by Massachusetts — What began as a simple attempt to escape the monotony of pandemic lockdowns has turned into a statewide journey of discovery, resilience, and connection for a Newton couple who have now visited all 351 cities and towns across Massachusetts.
Jenny McBride and Jo Gray officially completed their goal earlier this year, marking the end of a multi-year adventure that started during one of the most uncertain periods in their lives. Yet, even with the final town checked off the list, they say the experience still feels far from over.
“I don’t think we’re done,” McBride said, reflecting on the journey. “This doesn’t feel like an ending.”
A Pandemic Spark That Changed Everything
The idea took shape during the height of the COVID-19 lockdowns, when daily routines had become repetitive and isolating. Like many small business owners, McBride and Gray were dealing with personal and professional loss after their business closed permanently during the pandemic.
They found themselves walking the same neighborhood streets in Newton day after day, seeing the same faces from a distance, and feeling emotionally stuck.
“We were just getting grumpy,” the couple recalled. “Same walk, same people, not wanting to get close to anyone.”
One day, they made a simple decision: take a walk in a different town.
That small change quickly grew into something bigger.
Turning Limits Into Possibilities
As restrictions eased and travel became more feasible, the couple leaned into a new mindset. Instead of focusing on what they could not do, they chose to explore what was still possible.
“Instead of what we can’t do, let’s see what we can do,” Gray said.
That philosophy became the foundation for their mission: visit every city and town in Massachusetts, together, and fully experience each place.
It wasn’t about quick stops or checking boxes. The couple created clear rules for themselves. Every visit had to be intentional. They couldn’t just drive through. They had to walk, explore, talk to locals, and support small businesses along the way.
Supporting Local Communities Along the Way
A core part of their journey involved spending time — and money — in each community. Coffee shops, bakeries, restaurants, and local attractions became part of what they affectionately called their “town visit food.”
“Every time we came home, we were like, ‘We have town visit food,’” Gray said. “I got coffee from an independent roaster. I hadn’t bought coffee from a corporate place in so long.”
Those small purchases added meaning to every stop and allowed them to contribute directly to local economies, especially in lesser-known or overlooked towns.
From coastal communities to inland suburbs, historic mill towns to rural villages, each visit left a memory behind.
Discovering New Firsts Across the State
Even after decades of living in Massachusetts, the couple found themselves trying things they had never done before.
In Nantucket, they rode e-bikes for the first time. In Randolph, Gray rode a horse for the first time. Other towns offered quiet moments, scenic walks, or conversations with strangers who became part of the story.
Each town was marked on a map, not just as a location, but as a collection of experiences.
“We look at this and see memories,” Gray said. “Every place means something.”
Reaching the Finish Line — And Missing the Journey
By 2025, the couple realized they were nearing the end. The remaining list included Martha’s Vineyard, Nantucket, and several Berkshire towns. What once felt overwhelming now felt achievable.
“We knew we were in the homestretch,” Gray said. “We were like, ‘We’ve got this.’”
When they finally completed the last visit, the feeling was bittersweet.
“Honestly, we kind of miss it already,” she added.
What started as a coping mechanism had become a rhythm — a shared project that brought joy, healing, and purpose.
Finding Home All Over Again
Perhaps the most lasting impact of the journey wasn’t geographical, but emotional. Through their travels, McBride and Gray say they rediscovered a sense of belonging and optimism during a period that had once felt bleak.
“It’s taught us that we can find goodness,” McBride said. “We can find joyful moments everywhere.”
They also learned not to judge places based on reputation or assumptions.
“You just can’t prejudge a town until you go there, see it, talk to people, and understand what it has to offer,” she added.
Sharing the Story With Others
Throughout their travels, the couple often left behind friendly cards for locals, explaining their mission and inviting conversations. They also documented their journey online, sharing reflections and photos from each town.
Residents curious about whether their own town made an impression can find the couple’s detailed visits through their blog and social media presence under @Massachusetts351_jo_jenny.
Even though the official goal is complete, McBride and Gray say their curiosity isn’t.
Massachusetts may have 351 cities and towns — but for them, the journey proved that every place has a story worth stopping for.
What’s a Massachusetts town that surprised you the most? Share your thoughts and experiences in the comments.
