Running for a little

Mike Whittemore raises awareness for Big Brothers Big Sisters, and shares his ‘big’ story.

Mike Whittemore, left, and Sam Flanders have been a part of the Big Brothers Big Sisters program for three years now. — Eunki Seonwoo

Updated April 23

Vineyard Haven resident Mike Whittemore plans to complete a 100K on the Island to raise awareness and funds for Big Brothers Big Sisters (BBBS) programming here. The run is set for May 7. 

“It’s actually something I’ve always wanted to do. I love nature. I spend a lot of time in the mountains, and this year I want to spend more time on Martha’s Vineyard,” Whittemore told The Times. 

Whittemore has been a mentor, or a big, with BBBS for three years, and told The Times, “It’s just been a wonderful opportunity.” His little, the term used to describe mentees, is Sam Flanders, an eighth grader at Martha’s Vineyard Public Charter School. “When I first met Sam, I think he was a foot-and-a-half shorter than he is now,” Whittemore said. 

Getting Island men to volunteer was difficult for Big Brothers Big Sisters, according to J.R. Mell, executive director of Big Brothers Big Sisters of Cape Cod & the Islands. Matching women volunteers with girls participating in the program has not been an issue. Mell told The Times the reporting by Island newspapers about the need some young Island boys faced “spurred some amazing results, with the waitlist being cleared in February for the first time in our agency’s history.” However, there are currently three boys waiting for mentors. 

“There is always a present need for male volunteers with our program,” Mell said. “We welcome anyone interested in a meaningful, longer-term volunteer opportunity that makes a tangible difference in the life of a child, and their own.”

“It is really rewarding. I am surprised at how rewarding it’s been for me,” Whittemore said about being Sam’s big. 

Of course, Whittemore had to work to bridge the gap between himself and Sam. He is an outdoorsman, and Sam enjoys playing video games. Whittemore was warned about the difference in personality between them by his Big Brother Big Sister liaison, but he decided, “That’s OK, I want to meet [Sam].”

How did Whittemore connect with Sam? 

“I found out he really likes milkshakes,” Whittemore said with a chuckle. He and Sam would walk around town and get something to eat. Sometimes they would go for a walk and then watch a movie in Edgartown. “So, we came up with a compromise: OK, we can watch the “Batman” movie, but we’ve got to walk around the block and check out stuff I like to see, too,” Whittemore said. 

Little by little, Whittemore and Sam spent more time outdoors, kayaking, walking on trails, riding on e-bicycles, and other activities. “It’s just wonderful for me to share my passion for the outdoors, and of course he teaches me a lot as well,” Whittemore said. “To see him grow has been just really a great experience.”

Sam agreed, saying how he did not want to go outside at all in the beginning of the program. He just wanted to play the video game Roblox indoors. Now he and Sam can walk on the Menemsha trails well. Sam moved to the Island from Connecticut five years ago, so the program and Whittemore helped him acclimate to Martha’s Vineyard. The program provided Sam with a friend before he found more of them on the Island.  

“One of the awesome things about the program is if you’re one of those sort of kids who doesn’t like hanging around with people and you’re just doing it because your parents forced you into the program or whatever, then you only have to do it once or twice a month,” Sam said. “That’s what I did at the start, and now we [still] visit each other around the same [amount] because we have conflicting schedules. Otherwise it’s pretty darn great.” 

Whittemore, who grew up in Framingham, also came to the Island only a few years ago, for work with the Nature Conservancy. He urges people to give what they can offer to the youth on the Island. “My message to potential bigs out there is just, There’s definitely a lot of need on-Island. There are little brothers waiting for folks,” Whittemore said. “I’ll say it’s a small Island, but it’s such a big community, a rich community of folks with diverse skill sets and experiences and passions. We could easily pass that down to kids. The investment in our youth on the Island is the best investment we can make on the Island.”

The campaign has been set up to collect donations, with a goal of $1,000. All proceeds will go to the Martha’s Vineyard BBBS program. For those who want to donate, visit For those interested in becoming a volunteer big, contact Mell at

Updated with a new link to the fundraiser.