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Meet the Newton couple who visited every town in Massachusetts
Jenny McBride and Jo Gray visited all 351 towns and cities in Massachusetts. Here’s what they learned along the way.
In the winter of 2021, as the pandemic pressed life inward, Jenny McBride and Jo Gray began doing what so many did to stay sane: they went for walks.
Each day, the couple looped through their Newton neighborhood, circling the same streets, passing the same houses, nodding at the same passersby. At first, the walks felt like freedom, a way to stretch their legs and explore beyond the walls of their duplex. But before long, the routine began to close in on itself.
“We weren’t finding any joy in that,” McBride recounted. So, they decided to try something different.
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One day, they drove a few miles west to Natick. It wasn’t far — just a stone’s throw on the map — but it felt transformative. The change in scenery, the unfamiliar streets, the simple act of being somewhere new sparked something in them.
“Our eyes were open,” McBride said. “We were uplifted.”
That small thrill led to a much bigger idea. On January 2, 2021, McBride and Gray set out on an open-ended mission: to visit all 351 cities and towns in Massachusetts.
“Who knows how long it’ll take, and who knows if we’ll even finish,” McBride remembered thinking at the time. “But let’s start.”
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Flash forward five years to December 2025, when they finally crossed the finish line in Boston, having traversed the entire Commonwealth — from dense city blocks to rural back roads, from coastal harbors to mountain trails.
Along the way, they uncovered not just postcard landmarks, but the quieter stories that often go unnoticed: the people, businesses, and small surprises that give each town its character. And, like any hero’s quest, they learned a bit about themselves, too.
‘The Cookie Lady’ of Washington
One of the places that lingers most vividly in Gray’s memory is Washington, a rural town tucked into Berkshire County with just 494 residents spread across 38 square miles, according to the U.S. Census Bureau.
“This particular town literally has no commerce at all,” Gray said.
To an untrained eye, Washington might look like little more than a pass-through town: Route 8 slices through its eastern side, Washington Mountain rises in the west, and the Appalachian Trail threads quietly along the mountain’s edge.
But for McBride and Gray, it felt like stepping into a storybook.
They had heard whispers of a local legend known among Appalachian Trail hikers as the “Cookie Lady,” a woman who welcomed weary travelers with homemade treats from her porch. On a late-summer visit in August, they happened to spot a hand-drawn sign near the trailhead — an arrow pointing down the road, decorated with a cartoon cookie and a woman.
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They followed it.
What they found was a modest home with a blueberry patch and a tiny shop stocked with locally made goods, a picnic table, a portable toilet for hikers, and a wooden box on the porch that read: “Homemade cookies. Take one. Take three.”
They lingered there, eating lunch from their cooler, shopping for small handmade items, and talking with the woman who carried on the tradition — now its second generation owner. She told them about the thru-hikers who would visit, some of whom she even let sleep in her yard, and showed them a tally she kept of all who had come before.
“That moment was so special for me,” Gray said. “It’s just this whole little subculture that no one really thinks about, but if you ask somebody who’s an Appalachian Trail hiker, I’m sure they would know tales of the Cookie Lady in Massachusetts.”
Snowshoeing and samosas in Windsor
In Windsor, another small Berkshire County town, McBride and Gray visited Notchview, a Nordic skiing and snowshoeing property owned and managed by the Trustees of Reservations. While snowshoeing through the woods, McBride noticed a sign pointing toward the “Magic Woods.”
Intrigued, she followed it. What they found was a trail dotted with tiny handmade fairy houses, showing a barn dance frozen in time and gnomes gathered around tables.
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“It was just so magical,” McBride said.
Cold and hungry afterward, they drove down the road and spotted a convenience store advertising samosas.
“We’re in the middle of nowhere. What do you mean samosas?” McBride recalled thinking with disbelief.
Inside, they found a woman who was making them fresh, along with daal. They ate, warmed up, and took extra home.
“A day like that is an example of the unexpected delights of these little towns,” McBride said. “We have so many of those stories.”
‘Some people think there’s nothing in their town, but there is‘
McBride and Gray documented their journey through a blog and on Instagram — not for attention, but as a personal record. “Jo’s mom reads it,” McBride joked. “Our brother-in-law reads it.” Someday, they hope to turn it into a “really awesome” coffee table book.
The project reshaped their relationship, too. They approached each town differently, noticing different details, prompting conversations they might not have had otherwise.
“It made us talk to each other more, learn about each other more,” Gray said. “Interpersonally, we had a lot of growth as well.”
Now that the journey is complete, the feeling is complicated, they said.
“Relief and missing it,” McBride said. “All at the same time.”
They’re quick to say they aren’t done with Massachusetts. There are festivals to attend, towns to revisit in different seasons, favorite spots to return to. They’ve even coined a phrase for the edible souvenirs they brought home along the way: “town visit food” — anything from roadside eggs to North End pasta sauce to homemade chicken pot pie.
While it’s hard to pinpoint specific lessons they learned, they said the most encompassing one is perspective.
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“Changing your perspective a little bit to see what is in a town rather than what isn’t in town is the difference between having a joyful experience and not,” Gray said. “Some people think there’s nothing in their town, but there is.”
Five years and 351 towns later, McBride and Gray don’t claim to have captured Massachusetts in full. But they’ve learned this much: “You can’t really pigeonhole one thing about Massachusetts. It’s a lot of things,” Gray said.
From the Berkshires to the coast, from city skylines to country backroads, the state is made up of countless small worlds — each waiting, if you’re willing to wander.
“We’re state townies now,” Gray said with a laugh.
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