hunker-down with my family, as so many of us did. I had a pretty high-powered job at the time leading international expansion at a research technology firm, but my exciting international travel schedule was on an indefinite halt, and I was working from home. When my Dad brought-up the call he’d had about Bedford Magazine at dinner that night, and asked if I would be interested in leaving my job to run a magazine, I responded by proclaiming that ‘Print Is Dead’ and ordering a fresh pack of N95s. But my Dad persisted - and the more I thought about it, the more I realized how much opportunity there was to make the local magazine in this particular area so much more; thicker, glossier, even more interesting articles, more elevated photography, a more sophisticated design aesthetic, a much larger and newly defined audience... my creative juices started flowing and I began to get excited by the prospect of diving deep into a community that I love, sharing interesting stories, and having this incredibly creative outlet. So we took a leap! I quit my job, and three months later we published our first issue in September of 2020 as Bedford & New Canaan Magazine.
Image courtesy of Bedford New Canaan Magazine
LEG: The Bedford & New Canaan Magazine is distributed in Darien, Ridgefield, New Canaan, Bedford, Katonah, Armonk, Pound Ridge, North & South Salem, Pleasantville, Mt Kisco, Bedford Hills, and Waccabuc. What aspects of the magazine do you think resonate most with your readers in these areas and keep them engaged issue after issue?
We decided to add New Canaan to the readership immediately when we expanded. Bedford Magazine had always gone to some iteration of the Westchester towns and we just bumped up that circulation... but as someone who's lived in Pound Ridge for 25+ years, I found it to be so silly that what's considered our 'community' stops right at the state line - when I'd spent so much of my time in Connecticut, and especially in New Canaan. We felt that the folks in Westchester had all already been familiar with Bedford Magazine and seemed to understand that it was 'theirs' even if their town's name wasn't mentioned on the cover, but we figured that going over the state line, New Canaan folks would need to know immediately that this was theirs too! ...the name quickly became synonymous with our brand, so we decided not to change it - but we've added Darien and Ridgefield in the last few years as well because of the incredibly warm reception in Connecticut -- and because people started to ask for it!!
We defined the circulation area in a really intentional way: communities that are unique - but connected and intertwined in a way where residents of any of the towns would be interested in what's going on in the other communities that we cover. If you live in Bedford, you're going into Mt Kisco for your seafood, to Ridgefield for dinner, into New Canaan to go shopping, into Pound Ridge for a hike.... our towns are all individually fantastic, but only great because of their proximity to each other!
We keep everyone engaged by producing that relevant and proximate content; but also because our content is simply just really good and robust. We're getting inside of homes that you've always wanted to see. We're accessing some of the most successful titans of industries, major celebrities, and really accomplished folks... and it's in a relaxed and casual setting, in their house! And beyond those interviews just being interesting - our readers are even extra curious, because these are their neighbors. We're constantly talking about what makes where you live so great - from some of the most incredible nonprofits to unparalleled cultural institutions. And then there's just fun stuff too -- where to shop and eat, vacations to whet your appetite for planning a trip, local car culture, the equestrian scene... and of course - OUT & ABOUT!
LEG: Each of your publications has its unique character. Can you walk us through the process of selecting stories and themes, and how you ensure they resonate with your audience?
The Litmus test my Dad and I use is: is this interesting to both of us? If it is, we usually pursue the story - whether it's something one of us has come up with that we then go and pursue, or whether it's something that's being pitched to us.
LEG: You recently hosted a successful event featuring a private screening of Wicked. Are there other upcoming initiatives or events in 2025 that you're especially excited to share with your readers and the community?
Whether it's escaping into the pages of Bedford & New Canaan Magazine, curled up on your sofa on a weekend, or out at a party... we like to create spaces for people to escape into the wonderful world of B&NC. A place that's always local, and always positive. Last year we had the idea to throw a party around the Barbie movie - and it was such a hit; I'd had multiple people ask when we were going to do something like it again, so when I saw Wicked was coming out, I thought it was the perfect fit to do something similar. Fun and whimsical and a cute excuse to go have a good time. We're so grateful to the Bedford Playhouse and our friends at oHHo for indulging our idea and helping to make it happen!
