The baseball team won the Division 3 State Championship in 1996, 2006, and 2007, under the helm of legendary Massachusetts Hall of Fame coach Fred Thacher.

Harwich also had sent numerous players to prestigious schools for baseball including Boston College, Vanderbilt, Wheaton, UMass Amherst, South Florida, and George Mason.

Harwich currently has two baseball alumni in the Major Leagues, Cody Crowell and Ryan Soares.

The Rough Riders reached the Division IV South Sectional Finals in 2010, only to lose to Cohasset by a score of 6–1.

During the 2012 baseball season, the last season of Harwich being its own baseball team before they regionalize with Chatham and become Monomoy Regional in 2013, they won the Division IV South Sectional Championship, and eventually reached the Massachusetts Division IV State Championship.

In the past 10 years, Harwich has lost just two league games and has been the #1 seed in the Massachusetts State Tournament 6 times.

The Crusaders played West Roxbury in the first round, defeating them 35–27 and clinched a spot in the Division 3A State Championship game, which they lost 7–0 to Ipswich.

Beginning in 2013, Monomoy's football team will be a member of the South Shore League (Small), which competes at the Division 6 level of competition.