Where Are They Now? Catching up with former HCT intern Kris Ramsay
A wonderful parade of talented and dedicated people have spent part of their careers on the Harwich Conservation Trust (HCT) team. Their efforts have helped HCT become a leader in creating public-private land conservation partnerships that help sustain Harwich as a livable, vibrant community for current and future generations.

Former Harwich Conservation Trust (HCT) intern Kris Ramsay is now the General Manager of Pretty Picky Properties in Brewster. Photo courtesy Kris Ramsay
We thought it would be fun to catch up with some of these HCT alums, reminisce about their experiences in Harwich and find out what they’re up to now.
Kris Ramsay was an HCT intern from 2008 to 2009 and later served as Executive Director of the Orleans Conservation Trust (OCT).
He is currently the General Manager of Pretty Picky Properties, a Brewster-based company that curates summer vacation rentals at more than 200 private homes from Sandwich to Wellfleet, and is renowned for its topline portfolio, professional management, and guest-centric service.
We reached out to Kris by email and he was kind enough to thoughtfully respond to questions about his career and his time with HCT:
When were you at HCT and what did you do?
While interning with the Harwich Conservation Trust between 2008 and 2009, I researched and wrote the first iteration of the Lee Baldwin Memorial Woodlands Management Plan. I also helped with trail maintenance, invasive species removal, and some property restoration projects.
What do you do now?
I am currently the General Manager of Pretty Picky Properties.
What did you learn from your HCT experience?
I learned a lot! More specifically, I learned how to develop management plans, draft grants, and identify native vs. invasive plant species. I also learned how non-profit boards operate, their funding sources, and how small organizations can make a big impact within a community.
How did your HCT experience help as you moved on with your career?

Kris Ramsay and his wife Anna Ramsay celebrate the holidays with their daughters Cora and Ruby. Photo courtesy Kris Ramsay
HCT was instrumental in the development of my career. While I was interning, HCT Executive Director Mike Lach and his team connected me with the Board Presidents of the Dennis Conservation Land Trust (DCLT) and the Orleans Conservation Trust (OCT). Shortly thereafter, DCT hired me as their Administrator and OCT as their Property Manager. The two part-time positions resulted in a full-time job between the two organizations, making it possible for me to live on Cape Cod.
After a few years OCT hired me as their full-time Administrator, and then as their first Executive Director. I served in that capacity for six years before moving on to my current employment with Pretty Picky Properties.
While no longer working in the non-profit field, I am in a unique position as I oversee the management of 250+ private homes across the Cape. On a daily basis, I find myself advising homeowners on how they can responsibly enjoy and care for their properties without impacting surrounding resources, waterbodies, and sensitive habitats.
Why is preserving nature important to you?
In my opinion, preserving nature is preserving a healthy quality of life for generations to come. We all live on this round sphere we call Earth, and if we want to enjoy all that it has to offer, we have to take care of it.
People love living on the Cape or visiting here because of how much land has been preserved — the beautiful trails, the hundreds of ponds, variety of ocean environments, abundant wildlife and an overall sense of peace, thanks to the efforts of Land Trusts.
In my own personal effort to stay involved in local conservation work I spent 9 years on the Friends of Pleasant Bay Board and am currently in my third term with the Association to Preserve Cape Cod (APCC). I would encourage everyone to join one local organization. These organizations will have a lasting impact on future generations — my kids, their kids, and beyond.
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—Your tax-deductible contributions help fulfill the mission of the Harwich Conservation Trust to preserve land that protects woods, water, wildlife and our shared quality of life. And your land-saving financial support helps us preserve beautiful properties that can become stellar trail destinations. Find out how to donate by clicking here.