Although the first thing that comes to mind when you hear "Greenwich" might be mansions and fancy stores, it's actually a little colonial village settled over 300 years ago. It's the first town in Connecticut and the gateway to New England. With its gorgeous harbor and convenient location near the famous Post Road leading to Boston, Greenwich has certainly never been a sleepy town. However, within the last 15 years, Greenwich has transformed into a mecca for shopping, eating, yachting, and just being plain rich. And while those activities are commendable, I urge people to see beyond the glitz and appreciate Greenwich's lengthy history and surprising beauty.
Shopping can be accomplished on Greenwich Avenue, the main drag, and all its little side streets. To see mansions—some old and some comically modern—you must drive on the four main roads that lead you north and deep into Greenwich: North Street, Lake Avenue, Round Hill Road, or Stanwich. To get a sense of what Greenwich Avenue used to be like, go to Old Greenwich downtown. In the same area, you'll find the beautiful Binney Park, filled with little gazebos and bridges (thus a favorite photo-op for the brides) and Greenwich Point (the beach is only accessible if you're with a resident).
In main Greenwich, you can travel to Island Beach on the ferry (again, go with a resident), located on the harbor. The harbor has a beautiful, newly restored hotel that was built years ago and claims a lot of history. After the beach, go to the hotel bar right on the water and watch the yachts pull in. On the ferry, you'll pass boats tied up in the harbor areas, and you'll pass all the beautiful houses in the private Belle Haven community (home of Diana Ross and the infamous Skakels). Walk past the hotel down to the end of the road. On the right is the yacht club, and straight ahead is a small pier where many people fish. At night, you can watch the stars and hear the music play from the yacht club.
Quick Tips:
Greenwich is beautiful year-round; however, I particularly like the summer because it tends to be quieter around town and the trees are so lush and green. Greenwich is well-taken-care-of, and you'll notice flowers and trees on roundabouts and along the road. Rent a car to drive around and see the big houses, or to go to the Audubon.
Also in the summer, the park near the water will often have jazz concerts or even rock concerts featuring popular artists. These shows are often sponsored by the city or the Teen Center, a big brick building on the opposite side of the harbor from the hotel and right next to the park holding the concerts. To find out about events such as these, pick up a copy of the Greenwich Times newspaper or one of the free newspapers found at the train station platform that has event information for all of Fairfield County.
Best Way To Get Around:
The entire downtown can be covered by walking. North of the harbor is the highway (the town is exit 3 off of the I-95) as well as the train station (there are express trains to Grand Central). On the right, to the east before the overpass, you’ll notice Bruce Park and the Bruce museum. North of that is all of downtown Greenwich. Simply walk up Greenwich Avenue, and you’ll be in the center of the shopping district. As you can see, trips from New York on the train, without a car, are still easily possible. And taxis line up at the New York arrivals side of the train platform, in case you have a specific place to go. There is a bus system, but I don’t recommend it unless you really know what you’re doing.