Weston Voices: Kara Fleming Moves On from Town Hall

Many Westonians are now aware that Kara Fleming, Queen of Weston, has left the building–the Town Hall building that is. While Kara’s official titles were Assistant to the Town Manager and Public Information Officer, she was so much more and did so much more, and her shoes are going to be difficult to fill. [Note that Kara will be helping out part-time until the Town finds someone to step into the role] . In addition to all she did for the residents of Weston, the Town will surely miss her knowledge, dry humor, and interesting face masks. Fortunately, Kara now moves to her next role which is regular town citizen, and it was in this capacity that the Owl caught up with Kara at the Weston Beach on a sunny day last week.


[Owl]: How long have you lived in Weston, and when did you join Town Hall?

[Kara]: I’ve lived in Weston since 2005–my husband David is actually Weston-native–and I took the assistant to the Town Manager role in 2013. That role expanded to Public Information Officer shortly thereafter. 

One of your sons was also an elected town official, was he not?

Yes, Aidan was elected Measurer of Lumber in 2018 and re-elected in 2019. He graduated Weston High School in 2019 so is off to other successes. My other son, Danny, is WHS ‘23, but the political bug hasn’t hit him yet. 

What do you consider some of your greatest accomplishments at Town Hall?

One of the things I am proud of was BYOB (bring your own beverage) at Dumpling Daughter. The owner asked if anything could be done (since Weston is a dry town) and after a bit of research, I developed the policy for the Select Board to approve. It’s an example of work I did to help out someone and I did it on my own

I also feel happy about all the work I did on the Town Green policy. There was an issue with the holiday tree getting lit after it grew too tall for the town to string lights–and a “politically-correct” culture also threatened this beautiful tradition. This also corresponded with the 60-year tradition of the Carol sing on the porch of the Josiah Smith Tavern. I worked with the Weston-Wayland Interfaith Action Group to find a culturally sensitive means to get that tree relit and to keep the Carol sing going for when the JST work would again allow the Carol sing on the Tavern steps. I worked with DPW, Facilities and the Fire Department to help the Women’s Community League launch their event. And I redeveloped the town green policy to allow for culturally-inclusive community events on the Town Green and Town Hall. This policy also made room for the student-led political gatherings (BLM and CSW’s student march for gun control) and food trucks. It’s currently under rewrite because of the new town center so it should be coming to a Select Board meeting soon.

Obviously I am pretty proud of my work on the Town website. In 2014, on the original website: there were 9,300 hits per month. In 2016, one year after the website transition with new email communications system, it almost doubled to 18,300 hits per month. And now, in the last twelve months, there are 56,300 hits per month. [Owl: !!!!!!]

What did you like best about your job, and what was most challenging?

I enjoyed supporting boards and committees. I loved being helpful — communicating between different groups and letting people know of important rules or changes or whatever. The biggest challenge is there just wasn’t enough time to do some of the longer-term projects. I wish I could have finished a project on a welcome packet for new residents–something that would include a little bit about all the wonderful things in Weston. 

What is your advice to the next person in the role of Assistant to the Town Manager?

First thing every day is to just take a deep breath. While some things about the job may seem monotonous (meeting reminders, agendas, etc), it’s really not. There was something new every single day. 

What’s next for you?

I am going to take some time for myself, without deadlines and reminder emails. I enjoy working with my hands–I am going to do some furniture refinishing, and I’m in fact on my way to pick up a new table to work on. 


On a personal note, the Owl is having a very hard time imagining Town Hall without Kara. Since moving here in 2014, I’ve learned so much from her–and always knew where to go for details about well, anything. The good news is that Kara is still a town resident, and still knows everything.

Thanks, Queen of Weston, and see you on the civilian side of the zoom calls.

don’t smoke, kids, it’s bad for you.

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