8 Prettiest Downtown Strips In Connecticut

With a long strip of Atlantic coastline on the Long Island Sound at its southern point and a mountainous region of hilly highlands to the north, Connecticut is a state that boasts unique and diverse landscapes. Most of the state is rural, but like many others in the northeastern US, the "Constitution State" has a lengthy colonial background, which the beautiful cities there reflect in their architecture and historic downtown areas. The sense of community in Connecticut is strong, and any visitor will likely be welcomed with New England hospitality and promptly directed toward the best fresh seafood spot in town.

Westport

Another coastal town, Westport, is also not too far from New York and earned a reputation for being a quiet waterfront town where celebrities could stay incognito. It has, for that reason, among others, become a more affluent area, with some very expensive neighborhoods to live in. For tourists, it is a dream, a great place to spend a weekend and spend time on the sand, explore one or more of its great state parks, or, of course, hang out in its awesome downtown.

Most of the action takes place between Main Street and Myrtle Avenue around Sconset Square, which is a shopping center with several home decor stores, an art gallery, and some restaurants all organized into a pretty and compact area so that they are within steps of each other. Another mall filled with local goodness, The Market Place, is just on the other side of Church Lane and is home to even more shopping and food destinations.

Speaking of food, there are a few standout spots that are repeatedly recommended by Westport locals in this specific downtown strip. One of those, Spotted Horse Tavern, is in a restored Federalist house, which is interesting all on its own, and the modern American style flavors are a perfect accompaniment. Another, Walrus Alley, is a Southern food restaurant, a shake-up from typical seafood and New England style cuisine that is most commonly found in Connecticut.

Mystic

Part of the larger cities of Stonington and Groton, Mystic is a tiny port village that has managed to not only form its own identity but also establish itself as a tourist destination and develop its own cute little downtown. There is plenty to do all around the iconic drawbridge, which raises occasionally to allow boat traffic floating down the Mystic River. Right beside the bridge on West Main Street, you will find a beautiful strip filled with shops, restaurants, and tourist attractions such as the Mystic Museum of Art.

Some must-see spots in this neighborhood are the iconic Mystic Pizza, which actually inspired an 80's film by the same name, Sift Bake Shop, a locally owned and highly rated bakery, and Mystic Disc, a popular record and music store. Mystic River Park, on the other side of the river, often hosts free live music and has a beautiful boardwalk.

Middletown

Just south of the huge urban center of Hartford, nestled along the Connecticut River, is the smaller city of Middletown, home to about forty thousand people. It is in a great location surrounded by several state parks, including Cockaponset State Forest and Hurd State Park, and it is also only thirty minutes' drive from the Long Island Sound coastline. Combined with the proximity to the capital city, there are many reasons to find yourself in Middletown just due to the surrounding area, but do not doubt the charm and beauty of the town itself.

Main Street of Middletown is a thriving seven block stretch packed with entertainment. There are multiple shopping centers, including the aptly named Main Street Market, cafes, like the very popular and bustling Perkatory Coffee Roasters, and a variety of restaurants such as the highly recommended gastropub OSA.

There is plenty of nightlife along the strip as well, including Conspiracy, a cocktail bar commonly suggested by locals. You can also enjoy live music regularly at The Buttonwood Tree, a venue that has different performers every weekend. All of these attractions and more can be found right in the center of this lovely riverfront town, all within easy distance of each other.

Putnam

A much smaller town than the former on the list, Putnam is regarded by Connecticut residents as an underrated spot with a charming and historic downtown area. Once a bustling mill town, built up along the Quinebaug River, it is home to its namesake Putnam River Trail, which heads straight through scenic Rotary Park, a riverfront recreation area only a few blocks from downtown.

The quaint downtown area, concentrated around Main and Front Streets, is continuously up and coming, adding new things to do all the time. Putnam's downtown is particularly known for having a wide selection of antique stores, including the imposing Antiques Marketplace, a mega-mall for vintage goods which houses over a hundred vendors, and Jeremiah's Antiques and Collectibles.

Main Street has many options for food as well, like the Stomping Ground, a self-described eclectic restaurant with a lengthy menu, which also showcases live music every night of the week except Mondays. Craft beer is very easily found in Putnam too, with two options worth mentioning being The Crossings Restaurant and Brew Pub and Bear Hands Brewing Company.

