The Navigators are the successor to the Giants of the New England Collegiate Baseball League, a charter team in Middletown, Connecticut that moved to Holyoke, Massachusetts.

They finished the NECBL's inaugural 1994 regular season with the second-best record in the league, though the team did not qualify for the championship series.

After sweeping the Danbury Westerners in the postseason, Middletown defeated Torrington three games to one in a best-of-five rematch of the 1997 series, marking the franchise's second straight league championship.

Middletown Giants players who went on to Major League Baseball include Rajai Davis, Chad Paronto, Mike Smith, Doug Clark, and Earl Snyder.

The first round of the playoffs had Holyoke paired up with the Lowell All-Americans, and in the longest three game series in NECBL history, the Giants came out on top.

Having finished the regular season in first place, the Giants had home field advantage for Game 1 against the Vermont Mountaineers, though lost 7-3.

Game 2 seemed like it would be yet another extra inning contest for the Giants, but a walk-off home run in the bottom of the 9th by Vermont ended Holyoke's season.

By December 2007, word had spread that the Giants would move to Lynn and play at Fraser Field under the name North Shore Navigators.

[3] Fraser Field had been home to the North Shore Spirit of the Canadian-American Association of Professional Baseball, which ceased operation at the end of 2007 after five years.

The Navigators finished their first season in Lynn in second place in the NECBL Northern Division, at 26-16, two games behind eventual 2008 champion Sanford Mainers.

The team was sold to the January family of Swampscott before the 2020 season, which was mostly played without fans or income because of the city and state's response to the COVID-19 pandemic.

** In 2021, every team entered the playoffs; those in 3rd through 7th place played a one-game "play-in", which North Shore won at Montpelier.

A rain-shortened Game 2 against a decimated Upper Valley team was eventually ruled final and the Navigators were declared Division Champions.