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Greg and Chelsea met for their first date on the Boston waterfront. “The dollar draft beers were flowing, as well as the conversation,” she says, as they bar-hopped around the neighborhood. When the evening began to wind down, Greg and Chelsea made their way to the subway, dancing hand-in-hand through the brick and cobblestone streets of Boston. Greg’s grip wasn’t overly tight, and Chelsea accidentally tripped on a loose brick and fell. But, she says, “Greg picked me right up, and we shared our first kiss.”

As they continued to see each other, Greg knew that he had found someone special. He planned an elaborate proposal around a hike to the Poplar Hut (part of the Maine Huts and Trails system) in Carrabassett Valley—but a delay in shipment at the jeweler meant he didn’t have a ring to propose with. “Next came the best customer service experience of my life,” he says. A store manager from Day’s Jewelers drove three hours on a Saturday to deliver the ring, just in time for sunset. With only 30 minutes of daylight remaining, Greg had to devise a new plan, fast. He took Chelsea to the top of Ira Mountain and proposed while looking out at 10 inches of fresh snow and the setting sun.

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“We had been planning for so many months that we wanted the day to be carefree and filled with love—and we ended up with exactly that.”

GREG + CHELSEA

It was important for Greg and Chelsea to have their family involved in the ceremony. At the August 3, 2019 ceremony, both of their mothers gave readings, and Chelsea’s uncle played guitar for the processional. Greg and his father built the pergola that the couple was married under, and their brother-in-law officiated the ceremony. “All of these personal touches made the ceremony truly amazing,” Chelsea says.

Love at Its Peak

The Location
Greg has been going to Sugarloaf his entire life. He introduced Chelsea to skiing when they first started dating, and she instantly fell in love with it. They spent countless weekends together at Sugarloaf while Greg taught her how to ski. “Having Greg as my ski instructor was a real test to our relationship,” she says, “but we passed with flying colors.” Over the years they watched their love strengthen and grow on the mountain.