The Main Streets of America are often the best places for shopping, dining, and discovering the arts. Connecticut is no exception! Take some time out this weekend to visit, or revisit, some of these great Main Streets and fall in love with the charming towns that surround them. Whether you’re bringing the whole family along or planning a romantic date, these are the perfect places to be. Check them out!

1. Ridgefield
Maggie Deegan/Flickr
Not only is this Main Street historic, but it transforms into a beautiful and romantic place for a holiday stroll. It truly is picture perfect all year round!
2. Middletown
Joe Mabel/Flickr
One of the more modern locales, this Main Street is perfect for shopaholics looking to find some unique gifts.
3. Old Saybrook
Jay McAnally
The quintessential New England center, this Main Street is the center of life in the town, attracting folks of all ages with its endless activities.
4. Essex
Joe Mabel/Flickr
Folks flock to this center in the summer season, in part because this Main Street is oceanfront, offering gorgeous views of the harbor.
5. New Canaan
Terretta/Flickr
This place has an older look with a young feel. It's a great place to go for dinner and an evening walk around the block.
6. Niantic
dmcoxe/Flickr
This is a hidden gem! The stores blend right into the homes, so you'll have to walk around and explore to really discover what this place has to offer.

Related Stories

With Its Own Carousel, This Connecticut Seafood Shack Is Perfect For Families

With Its Own Carousel, This Connecticut Seafood Shack Is Perfect For Families

 Escape To The Countryside When You Stay At This Rural Airbnb In Connecticut

Escape To The Countryside When You Stay At This Rural Airbnb In Connecticut

 You'll Never Look At Donuts The Same Way After Trying Neil's Donuts In Connecticut

You'll Never Look At Donuts The Same Way After Trying Neil's Donuts In Connecticut
7. Hartford
Chez Julius Livre 1/Flickr
You can't go to the capital and not stop by Main Street! The Wadsworth Anthenuem Museum of Art is here, along with a number of restaurants.
8. Westport
caboose_rodeo/Flickr
Talk about a shopping district! If you're looking for high-end finds and unique one of a kind places, this is the perfect place to find them!
9. New Milford
Jerry Dougherty/Wikimedia
This historic downtown is the ideal place for young families to spend an afternoon. Pack a picnic and enjoy the window shopping!
10. Danbury
Daniel Case/Wikimedia
The tall century old style buildings of this Main Street make you feel transported to a different era without having to sacrifice any conveniences.
11. Darien
Doug Kerr/Flickr
Another high end option, this gold coast locale has everything you could ever want- or imagine.
12. New Britain
Sage Ross/Wikimedia
Besides the low-key dining options, this place is cool because it has made very few changes over the years. Old postcards reveal the awesome truth that this place is stuck in time.

Have you been to all of these Main Streets before? Tell us which one is your favorite! If you’re looking to explore more of Connecticut’s quaint and quiet side, try checking out these charming small towns. They are irresistible!

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

Related Articles