“We always pretended to feud a little bit about whether the North or South Shore had more to do, and that sparked up a conversation wondering what else was out there in Massachusetts that we haven’t seen yet.”

For Ross Bergen, a North Shore native, and his girlfriend, Lila Gardner, a South Shore diehard, the friendly sparring spawned an adventure: a whirlwind plan to visit all 351 cities and towns in Massachusetts in two weeks.

It all began with a debate over whose home turf was superior.

Bergen, 25, and Gardner, 24, both of Woburn, started to plot their route. And they decided to document the trip, writing a blog and posting photos along the way.


“It would be the ultimate quest,” Bergen said.

On Sept. 6, the couple hit the road for Williamstown, a college town in the northwestern corner of the Commonwealth. They dashed through 19 other communities that day, crossing much of Berkshire County off of their list. In each town, they took a photo of themselves in front of a municipal building — proof of their conquests.

At first, they were moving fast, barely taking in one town before rolling into another.

“If we stopped at every country store, corn maze, antique shop, and cute restaurant that we saw out here today, we probably would have only made it through a few towns!” Bergen and Gardner wrote on their blog.

But the pair said they eventually wanted the journey to focus on the excitement of discovering “hidden treasures,” more than completing the quest by their original deadline of two weeks.

“We took our time and did things we wanted to do,” Bergen said. We stopped at antique stores and rivers that run along the road.”

They were rewarded with many memorable moments, they both said. On the second day of their quest, they came across what they called “one of the most interesting things we have seen on this journey so far” in the Berkshire County town of Tyringham.


“We were heading down a long wooded side road, and out of nowhere is a house that looks like it’s made out of a giant tree, or mushroom,” they wrote on their blog. “It’s called Tyringham’s Gingerbread House, and it was originally a house designed in the 1920s by Sir Henry Hudson Kitson.

One town put out the welcome mat for them.

Lila Gardner (left) and Ross Bergen traced their drive through 351 towns and cities in the Commonwealth. Wendy Maeda/Globe Staff

“When we stopped in Greenfield, the president of the Chamber of Commerce welcomed us and about 30 people from the town came to meet us,” she said.

And of all the places they saw, Bergen and Gardner said they will always remember Gosnold, which has a population of 75 and encompasses the Elizabeth Islands stretching between the south coast and Martha’s Vineyard. They spent an entire day there because the ferry departs to New Bedford just once daily.

“We went up to one of the highest points of the island, and it had a great 360-degree view,” Bergen said. “It was a really peaceful place.”

The trip ultimately took three weeks after they got slowed down by car trouble and the unforeseen need for recuperation days.

“But that’s OK with us,” the pair wrote on their blog. “We encountered a few setbacks, and needed a few days here and there to take some breaks.


Bergen and Gardner, who are between jobs, both admit to being wayfarers compelled by wanderlust.

“We’ve been on a lot of road trips before,” Bergen said in an interview. “Driving to Ohio probably took us about 11 hours, but on the highway it’s so boring; there is nothing to look at and it seems like it takes forever.”

But on the backroads of Massachusetts, Gardner said, the time passed easily.

“There was a lot to see and talk about; it wasn’t just highway,” she said.

Twenty days and about 4,000 miles after starting out, Bergen and Gardner completed their odyssey Sept. 28 in the city that divides their beloved shores — Boston.

With no more travel planned for the immediate future, Bergen and Gardner said they are eagerly anticipating getting some rest, but with hopes that they can someday spend a bit more time in some of the places they discovered.

“We certainly have everything to offer in Massachusetts,” Bergen said. “Think of out west and its mountains and rivers; you come east and we have beaches and the Cape. Plus all the history in Boston and the sports . . . we have everything here.

“We definitely have a bit of extra love for our state, with all the new things we encountered and found out about,” he said.

Colin A. Young can be reached at colin.young@globe.com. Follow him on Twitter @ColinAYoung.