Beth Sobiloff had always wanted to embark on a cross-country road trip in an RV. But due to family obligations and a lack of disposable income, she was never able to fire up a vehicle to take the journey.
“I had been single for a long time. I was raising my three kids on my own. And I never really had extra money to take vacations or anything,” said Sobiloff, 72, of Plymouth.
But more than a decade ago, with her kids all grown up, she had an epiphany: as a web designer, her career allowed her the freedom to work from virtually anywhere. There was nothing stopping her from living out a version of her plan and turning a once seemingly far-fetched dream into reality.
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“Even baby boomers, they can still do things,” said Sobiloff, who has 14 grandchildren and 7 great grandchildren from two marriages. “Maybe they can’t completely live their dream, but they can do some version of it and they can have fun and enjoy it.”
And so, after finding a suitable travel partner to keep her company, “Two Grannies on the Road” was born.
Although her plan to travel across the country never came to fruition, Sobiloff launched a venture with the goal of visiting communities around Massachusetts instead, interviewing other “baby boomers who had reinvented themselves.”
But she later refocused her vision to emphasize the destinations themselves, and in 2019 made it her mission to eventually see all 351 cities and towns in the state.
For the last several years, Sobiloff has turned her expeditions — from feeding alpacas at a farm to being taught how ice cream is made — into a passion project, one that she shares with a growing audience on her website, YouTube channel, Facebook page, and a Plymouth-area public access show.
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As of Wednesday, she had crossed around 35 communities off her list, including Acushnet, Sudbury, Worcester, Yarmouth, and Pembroke. Her latest excursion was a stop in Hubbardston this week.
But don’t ask Sobiloff to choose which locale has left the most lasting impression — that would be like trying to pick a favorite grandchild.
“Oh, come onnnnn,” she said, laughing.
Sobiloff used to say that Marion topped her list. But with each additional stop, “it started to be like, ‘I love every town, and for different reasons.’”
Marcia being silly at Off the Hook restaurant in Fairhaven. We had a delicious lunch there.
Posted by Two Grannies On The Road on Friday, July 8, 2022
Since its inception, Sobiloff has had a rotating cast of grandmothers accompany her as she’s set out to accomplish the endeavor. Her most recent sidekick has been Marcia Rothwell, a Bourne resident who said she’s committed to sticking with the project for the long haul.
“I’m very excited,” said Rothwell, 79. “When people talk to me, since I’ve been to the Cape my whole life, [they assume] that I should know everything. I know nothing. So I’m learning all about it. It’s so exciting — it really is — to learn about all the little towns.”
Sobiloff typically begins planning for a trip by engaging with residents from a specific town on Facebook. If a number of people make the same suggestion for what to do once she gets there — whether it’s eating at a mom-and-pop diner or meeting a well-known local — she’s more likely to include it on her itinerary.
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But she always prioritizes scheduling a meeting with a town historian, someone the pair can interview to get a fuller picture of the area. In some cases, people have even volunteered to give personal tours of their respective towns, so the duo could see what Rothwell called the “hidden gems.”
“I would never have thought of it — to really research it first,” Rothwell said. “It would be just going on a travel [website] and looking on the internet. But it would be the big tourist places, not these other places that I think get missed by many people.”
Sobiloff agreed.
What a lovely day we had in Sudbury yesterday! One stop was at Duck Soup, a general store owned by Louise Mawhinney, who also bought the rights to the Skybar from Necco. I just had to come right home and try it!
Posted by Two Grannies On The Road on Friday, July 15, 2022
Her experiences so far have included going on a sailboat with a member of the Beverly Yacht Club in Marion; feasting on an assortment of breakfast foods, like French toast layered with gouda cheese, cranberry sauce, and whipped cream at a diner in Hubbardston; and learning that the first American combs were manufactured in West Newbury.
So what’s next? Dartmouth, Chelmsford, and Duxbury are all on the short list for now. But it’s a trip scheduled for September that Sobiloff is looking forward to the most.
“We’re going to take a week and take the RV and go to the western part of the state,” she said. “I know I definitely want to go to Washington. They’ve got some beautiful waterfalls and stuff there. And then we’ll probably do Lee, Lenox — those towns. We’re going to try to do five or six towns in one week.”
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On their way back, “The Big E” state fair will be happening in West Springfield — a must-see event for Sobiloff, she said.
While there are still many places she needs to visit, Sobiloff said the journey so far has taught her that you don’t need to travel out of state to learn more about the world.
“Our state has so much besides history. There’s culture, there’s the landscape — there’s lakes and ocean and mountains and rivers and gardens and woods. There’s everything you’d ever want in Massachusetts,” said Sobiloff. “I’m learning all about that and really wanting to share that with other people.”
Just over 300 more cities and towns await.
Shannon Larson can be reached at shannon.larson@globe.com. Follow her on Twitter @shannonlarson98.