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Located in New England, not far from New York City, Connecticut is a beautiful state and it has so much to offer all year round!
It’s small but there are a lot of things to do. Charming small towns, famous universities, castles, waterfalls, beautiful beaches… there is definitely a bit of everything!
I explored a lot of the state on my New England road trip and kept being amazed by how pretty it is.
Also, if you are a fan of Gilmore Girls, this is a no-brainer! While it wasn’t actually filmed here, it is set in Connecticut and exploring the state is really like being in Rory and Lorelai’s shoes.
So here are 8 of the most beautiful places to visit in Connecticut.
⚓ 1. Mystic
Mystic is a coastal town located on the Mystic River, at the border with Rhode Island.
It’s a very lively town and it really reminds me of Key West in many ways (but Connecticut version).
As you head downtown, you’ll discover the beautiful Bascule Bridge, a 1920s drawbridge that rises to let boats pass. Keep walking up Main Street, you’ll find loads of independent shops, bars and restaurants.
Make sure to go to Mystic Pizza (yes, that’s the one from the movie).
For shopping, Olde Mistick Village is ideal. It’s home to loads of quirky shops and it’s genuinely so unique.
Finally, make sure to visit the Mystic Seaport Museum and the Mystic Aquarium.
🍫 2. Essex Village
Essex Village is what most people picture when they imagine a perfect New England village.
The streets are lined with trees and there are loads of colonial and federal style homes.
Essex Village sits on the Connecticut River which gives it that coastal feel even though it’s not actually by the sea.
You’ll love walking up and down the main street from Essex Square. There are loads of quaint shops and cafes.
The Connecticut River Museum is also interesting and they often organize events.
Tip: set your GPS to “Essex Village,” not just “Essex,” or you’ll end up in the wrong part.
🎓 3. New Haven
New Haven is beautiful in a completely different way, thanks to the Gothic architecture of Yale University.
It’s a much bigger city compared to the other places you’ll see in Connecticut but it somehow has a small town feel to it.
The first place that you should visit is Yale. It’s one of the most famous universities in the world and an Ivy League university.
Also, if you’re a Gilmore Girls fan, that’s where Rory went!
Walking around the Old campus feels like stepping onto a film set. The stone towers, the ivy, the stunning Sterling Memorial Library, which was built to look like a cathedral… it really is amazingly beautiful. It looks like something you’d find in Europe rather than in North America.
I would recommend booking the free student-led tour to see Yale as you get to learn a lot more and will have access to some colleges you wouldn’t get to see otherwise. It takes about 1 hour and can be booked online.
Make sure to also have a wander through New Haven Green and go to Broadway to check out the Yale bookstore.
Finally, make sure to try the famous New Haven-style pizza.
⛵ 4. Milford
Milford is a lovely coastal town on Long Island Sound.
It has a pretty downtown and one of the longest town greens in Connecticut, so it’s nice to walk around. There are loads of independent shops so you can have a browse.
If you’re looking for a place to have breakfast, I’d recommend Cafe Atlantique. They serve some of the best omelettes I ever had!
The Milford Marina Landing is also very pretty and you can go there for a walk around. There are also boat tours that start from there.
Another reason to visit is to go to the beach! For that, head to Silver Sands State Park. At low tide, a sandbar appears and you can walk across to Charles Island. Just keep an eye on the tides as they come in fast!
🚣 5. Rowayton
Rowayton is a small seaside village in Norwalk, near New Canaan.
There isn’t a lot to “do” here, and that’s exactly the point.
It’s a lovely place to slow down. You can walk along the Five Mile River and look at the boats and the waterfront homes.
It’s also a great spot for seafood (make sure to book one of the restaurants, it’s worth it), and the sunsets here are beautiful.
💫 6. New Canaan
New Canaan is one of the prettiest towns in Connecticut. It’s also very easily accessible by car or train from New York City, making it a great day trip.
It has an elegant main street and the houses are so neat they look like dollhouses.
Park near Elm Street and have a wander. There are lots of nice shops and places to eat.
If you love architecture, go and see the Glass House, a famous modernist home.
🏰 7. Gillette Castle State Park
For something completely different, visit Gillette Castle.
It’s a quirky stone castle set high above the Connecticut River.
It was built in the early 1900s by William Gillette, the actor famous for playing Sherlock Holmes.
Inside, it’s full of secret passages and unusual details. Outside, there are lovely views over the river and woodland trails to walk.
Fun way to get there: you can take the historic Chester-Hadlyme Ferry across the river.
💧 8. Kent Falls State Park
Kent Falls is one of the prettiest natural spots in Connecticut. It’s located in the northwest hills so you’ll definitely need a car to get there but it’s well worth it.
The water drops around 250 feet down a series of falls through the forest.
A short trail lets you climb up alongside the falls for different views, and there’s a covered bridge at the bottom.
It’s especially beautiful in the fall.
🗺️ Map of the most beautiful places in Connecticut
