You'll love it. Great area. Tons of riding. I don't know the running in Armonk, but there are great parks and trails all over Westchester. Tarrytown/Pocantico Hills has some of the absolute best running in the entire world; Khalid Khannouchi chose to live there during his prime years (still does and still quite a few elite marathoners) at the Rockefeller State Park.

I think there are more swim groups now than there were when I was there, but I know there are plenty. I'm sure the White Plains Y has a master's group. Plus lots of open water swim options between LI Sound and various lakes over the summer.

The road quality is getting worse, which is a shame, because I find that is the real danger with riding. But in total, it's really one of the best places in the world to live and train.

Armonk is wonderful. Rye is a great area for riding and close access to the city if you want to go further South. Tarrytown is my personal favorite area because of access to the Rockefeller trails and also you're right on the Hudson line so 35min via express train to NYC.

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"Non est ad astra mollis e terris via." - Seneca | rappstar.com | FB - Rappstar Racing | IG - @jordanrapp

Well - the areas around NYC, including NJ and CT are terrible. High taxes, expensive real estate, about as left as you can get in terms of politics, very crowded roads that are in poor shape, terrible gun laws, etc. However, you are near the center of the business world (NYC) so you can make enough money to deal with the crap.

45 mile drive on the highway can easily take 3 hours on a Thursday or Friday afternoon.

Good luck.....

Biased much? Pretty negative assessment there overall... I'm in stamford, ct so not exactly westchester but close. My 0.02:

1. Yes, many of the NY roads stink, but they ain't all bad. I ride a lot in Bedford and pound ridge, and up to waccabuc, theyre close to armonk, some great roads there (rt 121 is a personal fav). But if you go south from armonk you get into the roads of greenwich and north stamford ct which are very very good. Well maintained and good to great pavement quality. Riversville, round hill, stanwich rds are all excellent and are staples of my usual routes.
Check those out . And all the other back roads among the gigantic mansions make for fun and scenic riding on quiet roads. Lots of short steep hills around here. PM me if you wanna talk more about riding routes and roads to try out.

2. NJ - why go there when you have NY and CT. I can agree on that point.

3. 45 min drive taking 3 hours is an overstatement. Long Island has the worst traffic, if you were going there that statement may be true. Sure driving literally into nyc you'll have traffic (not usually 2+hr delays on short trips barring serious incidents) but just getting around armonk or wchester on 684 or Taconic parkway? I don't think so.

4. Swimming-only thing I'll say is most of the lakes you see on maps in those areas are reservoirs for NYC water supply and recreation is very limited, perhaps downright prohibited. Down on LI sound there are OWS opportunities but that's about all I know. Perhaps someone else can chime in on that.

5. I love it here. Yes cost of living is high but such is life, it's a nice area with great access to nyc. Within 10 miles or less of armonk center on a map you have access to harlem and new haven line stations of metro north RR. Looks about 6 miles to Pleasantville station on harlem line. Nice.

Thanks for unbiased reply on where I'm committed on moving to. :)

Any tips on swimming in Stamford? Hoping to find a masters program. Majority of people at the soon to be work place reside in Greenwich/Stamford. Seems like a great area considering the income tax distribution as well.

I'm not masters material when it comes to swimming haha, sorry I cannot be of further assistance there since I have no knowledge! LA fitness gyms and Y's with pools are plentiful (I just scoot over to LA fitness, happens to be less than a mile away for me), there are also other aquatics clubs and the chelsea piers facility in stamford, they may have something. Im sure greenwich has some dedicated groups. Also, there's a group that hosts open water swim events at tods point in greenwich point park, that could be a link to some more dedicated swim groups, perhaps googling some of those things can get you some info.

In Darien - Just being honest. Try getting from LGA or NYC to Darien on a Thursday or Friday afternoon - easily 3 hours. A early morning commute is 45 minutes.

Add a little rain to any other time of day and traffic is terrible.

To the O.P.

Pools - there are plenty in Fairfield county - just pick a YMCA.

Report back next year and let us know which you prefer (mid-West or the greater NYC area)

Haha nice, Darien has good roads too, good town. Sorry but I have to ask - do you have to do that drive often? Drives along 95 all way from darien to nyc at peak hours...now I see where you're coming from, but I wouldn't call that a "normal" drive since you could be taking trains that take half the time. I thought you meant like a Sunday trip to the grocery store gets delayed by 2+ hours, haha.

Eneas Freyre and the group at TT Endurance would be a great resource for Stamford-area stuff. They may be the ones running the OW swims in LI Sound there - http://ttendurance.com/

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"Non est ad astra mollis e terris via." - Seneca | rappstar.com | FB - Rappstar Racing | IG - @jordanrapp

Greatly appricted for the help, Jordan.

Thank you!

The rides up towards Bedford are some solid options as well; head out towards North Salem for some good routes. If you want to head offroad, Mianus River Park has some good biking/running trails. As for swimming, most of the local Ys have Masters programs.

Every time I get back there I make sure to hit Whippoorwill a few times. I don't have any real climbing experience but that little steep section is something else....

25 +/- trips a year to LGA or JFK.

At least 1 per week to NYC but I do try to avoid it on a Friday.