Charming towns in Connecticut accessible by train from Boston

Look a little further out, between New Haven and Old Saybrook in CT - Amtrak runs right along the CT shoreline and stops in New Haven and Old Saybrook. There are also frequent non-Amtrak trains that run from NYC out to Old Saybrook and a bit beyond or it's about a 2 hour drive on Rt 95. They are cute, historical towns such as Branford, Guilford, Madison and Old Saybrook. Also try vrbo.com for some other options - I've rented houses through that site in Madison that were great (but in the summer, so a bit different). That would get you out of the very pricey Greenwich area. You can easily find them on a map and if you search for quaint CT shoreline towns. You could also look at Stamford - you might find something there as well that isn't quite as pricey as Greenwich. Much bigger town and not as quaint as further up the coast but another option.

As noted get out of Fairfield County. Either head north or east past New Haven. You could also look along the Hudson on Metro North.

I'd skip Greenwich completely. You don't have to get out of Fairfield County but you do have to get out of Greenwich. What do you consider an easy drive from NYC? Westport is a lovely town, about 30 minutes east of Greenwich -- we used to go to the Sherwood Island State Park there when I was a growing up in Connecticut. Rowayton is also lovely and there are neighborhoods in Norwalk that could be great. These towns don't have stops on the Amtrak Northeast Regional line (the Amtrak line that routes through Boston and these shore towns) but Stamford would be a relatively close by stop. If you want to go inland a bit, maybe Weston or New Canaan would suit. Of all the towns I have mentioned Westport is my favorite but it might be as pricey as Greenwich. Norwich should be less so. I love Old Saybrook, Old Lyme, Stonington, and Noank but they are all east of New Haven and are about a 2 hour drive from midtown Manhattan.

Stonington CT is a winner , I've been spending a fair amount of time there since the mid nineties . The two closest Amtrak stops are Mystic CT ( Mystic lies in the Town of Stonington ) and Westerly RI , a few miles east of Mystic . Look in Mystic , if you are there in off season , you will be able to find alot of options.

By the way , if you stay in Mystic , Stonington Borough ( the village ) is a three mile drive from Mystic , and is the quintessential New England seacoast village. A fishing port ,and historic vernacular architecture , the mile long peninsula juts out onto the ocean with views of Rhode Island , and Fishers Island NY . Other than the few residents , the place is thoroughly untrampled

I don't live in CT, but my tony post-war NJ suburb prohibits short-term house rentals. There are good reasons for that. Let's also remember that several Fairfield Cty towns have been repeatedly sued for making it impossible for urban kids' excursion busses to use nominally "public" beaches.

Stonington via Mystic’s train station. This is where I would go.

Thank you all so much! Really appreciate the tips and suggestions. We live in SF (home of AirBnB-ugh) unfortunately ABB has killed the owner rental business.
I will double-check Mystic and the other advice, but is that area easy accessible from NYC by car? Especially in the winter. Son is in Boston, so a train would be best (although he does have a car there).
All suggestions welcome!

I make the drive from my home in Westchester County ( 25 miles north of midtown Manhattan ) in about one hour and forty five minutes , when there is reasonable traffic . Be aware that driving into the Greater NY metropolitan area can be hectic . Avoiding rush hours is a good idea , or take the train .

The issue for your plan is how much time will you spend in each location , and in what order . Knowing that will make it easier for giving you advice on how to contrive this without subjecting you to unnecessary hassles .

All your advice super! Saw a very decent house in Westport. CAVEAT train from Boston & ez ride from NYC (rental car) is required-dont mind picking up Boston son if train station from Boston is not too far.
Mystic wow beautiful but too too far drive from NYC. Will check Stonington location tho fear this similar locale as Mystic.
It will be snowy when we come so walking around will be brief.
Sounds like you all have had wonderful experiences in CT!!

If you think Mystic is too far, concentrate on the area between New Haven and Old Saybrook. Both the train tracks and I-95 hug the coast and parallel each other, you'll still need cars to get around.

