Since 2005: More than you really want to know about Wellesley, Mass.
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You are invited to explore the shops, restaurants, people, stories, and experiences that make Wellesley Square such a distinctive destination. Multiple local businesses are bringing Discover Wellesley to life in their own ways. Free two-hour meter parking, thanks to the Town of Wellesley.
The Wellesley Police Department this week presented a proposed change to the town’s parking enforcement and citation management system that the Select Board approved (see discussion starting at about 18 minutes into Wellesley Media recording of May 19 meeting).
Lt. Michael Lemenager made the case for consolidating services with Passport Parking and moving away from an intergovernmental agreement with Plymouth County Parking.
A brief mutual admiration society meeting ensued: Lemenager had good things to say about the Plymouth County system in use here since 2023, and Plymouth County Treasurer Tom O’Brien had nice things to say about the Wellesley Police Department. But in the end, Lemenager said Wellesley was looking to consolidate its systems to improve operations, adopt more modern technology, and sync up with planned amenities improvements in Wellesley Square.
The department had run into incompatibilities between systems that resulted in bogus tickets for some people who had in fact paid for parking.
Wellesley had previously employed Passport technology for parking enforcement and citation management after the vendor used by the town was acquired some years ago by Passport. Customer service fell off during that transition, so the town switched to the Plymouth County system in 2023. (Wellesley has continued to use Passport for one of its mobile parking platforms.)
Lemenager spoke of the Traffic & Parking Division already increasing parking enforcement efficiency in part thanks to Wellesley’s move to more online permitting. This has enabled parking enforcement personnel to spend less time monitoring parking lots and more time on the streets doing meter enforcement, watching for turnover in the commercial shopping districts and laggards at limited time spaces on side streets (yup, that party could be over for shoppers who currently avoid meters and overstay on side streets).
“Overall the goal here is to continue to modernize parking operations… and switching to the Passport platform I believe is going to give us the tools and resources we need to do that,” he said.
Asked about a difference in cost between the systems, Lemenager cited a $500 monthly fee, but no transition cost.
The process for paying for parking remains the same, though paying for tickets would now go through the Passport rather than Plymouth County system.
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SPONSORED CONTENT: Wellesley in Bloom kicked off last weekend and is still alive with a celebration of spring. The town-wide event features floral fun, pop-up experiences, and creative collaborations throughout Wellesley’s shopping areas. The idea simple and fun—Wellesley in Bloom invites everyone to stroll through town and discover unexpected moments of beauty, creativity, and local charm.
We bopped around town over the weekend to enjoy the energy In Bloom brought to town.
Wellesley in Bloom continues through Mothers Day (May 10th) with more pop-ups and special events. Here are just a few:
The Cottage—Celebrate the season with a fresh new spring menu, featuring dishes created by Chef Michael Tondorf, formerly of Riva and Hook & Harvest on the South Shore.
Down Under School of Yoga
London Harness & TUMI—May 7-10, free gift with purchase of any handbag of $200 or more. Gift with purchase options include cosmetic cases and zipper pouches by MZ Wallace (value: $65.00).
Sara Campbell, floral-inspired fashion and styling experiences.
About Wellesley in Bloom
Funded by a state grant, the purpose of Wellesley in Bloom is to hold an event that creates a positive community experience and fosters business collaborations.
A rafter of wild turkeys was seen by a reader over the weekend at the Crest Road door for Faber Rug in Wellesley Square.
Perhaps the birds were looking for a runner or carpet square to accentuate a nest?
They had to be content with window shopping: The store is closed on Sundays…
More:
Wellesley RDF turkeys get their beauty sleep
A Wellesley Lower Falls Adventure for Bob the Turkey
See something? Send something: theswellesleyreport@gmail.com
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SPONSORED CONTENT: The most wonderful time of the year is here, and with it comes the delightful, yet sometimes daunting, task of finding the perfect gifts. Forget the stress—our curated 2025 Holiday Gift Guide is packed with unique, thoughtful, and desirable presents to bring the holiday spirit to all.
More local shopping options
Another wonderful Wellesley Marketplace is in the books, and its safe to say that the 200 vendors, 2,000+ shoppers, and 99 Wellesley Hills Junior Women’s Club members ended the day exhausted but happy. From setting up Wellesley High School the day before last month’s event, to seven hours of intense buying and selling, to the final 9pm wrap-up, the 47th Marketplace was a wild 36-hour ride.
Best support staff as cited by the Chairs in a social media post—hands down “Wellesley High School and their truly wonderful custodians! Couldn’t do it without their support. It takes a village!”
Best comment overheard by a vendor—”I meet more customers face-to-face on this one day than I do all year. It’s awesome.”
The yearly fundraiser draws so many vendors and loyal shoppers two ways. First, the Marketplace committee is discerning. The juried show draws a hand-picked cohort of creative artisans, boutique owners, and craftspeople from across New England. Second, the Juniors are a collective organizing powerhouse of epic proportions. If they ever want to add another major event to their roster, a “How to Harness your Inner (but latent) Executive Functioning Skills” seminar would draw a solid crowd.
Or they might just stick with Marketplace, the Kitchen and Home Tour (May 2, 2026), and the Wonder Run 5k & Kids Fun Run (May 17, 2026).
