Town of Medway Spotlight | Dennis Crowley, Chairman, Board of Selectmen

dennis crowley

With a can-do approach to wrangling all the moving pieces and parts that come along with municipal government, our Selectmen keep things running as smoothly as possible. As we continue to lift the veil, we move from the Town Administrator’s Office to our Board of Selectmen.

Meet Dennis Crowley, Chairman of the Board of Selectmen. He serves on the Board along with Glenn Trindade, John Foresto, Richard D’Innocenzo and Mary Jane White.  As he currently serves in his 5th term, Dennis brings a keen mind for business as well as Town processes. He’s a valuable resource in keeping Medway moving forward at a steady pace.

1.  What led you to run for the Board of Selectmen? 

As a professional working in business, I found myself continually on the move, trying to balance work and family. With a career involving constant travel, I was limited in the amount of time I was able to give to my community.  Luckily, I was able to volunteer as a coach for my kids sports teams while they were in Medway Youth Sports.  This enabled me to actively give back to the community while juggling work and family.  It was a win-win! 

Upon retirement in 2004, I finally found the time that I had been yearning for all those years.  I was able to focus on giving back and get more involved in the Town of Medway. At first, I slowly started attending local events; Christmas Parade, Memorial Day Parade and Medway Day, to name a few.  Enjoying the community and having fun at these events peaked my interest to get more involved.  I had been an active member of the Medway Lions Club since 1983 and found myself becoming more and more active in the daily activities of the Town. One particular day back in 2005, I found myself reading an article in the Milford Daily News about the Town being on the brink of bankruptcy.  I couldn’t believe my eyes when I saw that the Town needed to vote for a $2.5M override at Town Meeting. I began to think that my business and financial background might be a key resource in guiding the Town’s business strategies, decisions and plans back to stability. That is when it happened, I decided to run for the Board of Selectmen!  In 2006 I was fortunate enough to be elected.  I am honored and proud to say that I am currently serving my fifth (5) term.  I am also happy to announce that in conjunction with former and current Board Members, the Town has successfully turned around from the brink of bankruptcy to AAA rating!

2.  What do you love MOST about serving the people of the Town of Medway?

I love serving the residents. It is very satisfying to me to attend a Town event and interact with residents.When a resident approaches me at a Town function or even on the street, I love being able to address their concern or problem and be able to go back to them with an answer or strategy.

During my five terms as Selectman, I have loved being actively involved in the revitalization of many projects.  In the most recent past, the renovations on the Thayer House and Middle School holds a special place in my heart.  I have a passion for bringing old buildings back to life so, these projects were especially rewarding to me. As Selectman, I’ve also enjoyed working with the State to secure funding for the Rte. 109 renovations, and working with the town to increase the reserve funds from a "$0.00" balance to over $5.0M". Lastly, working with John Foresto, a fellow Board of Selectman, as the co-chair of Medway 300th Committee was extremely rewarding.

Presently, the Oakland and Choate parks projects are a priority to me. Watching the transformation of these parks are a dream come true! When everything is finished our Town is going to be the heart of the Medway, Millis, Medfield, Milford belt.

3.  What do you spend most of your day doing?

I actively spend about 10-15 hours a week working with Town officials and employees on Town of Medway business. I meet frequently with the Town Administrator, Michael Boynton and other members of his office.  At the moment I serve as Chairman of the Board of Selectmen. My function in this role is to communicate Town procedures and business practices to Boards, Committees and Town residents.I am always thinking about ways to make Medway a better place. Right now, I’m excited to be working on a new DPS facility, budget committee for the Medway School District, and Rte. 109 oversight.

4.  What is your favorite thing to do outside of work?

I have a passion for bringing old homes back to life.  My retirement has allowed me to be able to pursue my passion of taking something old and making it shine!As a result, I have purchased and renovated over 30 homes in Medway.Aside from my renovating hobby, I like to spend time with my wife of 45 years, Mary, and our three children, Dennis, Jonathan and Katie.  All three of our children attended Medway schools. We also enjoy spending quality time with our 5 grandchildren and eagerly await the arrival of our 6th grandchild!  My wife and I enjoy bringing our grandchildren to the beaches of Cape Cod and the lakes of Vermont.

5.  Favorite place to travel?

My wife and I have recently discovered cruises!- European river cruises!  We recently traveled abroad to Germany and have enjoyed cruising in the company of a few other long time Medway friends.  In addition we enjoy the Hilton Head area, Cape Cod and Mt. Snow, Vermont.

More about Dennis

Four years ago I became co-owner of the Muffin House.  Our locations are expanding outside of our original Medway location.  We have opened shops in Mendon, Natick and most recently, Hopkinton!  In addition to my business endeavors, I am most proud of the 35 years I volunteered as a Charter Member for the Medway Lions Club.  As an active member since 1983, I am most thankful for the opportunity to act as Co-Chair of the annual Christmas Tree Sale and the numerous monthly, bottle and can drives. 

Medway is my home and I’m looking forward to enjoying many more years of retirement here.