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Old 05-08-2023, 10:03 AM
 
225 posts, read 118,238 times
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Hi All,

So, yes, I know this an odd area in the subject line (both inland and coastal).

But...if you were to spend the day/evening with a group and wanted a nice quaint town to walk around and get a bite to eat, what towns might you recommend?

I know New Haven is good for pizza and Old Saybrook looks kinda interesting. Beyond that i know zip!

Any random input is appreciated. Thanks all!
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Old 05-08-2023, 11:09 AM
 
Location: Coastal Connecticut
21,773 posts, read 28,124,156 times
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New Haven certainly has the most to do and the most to walk around. And best food, much more than just pizza. You can walk around downtown/Yale Campus, East Rock, Wooster Square, Westville. It is beautiful. I especially love walking around East Rock this time of year. Yale Art Gallery is free and very impressive. It's perhaps the only place I would recommend spending the whole/day evening, as the other towns are too small to do a full day and you'll want to visit multiple.

Chester and Essex are really pretty too. Chester has some good food options. It is small but really charming.

Middletown has some great food. I love OSA. It is not as good to walk around as New Haven as a city tough, and lacks the old New England charm of some of the smaller towns.

Aside from that, maybe Guilford. The green is very charming. The food options at the green are OK. But Bufalina nearby has excellent pizza. Down Route 8 from Waterbury, Milford has a nice downtown/green/river/harbor to walk around with some good food options (I'm a big fan of Strega). Madison has a small but very nice downtown, and nearby Madison Beach Hotel is a great place to grab a drink.

Old Saybrook is a very nice town but I'm not sure it's special enough of a downtown to walk around to focus on.
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Old 05-08-2023, 12:45 PM
 
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and if the weather is nice Friday, New Haven also has there Night Market from 5pm on. They have vendors, live music, things to do all free, outside and they added more space this year. It goes from Orange St at George St (in Night Square) and extends across Chapel St one block toward Court St.
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Old 05-08-2023, 03:18 PM
 
Location: Connecticut
34,952 posts, read 57,005,315 times
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Quote:
Originally Posted by Stylo View Post
New Haven certainly has the most to do and the most to walk around. And best food, much more than just pizza. You can walk around downtown/Yale Campus, East Rock, Wooster Square, Westville. It is beautiful. I especially love walking around East Rock this time of year. Yale Art Gallery is free and very impressive. It's perhaps the only place I would recommend spending the whole/day evening, as the other towns are too small to do a full day and you'll want to visit multiple.

Chester and Essex are really pretty too. Chester has some good food options. It is small but really charming.

Middletown has some great food. I love OSA. It is not as good to walk around as New Haven as a city tough, and lacks the old New England charm of some of the smaller towns.

Aside from that, maybe Guilford. The green is very charming. The food options at the green are OK. But Bufalina nearby has excellent pizza. Down Route 8 from Waterbury, Milford has a nice downtown/green/river/harbor to walk around with some good food options (I'm a big fan of Strega). Madison has a small but very nice downtown, and nearby Madison Beach Hotel is a great place to grab a drink.

Old Saybrook is a very nice town but I'm not sure it's special enough of a downtown to walk around to focus on.
Great suggestions. I agree but it depends what they like. If they want big city then definitely New Haven. If they want small city then Middletown. If they want small quant towns then I’d go with the others.

Id also add into the mix East Haddam. They could see a show at the wonderful Goodspeed Opera House and have dinner at one of the great nearby restaurants. It makes a nice time. Jay
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Old 05-08-2023, 03:29 PM
 
Location: Coastal Connecticut
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Quote:
Originally Posted by JayCT View Post
Great suggestions. I agree but it depends what they like. If they want big city then definitely New Haven. If they want small city then Middletown. If they want small quant towns then I’d go with the others.

Id also add into the mix East Haddam. They could see a show at the wonderful Goodspeed Opera House and have dinner at one of the great nearby restaurants. It makes a nice time. Jay
And Gillette Castle is a neat stop.
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Old 05-08-2023, 07:20 PM
 
Location: Connecticut
34,952 posts, read 57,005,315 times
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Quote:
Originally Posted by Stylo View Post
And Gillette Castle is a neat stop.
Definitely! Jay
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Old 05-08-2023, 07:46 PM
 
Location: USA
6,924 posts, read 3,766,904 times
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You came to the right place. These guys are pros.
Walking downtowns and quaint town centers with a book store and grabbing a bite is the national sport of CT. Town centers are the backbone and central nervous system of the state. You sound as if it will be only a special occasion or one and done.
Make it a regular habit there’s lot to explore. Too numerous to list.
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Old 05-10-2023, 05:43 AM
 
6,592 posts, read 4,987,517 times
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Ok, 20 mins further out but if you're thinking Old Saybrook you should consider Mystic.
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