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High Side Project Nears the Finish Line as Holidays Approach

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Estimated time to read:

2–3 minutes

I have been a vocal sup­port­er of the so-called High Side project since it was first pro­posed. Once con­struc­tion final­ly start­ed in late April, it has been a slow, often painful expe­ri­ence for down­town shop­pers, and par­tic­u­lar­ly for busi­ness owners. 

But over the last month or so, as work final­ly start­ed to wind down and the final prod­uct began to take shape, I have seen a much more pos­i­tive vibe down­town. Now that folks can see what the fin­ished project looks like, it seems a new opti­mism and excite­ment are swirling about on Main Street. 

This after­noon, I took a walk down­town and also viewed the progress from the roof of our office in the his­toric McEldowney Building. Although much of the hard­scape has been in place for months, it seems the final touches—particularly the beau­ti­ful black-iron railings—are what bring it all to life for me.

Sidewalk level view of one of the brick-paved patios that now adorn the high side of Main Street on Nov. 13, 2025.
Sidewalk lev­el view of one of the brick-paved patios that now adorn the high side of Main Street on Nov. 13, 2025. Note the beau­ti­ful iron railings. 

It was touch-and-go on Main Street today as the street was being black­topped. The street was closed in seg­ments while inter­sec­tions were paved. Paving should be fin­ished this after­noon or tomorrow. 


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According to the lat­est update from the city, the final brick­work will take place ear­ly next week, along with the remain­ing strip­ing, includ­ing park­ing spaces and direc­tion­al arrows.

Next will come the final touch­es: new trash cans, bench­es, and flower box­es. Although not stat­ed in the update, I assume this will also include rein­stalling the white globes on the dec­o­ra­tive lamp posts and relight­ing them, as well as installing dec­o­ra­tive cov­ers for the drain pipes in the high side walls. 

The city says at least one lane of Main Street will be open at all times tomor­row as strip­ing takes place, though it appears the yel­low strip­ing has already been com­plet­ed. Parking spaces and direc­tion­al arrows will be paint­ed next week. 

Aerial view of Main Street looking South on Thursday, Nov. 13.
Aerial view of Main Street look­ing South on Thursday, Nov. 13. 

The final step will be cre­at­ing a punch list of things that need to be cor­rect­ed or com­plet­ed. Assuming that goes well, the project is expect­ed to be com­plet­ed by December 1, just in time for the Christmas parade and hol­i­day shop­ping. Won’t that be nice? 

Until then, know that down­town is still open and easy pedes­tri­an access is avail­able to all shops on Main Street. Tomorrow and Saturday, down­town will host the Holiday Open House. Many mer­chants are offer­ing sales, spe­cial events, and more this weekend. 

This event kicks off the hol­i­day shop­ping sea­son, which many down­town shop­keep­ers rely on to turn a profit—some stores gen­er­ate half or more of their annu­al rev­enue dur­ing the weeks lead­ing up to Christmas. Let’s turn out and sup­port them; they have endured a rough year for the sake of their own liveli­hoods and for our town. 

Aerial view of  the North end of the high side of Main Street on Thursday, Nov. 13.
Aerial view of the North end of the high side of Main Street on Thursday, Nov. 13. 
Downtown Winchester Holiday Open House: Friday-Saturday, Nov. 14-15.
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