[lazylghtng]

Hi Folks,

Don't hate on me. Brooklyn resident, here, and counting my blessings that I am lucky enough to be able to purchase a second home right now for year-round use. We have two kids (5 & 9) and neither is overscheduled or actively involved in sports leagues, thus weekends are relatively free. Taking a serious look at Ridgefield since it seems to check off all of our boxes which include:

- quaint/lovely village with a good pulse
- arts scene/cultural activities
- not too stuffy (we work in the arts/entertainment)
- antique/historical homes
- hospitable community (we are coming in cold!)
- good day camps for kids in summer
- within two hr drive of Brooklyn
- reasonably close to train station
- just enough country where it does not feel too "suburban"

We are also taking a look at Katonah and S. Salem area (although S. Salem's "town" obviously does not compare to R'field). I am curious about Fairfield if anyone can compare/contrast with R'field? Also don't know anything about nearby Wilton and Redding et al.

Definitely NOT interested in Greenwich, Darien, New Canaan, etc.!!!

Know nothing about Madison/Guildord nor the Lichfield towns like Washington or Sharon.

Generally speaking, trying to avoid any EXTREME sense of entitlement which is all relative, of course. And, yes, I know Ridgefield has lots of money ... and SUVs, etc. That's fine, we totally get it and can handle some element of that. Honestly, I also have some dough, too...and an SUV (although I'm not an a-hole who thumbs my nose at others). Again, we're somewhat desensitized to that stuff given that we live in present-day Brooklyn but we're certainly not looking to up the ante (i.e. the Hamptons...yuck).

FYI - we considered Rhinebeck and Cold Spring before settling upon Ridgefield. Rhinebeck is gorgeous but a bit too haughty/pompous (from afar). Neither Hudson or Woodstock very appealing to us. Love, love Cold Spring but have friends near Ridgefield so staying in that neck of woods is preferable. Ditto with Irvington and the "river towns" in Westchester. Taxes in CT also friendlier.

As for price, we are fortunate enough to have plenty of wiggle room. Not looking to buy an estate in Greenwich, but we're in good shape. As far as lot size, an acre is great. Again, commute to NYC is not a make-or-break as long as there is train service within 10-15 min (wife and kids will be spending time in summer and I will be doing some back & forth). Schools inconsequential as this is 2nd home.

One last point. Although we have plenty of excitement here in Brooklyn, we are not looking for 10 acres of solitude and a sleepy town to counter our urban angst. We would like to find a community that is alive and proud with a charming, walkable village with amenities and a handful of restaurants. So maybe Ridgefield is the needle in the haystack. Or maybe there are others not on my radar?

if you made it this far, thank you. Really.

[BPt111]

Fairfield, Madison, Guilford

[BicoastalAnn]

How about Westport? It's more expensive than Ridgefield but I think it's a little easier to commute to NYC while you're doing the back-and-forth, plus you get the beautiful coastline, cute town feel (by the train station), and the more woodsy, remote areas in close distance.

I do love Ridgefield, though, for its pleasantness and relative inexpensiveness compared to the other "lily-white" towns in the area - the only thing I could fault it is it's kind of a pain to get to the city. this is relative, but if you're in brooklyn now the difference might be unpleasant.

[CTartist]

Originally Posted by lazylghtng

Hi Folks,

Don't hate on me. Brooklyn resident, here, and counting my blessings that I am lucky enough to be able to purchase a second home right now for year-round use. We have two kids (5 & 9) and neither is overscheduled or actively involved in sports leagues, thus weekends are relatively free. Taking a serious look at Ridgefield since it seems to check off all of our boxes which include:

- quaint/lovely village with a good pulse
- arts scene/cultural activities
- not too stuffy (we work in the arts/entertainment)
- antique/historical homes
- hospitable community (we are coming in cold!)
- good day camps for kids in summer
- within two hr drive of Brooklyn
- reasonably close to train station
- just enough country where it does not feel too "suburban"

I know my suggestion is a little further away but take a look at Guilford. I am an artist and musician that lives in Trumbull (Fairfield County). Rather than moving down south in retirement I want to stay in CT because I want to be in a more "artsy" area and have access to NYC by train so I can go in 2 to 4 times a month. I have been looking into Branford, Guilford and Madison. I think Guilford would tick a lot of your boxes. The Pine Orchard section of Branford on the water might be a good place for you too.

