The ultimate bucket list of the best things to do on a Connecticut road trip
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Year visited: Most recently 2023
Time of year: October
I first visited Connecticut in 2019, just as a quick stop to see the town that inspired Stars Hollow in Gilmore Girls on our way home from Boston.
But a little research, and two visits later, I’ve discovered just how much there is to see and do in Connecticut. So I embarked on a road trip to try out all the best things to do in Connecticut, and I’ve put my list together here for you to plan your own perfect Connecticut road trip!
About Connecticut
Connecticut is the third smallest state (land-wise) in the US, and the fifth oldest, having officially become a state in Jan. 1788. As one of the original colonies and first states in the United States, the state is full of Revolutionary War era history.
It is part of the “New England” area, known for its fall foliage. It is also close to New York City, and is bordered on its southern edge by the Long Island Sound.
What is Connecticut known for?
I’ll be honest, I didn’t know much about Connecticut other than that the show Gilmore Girls took place there. I just kind of lumped it in with all the other New England states that I don’t know much about…
But here are some things that Connecticut is known for:
The Constitution State-Connecticut is known as the Constitution State because in 1639, the colony wrote the Fundamental Orders, considered to be the first written democratic constitution.
Fall Foliage-Like the rest of the New England area, Connecticut is known for its fall foliage. Come in mid-late October for the best foliage.
Yale University-Yale is the third (or fourth-depending on which list you’re looking at…) oldest university in the United States. It is an Ivy-League school, which basically means you have to be really smart to get in…
Small Towns-Connecticut has a plethora of charming small towns throughout the state. While there are several larger cities, it seems like Connecticut is just a lot of cute, small towns where Hallmark movies take place.
P.T. Barnum, Mark Twain & Harriet Beecher Stowe-Some of the well-known people from Connecticut. Barnum was the mayor of Bridgeport for several years, and Twain and Stowe were neighbors in Hartford.
Invention of the hamburger-Further down on this list of things to do in Connecticut you will find an entry to eat a hamburger at the place that invented the original hamburger sandwich, in New Haven, Connecticut!
Apizza-Apizza is a unique New Haven style pizza, known for its charcoaled edges, from the charcoal-fire oven in which it’s cooked.
Mystic Pizza-Connecticut is also known for this pizza. ‘Nuff said.
Best Time of Year to Visit Connecticut
October
The best time of year to visit Connecticut is definitely October. I have visited in early October, mid-October and late October, and I would say the best time to see fall foliage in Connecticut is late October.
It’s also fun to see all the Halloween decorations and all the fun fall activities that the small towns in Connecticut like to put on, which is why October is the best time to visit Connecticut.
December
I think it would also be beautiful to visit in December with all the Christmas decorations. So many small towns will look like they stepped right out of a Hallmark movie.
Summer
Connecticut is also beautiful in the summer, which is a great time to do outdoor activities or seasonal tours. So the best times to visit Connecticut would be summer, fall or Christmas time.
Planning a Connecticut Road Trip
How to Get to Connecticut
If you’re flying in, the closest airport is the Bradley International Airport in Hartford.
You could also fly into JFK in New York, or the Boston Logan International Airport. Both airports are relatively close to Connecticut, and are easy to start a Connecticut road trip from.
Rent a car at the airport for your road trip. Or of course, if you live close enough to drive instead of fly, just drive your own car to Connecticut!
Driving in Connecticut
One thing to note about driving in Connecticut is that some of the roads can be very small and narrow. You will especially run into this out in the countryside and around the small towns.
We have, on occasion, even run into one lane bridges, where we had to wait for a car to come the other direction before we could go.
Top 5 Best Things to Do in Connecticut
There are a lot of things to do in Connecticut, and being a small state, it’s pretty easy to plan a road trip across Connecticut and see a lot of different things!
