9 Most Charming Town Squares In Connecticut
Connecticut is full of small towns, fall colors, spirit, and history. Everywhere you turn, you can find statues, plaques, or some memento of history. During the fall, the explosions of color drive people to it in truckloads. During the holidays, the romance and cheer are on overdrive. However, choosing when and where to venture can be a challenging task. Many people search for that romantic small town we have seen on television or read about in books. To help guide you on this mission, below is a list of the 9 Most Charming Town Squares in Connecticut. Visit for the charisma and be swept away by the charm.
Putnam
Along the banks of the Quinebaug River in the northeast corner of the state (known as the "Quiet Corner"), Putnam has made some significant changes in the past 25 years. After implementing a revitalization plan, this former milltown has become a must-see destination. Main Street offers several shops and restaurants; Antiques Marketplace, Wolperdinger Bookends, the Courthouse Bar and Grille, and Bear Hands Brewing Company are just some of the possibilities to enjoy. Also, Putnam's “Arts & Al Fresco” motif has turned its downtown into an artist’s dream featuring small boutiques, theaters, and art galleries. They don’t want you just to see the artisans' work; they want you to experience it in the air. The goal is to combine arts and outdoors to enhance the town’s charm. While walking, be sure to look for the painted murals to tell the story of Putnam. In Putnam, they didn’t just incorporate the arts; they painted the town.
Litchfield
History books have talked about the events that have occurred in Litchfield. However, they don’t prepare you for the adorable and modern change that has happened over time. From Bohemian Pizza and Tacos to the seafood restaurant Sage and Salt, George Washington himself would be delighted by the food that has become staples. The community has been built and evolved into a top destination for its ability to maintain its charm and provide ample entertainment and opportunities. Litchfield has even created a town green for the community to gather and celebrate events. Shops and boutiques surround the green, so you can be included during events even as you shop or stop at the cafe.
New Milford
Walking the town square of New Milford looks like walking in Stars Hollow from the TV show Gilmore Girls. The green lawn space is covered with bodies lying in the sun, enjoying music, checking out the cool military tank, or waiting to meet friends. The gazebo in the center has seen speeches, music, fireworks, and more. The website has an entire guide to help you stay on the trail you seek, whether it is the antique trail, foodie trail, or nature exploration. Join or watch the creativity at The Village Center for the Arts. Walk for what will seem like hours at the Elephant's Trunk Flea Market, or walk the shops that go for blocks around the town square. This town isn’t overloaded, but it’s a relaxing, beautiful mix of country and accessibility.
Westport
Describing Westport would be like explaining how Cinderella felt rolling up in her magical carriage. The bridges, lights, and reflections off the water appear as pure magic. The mixture of history, charm, and preservation of tradition brings the community together thanks to the Westport Downtown Association. They hold events all year round, encouraging activity in the area and supporting local businesses.
The town square has mom-and-pop shops, boutiques, and modern stores. The area is so pleasant that there is even outdoor dining, so you can enjoy the atmosphere while eating. See contemporary art at MoCA CT or watch a show at the Levitt Pavilion. If you want history with your entertainment, enjoy a performance at the Westport Country Playhouse, a remodeled leather manufacturer from 1835. Westport is where magic and dreams are in the air.
Wethersfield
Walking into Wethersfield in the spring, you’ll see pops of color spread out like paint drops amongst the green. It is a beautiful array of yellows, oranges, and reds in the fall. In the summer, you find people filling in the grounds. This colonial history is far from dusty, as the vibrant community spirit and like-minded people gather to enjoy the heritage, colors, and nature surrounding them. The farmers' market at the Solomon Welles House is quite popular for local artisanal foods, locally sourced produce, and treats. You can also check out the healing center, The Blackbird House, scope all the beautifully decorated bikes, or find a laugh at a Brew HaHa Comedy Night at River: A Waterfront Restaurant & Bar.
The walk in this town square is enjoyable without even shopping, but shopkeepers are happy to see and help you. They decorate their windows and do what they can to maintain the small-town, almost old-world magic that is Old Wethersfield.
Madison
Madison holds true to the ideas and imagination of being in Connecticut. It is a small town with a whole lot to offer. With its beautiful nature, seaside smell, and wide selection of shops and restaurants, spending time in Madison is as easy as breathing.
The farmer’s market on the town green is only one of the many events held here. The E.C. Scranton Memorial Library is just outside the green, and together they are the ground for the community gatherings throughout the year, from concerts to the Ukulele Club. Restaurants and shopping line Wall Street, providing a dazzling mix of thrift shops to boutiques. Madison Arts Barn, Madison Cinemas, and The Sculpture Mile are just a few ways to bring art into your visit. There is much to see and peace to be found in Madison.
Ridgefield
Ridgefield is everything you think of when you think of a Connecticut small town. Fall colors and activities set the state ablaze in autumn. Greenery and nature create a peaceful park full of life, and in the center? You bet! A gazebo! This colonial town has a Main Street that is over a mile long with shops, boutiques, and history.
Summerfest transforms Main Street into a must-see event, with tents, booths, and activities lining the street. Catch a show at the Ridgefield Playhouse. See a movie while supporting a cause at the Prospector Theater. Plan an event at the Lounsbury House, or enjoy walking the town and shopping or dining at various restaurants and artisanal shops. Ridgefield is full of community, history, and charm.
New Canaan
Three streets form together to create a triangular pinnacle that is the spirit of New Canaan. These three streets hold artisan works, boutiques, restaurants, and cafes, creating a pocket of community. With a dedicated Chamber of Commerce, this small town's beauty, charm, and versatility shine. Events, gatherings, eclectic sales, and interesting events are constantly occurring. Stop in for the Village Fair & Sidewalk sale and tour the Garden Club.
Leisurely walk around, or pop into one of the many shops for a special gift for someone you love. Stopping into the Egia Day Spa, Eco Chic Nail & Spa, or Canaan Nails for a gift to yourself is welcome and encouraged. New Canaan is all about caring for the environment, the community, and yourself. Also, see what event is being held at the New Canaan Library.
Chester
If you are on the search for a place that could be mistaken for a small town from a romance movie, you can stop looking at Chester. Walking around the town square might get your calories burned, but the smell of the variety of cuisine will tempt you. Whether you seek locally grown, minority owned, eco-friendly businesses, there is a downloadable map of the town square available to help you find what you are looking for. Beauty can be seen from the Chester Gallery to the Lori Warner Gallery and The Space gallery. History runs in the veins of this town, but an ever-growing, enchanting swirl of variety accompanies it.
From History to the Here and Now, Connecticut Has It All
Connecticut is a state full of history and spirit. It has roots in the pilgrimage and the United States' founding fathers. This history can be seen in festivals, reenactments, statues, street names, etc. The atmosphere cannot be overlooked, as you feel when you step outside. Whether you are looking for fall festivals and fun, winter activities and holiday cheer, or warm outdoor adventures, Connecticut doesn’t disappoint. Small towns, boutique shops, artisanal works, great food, and charming town squares are scattered across the state. Charming town squares and walkable downtowns can be found all around.
