Rob Caldwell’s Favorite Place

Casco Bay Islands, Rob Caldwell's favorite place
Photograph by Benjamin Williamson

Casco Bay Islands

From our November 2018 issue.

If you’d have told WCSH news anchor and reporter Rob Caldwell back in 2003 that 207 — the breezy, post–news-hour magazine show that the station launched that fall — would still be airing in 2018, he would have . . . well, he probably would have listened attentively and then responded with a thoughtful observation about the fluidity of network TV schedules. Warm approachability and smart, earnest dialog are kind of his calling card. But privately, he’d have thought you were nuts.

Rob Caldwell

Portland/Simsbury, Connecticut

Inducted in 2015 into the Maine Broadcasting Hall
of Fame

First Trip on Casco Bay
On his very first day in Maine, in 1977. “I fell hard for the water, the islands, the views — everything.”

And yet, 207 just celebrated 15 years, a nightly ritual for some 30,000 Mainers who tune in to watch Caldwell and his equally winning cohost, reporter and anchor Amanda Hill, chat with guests ranging from former presidents to loggers and lobstermen to A-list actors to the Marden’s Lady. (Full disclosure: 207 has Down East on monthly to talk about our new issue. Fuller disclosure: We’d watch even if they didn’t.)

In Caldwell’s mind, the show’s success owes to its topical breadth — and to a state that facilitates it. “I’ve ridden a motorcycle across Kansas and thought, ‘I’m glad I’m not trying to do feature television stories here,’” the 58-year-old journalist says. “You just don’t have that range of places, and therefore people, that Maine has. If you’re doing a story on Vinalhaven, it’s a lot different from a story in Rangeley, which is a lot different from a story in Presque Isle, which is a lot different from a story in Waterville.”

Caldwell’s first exposure to Maine’s maritime culture was as a deckhand for Casco Bay Lines in 1979 and 1980, a couple years after moving to Maine with his family — and several years before the company adopted mechanical lifts to load and unload freight. He spent two backbreaking summers hauling gear on and off ferries, learning to toss a line onto a pylon, and admiring dramatic views of the landings, skylines, and shorelines on Peaks, Great Diamond, Chebeague, and the other Casco Bay islands.

“I still look out on those islands when I’m driving around the Eastern Promenade,” he says, “and I’m still charmed by them. I still think they’re so beautiful.” These days, he lives not far from the Portland waterfront and sometimes detours on evening walks to sneak a peek at the ferry terminal where he once toiled. “The old memories come back every time,” he says.