Hi Again,
How's West Norwalk? Looks like only 14" to Stamford train station. Is it cute or kinda industrial? Hard to tell from the visitor photos. We won't be going out much (snowy).
Also fyi: I think I found 2 scams on VRBO: beware of "House Westport"---owner doesn't respond, VRBO has no contact for this so called Property Manager, plus the price was a bit too good to be true.
Beat goes on...thank you!

It’s merely a suburb. Do you prefer a suburb of NYC versus a charming coastal town in Connecticut convenient to both NYC and Boston?

As a bedroom community, aka suburb , of NYC , there is nothing wrong with living there . I live in a similar community . There is , however , nothing to recomend it as a place to visit ( except , perhaps , Stew Leonard's food store , a sort of Disneyesque place ) .As for it being close to the Stamford Metro North Station , this one , like every other train station in the greater metro area , has extremely limited parking , almost totally consumed by people who have parking permits . Driving into Manhattan from the surrounding suburbs is a headache at the best of times , and during the holidays it is a positive nightmare .

Most places west of Bridgeport will have a “suburb of NYC” feel but the upside for those locations will be ease of access from NYC and since you are going in the winter, I’m not sure that a beach town is a must. You may end up enjoying a place with restaurants and a bit of city life more. It all depends on what you are envisioning. Have you looked at Fairfield. Check this out (it showed up on my iPad today): https://www.planetware.com/connecticut/best-beach-towns-in-connecticut-us-ct-45.htm
One of my goddaughters lives in a building that I think should be condemned near Canal Street in Manhattan and when she and her friends rent a house for a weekend in the country, they go to Ardsley — LOL. https://www.ardsleyvillage.com/

Hi All
Sorry te so difficult-but I need a spot <20” drive to Stamford train station and convenient to Manhattan. I am a bit freaked out by post saying “driving into Manhattan during the holidays is a nightmare”-yikes!
I would love a sweet picture perfect village but must fulfill the requirements above. Thise east of New Haven are a slug from Manhattan now (much less in December) and the trains from Boston are 3+ hours.
Them’s the breaks.

If Manhattan is your destination then staying in or near a town serviced by Metro North commuter rail or Amtrak train may be a better option. I loved driving into NYC but haven’t done so in about 15 years - city traffic, parking availability, high parking expense, etc. Of course that expense needs to be balanced by the number of people in your travel group.

New England resident for over 50 years (35 years in CT).

We used to live in NYC and then in Putnam County and return there for weeks during the summer and for two weeks over the Christmas holiday and stay about 80 minutes from midtown Manhattan. We drive to NYC on the same day that we need to be there, except for the period between December 20th and the first weekend after January 1. If you are going to drive, the traffic on the west side of Manhattan is next level bad. Plan for it as best you can if you going over there including prepaying for your parking. We stopped driving in after we allotted 3.5 hours for the trip and the driver ended up missing the entire first half and the intermission of the 163-minute show that we were going to see. The passengers got out of the car about three blocks from the theatre and ran there after the driver (my husband) told us he would park the car and meet up with us. Well, you know how that ended. Many of the parking lots were sold out and there were police officers who because of the traffic and number of pedestrians were not allowing turns onto avenues that usually allow turns. Hubby arrived right after the first number of the second half.

Oh My! CT was our plan for holiday (starting 12/21) flying in from SF. We planned to drive from NYC with our daughter & son would meet us by train from Boston. We would need a car there for sure. 3.5 hours from NYC...that's almost as bad as getting to Tahoe on Thanksgiving weekend (that's 5+ hours from SF.
I guess we won't be seeing our kids over holiday ):

I think that trying to lace all of this together is a bit like posters who come to Europe and try to cram too much together without regard for the practical logistics of doing it . Here is one idea that may work for you - Rent a place in the Mystic- Stonington area , it should be easy to find , and have your kids take the train there from Boston ( Mystic or Westerly RI Amtrak stops ) Fly into NYC , and pickup a rental car at the airport . Drive to Mystic ( about three hours , Whitestone Bridge to I-95 to Mystic exit 90 ) Spend your collective time there . The place is just what you are looking for , Mystic Seaport Museum and Stonington Borough are bucolic , beautiful places . Having the car will give you the mobility to explore the area . After your stay there , drop the car and take Amtrak to Manhattan , and take a hotel room there . No traffic hassles , you will be free as a bird and be able to enjoy the city's Christmas sights . Fly home from NYC . Give this some thought . Writing from ( rainy , at present ) Wengen, Switzerland.
EDIT - You could also fly into Boston - Logan , pick up your kids and drive to Mystic from there . They could take the train back home when you head for NYC .

