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Unread 05-16-2014, 04:48 PM   #1
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Fairfield Connecticut- The Setting for "Who's the Boss?"

While the house used in the exterior shots is in Rye, New York and "Oak Hills Drive" appears to be a made up neighborhood/ street in Fairfield; the real town where "Who's the Boss?" supposedly took place is a perfect match for the sitcom. It's a beautiful and historic, picturesque community that you would expect the Bowers to live in. You can also clearly see why Tony would want to move his daughter there. It's truly an upscale community with a small town feel at the same time. A lot of well-to-do people really do live there. Colonial mansions are a common sight; which makes Angela Bower's home fit right in. It's very clean and suburban and boasts the best public school system in Connecticut. They also were voted the best place to live in the northeastern US in 2006. Although "Oak Hills Drive" doesn't exist; you can see the similarities between the fictitious "Oak Hills Drive" and real well-to-do Fairfield neighborhood, Greenfield Hill. I have no idea why they didn't just claim that the house was in Greenfield Hill; but, who knows why writers make up streets. I guess we could assume that Oak Hills Drive is a street in the Greenfield Hill community. They apparently knew quite a bit about the area when writing the show; because, they captured some things accurately. The type of house used in the series along with the scenery and the show's overall feel/aura were very accurate to Fairfield. When looking at Fairfield's website and the many pieces of information about the town; you feel almost as if you might run into the Bowers and Micellis out for a stroll somewhere. With a population of 59,404 as of 2010; you can see why there is a close knit/ small town feel in Fairfield. It's very convenient as there are now four operating train stations; if I'm not mistaken, for commuters to New York City. So; you can work in the crowded metropolis of New York City just like Angela Bower did and then come home to your quiet small town with safer streets in the evening. I now want to visit Fairfield after reading about it. There are quiet a few historic attractions to see among other things. It looks like a great place to spend a short vacation or weekend. It's no surprise that New England's best place to live would also be the home of "Who's the Boss?"!

Below are some links to check out:

Rawleys Drive In- Nothing says small town charm better than an old fashioned drive in/ hamburger and hotdog stand. And Rawleys has the best hotdogs in CT. The deep fry them first before putting them on the grill. Sound strange.? Apparently; it's delicious... There is a twenty minute wait on average. I can see Samantha going on dates here. http://www.hollyeats.com/Rawleys.htm


Official Town Website: http://www.fairfieldct.org/

The historic Greenfield Hill Church- Be sure and read up on the annual Dogwood festival:

An example of the real estate in Greenfield Hill- A very eerily familiar looking old mansion... You should click on street view to view a great old stone fence! I wonder if Angela decided to sell. This house actually looks closer to being accurate to the show's set than the Rye New York house- http://www.zillow.com/homedetails/47...58784152_zpid/

One of the many local papers- "The Fairfield Minuteman"- http://minutemannewscenter.com/

The Fairfield Theater- a cultural hub for the community- http://fairfieldtheatre.org/

Fairfield Community Theater-

Fairfield University

There is more;but, I have to leave for now.

A Real Estate video about the area

Rawleys: http://www.youtube.com/watch?v=xyMiJ4MApf8
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Unread 05-17-2014, 12:24 PM   #2
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Here we find another colonial that looks more accurate to the show's set than the Rye House. On the outside it does anyway. Once you get on the inside; you realize; that, with any of these houses, a three camera sitcom set; which is set up like a live theater stage, would never be proportionally accurate to a real house unless you designed the house around it. That would make an interesting study in design. How could you make various sitcom sets fit into their exterior shot counterparts?

Why they didn't use exterior shots of an actual colonial in Fairfield ( which there are many) I'll never know. However; the Rye New York house has become so iconic and such apart of the show; I can't imagine nay other house being used.

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Unread 05-17-2014, 12:34 PM   #3
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Another very accurate exterior. And naturally, the interior is not even close. As I mentioned above; it's almost impossible to fit sitcom sets into their exterior counterparts. You have to use some imagination and just forget about specific detail. After all; it is a work of fiction!

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Unread 05-20-2014, 12:05 PM   #4
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Really neat info, SitcomJon! Thanks for finding all that and sharing. I have a picture somewhere of me in front of the house in Rye. Even though it's not actually in Fairfield (which does sound like a lovely place), it was very cool to see it person.
Robin C.

Angela: You would ruin our friendship for love?

Tony: In a second. I'd throw it in the garbage. I'd spit on it. I'd flush it down the toilet.

Angela: (Touched) Oh, Tony, that is so beautiful.
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Unread 05-24-2014, 09:06 PM   #5
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I took the train from NYC to Fairfield once about 5 years ago....very nice, calm, upscale, yet homey. I had coffee & a cookie at what used to be the old Firehouse.
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