By 4Squares Residential Group with Judi 411
Medford has a way of drawing in people who don’t just move here—they dive in and make a difference. Anna Callahan is one of those individuals. A newer resident, Anna wasted no time getting involved in the community. She quickly immersed herself in local issues, connected with neighbors, and, before long, took on a leadership role as a City Councilor. Now, she’s helping to shape Medford’s future at a pivotal time—especially as the city undergoes its first major rezoning effort in nearly 40 years.
We spent time with Anna to learn more about her experience living in Medford, what attracted her to this community, and how she’s working to make it an even better place for residents—both longtime and new.
What roads brought you to Medford?
I’ve lived near Medford for a long time—I moved just about a quarter mile away back in 2003. I spent years in Somerville, always within about a half-mile of Medford. Then, in 2020—right in the middle of COVID—we finally made the move into Medford itself.
I’ve always loved having housemates. Even when we were married and had our kid, we always had people living with us. There’s just something great about waking up in the morning and having someone to share breakfast with. I’ve always found that really fun.
But during COVID, things changed. A lot of shared living situations fell apart. Our housemates—all connected to Harvard—moved out when Harvard decided not to reopen. They figured they could live somewhere a third of the price instead of sticking around here.
So we started looking around, which made sense since we already knew many people in Medford. We found a place—just a half-mile from where we were—but this time, actually in Medford. And that’s how we landed here in 2020!
What do you love about your Medford neighborhood?
There’s so much I love about our neighborhood in South Medford. First, we absolutely love Missituk Elementary School. My son goes there and is so happy—it’s been a great experience. Plus, we get to walk to school every day, which is something I really enjoy.
And then there’s Oasis Brazilian Barbeque—I love that place. They’ve got great food, and sometimes there’s live music, which makes it even better. Oh, and of course, Colette Bakery! We walk past it every morning on the way to school, and, well… let’s just say it’s hard to resist stopping in.
One of my favorite little spots, though, is this tiny strip of land across the street from the school. I call it a "pocket forest." This little green space is too hilly to develop, so it’s just… there. And I love it. In the summer, I’ll even go over and do a little cleanup—it’s like my own secret little nature retreat.
Beyond the places, though, the walkability makes this neighborhood special. Everything’s close, everything’s accessible, and great food spots surround us. And the neighbors? Amazing. Our next-door neighbors have a kid the same age as mine, and they just knock on each other’s doors and run around outside like kids should. It’s just a great place to live.
What inspired you to run for City Council?
For years, I’ve been helping people across the country run for City Council, encouraging them to step up and make a difference in their communities. Since 2016, I’ve been passionate about building leadership from the ground up—starting with local offices like the City Council and school boards, where elected officials can listen to and advocate for residents, not just big corporate interests.
In 2020, I ran for State Representative. I didn’t win, but the experience was incredible. The campaign brought together a fantastic group of people, and I loved every part of it. At the time, it made sense because I’ve been co-hosting a podcast on state politics for years—Incorruptible Mass—so my interest in state-level policy was already there. But after that experience, I started thinking… why am I encouraging people to run for local office when I could do it myself?
Living in Medford, I’ve had a front-row seat to how local government works, and I’ve also had the opportunity to talk to city councilors and mayors all over the country. That’s given me a unique perspective on what this role can be. Yes, it’s about policy—that’s the job—but for me, it’s really about connecting with people who don’t usually engage with City Council. I want to hear their ideas and help bring them to life, not by doing it for them but by connecting them with others who share their vision and can make things happen together.
I’ve spent most of my life diving into various volunteer projects—things that might seem crazy, but they bring people together. I’ve done 48-hour film challenges where you must write, cast, shoot, and score a film in just two days. I’ve built a cardboard canoe for the Medford race, spending weeks constructing something that we were sure would sink (but somehow didn’t!). I’ve been part of the Cambridge Family Opera, where 60 volunteers—kids and parents—come together to perform an entire opera. These experiences have shown me what people can accomplish when they care about something and work together.
That’s the energy I bring to the City Council. Volunteers meet with me regularly to review the council packet and discuss what matters to them. It’s not just about me listening—it’s about working through issues together and ensuring more voices are in the conversation. It’s a different kind of engagement, a different kind of democracy, and I love that.
Most importantly, I deeply respect people who disagree with me—even those who oppose me on many issues. Politics has become so divisive, but honest conversations and different perspectives make better decisions. At the end of the day, I ran for City Council because I believe in community-powered change, and I want to help bring people together to make Medford an even better place to live.
What’s a hidden gem you’d like to highlight for readers?
Medford has some incredible hidden gems, and one of the best—hands down—is the Medford Family Network. It’s one of those resources you don’t fully appreciate until you have a kid, and then suddenly, you realize just how amazing it is. Other communities don’t have anything quite like it, and we are so lucky to have such a strong, supportive network for families right here in Medford.
Another hidden gem I love is the walk along the river. When I’m in Medford Square, I start my walk near Shipyard Way, across from Colleen’s Ice Cream, then follow the path over the footbridge and continue along the river until I reach the community gardens. It’s such a peaceful, scenic stretch—especially by the Condon Shell. That little section of the walk is one of my absolute favorites. It’s the perfect spot to slow down, take in the beauty of Medford, and just enjoy the moment.
Photos, clockwise from top left: Callahan, with friends and neighbors in South Medford; Medford's historic footbridge over the Mystic; fun and games, local coffee, and local news at Colleen's; and the playground mural at the Missituk Elementary.
What are some City Council initiatives you’re excited about?
If my best friend were considering a move to Medford, I’d tell them it’s a city full of opportunity, engagement, and community. Right now, we’re in the midst of rezoning for the first time in nearly four decades, which is an exciting chance to shape Medford’s future. Some of it is just aligning zoning with what’s already here, but there’s also potential for more mixed-use development—like adding residential spaces above shops, especially along Mystic Avenue. I love that kind of city design and think it will add to Medford’s character. But the zoning initiative I’m most excited about is “community mixed-use” – the idea that within a half mile of every home in Medford is a corner where residents can find a cafe, a coworking/community space, a little family grocer, and maybe a spot for kids activities.
Building our community so everyone has a community space to walk to is very exciting to me.
Beyond that, Medford is in an interesting transition. Our older population is more significant than it has been in a long time. I’m committed to supporting aging residents who want to stay in their homes, whether through volunteer efforts or city initiatives. At the same time, more families with young kids are moving in, bringing fresh energy and ideas. Cities evolve, and right now, Medford is in one of those moments of change—balancing the needs of longtime residents while welcoming new ones.
I love where I live, but you’ll find a strong sense of community no matter where you settle in Medford. If you’re looking for a place where people care about shaping their city’s future—and where you’ll be welcomed—I’d say, come join us!
Want to learn more about Medford’s rezoning efforts and how you can have a voice in shaping our community’s future? Anna Callahan is always eager to connect with residents who care about making a difference. Whether you're curious about zoning changes, looking for ways to get involved, or just want to chat about the best ways to serve Medford, Anna is ready to hear from you. Contact her directly at acallahan@medford-ma.gov to join the conversation and explore volunteer opportunities that align with her hands-on, community-driven approach to service.
For all our Medford City Council profiles, click here.
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