But after road tripping Connecticut three times, these are my top 5 picks for the absolute best things to do in Connecticut:
#1: Gillette Castle State Park
This state park is quirky, unique, and beautiful. And you don’t have to pay for parking, like at a lot of the state parks in Connecticut! It was my absolute favorite spot on my Connecticut road trip. And I didn’t even get to see the inside!
#2: Mystic
Home of Mystic Pizza, one of the best museums in Connecticut, the oldest cider mill in the US, one of my favorite donut shops EVER, and so many other fun things to do and see! Mystic is a great place to bring families for vacation in the summer or fall.
#3: Small Towns in Litchfield County
These are the towns that inspired Stars Hollow from my favorite TV show ever: Gilmore Girls! They are full of small-town charm, with gazebos, local shops and cafes, bookstores, festivals, town greens and more. I myself always prefer wandering around an adorable main street to exploring big cities.
#4: Hartford
Speaking of big cities… If you visit one big city in Connecticut, it should be Hartford, the capital (although it is actually one of the smaller cities in Connecticut). There are a lot of unique and fun attractions to experience in Hartford, including “small-town” suburbs that also look like Stars Hollow.
#5: Stay in a Unique Airbnb/Rental
The final entry on my top 5 things to do in Connecticut list is to find somewhere special to stay. There are a lot of unique stays on VRBO and Airbnb in Connecticut.
You can find a cabin in the woods surrounded by fall foliage, stay in your own little castle, or in an English countryside cottage, like the one where I stayed, which was another highlight on my Connecticut road trip.
Things to Do in Connecticut
Of course, everyone will have their own favorites, but for me, those are the absolute best things to do in Connecticut. Plan your own Connecticut road trip and pick your favorites too!
Here are all the best things I’ve found to do in Connecticut, as well as additional information to help you plan your visit to the Constitution State. The Connecticut attractions are listed from west to east across the state.
Map of things to do in Connecticut:
Hike Kent Falls State Park
Kent Falls is Connecticut’s tallest waterfall, stacking up to be a 250 foot drop in total, although it is not a straight, dramatic drop. The hiking trail goes up and up and up, past many mini waterfalls as the stream makes its way from the top of Kent Falls to the bottom.
If you’re not into hiking, you can enjoy the view of the falls at the bottom of the hill, as well as the covered bridge and picnic area, without having to hike all 250 feet up!
If you’re from out of state, you will have to pay a parking fee on an app at Kent Falls. If the parking lot fills up, the park will close to more visitors until enough spaces open up again.
Drive Across the West Cornwall Covered Bridge
One of the last covered bridges in the state, not only is the West Cornwall Covered Bridge a good photo op stop on a Connecticut road trip, but you can actually drive across the 172 foot bridge in Connecticut’s northwest corner.
Explore the Small Towns in Litchfield County
I’ve already mentioned that exploring the small towns in Litchfield County is one of my favorite things to do in Connecticut. There are small towns all over the state, but of all the ones I’ve been to throughout the state, this area has my favorite small towns.
This is the area where Amy Sherman-Palladino (creator of Gilmore Girls) was staying when she developed the idea for the show and the setting of Stars Hollow. While you can’t find any one town that specifically feels like Stars Hollow, you can find bits and pieces of it in all the towns.
The four main towns to visit are:
These towns are great for local shopping, restaurants, hanging out in the town green, enjoying local festivals and farmers markets, and are especially good for antiqueing.
Have Brunch at the Mayflower Inn
Three times I’ve been on a Connecticut road trip, and three times I made plans to visit the Mayflower Inn, and three times I haven’t actually been to the Mayflower…
The biggest draw of the Mayflower Inn is that it was the inspiration for the Independence Inn in Gilmore Girls (no, this entire list of things to do in Connecticut is not based solely on Gilmore Girls. Honest…).
It is quite a chunk of money to spend the night here (but something to splurge on for a special occasion!), so I would suggest just coming for a meal. That way you can experience the boutique hotel, the farm to table food, and the beautiful grounds, without having to break the bank.
