Another competitive election emerges in Brooksville

Feb. 23, 2026

By John Epstein

Last month, The Rising Tide reported that Brooksville would be having the first competitive race for select board in over 40 years. Now it appears the election for two of Brooksville’s school board seats will also be a rare contest.

“It’s an unusual situation,” said Amber Bakeman, Brooksville’s town clerk and registrar of voters.  

When incumbent school board members Sam Vaughan and Annie Silver filed the necessary paperwork at the end of 2025 to get on the town’s March ballot, it looked like their election would be a formality. But the candidates will now face a challenge from Lindsay MacDonald, who has put up signs in town declaring herself as a write-in candidate for one of the two board seats.

The Rising Tide interviewed all three school board candidates, whose profiles are below.

Annie Silver 

Silver was appointed by Brooksville’s school board to fill an empty seat in April 2025. A graduate of the University of California Davis with a BS in Agricultural Systems and the Environment, she has lived in Brooksville for 20 years with her husband and two daughters. One daughter is in college now, the other goes to George Stevens Academy (or GSA); both attended Brooksville Elementary School (or BES).

Annie Silver.

“I want to give back to the town and school for the education they received,” said Silver, who has worked as a farmer, a private chef, and now as an administrator of her husband’s design landscaping business.

“The school has done a great job,” said Silver, pointing to its foreign language and music offerings. But she sees the declining enrollment as the biggest issue facing the school.  

“We need to get the word out,” Silver said. “Kids are the future, and we should do right by them so their future is bright, but also the future of our community will be in their hands.”

Sam Vaughan

Vaughan is running for a second term on the school board. Raised in Brooksville, Vaughan was educated at Brooksville Elementary School, GSA, and Skidmore College, where he earned a degree in International Economics. He worked in New York City for several years as a construction project manager and then as an executive for an educational testing company.

Vaughan met his wife in New Zealand and returned with her to Brooksville where they are raising two daughters who attend BES while he runs the Seal Cove Boat Yard.

Sam Vaughan.

“The school has a fantastic group of teachers and support staff and my children are getting a great education,” Vaughan stated in an email, while noting that the operations costs are a challenge.

“Like most small-town public schools, the Brooksville school is expensive and it comprises a large portion of the town budget,” Vaughan said. “We need to provide a good education and we also need to pay a competitive wage for everyone that works at the school, but we also need to be mindful of a voiced public concern about the costs,” he added.

Lindsay MacDonald

MacDonald, who grew up on Deer Isle, moved to Brookville seven years ago with her husband.  Both of their children attend Brooksville’s elementary school.

Lindsey MacDonald.

A 2004 graduate of Deer Isle-Stonington High School, MacDonald said “I’ve done a little of everything.” She was a cashier, a cook, a certified nursing assistant and residential nursing aide, as well as a mate on her husband’s lobster boat. She now owns and runs Coastal Road Redemption in Brooksville.

MacDonald said she had long wanted to run for the school board, but had been too busy. She thinks she now has time. “[O]ur youngest is in pre-K and I have gotten the major kinks worked out of my business,” she added.

MacDonald believes the biggest issue facing the town’s elementary school is the declining enrollment. “When we moved to Brooksville in 2018, there were close to 70 students,” she said.  “Now there are a little over 40.”

MacDonald would like the school board to conduct a survey of Brooksville families with school-age children who home-school their kids or enroll them in schools outside of town. She thinks the information could help the board learn what the elementary school could do educationally to appeal to those families.

The Brooksville elections will be held on Monday, March 2 from 10 a.m. to 8 p.m.