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While Trader Joe's likes to be in "upscale" communities, they prefer to be in more densely populated suburban areas, that's why locally you find them further south in places like Hartsdale, Larchmont, and Eastchester/Scarsdale. There are many smaller but still substantially populated metro areas that have only one Trader Joe's in the whole area.
If they were ever to open one in Northern Westchester, it would likely be either in Mt. Kisco or on the 117 strip in Bedford Hills, or further north and west either near Peekskill or along Rt. 6 or 202 between Peekskill and Yorktown Heights (or perhaps in the center of Yorktown on 118). Probably not in Chappaqua itself.
It would be nice to get a TJ's or Whole Foods in the Borders space in Mt. Kisco. I go to the Shop Rite or the old A&P in Millwood for a quick run and to the AP Fresh next to Target in Mt Kisco for full shopping. None of this seems like a punishing inconvenience - it's all within a 15 min drive (which is less than what I was used to doing in Los Angeles before moving here anyway). I wouldn't judge a community based on not being able to walk to a grocery store. Chappaqua Market has (expensive) basics if we need something in a pinch.
Why did D'Agostino's come to Chappaqua in the first place? Does Walgreens sound like a better fit? Could be.
I think any retailer should come to Chappaqua only if it makes sense commercially and they want to. Nobody should open a store only because local people think they should
But the question is - WHY isn't there a market to begin with, despite the fact that D'Agostino's operated from there, the location was accessible from at least 3 affluent communities, no competition within a 20 minute radius? Your reply doesn't answer the question.
I've heard there were landlord issues with the Dags location in terms of work/updates needing to be done and the overall terms of the lease. I guess Walgreen's had fewer concerns.
On the other hand, the Chappaqua Crossing people are all too eager to get tenants in there including in the form of lame strip mall stores along with the grocery store, which the majority of the community is vehemently against.
Back in Queens, I would see Latinos buy loads of stuff from COSTCO and BJs (the rotisserie chicken is a popular item) for resale. Never got to ask them how they redistribute. Could be a good opportunity to put some of those Escalades to work and pick up stuff from WF in Yonkers to haul back to New Castle!
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