Thoughts from the Chair of the Plymouth Planning Board
Steve Bolotin’s path to town leadership wasn’t a traditional one. After a successful career as an attorney—working in Washington D.C., London, and Boston—he and his wife sought a retreat from their demanding professional lives. They found that escape in The Pinehills.
But Steve didn’t just settle into Pinehills life—he saw an opportunity to give back. Drawing from decades of experience advising municipalities and businesses, he transitioned from full-time law practice to town government, and now applies his expertise as Chair of the Plymouth Planning Board helping to shape Plymouth’s future.
Steve is a thoughtful, strategic thinker committed to Plymouth's long-term development and community engagement. In this Q&A, he shares his journey, a vision for Plymouth and the Plymouth Master Plan, and why he believes that the best way to feel at home in a community is to jump in and help move it forward.
Q: Steve, tell us a bit about your background and how you ended up in The Pinehills.
A: By profession, I’m an attorney—I was admitted to the bar in 1989 and have worked in Washington, D.C., London, and Boston. My wife and I found ourselves constantly rescheduling vacations due to work demands, so we decided to find a place that felt like a retreat but was close to home and work. We discovered The Pinehills and bought our first home in 2005. By 2009, we loved it so much that we bought our forever home here.
Q: What inspired you to get involved in Plymouth’s town government and run for a seat on the Planning Board?
A: I wanted to give back to my community. Throughout my career, I represented municipalities, businesses, and individuals in governmental operations. I worked on everything from small renovations to nuclear power plants, across more than 40 municipalities in New England. That experience gave me a unique perspective on what works, what doesn’t, and how government decisions impact communities. When I stepped away from my law practice, I saw an opportunity to apply those insights to help Plymouth.
Q: What’s been the biggest challenge in working within town government?
A: Government operations are incredibly complex. Every decision has consequences—it's like a balloon: when you squeeze one side, something else shifts. People often don’t realize how long it takes to make changes, how much state regulations impact local decisions, or why certain things—like adding stop signs—aren’t as simple as they seem.
Q: You’ve been a key figure in Plymouth’s Master Plan update. What’s your approach?
A: The Master Plan is about ensuring Plymouth’s long-term sustainability—not just environmentally, but economically and culturally as well. One of my priorities has been making sure we get input from every village across Plymouth’s 134 square miles.
I insisted that we take meetings to different neighborhoods instead of just holding them at Town Hall. It’s critical that everyone has a voice in shaping Plymouth’s future. Too often, town planning gets dominated by downtown issues because that’s the most visible area, but we need to hear from everyone.
Q: One of your most innovative proposals has been the Land Bank. Can you explain it?
A: The Land Bank is a unique approach to addressing Plymouth’s challenges. Traditionally, land banks are either about preserving open space or creating affordable housing. Our approach balances both, along with securing land for future municipal needs like fire stations or schools.
It would be funded by real estate transfer fees—not through additional property taxes. It recently passed Town Meeting and is now awaiting approval at the state level.
Q: What are some of the biggest issues Plymouth is facing?
A: One of the biggest concerns is our aging population and its effect on housing. Right now, 45% of Plymouth residents are over 55, and that number is trending higher. Rising home prices are making it harder for young families to move in. If we don’t address these trends, we risk becoming a town where only retirees can afford to live—like what’s happened in many Cape Cod communities.
Q: If someone in The Pinehills wants to get involved in Plymouth town government, what advice would you give them?
A: Get involved. There’s a misconception that you have to be part of an “insider group” to participate, but that’s not true. Diverse perspectives are important. Whether you’re interested in conservation, economic development, or senior services, there’s a committee that needs your input.
Q: What do you hope your legacy will be in Plymouth?
A: I hope to help create a sustainable, well-balanced community—one that preserves its character while also ensuring it remains livable for people of all ages and incomes. The Land Bank, if approved, could be a generational game-changer.
Ready to get involved?
Steve Bolotin’s journey—from court rooms to Plymouth Town Hall—proves that the best way to feel at home in a community is to help shape its future. His transition from full-time attorney to Chair of the Plymouth Planning Board is a testament to one of the things that makes The Pinehills special—the wealth of residents with expertise, passion, and fresh perspectives to enrich Plymouth for everyone.
Now, it’s your turn.
- Take a deeper dive into some of the topics Steve talked to us about at Steve4Plymouth.com and learn more about Plymouth initiatives, upcoming events, and ways to connect.
- Explore Plymouth Town Government, join a local committee, or attend a community meeting. Your voice matters. Engage with your town and help shape its future!
The strength of Plymouth lies in its people—step out from Behind the Pines and be a part of something bigger.
