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If you're going to look in Southport, I'd give Westport a look. While it's not as charming and bucolic as it used to be there are sections of town that are what you're looking for and much more convenient to the city than some of the other lovely towns being discussed.
If I were a city dweller looking for a summer home, it would be New Fairfield or Brookfield waterfront on Candlewood Lake, but thats just my taste, nothing like sitting on your back porch watching the boats on the lake, or taking yours out for cruise on the water
+1. The reason I recommended this before is, the huge majority of my friends who have summer homes within a 50 mile radius of New Milford are all right on the lake, be it on the New Milford side or another town. New Fairfield and Brookfield are also lovely towns, but NF in my experience tends to be rather uppity, especially come the summer months.
Definitely don't do Milford, I'm not sure why this keeps coming up. And to be honest, if you like Woodbury, I still think that Litchfield is rather akin but just better in ever aspect beyond distance to the train.
lots of options besides Ridgefield - Wilton, Weston, Westport, Southport/Fairfield, even Rowayton. I live in Weston and know that many are weekenders, live in the city and love the privacy and country feel.
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.
I am not looking for that either. Branford and Guilford are not the above. But they do have many creatives and have a laid back VERY friendly non Wall Street type of vibe. All of the towns in Fairfield County are going to have a competitive keeping up with the Jonses type of vibe. They are commuter towns into NYC. It seems like you want to get away from that. If you want that friendly laid back non competitve vibe you need to look outside Fairfield County.
I am originally from North Stamford and have hundreds of friends and relatives in Fairfield County.
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.
Before you decide on a town do this when it gets a little nicer out. Take a ride and spend some time in Guilford and the Pine Orchard section of Branford (which is adjacent to Guilford). When you go there you might think "a little further ride is worth it". Spend some time in the little village of Pine Orchard and in and around the Guilford Green then go down to the little beach and cove area where the kayakers are. I would love for you to see the Arts Fair the Guilford Art Center has on the green but that is in the summer.
As a whole, Litchfield is more homogeneous and more visually appealing than Woodbury.
It has a fair amount in common with Rhinebeck, and if OP didn't like the vibe in that community, I'd say there is a good 75%+ chance of not "feeling it" with Litchfield either.
urban vs suburban whatever, Jayct likes to speak of and yearns for the Fairfield of yesteryear when it was a quiet suburb of Bridgeports manufacturing heyday. That town is long gone and been replaced by transient families relocating in and out to commute to jobs further south (NY-Stamford), not very quaint and definitely has it's fair share of building/apartment/condo cluster.
End of the day, the coast is more dense, hectic wherever (what I like and prefer so not being biased), Sounds like a Ridgefield type would be more to your liking.
If your considering Southport, then also check out the Rowayton section of Norwalk, similar vibe and waterfront affluence but closer to NY.
Milford doesn't fit here, the chain store/restaurant capital of CT.
Sorry but I am not speaking of or yearning for Fairfield of the past. Suburbs have apartments and transient families. People commute to places further away. Like I said there are no high rise buildings and most neighborhoods have decent sized lots. I guess we just have to agree to disagree on this one.
I do think your suggestion of Rowayton is good. Since the OP is not concerned about schools it would be a good choice. Plus it has a train station for easy access into Manhattan. The only thing is if you think Fairfield is a city then Norwalk, where Rowayton us located, would be considered a big city since it is much larger than Fairfield, has high rise buildings and a lot more traffic. And Norwalk has a lot of chain stores and restaurants. Likely as many as Milford which you dismiss. Still Rowayton may be an option depending on the OP's budget since it can be pricey. Jay
Sorry but I am not speaking of or yearning for Fairfield of the past. Suburbs have apartments and transient families. People commute to places further away. Like I said there are no high rise buildings and most neighborhoods have decent sized lots. I guess we just have to agree to disagree on this one.
I do think your suggestion of Rowayton is good. Since the OP is not concerned about schools it would be a good choice. Plus it has a train station for easy access into Manhattan. The only thing is if you think Fairfield is a city then Norwalk, where Rowayton us located, would be considered a big city since it is much larger than Fairfield, has high rise buildings and a lot more traffic. And Norwalk has a lot of chain stores and restaurants. Likely as many as Milford which you dismiss. Still Rowayton may be an option depending on the OP's budget since it can be pricey. Jay
Has nothing to do with agreeing or disagreeing. I think someone who lives and works in the area fulltime opinion carries a lot more weight than someone who lives in the Hartford area. There are decent sized lots in all towns/cities along the coast, but per the OP paragraph in post #11, I think a Ridgefield/Litchfield type would suit better. What I said was not a knock, just the way it is. You really dont need to defend and knitpick every perceived (on your end) negative post on here all the time. 85K population vs 60K, 1 high rise vs 0 - whatever!!
Traffic - come down one day and try and get thru downtown Post Rd Fairfield or I95 during rush hour.
There are no national chain resteraunts in neither Fair or Norw (Applebys, Chilis, Cheesecake,etc)
I think Jay (who still has connections and deep roots in Fairfield) has a pretty accurate view of Fairfield. That being said, the OP is looking for quaint. While many shoreline towns are very nice, I'd argue most aren't "quaint", with maybe the exception of Southport. They are all fairly fast paced, energy-hungry suburbs of New York. I think we've given the OP a good starting point. Now they'll have to visit to see which towns are to their liking.
