Dylan Curran: Westport’s Downtown Ambassador

Every Main Street landlord (and their tenant) is responsible for cleaning the sidewalk in front of their property.

Once a week, a town street sweeper clears the road.

That’s it.

If you’re wondering why parts of downtown look a bit grotty, there’s your answer.

But if you’ve noticed a change recently, there’s a reason.

Dylan Curran.

The 2020 Staples High School graduate is the first “Downtown Ambassador.” That’s the new position created by the Westport Downtown Association, in collaboration with the town’s Department of Human Services.

Since May, Dylan has been responsible for keeping Main Street clean. But he’s also the WDA’s public face, bringing smiles to shoppers and shop owners with his broad smile and optimistic attitude.

Dylan Curran: Looking good, while making Westport look good.

The project is part of Westport’s Employment is for Everyone” (E4E) program. A collaboration between the town and its Commission People with Disabilities, the goal is encourage and support local businesses to recruit, hire and advance people with disabilities, while creating a disability-friendly, inclusive culture throughout Westport.

The Downtown Ambassador program is funded by the Westport Downtown Association.

Every Monday and Friday, Dylan patrols Main Street. Armed with a bucket and trash stick, he gets right to work.

“It gives individuals a chance for employment, and there’s no better stage for that than downtown,” says WDA president Maxxwell Crowley.

“Everyone sees how hard-working, dedicated and personable someone like Dylan is, and how much he cares for the town. He’s already become a familiar face.”

From left: Westport Downtown Association president Maxx Crowley, Downtown Ambassador Dylan Curran, WDA operations employee Sean, and 1st Selectwoman Jen Tooker. She connected Crowley with Human Services director Elaine Daignault, for the E4E program.

The WDA might add another day to the schedule, and hire at least one more Downtown Ambassador.

“It’s a win-win-win,” Crowley says.

Main Street looks much better. Dylan has a job he enjoys. And everyone who sees the ambassador — working hard and smiling — smiles right back.

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25 responses to “Dylan Curran: Westport’s Downtown Ambassador

  1. Thank you Dylan~the BEST! 🌞

  2. Meredith Poster

    Great write-up about an amazing young man…he always has a smile on his face and is very friendly!!! The downtown ambassador will surely be a positive addition to downtown Westport!

  3. Dylan is a rock star! Every time I see him he is brimming with enthusiasm, grace, and kindness. We need more Dylans around town!!!

  4. Melissa Augeri

    Can’t imagine a better choice than Dylan to be an Ambassador. We are lucky to have him because he makes our world a better place.

  5. Debra Levin

    What a great article! Thank you Dylan and thank you for bringing a much needed smile to my face this morning. Westport downtown, let’s add another ambassador !

  6. Now everyone in downtown Westport will see what the Westport Book Shop has know for years — that Dylan Curran is a very capable, diligent, hard-working team member with a can-do attitude, who always has a smile and a pleasant word for our customers. Downtown Ambassador is a perfect title for you, Dylan! The Westport Book Shop is very proud of Dylan — and of all of our employees with differing abilities — who make meaningful contributions to our community and our quality of life every day.

  7. Ronnie Stanford

    Loved this article and this is the perfect role for Dylan! His amazing can-do spirit, friendly face and inspiring leadership will add so much more to our beautiful town – thank you, Dylan!!

  8. THE most beloved person in Westport! Dylan is THE BEST!!!

  9. Sal liccione

    Dylan is a great person he cares so much for Westport and everyone here he will do a wonderful job of anyone see his on the street say hi He will do anything for this town of Westport which he loves so much Great job Dylan I am here for you thanks max for doing this

  10. Maggie Dobbins

    Dylan makes everyone around him smile! I have seen him at Club 203 the last few years and he always makes a point to go to each person there and say hello. And give you a big wonderful hug once he knows you. An exceptional human!
    Well done to Westport for providing and supporting these opportunities.

  11. I want to expand upon my comment about the fabulous Dylan Curran. He has been on our Westport Winners Challenger baseball team since Day One in April 2013. He quickly rose to Co-Captain and then Asst. Coach this past spring. He is a mentor, a cheerleader, a friend to all, enthusiastic, helpful, a skilled baseball player and as I stated above, BELOVED! I’m so happy for his successes of which there are many!

  12. Nicholas Cody

    My family has known Dylan for a little over a decade, as my mom and brother brought the Challenger program to Westport. Dylan is one of the finest people we have ever met. His positive attitude is infectious and he’s never in a bad mood. He’s a great hitter and knows rock / metal music like the back of his hand! Everyone who has interacted with him loves him.

  13. Kathryn Turley-Sonne

    Dylan is the best! We are so lucky to have him representing the town that he loves. 🩵

  14. I appreciate Dylan’s work and believe Main Street
    has become such an appealing stroll. I do have a suggeston.
    Most of the other towns have stands with doggie bags. ( i.e.New Canaan). While, of course, most owners carry doggie bags
    there are times when we may be caught off guard, or out of towners are just not as respectful. I believe the Town should install these perhaps midway up the street.

  15. Even though I’m a few years older than him, Dylan is my hero! He’s the most popular guy in town and he always lifts everyone’s spirits. He cares so much about Westport and works extremely hard to make it such a great town. We’re so proud of you Dyl!

  16. Michael Calise

    Congratulations Dylan for a great undertaking. You are an inspiration for all who know you and your successes. Not only are you improving our downtown environment, but the results of your work will cause others to be more responsible.

  17. Who better than the wonderful Dylan Curran? He is sunshine personified.

  18. Tim Foisie

    Congratulations Dylan and thank you!

  19. Russ Considine

    Wonderful program! Thank you very much Dylan, GREAT work🙏

  20. Sharuna Mahesh

    Way to go, Dylan—our rockstar Downtown Ambassador! Kudos to the Westport Downtown Association for collaborating with Westport’s Employment is for Everyone (E4E) program!

  21. Diane Johnson

    Wise choice for a Downtown Ambassador; Dylan is so friendly and hard working! Way to go, Dylan!! An inspiration for us all to go above and beyond for our town and for each other!

  22. Donna ODonnell

    Clearly the best person for the job! Dylan is the greatest

  23. Mary Sikorski

    Dylan is a remarkable young man who embodies the true spirit of community service. He exudes contagious enthusiasm in all his endeavors! I’ve seen him helping out at the Westport Police Department as well the Westport Book Shop. I’ve had the privilege of watching his performances at the School of Rock and Little Barn as well as other venues. He is a fantastic musician! Thank you Dylan for all you do! You truly are an inspiration!

  24. Brian Sikorski

    To also embellish on my wife Mary’s comments while he was at Staples High School Dylan was a member of our 2017 and 2019 LL State Champion baseball team! His enthusiasm and spirit was a key component of our success. He was a great teammate!!!

  25. Andrew Colabella

    The right person to be ambassador and leader of Downtown Westport, Dylan Curran. Passionate, dedicated, always HAPPY.

    See you at Dodge-A-Cop Dylan🇺🇸. Proud of you 🤘🏻