After speaking with a few departments, here is what I was told:
“PEAK HOURS”
The traffic signals between Hartford and Westwood Glen, are synchronized to give priority to the High Street during the AM and PM commute. Vehicles that exit Gay, Hartford, Barlow/Westwood Glen do have to wait extended periods before they are given green. Windsor/Library is not synched as it is too close to the Gay St intersection.

“OFF PEAK HOURS”
During off peak hours, all signals run independently and you could have a red light at each intersection, by chance.
Activation of pedestrian signals and the opticon (emergency vehicles) can interrupt the synch for one cycle.

The timing has been adjusted in the past and has been the topic of discussion since installed in the early 2000’s. We can look into whether any further tweaking can be done.

I do not believe that the lights are synchronized to work together to provide priority to the High Street traffic. Often times one of these lights will turn green allowing High St. traffic to flow and almost immediately the next light turns red stopping the High St. traffic.

We had our on-call technicians come out to check the timings of all intersections along High Street. They have confirmed that all is working properly, outside a few minor issues with pedestrian signals that is being addressed. Please let us know if you have any further questions.

Thanks for fixing this issue!

Hi, I very much appreciate the followup.
However, the following statement in your response does not seem to be logical "Windsor/Library is not synched as it is too close to the Gay St intersection." The fact that it is too close to the Gay St. Intersection is exactly the reason I think it should be synched with the Gay St. intersection. Often times the Gay St. intersection signal will be green for the east/west travel on Rt. 109 and the Windsor/Library signal will be red which stops all traffic on rt 109.
What am I missing?

To allow the “block” of traffic to flow between the three synched intersections there is a time period at which each of the signals is green, as the block progresses east or west. If Gay was green and there was a car waiting at the library that caused the signal to trip to red, that happened independent of the synched flow. If we added the Library/Windsor to the synced group, then there would be more times when Gay is green and Windsor/Library is red, causing the same problem. If you have further questions, please contact the Town Engineer for follow-up.

Why can't the light at Windsor be green when the light at Gay is red and when the light at Gay is green then the light at Windsor is red? That would keep the traffic on High Street moving and also give the Windsor traffic the opportunity to enter High Street.
It seems having a light at Windsor is problematic as to its proximity to the Gay Street traffic signal.

Please contact the Town Engineer for follow-up.

Thanks for fixing this issue!