Oak Bluffs harbor master Todd Alexander will retire after 29 years on the job, it was announced at the town select board meeting Tuesday. The retirement is effective July 1; Mr. Alexander will work part time this summer.
Oak Bluffs harbor master Todd Alexander will retire after 29 years on the job, it was announced at the town select board meeting Tuesday.
“Just wanted to make it public and thank everybody,” Mr. Alexander said at the meeting. “It’s been a hard decision and I don’t know what to say — it feels it’s time to move on.”
Mr. Alexander’s retirement is effective July 1, but he said he will continue to work part time through the summer.
“I can’t leave there that quickly. It’s not like pulling a band-aid,” the harbor master said. “It’s an emotional decision . . . I want the transition to be as seamless and unobtrusive as possible . . . I will be there all summer — for all the main events.”
A succession plan was not clearly outlined at the meeting.
In a letter to the board, Mr. Alexander recounted his beginnings working on the harbor at age 12 — first working on the party boat Ranger, then as co-owner of the Skipper.
“In what seems like the blink of an eye, three decades later I find myself realizing just how much this harbor has meant to me,” he wrote in the letter dated March 7. “In all this time, I have come to love the harbor community, the locals, the businesses, the regulars, and yes, even the tourists.”
Board members thanked the harbor master for his long service to the town.
“You, more than any other employee in town, have had interactions with probably more than tens of thousands worth of people through your career — which is pretty amazing,” board member Ryan Ruley said.

Comments
Oak Bluffs just lost a good
Kara O OB/Fall RiverOak Bluffs just lost a good one. Todd has been amazing over the years.
Good luck to you Todd with
rob the roofer new jerseyGood luck to you Todd with wherever your future brings you. thanks for a job well done .
A tremendous heart and
George Stein Oak BluffsA tremendous heart and dedication that will possibly be irreplaceable. Bless you sir !
A good guy focused common
Patrick Paquette Hyannis MAA good guy focused common sense based management and customer service. Hard not to consider this a loss.
One of the best things about
John Zarba VineyardOne of the best things about OB - sad to hear this news but so happy for you Todd! Fair Winds and Following Seas!
I have known Todd since his
James Pringle Vineyard HavenI have known Todd since his days on the Ranger and am proud to call him a friend. He did (and is still doing) a fantastic job in Oak Bluffs and is probably the only Harbormaster in the country, or even the world, who has started a school in Africa.
Good news first. Good for you
Phillip Lesh MV/Boston/MarinGood news first. Good for you 1 fine Harbormaster, unbroken chain. Bad news, How will I tie up aboard my ship of fools?
Awesome career Cuz! I’m not
Scott Oak BluffsAwesome career Cuz! I’m not far behind you!
Phillip,
Todd OBPhillip,
“ For this is all a dream we dreamed
One afternoon long ago”
What a swell young man,
Mick Hart Stinson Beach,Ca.What a swell young man, smooth sailing to ya! Yes it's me and my boat The Pride of Cucamonga!
Funny thing is…
TA OBFunny thing is…
All the years combine
They melt into a dream.
Congrats, Todd! The end of an
Deborah Hammett Somewhere SpectacularCongrats, Todd! The end of an era. Thanks for supervising my dock girls. We love you!
Congratulations Todd, upward
Jamie West TisburyCongratulations Todd, upward and onward, to new adventures. The harbor will not be the same without you, but we know you'll always be a salty Wharf Rat at heart...
That boat,that boat...Pearly
August West Hoboken/TisburyThat boat,that boat...Pearly Baker, loved her more than my wine! Godspeed Retiree, shake it,shake it Retiree...
Todd, on the obhmc we had
Captain G plymouthTodd, on the obhmc we had some minor personnel issues that we had to deal with, some good victory's. Back when, I knew you would always do the right thing, and indeed you have//// Enjoy your retirement!!
We all were glad you stepped
Donny Oliver OB/Beacon HillWe all were glad you stepped up so many years ago, taking the OB Harbormaster position and we’re proud to know you had the helm. Your calm, commanding and charismatic demeanor will be genuinely missed along the waterfront. Wishing good health and happiness in all your future endeavors.✌️
I worked on the Oak Bluffs
New Englander Providence RiI worked on the Oak Bluffs harbor many years. Todd Alexander ran a smooth, efficient operation. Probably many people outside Oak Bluffs do not know his name, which is a testament to his understated but well executed performance.
Wow and congratulations! I
Casey Sharpe Oahu HawaiiWow and congratulations! I wish all the best for you and your family.
I remeber first getting to
Sig Van Raan West TisburyI remeber first getting to know Todd way back in the early 90's when I was running Cafe Luna at the Oak Bluffs harbor.Hewas always friendly, welcomming ande very supportive when we initiated live music nights on the Harbor.He's had a pretty inspiring life so far as during his offtimes from the Harbor he has traveled the world and in fact started a school for stret kids in Cambodia . Hopefully his "retirement" willfoster an evolution to even more interesting life challenges to a really good person - all best Todd
Thank you Sig,
Todd OBThank you Sig,
I remember you well my friend!
Good luck, Todd. I enjoyed
Jim Dorsey Charlotte, NCGood luck, Todd. I enjoyed working with you. I'll pass this news along to Terry Ann too.
It’s not often one gets a
Hugh Taylor Gay headIt’s not often one gets a chance to offer up good wishes to old friends so I will step in here to say just a couple of things that come to mind ..
Practical, pragmatic, logical, all brought to the task at hand within the framework of intelligent humor. Few people hold the badge Todd has held for all these years where ego hasn’t tainted getting the job done. We all wish his successor as fine a run. H
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