28-Time Eastern Independent League Baseball Champions

9-Time New England Small School Baseball Tournament Champions

The Pingree School Varsity Baseball Team competes in the Eastern Independent League (EIL), which is composed of 11 schools (8 competing in baseball) from the states of Maine, Massachusetts, and Rhode Island. The Highlanders typically have a 20-game regular season schedule, facing each EIL school once and playing additional games against New England Prep School Athletic Council (NEPSAC) opponents from the Independent School League (ISL) and Central New England Prep School Baseball League. 

Each season, the Highlanders seek to qualify for the 4-team EIL Tournament, as well as the New England Small School Tournament. Pingree Baseball has enjoyed tremendous success in the EIL over the years, having been crowned champions 28 times since 1981 with the most recent title coming in 2024. In addition, the Highlanders have taken home the New England Small School Championship 9 times, with the first title coming in 1988 and the most recent in 2011.

Every year the Highlanders look to add new players who will have the opportunity to step into contributing roles quickly. With both Varsity and Junior Varsity levels offered within the Pingree Baseball Program, there are opportunities for all athletes to be involved, contribute, and work towards developing their baseball skills. Interest and participation in baseball has been expanding rapidly on the North Shore and in the surrounding areas, and many Pingree Baseball Players take advantage of opportunities to play and train with AAU and travel programs during the summer and offseason. Our top priority is to help our student-athletes achieve their athletic goals both here at Pingree and potentially beyond at the collegiate level. In recent years, a number of alumni from the Pingree Baseball Program have gone on to play NCAA college baseball at the Division I, II, and III levels, and in July 2025 Pingree had its first alum reach the professional baseball ranks as Cooper McGrath '19 was selected by the San Francisco Giants in the 18th Round of the Major League Baseball Draft.

Prospective students and families interested in the Pingree Baseball Program are encouraged to contact Mr. Luke Wamboldt, Head Varsity Baseball Coach, via email at lwamboldt@pingree.org.

Recent Season Recaps:

This past spring (2025), the Highlanders finished the regular season at 10-4 before capturing the EIL Tournament Title with 2 more victories. Pingree earned another home playoff game with the #4 Seed in the New England Small School Tournament, but could not escape the Quarterfinal Round in a game that once again went into extra innings.

The 2024 Highlanders set a new high-watermark, finishing with an outstanding 16-4 record that included another outright EIL Regular Season and Tournament Title. Pingree once again rode their success to the Semifinals of the New England Small School Tournament, where they fell 1-0 in extra innings.

In 2023, after another successful 12-win season, Pingree earned the #3 Seed in the New England Small School Tournament and advanced to the Semifinal round where the Highlanders carried a lead into the bottom of the 7th inning before coming up 3 outs short of a spot in the Championship.

The spring of 2022 saw Pingree post an undefeated league record (13-5 overall) en route to capturing their 27th EIL Championship. The team also earned a berth in the New England Small School Tournament as the #2 Seed in the East Region, before falling in extra innings in the Quarterfinals.