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Upcoming Alumni Events
Sat, August 01, 2026
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Alumni Adventure to Maine
🦞 This exciting day is designed à la carte — attend every stop on the itinerary or simply join us for the events that fit your interest. Want to leave the driving to us? Hop aboard our mini bus! Limited seating is available, and transportation includes round-trip service from PA to all scheduled events throughout the day before returning to Pinkerton. Reserve your seat early!Here is what the day and timeline looks like:
8:15AM - Meet at PA's Pinkerton Hall - Senior Steps for the bus
9:30AM - Arrive at Stonewall Kitchen in York, ME
12:00PM - Arrive at dock for the Port-City Lights Cruise (cruise is 12:30 - 1:30)
2:00-5:00PM - Alumni Regional Event at Larry Donovan '85 home
6:00PM - Portland Sea Dogs Baseball Game & Fireworks
9:00PM - Bus back to PAFor more information and to register, click here!
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Sat, August 08, 2026
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Pinkerton Academy 5k Astro Run
9:00AM - 12:00PM EDT
Pinkerton Academy CampusJoin us for the first Pinkerton Academy 5K Astro Run! The race will begin at 9:00 AM, with registration opening at 7:45 AM. The course will take runners through parts of the Pinkerton Academy campus and along the cross-country trails, offering a scenic and fun route for participants. Runners and walkers of all ages are welcome, so bring your family and friends and enjoy a great morning at the Academy. All profits from the event will support the Pinkerton Fund, with proceeds going directly back to benefit the students.

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Thu, August 20, 2026
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Field Hockey Alumni Game
5:30PM - 7:30PM EDT
Pinkerton Academy - Multipurpose FieldDo you remember playing Londonderry at Mack Plaque or wearing your jersey to school? Now is your chance to come back to campus, visit with former players and coaches, play a 40 minute game of field hockey against alumni (need 25 alumni to register), enjoy game time snacks, and a chance to meet the current team! We will be celebrating the 1996 championship team! Please bring your families to watch and cheer you on!
Reach out to Jen Resmini at [email protected] with any questions.
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Fri, August 21, 2026
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Girls Volleyball Alumni Game
6:00PM - 7:30PM EDT
Pinkerton Academy - Hackler GymnasiumFor more details, reach out to Todd Royce at [email protected]
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Thu, August 27, 2026
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Boys & Girls Cross Country Alumni Meet
6:00PM - 7:30PM EDT
Pinkerton Academy - Cross Country TrailFor more details, reach out to Jon Alizio at [email protected]
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