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New York City is well connected to places well outside the city limits with commuter trains. Metro-North generally connects areas like the upper Hudson River Valley and Connecticut with midtown Manhattan. If during your trip you have time, are feeling adventurous and want to go out into the surrounding countryside (one line has a very scenic route that roughly hugs the east bank of the Hudson) this would be the way to do it. The trains do not go very fast, but they do allow you to see scenery other than skyscrapers.
New Haven Line Metro North lines that leave for Connecticut generally leave out of Grand Central (ask the person at the information kiosk about which line to get in to purchase a ticket.) The end of the line generally is New Haven (this is the same town that Yale University is found in) and the time to get to the end of the line is about 2 1/2 hours. Along the way there are other stops that will take you into small New England towns and suburbs, some worth visiting, others not so much.
Yale University is one of the oldest institutions of higher learning in the nation and would be a nice addition to a trip for the college bound hopeful, early architecture nut, rare manuscript peeper, or just the plain curious. Presidents have graduated from these halls (do not mention that the current president went to the rival school, Harvard, as it may touch a nerve. As for Bush, the professors who knew him thought they recovered when they had him around the first time and then got a rude shock....) as have Meryl Streep, Sinclair Lewis, Jodie Foster, and Noah Webster; Former UK Prime Minister Tony Blair has taught here and his son was a student here (though not concurrently.) The grounds are typical for an Ivy League school (compare Columbia's in NYC if you have the time) and the college does do tours.
The surrounding town of New Haven still has a few signs of its early American history as well for those who know what to look for: in the early nineteenth century, New Haven was a popular spot for runaway slaves to flee to (it is well north of the Mason-Dixon line and connected routes into Canada and Boston) and, like much of New England, was a hotbed of abolitionism. It was thus kismet that in 1839 a group of kidnapped Africans from what is today Sierra Leone found themselves in New Haven Harbor. Their fate would help determine the course of history in the definition of blacks as men rather than chattel and would go all the way to the Supreme Court: Amistad vs. the United States. The leader of the Africans, Cinque, has his statue right outside of city hall, and there is an exact replica of the slave ship Amistad sitting in the harbor that is open to the public as a museum.
Hudson Line This route will take you alongside roughly the Hudson River's east bank and terminates in Poughkeepsie, about 75 miles away. Along the way there are three main stops that are of interest to the tourist: 153rd street, Philipse Manor, and Poughkeepsie.
153rd street is a stop in the
South Bronx: before you begin to panic either due to past history of
this neighborhood or due to general squeamishness, know that this is
one of the "cheats" of the entire public transit system: Yankee Stadium
does have its own subway stops and even ferry service that will take
you from lower portions of Manhattan to see the game. However, during
the summer it can be soul crushing to wait in a very hot underground
subway station and then have to be packed in like a sardine with
everyone else......for a ride that makes ever more stops to pick up
more people. (The ferry can set you back $30 a person, too.) If you
purchase a ticket to ride Metro North up to Yankee Stadium from Grand
Central however, you are almost guaranteed a shorter ride on a
(usually) less crowded train. (Sometimes these trains run express to
the stadium; if the Yankees go to the World Series the trains look like
they are running a relay race and since World Series games have happened at least three times in the past ten years, it is a miracle the tracks haven't been worn by the sheer friction.) The station itself is brand new, the
neighborhood has seen some improvement, policemen are usually not far away during big games (like playoff games or games against the Red Sox, a team the Yankees have had a rivalry with for 100 years) and the way to the stadium is
well lit for night games. It is worth it. (Buy a hotdog from one of the vendors on the way-yum.)
Poughkeepsie is the end of the line; the town itself is pretty much an ordinary place but during the warmer months the National Park Service offers shuttles to a place of great interest: Springwood Estate. Springwood is a mansion that once belonged to the Roosevelt family and was the home FDR was both born in and later lived in with his family. (He is buried in the garden, alongside Eleanor.) Park rangers lead tours through this home and answer questions about FDR's life as well as tell about what the life of this family was like in this house.
Philipse Manor station is so named for a land grant given to a Dutchman named Frederick Philipse by William III; within walking distance of the station is Philipse's colonial era manor house turned museum with a working grist mill and barn showing off what life was like when New York was still dominated by British and Dutch settlers. Another destination not far away is Kykuit: this is a very large mansion built during the guilded age by tycoon and robber baron John Rockefeller. Kykuit has a commanding view of the Hudson River and is an opulent, palatial home of the kind that was very popular during the Guilded Age and a testament to what a man with a very large amount of money can buy, including manicured gardens and works of art.
Overall, this stop is interesting enough to leave New York CIty during late October not just for the ability to see fall colors but also because of its literary background. Early American author Washington Irving's home still stands a few miles away from this spot (you can visit it if you like by going back one stop to Tarrytown and getting in a cab.) However, the most famous story he put in his Leatherstocking Tales he based on a settlement he knew as Beekmantown.....better known to the world as Sleepy Hollow. (The old Bridge of Souls, the Church, and the graveyard still stand..enter if you dare come Halloween time.)
Harlem Line This is the longest route on Metro-North and it takes you well north of the city. It originates in Grand Central, passes through Harlem at 125th Street (good to know if you want to get to LaGuardia by switching to the M60 bus) and snakes its way more than halfway to Albany (which is more than 100 miles away.) When peering out the window, be prepared for the jungle of concrete and steel to give way to absolute quiet once you pass Chappaqua (yes, Bill Clinton's Chappaqua.) Cheap colored lights will eventually give way to trees and the occasional farm. It is a very pretty sight and a nice way to have a meal, sipping a cup of coffee and admiring leaves that explode into a riot of red, orange, and gold in the autumn.
For those seeking a quick way to reach a popular destination, the Harlem line features another public transit "cheat." From Grand Central, purchase a ticket that takes you to the Fordham stop. Transfer to the bus at the stop and it will take you to the Bronx Zoo (on the regular subway it would take you about two hours whereas this trick takes a little less than one.)
For those wishing to head outside the city (meaning WAY outside the city) in warmer months, get a ticket that will take you to the stop marked Appalachian Trail. It is EXACTLY what it says it is: the 2,000 mile long Appalachian Trail has only a handful of spots where there are signs of civilization. This train station is one of them and the trail itself is a short walk from the station where it crosses the tracks back into nature. For those that want to hoof it over the Hudson River and see if they can make it to Virginia, or for those with a burning desire to see moose but not to start at the northbound trailhead in Georgia, this would be the place to drop off. (Note: trip not advised for inexperienced campers, persons staying two weeks or less, or persons with a deep seated fear of bears, creepy crawlies, larger felines (bobcat and lynx) or bats. You have been warned.)