See a Revolutionary War Cannonball
Keeler Tavern was originally built in 1713 as a home for Benjamin Hoyt and his family. His grandson later turned it into an inn and community tavern, just on the brink of the Revolutionary War. Which leads to its significance today (other than the fact that it’s 300 years old).
During the battle of Ridgefield, British soldiers fired on the tavern, and a cannonball from the war was embedded into the wall of the tavern, where it remains today!
Putnam Memorial State Park
Connecticut is full of history! Another site of significant Revolutionary War history is Putnam Memorial State Park, not far from Keeler Tavern.
The Continental Army wintered here in 1779, during the American Revolution. You can see the remains of their encampment as well as other buildings that have been rebuilt in the style of the times.
The Barnum Museum
This is the greatest show! P.T. Barnum, the famous founder of the circus, was from Connecticut, and towards the end of his life served as mayor of the city of Bridgeport. Naturally, they have a museum to honor him.
One caveat though…the Barnum Museum has been closed for renovations since a tornado struck it in 2010! One would think that being closed for so many years would lead to ultimate closure… but no! The Barnum Museum is constructing an even greater show!
Sooo… when it does reopen, it will certainly be one of the best things to do in Connecticut.
Meanwhile there are some other P.T. Barnum things to do in Bridgeport:
Visit P.T. Barnum’s grave, in a cemetery that he designed!
See the P.T. Barnum statue at Seaside Park, a city park developed by, who else, Barnum!
The PEZ Visitor Center
Did you know that PEZ was invented in Austria as a way to help smokers quit smoking? Did you further know that when PEZ production finally made its way to America, it landed in Orange, CT, where there is still a factory today?
The PEZ Visitor Center is a quick, but unique stop on any Connecticut road trip. It is close to New Haven and Yale University. Plan to spend around half an hour here, touring the museum and browsing the gift shop.
Tour Yale University
Touring the campus of Yale University is one of the best and most popular things to do in Connecticut! You can learn some really fun history about America’s third oldest colonial college, see the oldest building on campus, and touch the toe!
Public tours of Yale are offered during the school year, and are free. You do have to reserve your spot online before the tour though. You will see the Old Campus, and gain access to other parts of Yale that are not open to the public.
Parking in New Haven is tricky. The best place to park is either at your hotel (if it’s downtown) or at the Shops at Yale parking lot.
Here are some things to make sure you see at Yale:
Eat the Original Hamburger
One of the best places to eat in New Haven is a tiny little building housing a restaurant that was established in 1895. Louis’ Lunch is a small and adorable diner that is famous for inventing the hamburger!
They still serve the hamburger the same way they originally served it: with cheese, tomato and onion on toast. Or as they put it, the right way.
Tip: Go in the afternoon to avoid the meal time crowds. There is not a lot of room inside!
Take Pictures at Saville Dam
I saw Saville Dam on almost every list of things to do in Connecticut that I read. Still, I wasn’t convinced there was enough there to make it actually worth a stop. But since it was only 15 minutes from where I was staying, I decided to check it out.
A dam is not usually high on my list of places to check out on a road trip, but whoever designed this water pump went to great lengths to make it photogenic. On a sunny day, it’s an enjoyable place to spend an afternoon, walking along the lawn, gazing out at the reservoir, and of course, taking pictures at the castle (which is a lot bigger in real life than you’d expect!).
I wouldn’t go out of my way to stop here, but if you are on a Connecticut road trip, and happen to be nearby, it’s definitely worth a stop.
How to Get to Saville Dam:
The directions are a little tricky, as the castle is not actually where Saville Dam is marked on Google Maps. There is an oddly-shaped parking lot off of Route 318/Saville Dam Road.
There will be a little pathway leading you across the street from the parking lot (you will have to cross the busy highway twice, as the parking lot and the dam are on the right, but the area to walk is on the left).
