Greenwich has a relatively poor food scene for a town of 60,000 and only 35 miles from NYC. But if you are in town and need places, here are a few:
Little Pub in Cos Cob, good pub fare/burgers.
Fat Poodle in Old Greenwich is a go to for decent date night dinner.
Applausi is serviceable Italian I’m Old Greenwich. Valbella, near your hotel is overpriced red sauce but odds are you will run into Regis and Joy.
If you have a car, The Whelk in Westport is great, as is the Tavern at Silver Barns in Norwalk.
I’d second the idea of driving up to Zuppardi’s (get the sausage pie special) in West Haven or Sally’s in New Haven for a pie. Best pizza ever.
to get beach passes, if that's your jam. Hot there this week.
Bruce Museum is decent, as is the art center up at the polo fields.
Lots of good but expensive option on Greenwich Ave for dining, I recommend Le Penguin. The Fat Poodle in Old Greenwich is solid, too.
Mystic is a solid day trip, as is taking the train into the city, it's quite close. Yankees games are possible as well.
I doubt he's still there though.
I’m a greasy no-good WOP from Stamford, CT who used to have big greasy hair, straight out of central casting. Those Blue-Blood back-country chicks couldn’t get enough of slumming it w/ young Ferndog. I couldn’t talk to a girl in my own high school, but could talk to girls completely and entirely out of my league for reals.
If you’re a young man, go buy a track suit, wear a black t-shirt w/ gold cross worn specifically on the outside, perhaps an Italian horn / pepper, or a little boot of Italy. Try and channel the spirit of one of Tony Soprano’s crew. Slick back your hair.
Unless you’re a pasty Irish dude that wears khakis and lived in Stanford or Zahm. Then, don’t even bother, as it’s pointless.
Greenwich has some cool stuff, but if you are in town as a visitor, it may be difficult to experience. For non-residents, there are many hoops to jump through to visit Todd's Point or Captain's Island, for example.
Your location is also limiting. You are on the very border with Stamford, thus far away from Greenwich Ave., which has some nice shops and places to eat.
My suggestion to you is to get thee to Stamford train station. From there take the Metro North into NYC. I'd skip New Haven. It is mostly a dump. If you are inclined to take John 88's advice, take Amtrak from Stamford to New London, CT and Uber to the Sub Base.
You can also take Amtrak to New London and then take the ferry to Block Island. That might be fun.
But your best bet is NYC.
Find his house, knock on his door, and ask him to play you a few tunes.
Drop in on Dave, and tell him what you think of his beard.
Dave would love to see him. Anyone who calls himself "ODDMAN" probably has a stupid human trick or two in his repertoire.
It's a tiny place that supposedly served the first hamburger. Their interpretation of it is unique. While you're there, make sure to carve your name into the seat or wall.
But I've heard New Haven pizza (or Apizza as they call it) is some of, if not the best, in the country.
I think it’s just ok, but a lot of people love it
Skull and bones is a few blocks away
Drive to Groton, CT and tour the USS Nautilus, our first nuclear powered submarine. That's what I'd do.
in Groton in mid-70s, just 100 ft across the street from the local lobster pound and the Thames River. Easy walk to buy fresh lobster just unloaded from the boats. Could see New London, the sub tender docked and US Coast Guard Academy (and their masted training ship) from our deck. A great three years there, added to by the birth of our first son, ndslc! Our neighbors were a great couple, no children, who "adopted" us. He as asst chief of police for the town and she owned a local women's store close to the base of the Thames River Bridge (rt 95 ). Just upriver less than a mile was the SUb base and home to active Nautilus, and a few hn=undred yards in opposite direction, General Dynamics Electric Boat, where the Trident Subs were being built and launched. Saw a fewe as well. I was wor=king there in the final stages of completion for Milestone Unit #2 in Waterford just across the river as well.
Besides the ease of purchasing lobster (cheaper than meat then, we had the regular sounds and sights of subs going to from the LI Sound and sub base. A neighbor in the 12 townhouse community was the MPA on the Nautilus at the time and eventually went on the last around the world / under ice too, cruise of the Nautilus.
We returned a few times to the area when we lived in Sandwich, on Cape Cod (another nuclear plant project - in Plymouth). By then the Nautilus was a museum - YES GO - as well as a Diesel Sub.
Also, recommend Mystic. There are many small towns along the coast from Greenwich up along the Connecticut Coast that are great to visit. We used to attend many Art and Craft shows/flea markets back in the day. New London is a nifty town. Might want to check out the Tall Ship cruise there. There are also Whale Watch cruises from Narragansett, but best are from Cape Cod - Falmouth, etc.
Enjoy your visit. It is a great area.
Would love to hear some stories from that generation.
The day I started NROTC at Notre Dame is the day the USSR collapsed. I thought our platoon leader was joking when he told us the news during orientation. By the time I put out to sea on my first boat in 1996 until the time we moored after my 6th patrol in 2000, the Russians did not put a single submarine out to sea.
place to spend a day. Or even more.