Inside Windjammer Days: Maine's Most Iconic Harbor Festival

Inside Windjammer Days: Maine's Most Iconic Harbor Festival

Windjammer Days has been a Boothbay Harbor tradition for 64 years, but what does it actually take to keep one of Maine's most recognizable waterfront festivals going? In this episode of the Maine Famous Podcast, April sits down with Bruce White, longtime volunteer, board member, and Boothbay local, to go behind the scenes of Windjammer Days. Together, they discuss how a simple idea involving a handful of schooners grew into a week-long celebration featuring tall ships, fireworks, tug-of-war across the harbor, codfish relay races, live music, and thousands of visitors each summer. The conversation is also about something bigger: the volunteers, traditions, and sense of community that have allowed Windjammer Days to endure for generations.

How Two Friends Took Over an East Boothbay Inn

In this episode of the Maine Famous Podcast, April sits down with Matt Partridge and Ryan Edwards, the new owners of Five Gables Inn in East Boothbay, Maine. The two longtime friends talk about what it’s actually like to step into ownership of a beloved coastal Maine inn with decades of returning guests and a reputation already firmly in place. Over the course of the conversation, they discuss the pressure of preserving tradition while modernizing the guest experience, the realities of staffing and housing in Maine’s tourism economy, and the unexpected lessons they learned after arriving in Boothbay. They also share stories about proposal weekends, repeat guests who’ve been visiting for 30 years, lobster dinners at the inn’s cottage, and the kinds of porch conversations that turn into lasting memories. “One minute you’re serving breakfast,” Ryan says. “The next, someone’s yelling that there’s a leak upstairs and you need a wrench.”

This Coastal Maine Inn Has a Whiskey Club, Art Gallery, and Sunrise Views

Greg Soutiea didn’t set out to become an innkeeper. After years working in corporate property management in Boston, he and his wife Lauren were burned out by the constant cycle of “putting out fires.” Then a stay at a small inn on the coast of Ireland changed the trajectory of their lives. In this episode, Greg shares how the couple took a leap of faith and purchased Craignair Inn, a nearly 100-year-old property perched beside the ocean on the St. George Peninsula. Today, the inn has quietly become one of Midcoast Maine’s most distinctive destinations, with a celebrated brunch program, a 250-bottle whiskey collection, rotating local art exhibitions, chef dinners, and direct access to the trails of Clark Island Preserve. But this conversation goes beyond hospitality. Greg opens up about workforce housing, building community, creating meaningful guest experiences, and why he believes the best inns should feel less like luxury resorts and more like home. We also talk about sunsets that turn the granite causeway gold, the surprising number of artists living on the peninsula, and why some guests come for the whiskey while others come for the peace and quiet.

They Met on a Tour Boat. Now They Run One Together.

Dom and Liz Gioia met while working on tour boats in Portland. Years later, they’re now the owners of Camden Harbor Cruises, one of Camden’s most beloved on-the-water experiences. In this episode of the Maine Famous podcast, we talk about how a summer job turned into a life on Penobscot Bay, what it’s really like running a family business on the water, and why generations of visitors keep coming back aboard the Lively Lady. From hauling lobster traps and spotting seals to sunset charters, lighthouse cruises, and stories from years at sea, this conversation captures a side of coastal Maine that most visitors only glimpse from shore. We also talk about raising kids around the harbor, the strangest things they’ve pulled up in lobster traps, and why even lifelong Mainers still get excited watching someone see a lobster hauled for the very first time. If you’ve ever wondered what makes Camden feel so quintessentially Maine, this episode is a pretty good place to start.

The Best Wings in Maine Might Be at a Pizza Shop

Nick Krunkkala trained in some of New York City’s most demanding kitchens. Today, he’s smoking chicken wings for four hours behind a pizza shop in Damariscotta, Maine. In this episode of Maine Famous, April sits down with the owner and chef of Oysterhead Pizza to talk about why he left fine dining behind to build something more personal: a neighborhood restaurant where locals can grab a slice three nights a week, high school students learn the restaurant business, and every sauce, dough, sausage, and dessert is still made in-house. They talk about the cult following behind Oysterhead’s wood-fired wings, the deep dish pizza Nick describes as “Damariscotta style,” the influence of New York kitchens on his cooking, and why he believes affordable food still matters. The conversation also dives into mentorship, community, live music nights, and the strange movie references hidden throughout the menu and decor. If you’ve ever wondered how a pizza shop becomes a Midcoast institution, this episode tells that story.