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I'm looking for some suggestions on quaint downtowns in CT. Something like a downtown Madison, where you have various shops like coffee, ice cream, a movie theater, etc.
Westport has a nice downtown. No movie theaters any more, but a great library, lots of shops, coffee places, deli, art supply store and a bunch of restaurants. Most of the places are on the higher side price wise, but it is nice and walkable...
I second both New Canaan and Westport, lovely and fun! Ridgefield has a great downtown, too. Fairfield, by the train station, Southport and Milford are also fun and walkable.
There is a very cool movie theater in downtown Fairfield that shows movies for $4 (I think). They were showing Casablanca last time we were there. The library is just about across the street from the theater, and you can walk to the beach, too.
West Hartford has a great downtown with movie theaters, great shopping and some of the best restaurants in the state. Greenwich also has a great downtown area. Milford, Branford and Guilford are nice but they don't have movie theaters either. Jay
If you are into retirement homes, East Haddam's downtown can be considered quaint
Niantic has the quintessential Main Street with a movie theater, some restaurants, grocery store/gift shops, access to the boardwalk/beaches, and some coffee shops/bakeries.
I have lived in East Haddam for 12 years. It is a VERY quiet town and very rural. Most areas do not have a 'neighborhood' feel because houses are very spread out. Which is not to imply that the people here are not friendly - we like all of our neighbors; we just don't see then too often. It is in the country so you if you want a town that has a lot of services and restaurants and grocery stores, etc. you will not like East Haddam. We like it for those very reasons though. In total there are 3 or 4 restaurants, 1 small grocery store, a couple of convenience stores and 1 gas station. There is not 1 stop light in the town - well, except for the one at the swing bridge. During the summer, the bridge opens up to allow boats on the CT. river to pass so you will get stuck while it is open - leave a book in your car to read while you wait. It adds to the quaint feeling of the town! The Goodspeed offers 3 plays a year and there are 2 restaurants in the 'downtown' area. I put that in quotes because it really isn't a downtown like Madison or even Chester. It is a very pretty town but very country and very quiet. If you want to live here you will need to like deer, turkey, coyotes, and not want to plant a vegetable or flower garden (unless you have a high enough fence that the deer can't jump). The schools are good (A new middle school just opened up this year) and there is very little crime - a few break ins now and then but for the most part a very safe town. Taxes are on the high side and there aren't a lot of services - you will pay for garbage pick up for example. You will have a well for water and when you loose electricity you won't have water - that includes your toilet! So, if you like country living, you will like East Haddam.
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