Once you cross the street, just walk along the grass until you come to the castle structure. There will be another spot showing you where to cross the street over to the dam. If you come on a sunny day, chances are there will be a lot of other people walking around here too.
Hartford, Connecticut
Hartford has to be on any list of the best things to do in Connecticut, because it is, of course, the capital (although being a state capital doesn’t guarantee you a spot on the list. I’m looking at you, Albany).
In Connecticut’s case, however, Hartford makes the list. There are so many fun things to do in the area:
Tour Mark Twain’s House (listed next!)
And Harriet Beecher Stowe’s house (Mark Twain’s neighbor!)
Explore cute neighborhoods, like Old Wethersfield
Tour the Capitol building
Relax in the award winning Elizabeth Park Conservancy
Cruise down the Connecticut River
Tour Mark Twain’s House
I think that touring the Mark Twain House deserves its own place on this list. This is a great museum to visit if you are a literary nerd like me!
The house is only open for guided tour, and I highly suggest signing up for the costumed actor tour! In fact, you could sign up for this tour several times and hear different stories, as they have a whole crew of actors portraying each different member of the household. My tour was delivered by the maid.
You cannot take pictures inside the house, but you are welcome to take pictures outside. There is also a museum, cafe and gift shop adjacent to the house, where you will go to begin your tour.
Dinosaur State Park
What happens when 2000 dinosaur tracks are uncovered during an excavation for a new building? You open a state park!
Dinosaur State Park is a great place to bring families on vacation. See some of these dinosaur tracks on display in their geodesic dome, or wander around the trails outside, and maaaaybe uncover some tracks of your own!
Hammonasset Beach State Park
Going to the beach is not the first thing that comes to mind when I think of things to do in Connecticut. But the state’s location along the Lond Island Sound does provide plenty of shoreline, the most popular being Hammonasset State Park.
There are even reports of a spot where you can hear a “singing beach!” Visit Meigs Point at Hammonasset Beach to hear the tide make music on the seashells that litter the shore.
Gillette Castle State Park
Rounding out our list of Connecticut state parks, and my absolute favorite Connecticut attraction is Gillette Castle State Park!
This state park used to be the home of actor William Gillette, who was the first person to play Sherlock Holmes. His quirky house is set high atop a cliff overlooking the Connecticut River.
It is a bit tricky to get to, because you have to drive the narrow, winding roads up to the top of the hill, but it is definitely worth it. This is also one of the few state parks in Connecticut where out of state residents do not have to pay a parking fee (definitely my biggest beef with Connecticut… But I digress).
The inside is only open by guided tour, and tours are only offered the end of May through early October. Even if the castle and visitor center are closed, the bathrooms will still be open as long as the park is open (yay!).
There are also beautiful walking trails on the state park grounds. It was spectacular to see the fall foliage.
Ride the Essex Steam Train
Another must-do Connecticut attraction is to ride the historic Essex Steam Train. You can choose to ride just the train, or extend your journey to also include the riverboat Becky Thatcher (named after the Mark Twain character!).
These historic transportation modes will take you through the New England countryside, small towns, and along the Connecticut River, where you can see highlights like Gillette Castle from the water.
Then be sure to check out the downtown area of Essex, with lots of shops, cafes, and museums.
The steam train and riverboat tours are available May-October, with seasonal train experiences also available in December.
Eat at the Griswold Inn
The Griswold Inn in Essex is one of the oldest inns in the country! It opened its doors in 1776 (talk about patriotic!). So while you’re in the area, be sure to stop in for a pint in the historic dining room, or even stay overnight in one of their cozy rooms.
Take a Boat to Forts Griswold & Trumbull State Parks
Another Revolutionary War site to see in Connecticut is Fort Griswold Battlefield State Park. The park is situated at the site of the 1781 massacre of American troops by traitor Benedict Arnold.
