On June 25, Alternative Organizational Structure 98 will say goodbye to Teresa (Orchard) Tess. The beloved guidance secretary is retiring after 30 years of service (1995-2025).

“I plan to take it easy and travel to the 10 states that I have left to visit to reach all 50. I will miss all of the students and the friends I’ve made throughout my time at the two schools,” Tess wrote in an email to the Register. Tess worked for 23 years at Boothbay Region Elementary (BRES) and seven years at Boothbay Region High School (BRHS), beginning her career as the secretary to BRES Principal Eileen King.

“Teresa is an invaluable member of our school. Teresa moved from BRES to BRHS the year before I arrived. She welcomed me immediately and we quickly became a strong team in the Guidance Office. Her historical knowledge, both of the school and the community, has been immensely helpful to me over the years ... She is more than a colleague; she is a trusted friend. I will certainly miss having her in the office next year,” wrote BRHS Guidance Director Leanne Burnham.

Tess always made a point to say “Hi” to students in the halls and call them by their names. “You never know when that one simple thing can make a difference to a student,” Tess wrote.

“Teresa has dedicated 30 years to the students of Boothbay/Boothbay Harbor, both in and out of the building. She is a familiar face as students transition to BRHS and she has provided a listening ear, a shoulder to cry on, and a welcoming smile to generations! She greets every student and keeps track of their extracurricular activities, leading to conversations about ball games and school plays. She knows the students and they recognize how much she cares for them. She makes a positive impact every day,” wrote Burnham.

Tess also knows she will miss past graduates coming back to visit. But for her and husband Mark, who have lost several close relatives over the past few years, she knows that now is the right time to retire. “Nobody is promised tomorrow … Now is the time to retire and spend time with my husband and dog Calistoga (Cali)," the unofficial mascot of the BRHS cross-country team.

Tess grew up on Southport Island and still lives there. Her family goes back generations in the Boothbay region. If you are an Orchard, Brewer, or Pinkham, there is a good chance Tess is a relative. She is a graduate of Southport Central School and BRHS, Class of 1978. She later earned an associate of science degree from University of Maine at Augusta.

During high school, Tess played softball all four years, as the team’s second base starter. That experience led to her coaching softball at BRHS; one year alongside Ken Maxim and one year as head coach. Then, she coached middle school softball for 14 years at BRES.

The list of people who inspired, supported and encouraged Tess in her career is long. A few that quickly came to her mind were King, John Deetjen and Cory Chase at BRES and Burnham, Skip L’Heureux and Tricia Campbell at BRHS. Before beginning her AOS 98 career, Tess worked several secretarial/bookkeeping/managerial jobs at Goudy & Stevens Shipyard, Boothbay Region Lobsterman’s Co-op and Log Cabin shoe store.

Some know her for her gorgeous sunrise and sunset photos. All know her for her dedication to the region’s students and families.