I love your creative thinking. Daughter lives in NYC/Upper East Side: she was going to drive (til I heard from several posters about the holiday parking lot on 95. Driving from NYC - Mystic on 12/22 could become a daylong journey.
I don't know, maybe we should all fly into NYC, get a hotel and forget about a cozy Christmas home. Tried this last year & daughter tested Covid+ when we checked in. We left two days later.
Recall we are going during the HOLIDAYS, likely to be cold & snowy: when Mystic/Stonington's charms may not be accessible.

Traffic is atrocious on the west side because of the theaters and the Christmas tree which is just west of 5th avenue. It should merely be bad on the East side. If you leave early enough in the day 12/20, you should avoid the I-95 traffic. Try to avoid any routing that takes you on the Cross Bronx Expressway – it is the 880 of New York and vice versa. Many people who go to NYC during the winter holidays attend a Broadway show. If you are going to drive in to do that then my traffic horror story applies. If you plan to just drive out of town and stay out of town, then you should be fine. You say your daughter lives on the Upper East Side and your son lives in Boston. How long is your daughter willing to drive to get to the destination? Are you planning trips back to NYC during your week? How far are you really willing to drive to get to your son’s train station, especially since it only has to be done twice? What are you all planning to do during the time together? Hang out at home and play games, cook together, maybe go to a spa or mall one day etc. and just chill or are you wanting to do cultural activities within the town or nearby? I am asking all these questions because if you not really planning to explore the town, then any suburban town with good housing stock and decent grocery stores will fit the bill. In that case, why not Norwalk or even Ridgefield (further inland) or New Canaan (also more inland) if your daughter is willing to drive about an hour. I’m still feeling Westport for you because it comes the closest IMO to having the decent restaurant and shopping scene, good houses, and easy access to the train from Boston and you could easily go into Manhattan for a day trip if that floats your boat. If your daughter is willing to drive around 2 hours and the shoreline is still your thing, then Old Saybrook and New London would be good choices, especially New London because it is bigger and has more variety. You could also flip the script and got to Millerton, NY (cute little town up I-684 and Route 22 or the Taconic). Great restaurants in town, lovely housing stock but really not much to do for miles. For your son and family, it’s a train ride across Mass to Pittsfield and then you guys would have to pick them up from Pittsfield which is about 75 minutes from Millerton. Or what about Avon, CT? Cute little town – 3 hours from NY and about 30 minutes from the train station in Hartford. As you can see, I could throw you suggestions all day. All of that being said, you could just try doing what you planned to do last year because the odds of Covid ruining this trip are low. It’s a great idea – we did that in 2019 and saw Hadestown, ate out every night and wandered together and in subgroups around the city each day and celebrated my niece’s and nephew’s birthday at Juniors on the West Side and the whole trip was amazing.

Hello JHK ! Just to let you know , I'm enjoying reading your posts . Route 7 up into The Berkshires is another favorite place for us ( Kent , Falls Village Ct, Great Barrington , Stockbridge MA ) particularly Williamstown, MA . I'm sure you are familiar with it , any thoughts ?

@ steven, Thank you. I grew up in the north end of Hartford and was scholarship student at a Connecticut prep school so I was all over Connecticut for games during my four years of high school. Kent Falls is a favorite -- been there many times to play Kent School and as adult to visit the falls, see relatives play Kent School, or for lunch. My children are now a young adult and a sullen teenager but we used to go berry picking in northwestern Connecticut during our NY summers when they were younger. Luckily, I have some much younger nieces and nephews and we did all that stuff this summer when I spent 8 weeks in Putnam County.