A fun way to visit the fort is to take the Thames River Heritage Park Water Taxi from New London. The boat will take you from the New London Pier to the state park, and also goes to Fort Trumbull State Park. Although not as old as Fort Griswold, Fort Trumbull boasts a 19th century fort structure that is still standing today.
The boats only operate on weekends, mid-June to mid-September.
Mystic Seaport Museum
There are so many great things to do in Mystic, that instead of just listing Mystic as one of the best things to do in Connecticut, I have to split up at least some of them into their own categories.
The Mystic Seaport Museum is one of those things that deserves its own spot on the list. It is certainly one of the best museums in Connecticut! And it’s huge! There are so many fun things to explore at this museum along the water in Mystic.
There is a large parking lot just across the street from the main (north) entrance to the museum. There is also additional parking at the south entrance, if this lot is full.
Eat Mystic Pizza
It may be cliche and touristy, but I am a tourist, and I want to eat a slice of Mystic Pizza when I’m in Mystic! And I thought it was absolutely delicious! So I feel no shame in saying that eating Mystic Pizza is one of the things you have to do in Connecticut.
You can order just a slice or a whole pizza, dine in or order carryout, or order online for pickup or delivery. There are lots of ways you can get that slice of Heaven!
Get Cider from the Oldest Cider Mill in the Country
There are a lot of cider mills worth visiting in Connecticut, but B.F. Clyde’s Cider Mill deserves its own space on the list because not only is it a delicious cider mill, it is also the oldest steam powered cider mill in the US! They’ve been in operation since 1881, so this cider mill in Mystic is definitely worth a visit.
Visit the Boxcar Museum
Nestled in the top corner of Connecticut is a little boxcar, housing the Boxcar Museum, a little museum dedicated to the beloved children’s books. The Boxcar Children books were written by Connecticut native Gertrude Chandler Warner in the early 1900s.
It’s not a very big museum, but it is a special and unique Connecticut attraction. The museum is open May-October.
Things to Do Across the State
These are things to do in Connecticut that you can find at multiple locations across the state. Perfect for planning a Connecticut road trip!
The Connecticut Pizza Trail
From the famous New Haven “apizza” to the (also famous) Mystic Pizza, and countless other pizza shops in between, CT Visit has put together the ultimate Connecticut Pizza Trail.
They claim no state does pizza better… Well I don’t know about that; it sounds like we better get our taste buds out and start testing this theory, on a pizza themed Connecticut road trip!
Visit a Cider Mill
In addition to the oldest cider mill in the US (B. F. Clyde’s) there are so many cider mills across Connecticut that you should visit in the fall. Here is a review of the best cider mills to visit across the state.
Go Antiqueing
Connecticut is known for its (many) antique stores, especially the small towns in Litchfield County. If you’re in search of a good find, Connecticut may be the place to look.
Attend a Festival
A scarecrow festival in Old Wethersfield.
There are so many small town festivals to experience in Connecticut! Try to plan your trip around one of these events, be it something simple like a farmer’s market in the town green or a scarecrow contest on Main Street, or a full blown harvest festival.
It really brings the small town charm to life when you can participate in one of their quirky festivals!
Eat Donuts
A French toast donut from Deviant Donuts!
I have made an effort to try ALL the best donut shops in Connecticut! There are still plenty more for me to try, but here is my opinion of all the ones I have tried:
Luke’s Donut Shop-While their donuts are surprisingly affordable, I would skip this donut shop in Connecticut. Unless you are a fan of Gilmore Girls. Because it’s Luke’s. Then yes, definitely stop.
Dottie’s Diner-This simple diner in Woodbury is well-known the state over for their donuts. They don’t have a lot of variety, but they don’t need it, because their donuts are delicious!
Neil’s Donuts-Neil’s Donuts has a couple locations around central Connecticut, so if you’re near one, be sure to stop for a donut. You won’t find anything out of the park, but they are good donuts.