This continues to be a fascinating thread chock full of info and a wide variety of suggestions. Thanks to all for chiming in!!
For whatever it is worth, my budget is $1.5 - 2M for a min. 4BR antique house with a pool (ideally, with a guest cottage or 5th BR for in-laws) on an acre. That is blue skies.
Yes, we want quaint and charming with character. Yes, we want some activity and flavor and culture. Yes, we want family-friendly. No to high rises and lots of condos. Don't mind chains as long as they are not in village center. Preferably tucked away or a town away.
For context in a different locale, we love Sag Harbor but can't stand the attitude/sense of entitlement of the majority of Hamptons seasonal inhabitants (generally speaking). Sag Harbor is a walkable village with a Main Street that stretches a few blocks and is largely comprised of mom & pop indie stores (along with Calypso but nothing's perfect). There is a terrific art house cinema and also a theatre presenting plays, concerts, etc. I'd estimate there are ten restaurants, as well as pizza, tavern, and burger joint.
Sag Harbor is roughly 2,500 population year-round but grows to at least 4K in the summer, not including scores of daytrippers and visitors that easily push it to 10K on weekends. East Hampton jumps from 15k to 70k. So we are no strangers to traffic given the proportion of people to the small confines of the village. The torture of commuting on the LIE is self-explanatory. That said. I can zip out there in 2 hrs flat off-peak and there is also bus and train service which is convenient. As I said, it would be helpful to jump on a train to CT but with change comes adjustments and if that means no train then so be it. I mean, hell, this is obviously a fabulous problem to have so not complaining.
Having been seaside in Sag Harbor, it sounds like Rowayton and Southport would be feel very comfortable for us. Of course, I am concerned about being just 45 min or so from NYC (i.e. Rowayton) as that qualifies as a commuter town which stands in contrast to a getaway refuge for us. And the taxes in Rowayton are very high compared to Ridgefield. Again, I am oversimplifying, but you get my gist. Will still check them all out. Westport strikes me as just too suburban despite it seeming phenomenal for that particular category. If I were relocating full-time, then I would take a look but I don't think it is for us as weekenders/summer residents.
Guilford sounds pretty awesome and possibly worth going the extra mile(s).
Staying inland as opposed to water is strong option which is why we first took a shine to Ridgefield. Slightly rural with a historic, bucolic vibe struck a chord. We'll do a deep dive into Weston while we're at it. We will also explore Lichtfield. What are the best towns around Candlewood Lake? I am assuming New Fairfield and New Milford? How far is the drive from water to village?
Did I say "thank you" yet to you guys?!?!?!
Last edited by lazylghtng; 01-10-2016 at 08:24 AM..
This continues to be a fascinating thread chock full of info and a wide variety of suggestions. Thanks to all for chiming in!!
For whatever it is worth, my budget is $1.5 - 2M for a min. 4BR antique house with a pool (ideally, with a guest cottage or 5th BR for in-laws) on an acre. That is blue skies.
Yes, we want quaint and charming with character. Yes, we want some activity and flavor and culture. Yes, we want family-friendly. No to high rises and lots of condos. Don't mind chains as long as they are not in village center. Preferably tucked away or a town away.
For context in a different locale, we love Sag Harbor but can't stand the attitude/sense of entitlement of the majority of Hamptons seasonal inhabitants (generally speaking). Sag Harbor is a walkable village with a Main Street that stretches a few blocks and is largely comprised of mom & pop indie stores (along with Calypso but nothing's perfect). There is a terrific art house cinema and also a theatre presenting plays, concerts, etc. I'd estimate there are ten restaurants, as well as pizza, tavern, and burger joint.
Sag Harbor is roughly 2,500 population year-round but grows to at least 4K in the summer, not including scores of daytrippers and visitors that easily push it to 10K on weekends. East Hampton jumps from 15k to 70k. So we are no strangers to traffic given the proportion of people to the small confines of the village. The torture of commuting on the LIE is self-explanatory. That said. I can zip out there in 2 hrs flat off-peak and there is also bus and train service which is convenient. As I said, it would be helpful to jump on a train to CT but with change comes adjustments and if that means no train then so be it. I mean, hell, this is obviously a fabulous problem to have so not complaining.
Having been seaside in Sag Harbor, it sounds like Rowayton and Southport would be feel very comfortable for us. Of course, I am concerned about being just 45 min or so from NYC (i.e. Rowayton) as that qualifies as a commuter town which stands in contrast to a getaway refuge for us. And the taxes in Rowayton are very high compared to Ridgefield. Again, I am oversimplifying, but you get my gist. Will still check them all out. Westport strikes me as just too suburban despite it seeming phenomenal for that particular category. If I were relocating full-time, then I would take a look but I don't think it is for us as weekenders/summer residents.
Guilford sounds pretty awesome and possibly worth going the extra mile(s).
Staying inland as opposed to water is strong option which is why we first took a shine to Ridgefield. Slightly rural with a historic, bucolic vibe struck a chord. We'll do a deep dive into Weston while we're at it. We will also explore Lichtfield. What are the best towns around Candlewood Lake? I am assuming New Fairfield and New Milford? How far is the drive from water to village?
Did I say "thank you" yet to you guys?!?!?!
If you like Sag Harbor....definitely look into Southport...
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