[reslinal]

Westport is best for me because it has the river walk and bridge along with a nice mix of shops and restaurants. It also has a nice church in the back if you walk the full circle.

Ridgefield downtown is really cute with all the historical houses with the big nice lawns around downtown area, a variety of shops and restaurants, the art museum and park in the downtown area also adds to the charm.

Fairfield/West Hartford/new Canaan/Greenwich are nice to walk around but lack the unique charming/scenic factor.

Essex and Chester are charming but too small and lack shops.

Wilton/Darion: didn’t realize they have downtown, thought just shopping plaza

Milford: the only time we visited it seems a little bit dirty and rundown.

[Danny K]

Originally Posted by reslinal

Milford: the only time we visited it seems a little bit dirty and rundown.

??? You sure you’re in the actual downtown of Milford? I’ve never heard this before ever.

[Stylo]

Originally Posted by Danny K

??? You sure you’re in the actual downtown of Milford? I’ve never heard this before ever.

Yeah that's a first!

It's got the unique mix of the waterfalls/duck ponds, harbor, and green. Not sure any other town has all that, plus a train station.

Also Essex and Chester absolutely have shops. And several restaurants.

[reslinal]

Originally Posted by Danny K

??? You sure you’re in the actual downtown of Milford? I’ve never heard this before ever.

Maybe we went to the wrong one? Is that the one with a restaurant that has a small pond/waterfall view?

[SteveM85]

Originally Posted by reslinal

Maybe we went to the wrong one? Is that the one with a restaurant that has a small pond/waterfall view?

Probably thinking the Stonebridge in Milford. That area is not rundown.
All CT towns/cities centers are tremendous. This is where CT really shines.

[SteveM85]

Originally Posted by Danny K

As for Downtowns: Milford and Guilford are my favorites by far!

Then I'd say Essex, Chester, Litchfield, Stonington Borough (if that counts as Downtown Stonington), Old Saybrook, Madison, and Branford.

Fairfield and West Hartford also have some really nice downtowns but they're pretty busy and can be quite crowded, which is why I wouldn't call them my top.

You sound like you just go by the Town Tournament 101 playbook for downtowns

[reslinal]

Originally Posted by SteveM85

Probably thinking the Stonebridge in Milford. That area is not rundown.
All CT towns/cities centers are tremendous. This is where CT really shines.

Yeah I think rundown is the wrong word to use. We went in a windy/cloudy day and the streets were a little bit dirty, probably that’s why it left a bad impression on us.

[reslinal]

Originally Posted by ct1615

if you like westport & ridgefield downtowns, you will probably enjoy New Canaan as well

Yes New Canaan is nice. It feels better than Fairfield but just doesn’t have the water views of westport or the houses/greens of ridgefield.

[Stylo]

Originally Posted by reslinal

Yeah I think rundown is the wrong word to use. We went in a windy/cloudy day and the streets were a little bit dirty, probably that’s why it left a bad impression on us.

In winter? The streets around there are typically immaculate. Next time visit the harbor, green, and northern duck pond area above city hall

[JayCT]

I can’t believe that no one recently mentioned one of the best downtowns in the state, if not New England: Middletown. It has a ton of great restaurants and bars plus some great stores and shops including the iconic Amato’s Toy & Hobby and the wonderful Wesleyan RJ Julia Bookstore. Thats hard to beat.

https://www.amatosmiddletown.com/

https://www.wesleyanrjjulia.com/