South Shore Family Adventures offers friendly trails, outdoor activities


EASTON – Each summer, siblings and educators Amy and Jim Kirkcaldy were challenged to find a way to cut down on their children’s TV and games time by getting them out.

When the COVID-19 pandemic hit, they were in a similar situation to find free outdoor activities. They decided to explore the trails and parks in the area and share their experiences and advice through a business they started called Family adventures on the South Shore.

“There are so many places all around you don’t even know,” said Jim Kirkcaldy, a resident of Weymouth and a teacher at Watertown Middle School.

He and his sister research parks in Southeast Massachusetts with a variety of trail lengths, difficulties, and scenery.

Some are in state parks. Some are more local and hidden, like a wooded half-mile trail behind Moreau Hall Elementary in Easton, where they hiked on Saturday afternoon.

The siblings wanted to focus on free outdoor activities. Some hiking areas are chargeable for parking.

Amy Kirkcaldy, of Easton, said there are resources on the trails and groups of people to get there, but heard from parents about finding family-friendly places.

“We are trying to eliminate all the unknowns,” said Amy Kirkcaldy, who works as an academic advisor at Milton Academy. “We are trying to think of what people want to know.”

To help, the Kirkcaldy siblings created a system called a “PINT” score that rates parking and access, level of interest, navigation, and terrain of the parks and trails they visited. A score of 1 is the worst and a 5 is the best.

Every trail they’ve visited is noted with a PINT score and listed on their website along with other information, including directions, trail description and maps, blurb about their visit, photos, and a video. Over 20 trails are listed on the website, run by the Kirkcaldy siblings.

Amy Kirkcaldy’s twin sons, Sebastian and Adrian Gattas, are 9 1/2. Her brother’s children are James, 8, and Alice, 6.

Some of the trails have included rocks that Amy and Jim’s kids love to climb. One of the kids’ favorites was the Rockland Town Forest and Twin Ponds trail, which is decorated with knickknacks along the way.

Amy Kirkcaldy said her kids are having fun hiking most of the time.

“We never felt like we wasted time outside,” she said.

She said her sons didn’t always want to go out with her and her husband, but when their cousins ​​came, they wanted to go. Sometimes she and Jim’s dad go with them on hikes.

Jim Kirkcaldy said their dad would take them on hikes and outdoors. It is a state of mind that they have nurtured with their two families.

There is no shortage of places to explore and include on the website, said Amy Kirkcaldy. His brother added that they could expand to other parts of the state, like Cape Cod, or visit trails in Rhode Island.

People started leaving comments and tagging them in posts on South Shore Family Adventures social media pages about the places they’ve been and their experiences.

A neighbor said they hiked and used their website to help plan, Amy Kirkcaldy said. A college friend used it to find a place to hike when she was in the area.

South Shore Family Adventures isn’t just about hiking. The Kirkcaldies said they plan to include more activities other than hiking, like scavenger hunts or paid activities.

Amy Kirkcaldy hopes to do more in the community, like working with local businesses to promote each other.

“It would be cool to build a community around that,” Jim Kirkcaldy said of their business.

To learn more, visit

Editor-in-Chief Mina Corpuz can be contacted by email at [email protected] You can follow her on Twitter @mlcorpuz. Support local journalism by purchasing a digital or print subscription to The Enterprise today.

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