"not too stuffy (we work in the arts/entertainment)"
I would not look in Ridgefield with that criteria. Sorry Ridgefield, but this creative is telling it like it is.

[BPt111]

Originally Posted by CTartist

I know my suggestion is a little further away but take a look at Guilford. I am an artist and musician that lives in Trumbull (Fairfield County). Rather than moving down south in retirement I want to stay in CT because I want to be in a more "artsy" area and have access to NYC by train so I can go in 2 to 4 times a month. I have been looking into Branford, Guilford and Madison. I think Guilford would tick a lot of your boxes. The Pine Orchard section of Branford on the water might be a good place for you too.

"not too stuffy (we work in the arts/entertainment)"
I would not look in Ridgefield with that criteria. Sorry Ridgefield, but this creative is telling it like it is.

Monroe will work too.

[beerisgood02]

Originally Posted by BicoastalAnn

How about Westport? It's more expensive than Ridgefield but I think it's a little easier to commute to NYC while you're doing the back-and-forth, plus you get the beautiful coastline, cute town feel (by the train station), and the more woodsy, remote areas in close distance.

I do love Ridgefield, though, for its pleasantness and relative inexpensiveness compared to the other "lily-white" towns in the area - the only thing I could fault it is it's kind of a pain to get to the city. this is relative, but if you're in brooklyn now the difference might be unpleasant.

I second this. Westport also has the music pavilion with summer concerts every other day, earth place, wakeman town farm, and possibly the best town pool on the eastern seaboard with it being right on the sound.

[lazylghtng]

Thanks for promt responses! Much appreciated. Guilford and Madison are too far. It would take me 2.5 hrs to drive and that's w/o traffic so that's a deal-breaker. In terms of "creative," let me just qualify that by saying that I'm not looking for an artist's colony, or a neighborhood where all the moms have tatts and the dads are rocking hipster 'staches! In other words, I'm less concerned with the cover than the book that lies within. Again, looking to avoid the hedge fund mngrs and that elk (if I must generalize), but don't have issues with old-fashioned tastes. I would much rather hang out with my kids on Main Street USA in Disney World than fart around Aspen.

[beerisgood02]

Originally Posted by lazylghtng

Thanks for promt responses! Much appreciated. Guilford and Madison are too far. It would take me 2.5 hrs to drive and that's w/o traffic so that's a deal-breaker. In terms of "creative," let me just qualify that by saying that I'm not looking for an artist's colony, or a neighborhood where all the moms have tatts and the dads are rocking hipster 'staches! In other words, I'm less concerned with the cover than the book that lies within. Again, looking to avoid the hedge fund mngrs and that elk (if I must generalize), but don't have issues with old-fashioned tastes. I would much rather hang out with my kids on Main Street USA in Disney World than fart around Aspen.

Westport is well-known for its artists.

[Raider111]

Sounds like Ridgefield, Wilton, and Westport would all fit nicely, albeit Wilton has a much smaller downtown, but the others can be a short drive. Westport will be much more congested along the Post Rd, but the downtown/riverfront can't be beat on a warm summer evening with the Levitt mentioned by beerlover. There is a walkway behind some commercial buildings along Riverside ave over the bridge where you frequently see artists painting the riverscape on canvas.
Redding, Weston, and Easton are very rural with little to no commerce.
Outside of the Greenfield Hill section (and too far from NYC), Fairfield is basically a city in comparison, much more dense - urban/suburban.

[mlassoff]

You'll find a fairly equal ratio of good to crappy people in both Ridgefield and Westport, IMO.

I think you have to visit both towns and see which you like the character of more. You won't see many tats or Hipster 'staches in either place.... Not nearly as many as you would in Brooklyn, anyway. Westport provides a nice family atmosphere town beaches and more to do. More restaurants, more events, concerts, etc.

Ridgefield will be more peaceful and rural and significantly less expensive.

I think you can make a lovely weekend home in either place. Westport will be the slightly more convenient commute most days.

If you fall in love with Fairfield County and decide to abandon Brooklyn all together you'll be pleased to know that both towns have some of the best schools in the country and that private school is hardly necessary-- or even desirable for most families.

Good luck in your search!