Wethersfield

Old Wethersfield, the city's historic downtown area, is packed with over a thousand examples of colonial architecture, some dating back to the 18th century. The primary area where local businesses thrive is centered around Main Street, beginning near the Wethersfield Historical Society. Right down the road is the Webb Deane Stevens Museum, an 18th-century residential home which has been restored, and, most notably, when discussing pretty downtown areas, its beautiful backyard, the Webb House Colonial Revival Garden. This garden is open to the public and was designed by a female architect, which was highly uncommon for its time.

Also on Main Street, another scenic destination is Cove Park, which is situated on the stunning natural inlet Wethersfield Cove. It has a paved walking trail all the way around it, and multiple boat docks so that you can experience the water any way you would like. If you prefer snacks over sightseeing, a versatile stop like Heirloom Market cannot be missed. It is a restaurant, cafe, and more that serves breakfast, coffee, and baked goods. It also sells fresh produce grown in its own greenhouse. For dessert, wander down to Main Street Creamery and Cafe, an ice cream shop that offers its unique flavors individually or in flights, if you want to try a variety.

Branford

A waterfront town located right on the Long Island Sound, Branford is also close to the larger city of New Haven. It certainly stands on its own, being a coastal town with several breathtaking saltwater beaches only a short drive away from a charming downtown area. This Main Street is mostly centered around the Branford Green. The green is covered in plentiful old trees and dotted with monuments, and many town events are held there, including the annual Branford Festival, which takes place in June.

Near the green and also on Main Street, there is a wide variety of food options, the vast majority of them being locally owned. A couple of those that are highly rated are Pasta Cosi, an Italian restaurant that aims to serve upscale food in a casual atmosphere, and Home, an American comfort food spot with a vibe to match. There is also a downtown coffee shop, Common Grounds, which is open until at least 8 p.m. every night, making it a perfect relaxation and gathering spot in a cute setting right near the green.

Madison

New England rocky beaches and small town charm can both be found in Madison, a walkable town in the southeastern part of the state. It has abundant outdoor recreation opportunities and the longest stretch of publicly available beach at Hammonasset Beach State Park. Luckily for people who prefer to explore a pretty downtown area for entertainment, Madison has that too.

There is a lot to do in the town, and one of the most popular areas is the Boston Post Road strip. Here, you can find one of Madison's longest-running local attractions, the Madison Cinema, which has been there for decades but was recently fully remodeled. They play both popular and independent films, including foreign exports. Right across the street from the cinema is another Madison staple, RJ Julia Booksellers, which has been named Connecticut's best bookstore and even has an attached coffee shop.

Something unique about Connecticut is the New Haven style version of pizza, which is thin crust Neapolitan style and locally known as "apizza." If you want to feel like a Connecticut local and have never tried apizza before, you can do that in Madison as well, at Grand Apizza Madison, also on the Boston Post Road main drag.

Niantic

A tiny place geographically with only four thousand permanent residents, Niantic is, like many on this list, a waterfront town, but on the Niantic Bay. Unlike the rest though, Main Street in Niantic is actually a boardwalk as well, which gives it beach town charm but without the tourist traps. Its quiet hospitality and insane views will surely make it a fast favorite for you, and it is a very family friendly spot too.

Among the attractions on Main Street is the Niantic Children's Museum, an interactive, touch-based educational experience for kids that is, of course, also fun. Another that has been a local favorite for decades is the Book Barn Downtown, a sprawling building with a massive selection, and it is also kid-friendly with an enormous children's selection.

After shopping and walking the boardwalk, dinner at Skippers Seafood Restaurant is a mom and pop counter shop will truly give you an authentic downtown Niantic experience. For a more grown-up food and drink spot, visit The Black Sheep, a classic Irish pub with a wide selection and live music on the patio regularly. In downtown Niantic you are guaranteed to have a good time.

If you like feasting on top-notch seafood, meandering through museums, witnessing vivid sunsets on gorgeous harbors, or exploring pretty New England towns, this state has it all. Wander along the charming Main Street boardwalk of Niantic or spend time fishing in the beautiful Wethersfield Cove for a relaxing evening. Get excited about unique movies at the Madison Cinema or shop for antiques in Putnam. Whatever sparks your interest, Connecticut is sure to be an enjoyable destination for you!