Donut Crazy-Donut Crazy has a cute location in downtown New Haven (walking distance from Yale!), and quite a few other stores as well. They have creative, fun, and delicious donuts! This is definitely one worth stopping for.
Beach Donuts-I have to be honest… I read a lot of reviews that listed Beach Donuts as one of the best donut shops in Connecticut, but I just didn’t see the appeal. I only tried the apple cider donut, so maybe their others are better, but I personally would put this down as a skip.
Deviant Donuts-Yes! This donut shop you have to visit! They have the most artistic looking donuts and the most creative (but delicious) flavor combinations. I won’t say that it’s necessarily the best donut ever, but the flavor and appearance raise it up pretty high in my book! Definitely give them a try.
Movies to Watch
(and books to read, before visiting Connecticut)
Books to Read
The Adventures of Tom Sawyer
Or anything by Mark Twain, really. The author lived in Connecticut for much of his adult life, and wrote his most famous works, including The Adventures of Tom Sawyer, from his home in Hartford,CT.
Uncle Tom’s Cabin
Mark Twain’s neighbor was Harriet Beecher Stowe, author of Uncle Tom’s Cabin. The book, first published in 1852, was significant in the fight against slavery in pre-Civil War America.
Boxcar Children Books
Read the original Boxcar Children book, and any of the first mysteries that were written by Connecticut native and Yalie Gertrude Chandler Warner (only read the ones that were actually written by GCW, AKA the good ones!).
Movies to Watch
Gilmore Girls
Let’s face it, Gilmore Girls is the only reason I visited Connecticut in the first place. The heart-warming show is set in the fictional Connecticut town of Stars Hollow, and hits up a lot of other Connecticut hot spots, like Hartford and Yale.
The Greatest Showman
Before you visit Bridgeport, Connecticut, you should watch The Greatest Showman, the catchy musical about the city’s former mayor who created the circus.
Marshall
This 2017 biopic starring Chadwick Boseman as Thurgood Marshall was actually filmed in the beautiful city of Buffalo, NY, but it primarily takes places in Bridgeport, CT. It is based on a true story that happened there in 1941, one of the early civil rights cases that Marshall took on as a lawyer for the NAACP.
Mystic Pizza
Mystic Pizza is probably the most famous movie that takes place in Connecticut. Definitely watch it before traveling to Mystic and trying the iconic “slice of heaven.”
Little Women
Especially if you’re coming at Christmas time, watch Little Women (any version will suffice, but I’m specifically thinking of the 1994 version) before you visit Connecticut. The movie takes place in the state during the Civil War.
The Noel Diary
This Netflix Christmas flick takes place throughout the New England area, with some very recognizable Connecticut filming locations, such as the Griswold Inn and R.J. Julia Booksellers.
Tom & Huck
One of the best movie adaptations of Mark Twain’s work (especially if you’re a fan of JTT), Tom and Huck is a fun Disney film of Twain’s most famous and enduring work.
The Adventures of Huckleberry Finn
If we’re going to watch Tom & Huck, we might as well watch The Adventures of Huckleberry Finn as well. Although these stories take place in Missouri, they were penned in Connecticut, and are fun to view before you visit Mark Twain’s house.
Revolutionary War movies
I find there are surprisingly few Revolutionary War movies for something so central to our history, but if you can find any, choose a favorite to watch before your trip to the Constitution State. A couple suggestions you can always go with are The Patriot or Hamilton.
Plan a Gilmore Girls themed Connecticut road trip:
To be honest, I thought I had covered Connecticut pretty well on my three road trips, but after writing this article, I feel like I need to go back and do more! If you have any suggestions for things to do in Connecticut, feel free to leave them in the comments below!
Further Reading
I was one of many people (most of them CT locals) who contributed to this list of the best things to do in Connecticut in each season.
Any more questions?
If you have any more questions about visiting Connecticut, feel free to email me or comment below.
Planning a Connecticut road trip?
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