Amy Kirkcaldy, is the co-founder of South Shore Family Adventures, along with her brother Jim. She is a full-time college counselor at Milton Academy and the mother of extremely active nine-year-old twin boys.

Amy and Jim started South Shore Family Adventures in March 2021 as a way of sharing information about local hikes and adventures to help families get off their screens and out into nature.  In addition to hiking, she loves eating and cooking south shore bar pizza, drinking a hazy IPA, reading a good book, and entertaining friends and family in her backyard.

Amy graciously answered some questions for BFH about her work, her personal experiences with nature & the outdoors, and where we can expect to find South Shore Family Adventures next!

BFH: How important have nature and the outdoors been in your life?

Amy Kirkcaldy: Growing up, we actually didn’t intentionally spend a ton of time outdoors in nature, although we were always outside. My dad took us to Blue Hills regularly to hike up to the top. But that was really the extent of our outdoor/hiking experience. I was not a Girl Scout and my brother was not a Boy Scout. But I always played sports outdoors, and we lived in a neighborhood during the late 80s/90s where everyone played outside together all the time. We rode bikes, “ice skated” in our shoes on small ponds, explored the surrounding woods, and swam in each other’s pools.

It wasn’t really until I had kids of my own and summers off that I started to spend so much time hiking. My boys have tons and tons of energy–and so do I–and we needed free things to do to keep us busy. We also hit every playground we could find. Now that they are a bit too old to spend too much time at playgrounds, hiking is where it’s at. We try to get out at least once a weekend, and I get out with a friend every Saturday morning for an adult-only hike. These days, there is literally nothing I’d rather do than go for a hike. Even when I’m not hiking I’m thinking about it, planning my next trip, or sitting in my backyard being as close to nature as I can be while still at home! 😉

What’s your favorite place to get outdoors in the Berkshires or beyond? My personal favorite is Borderland State Park in Easton. I used to hate it there because it’s so crowded. But once you leave the main loop that 99% of visitors travel, it’s so beautiful and people are sparse. There is a great variety of scenery on the trails as well. Last fall, a friend and I hiked every trail in the park together–it felt like an accomplishment, and it got us quality socialization and some needed time away from our kids during COVID.

What’s your earliest memory in relation to the outdoors? The house I grew up in had a large woods in the front and back yard.  I could hike through the backwoods to a friend’s house.  In the front woods, my brother had his “afternoon chair” (a rock) and I had my friendship pine (a pine branch that my BFF and I stuck in the ground that I swear somehow rooted and became a tree). In the front woods, I used to make “mud pies” out of the clay/mud. 

Once, I was grounded and wasn’t supposed to be outside making mud pies. I snuck out anyway, and, while playing, I found a postcard in the woods. It turns out it was attached to a balloon that had been released from Stamford, CT by a girl my age.  Finding that postcard ended up being a rare “get out of jail free” card as my parents were so amazed by the find that they forgot to punish me for leaving the house!  I ended up being interviewed in the local paper for finding it, and the girl and I wrote to each other once or twice.   Having access to nature right outside my front and back door probably played a larger role in my current love of nature than any other experience.

How long have you been working in this industry? We started the blog in March 2021, so it’s only been a few months!  



How important do you think it is for children to get outdoors and why? I have very active boys–I often joke that I have to run them like puppies every single day. If they don’t get out and burn off that energy, we’re all a mess. So playgrounds, outdoor time, hikes, etc. are a necessity!

Also, now that they are almost 10 and coming off a year of being tethered to technology due to COVID, I feel like there’s been a seismic shift: if they are not outside and engaged, they will ALWAYS opt to be on technology. I have to set tough limits and follow through or they would do nothing else but watch YouTube and play video games. To be honest, it bothers me and makes me incredibly sad that if allowed, they would always choose technology over pretty much anything else. So I make sure, now more than ever, that we get outside as much as possible.

What are you curious about right now? Honestly, I’m curious about the long-term mental health effects of the pandemic and all this screen time.  We’ve all suffered through COVID, either directly and indirectly, and as an educator and mother, I’ve seen how it’s affected our children close up.  I’m curious how we help children heal as a country and society, and I think at least in part, nature is our answer.

What do you enjoy most about nature and the outdoors? I love being outside and hearing, smelling, seeing, and feeling nature.

What I’m most enjoying about it right now is the opportunity it provides for bonding. I’ve become closer to my boys and my family by taking walks with them and slowing down. We’ve had conversations about everything. With my hiking partner, being out in nature every single week and carving the time into our schedule has helped us become very close in a very short amount of time. Trust and connection build quickly in the solitude of nature. 

Also, I have a theory that hiking is like car rides: connection happens easier because you’re NOT actually making eye contact with the other person/people. While I fully believe in the importance of eye contact, I think when you are digging deep with people, it’s often easier to be vulnerable when you’re side by side or one behind the other, but not face-to-face. 

What’s the road ahead look like for you? I’m not sure…but I would like to grow the blog.  Ideally, it would be my full-time job! But I’d also like to explore some combination of education and nature, like working for The Trustees of Reservations or Mass Audubon or something.  I’m also toying with the idea of pursuing a master’s in social work.

If you had extra funds in your budget, how would you spend it and why? I would spend more money on eating out, reviewing restaurants, and helping the restaurant industry recover–I love to eat, but my kids are picky so it’s really not worth eating out with them unless it’s ice cream! 

What is your favorite word?

Mezzanine.  Who knows why–I just like the sound of it!

    What’s your favorite sound in nature? A babbling brook, heavy rain and/or thunder, and wind rustling through birch trees (yes, they have to be birch trees!)

    How do you continue to learn in order to stay on top of things within your role? Honestly, I hate social media. I’ve had to learn a lot about it in order to keep up with the blog. My brother is good at video editing and knows more about social media than I do. So I do the blog writing and the planning of our adventures. I have also been doing most of the community outreach and publicity. So we complement each other nicely with our areas of interest and skills. But I have attended a social media webinar and done some reading so I have a better idea of Instagram, Facebook, etc. Still, it feels ironic to me that I have to play the social media game to get followers for a blog that strives to get people OFF of their screens…such is life in 2021.

    What are some of the things you’re researching the most right now? I’m always trying to learn. Right now, I’m in the thick of it reading parenting books! I need all the help I can get!

    What do you think is the biggest obstacle preventing people from getting outdoors?

    Self-confidence.  People who don’t get outdoors much simply can’t imagine themselves hiking and camping and enjoying nature.  It’s foreign to them, so it’s easier to not go.  At SSFA, we try to take all the unknowns out of hiking and being outside with kids so that it won’t be as intimidating.  Our hope is that if people know what to expect and can prepare for it, they will have the confidence to try it.  And that confidence will hopefully build over time until they are experienced hikers and can’t imagine their lives without nature!

    If you could have a billboard with one message on it, what would it say?

    “Never Worry Twice!”  It’s not related to nature, but it’s a good way to remember not to be anxious.  Worry when you have to worry, but not until it’s absolutely necessary! 

    For more information about Amy’s work and South Shore Family Adventures, visit

    Follow along on IG @southshorefamilyadventures