Most of what we do in the events space is in partnership with incredible community organizations; we really serve as a tool for amplification - both leading up to the event to help promote and sell tickets or garner turnout, and then after the event through our Out & About pages - giving anyone that missed out just the right dose of FOMO that they'll likely be sure to clear their schedule when the event rolls around next year. It's given us the opportunity to be part of fun happenings in each of the 13 towns that we serve, and to do the most good - as many of these events are, at the end of the day, are raising money for great causes.
LEG: If you had to sum up Bedford & New Canaan Magazine in a single sentence, what would that be, and why?
A beautiful representation of noteworthy things in an amazing place.
LEG: In your opinion, how has the magazine influenced perceptions of the Bedford and New Canaan areas? What do you personally cherish most about these communities?
We really came on the scene right when this area was having its renaissance; covid made people realize how special it is to be just an hour from Manhattan and to be in a completely peaceful place surrounded by abundant nature, with charming towns, interesting neighbors, great schools... what a beautiful place to live! And with the influx of creatives that came with the Brooklyn migration, the result has been this reimagined version of a great place. Keeping the historic character, the charm, and preserving the nature around us... while having a little bit more to do that's a little bit more elevated.
We've been lucky enough to be at the precipice of that - and really just highlighting and showcasing what this area is and has to offer. I think the hand that we've played in influencing perceptions has a lot to do with helping people to realize how robust our cultural scene really is when they get here, and helping locals to discover the gems around them.
LEG: You've featured notable personalities such as Martha Stewart and Chevy Chase on your covers. How do you choose your cover stars, and what have been some of your most memorable interviews or stories?
First of all... how amazing is it that all of these incredible people live right here in our community! That they too have chosen to make this great place home.
We feel very lucky and honored that so many notable locals have been generous enough to open up their homes to us and to share their time and energy with us - so that we can share their stories and love for their community with you. Part of that is each one seeing the good job that we've done on those before them. But the other part is that the celebrities that have participated want to be part of our community and feel like they're contributing -- because this is home for them too. It's such a nice thing. A big shout out to everyone that's been on our cover and in our book - for spending time with us, opening up your homes, and being so incredibly kind and generous. Getting to know each and every one of them has been the experience of a lifetime
Martha Stewart on the cover of B&NC
LEG: Working alongside your father as the Publisher must be a unique experience. Can you share how this dynamic shapes the magazine’s vision and direction?
That's for sure! How many people are lucky enough to get to say that they work with their Dad and best friend?! I guess lucky seems to be a theme here - I definitely feel very lucky for all of this; to live here, to have this opportunity, and to get to do it with my Dad. It's a lot of fun - and a lot of work. And nobody writes like Michael Kaplan. We've taught each other so much - he came to this with decades of experience as a 'deal junky', and with lots of success - and his lessons seem to always harken back to quality and integrity... the most important principles to have in business.
LEG: The publishing world is constantly evolving, especially with digital trends. How is Bedford & New Canaan Magazine adapting to these changes?
Though we've incorporated important digital elements, like the largest locally-focused Instagram in the region: @BedfordNewCanaanMag and a massive base of e-mail subscribers, as well as a significant online presence where the magazine is published in full - and where locals can access the largest amalgamated calendar of events in the area (which has proved to be incredibly valuable to so many)... it's really the print magazine that continues to be our gem.
The world has done so much "evolving" in the last few decades - that sometimes its nice to just slow down, to read something interesting and well written and to look at beautiful and maybe even aspirational photos -- where there's no bad news, no screen time, and where you get to feel good about the place that you've chosen to call home... and maybe even learn something! There's something special about that. An almost archival experience. We hear from people all the time that they wait eagerly for the arrival of the magazine in their mailbox - and even that there are lots of families in the area that fight over who gets to read it first when it comes.
LEG: What’s next for Bedford & New Canaan Magazine in 2025 and beyond? Are there any significant changes or expansions planned?
We plan to continue to work tirelessly to bring you more great stories and into the most interesting corners of our community. We have a few special series planned for this year that I think you'll really enjoy! And we will constantly be coming up with new ways to surprise and delight. If you are not already a reader and you're intrigued... go on our website to subscribe! And if you have an interesting idea for a story that we should cover... get in touch! info@BedfordNewCanaanMag.com