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Are you planning a trip to New England and want to explore Connecticut?
You’ve come to the right place!
Connecticut may be small, but it packs an incredible amount of things to do! Rolling hills, waterfalls, a gorgeous coastline, Ivy League towns, historic villages and scenic byways… it has it all!
And if you are a fan of Gilmore Girls like me, no doubt that you can’t wait to discover all these cute small towns!
This route starts and ends in Hartford, taking you through the northwest hills, down to the shoreline and back up through the peaceful Quiet Corner but you could adapt it to start it from somewhere else like NYC or Boston.
🚗 Getting started: Fly into Hartford (Bradley International Airport) and hire a car from there. It’s the most central starting point, and this loop is designed to bring you right back to it.
I’d allow around 7 days to do it justice.
If you need to hire a car, I personally use Discover Cars, they always find great deals and their customer service is great.
🏙️ 1. Hartford
Begin in Hartford, the state capital. It’s often overlooked, but it’s full of history.
The first thing you should do is to visit The Mark Twain House & Museum. This is where the author wrote The Adventures of Tom Sawyer and it’s truly fascinating.
Make sure to also go to the State Capitol as nobody should ever go to a state capital without seeing that beautiful dome.
If you like museums (or if it’s raining), the Wadsworth Atheneum Museum of Art and Connecticut Science Center are great options.
Finally, go for a stroll at Bushnell Park, the oldest publicly funded park in the country.
🍂 2. Litchfield
Head northwest into the beautiful Litchfield Hills and the elegant town of Litchfield.
It’s the quintessential New England town, with a stately green, grand colonial homes and lovely antique shops to browse.
Take your time wandering the pretty streets, then just outside town, head to the White Memorial Conservation Center, which offers miles of peaceful woodland trails.
It’s especially gorgeous in the fall, when the whole area turns gold and red.
🎨 3. Kent & Kent Falls State Park
Continue to Kent, a tiny town with a surprisingly sophisticated art scene and a cluster of excellent galleries.
Wander the walkable main street, browse the shops, and grab a coffee before heading back out into nature.
Just outside town, don’t miss Kent Falls State Park, where you’ll find a series of waterfalls in the forest. A short trail lets you climb alongside them for different viewpoints.
It’s stunning, especially in the fall. If you have time, the nearby covered Bull’s Bridge is worth a quick stop too.
🌳 4. New Milford
Next, stop in New Milford, home to the longest town green in Connecticut.
It’s a classic, walkable New England town with a pretty 1891 bandstand gazebo, independent shops and a relaxed, local feel.
It’s the perfect place for a coffee and a gentle stroll, and Gilmore Girls fans will love how much the green feels like Stars Hollow.
💫 5. New Canaan
Drive south into Fairfield County and elegant New Canaan, one of the prettiest towns in the state.
You can park near Elm Street and start having a wander. There are a lot of cute boutique so if you’d like to do some shopping, that’s an option.
There are also quite a few places where you can eat along Elm Street. They are particularly nice in summer since they have outdoor space.
Make sure to walk up to the iconic modernist Glass House.
🚣 6. Rowayton
Once you’re done in New Canaan, drive down to Rowayton. It only takes about 20 minutes.
It’s a peaceful little seaside village in Norwalk and honestly it’s a great place to end the day if you can.
You can stroll along the Five Mile River, admire the waterfront homes and boats, and enjoy the calm coastal atmosphere.
You’ll also find some nice restaurants including the Rowayton Seafood which is a must go if you like seafood.
The sunset here is always great as well!
⛵ 7. Milford & Silver Sands State Park
Continue east along the coast to Milford.
There are two main things to do here: going to downtown Milford and Silver Sands State Park.
Now Silver Sands will come before Milford so if you are driving in the morning, I would recommend stopping there first so you can spend at least half a day there.
However, if you are traveling in the evening, you should go downtown first and then head back to the state park in the morning.
Silver Sands State Park is where a sandbar appears at low tide, letting you walk out to Charles Island (but watch the tides!).
Milford is quite a pretty town and there are a few things you can do downtown.
Firstly you can walk along the town green and browse the shops. You’ll also find several cafés where you can have food (I personally loved Cafe Atlantique).
You can also go down to the marina and have a walk around as it’s very pleasant.
🍕 8. New Haven
Next up is New Haven, home to the world-famous Yale University.
This is one of my favorite spots and if you love Gilmore Girls, you must go!! Remember, that’s where Rory studied.
Your first stop should be the world famous Ivy League University, Yale.
You can visit by yourself but I recommend booking the free student-led campus tour. It only takes an hour and you’ll learn a lot more about Yale.
You’ll go to the Old Campus (which is stunning) as well as to the spectacular cathedral-like Sterling Memorial Library and inside a college (that bit you can’t do without the tour).
I thought it was fascinating because we got a lot of information about Yale, the architecture but more importantly the student life and what it actually is like to be a student at Yale University (spoiler alert: it sounds great, I had proper FOMO).
You can then head to Broadway and check out the various shop including the Yale bookshop.
Finally, let’s not forget another highlight: the pizza.
The New Haven-style pizza is legendary, and the local “Holy Trinity” of Frank Pepe, Sally’s and Modern serves some of the best in America.
Grab a pie, and see what all the fuss is about.
🏖️ 9. Madison
Carry on to Madison, home to Hammonasset Beach State Park, Connecticut’s largest shoreline park, with two miles of sandy beach and a lovely boardwalk.
It’s the perfect place to break up the drive with a proper beach stop.
The charming Main Street is worth a look too, especially R.J. Julia Booksellers, one of the best independent bookshops in the state.
🐚 10. Old Saybrook
At the mouth of the Connecticut River, Old Saybrook is a classic, laid-back shoreline town.
Start with a coffee at the charming Ashlawn Farm Coffee, set in an old farmhouse next to the historic train station, then wander Main Street with its antique and independent shops.
Head down to Saybrook Point for water views and have a drink at the marina (in summer that’s a fantastic spot).
Fun fact: this was the longtime home of Hollywood legend Katharine Hepburn.
🍫 11. Essex Village
Once you’re done in Old Saybrook, head to Essex Village. This is one of the most charming spots in the whole state so do not skip it!
It wasn’t in my original plan and I’m so glad that I went because it’s truly a fabulous little town.
Start by walking down the main street. You’ll find loads of quaint shops and cafes, as well as a lovely chocolate shop and pub.
You can walk all the way down to the Connecticut River Museum which is right on the water.
PRO TIP: Make sure to set your sat-nav to “Essex Village,” not just “Essex.” otherwise you won’t go to the right place.
⚓ 12. Mystic
Drive about 45 minutes and you will reach the beautiful town of Mystic.
This is the most famous town in Connecticut and I like to describe it as the Key West of New England. I find it very fitting and if you’ve been to the Florida Keys, you’ll see exactly what I mean.
When you get there you can stop at the Mystic Aquarium and/or the Mystic Seaport Museum. Both are fantastic.
Then head to Olde Mistick Village which is full of very unique shops.
After that, it’s time to head downtown.
The historic Bascule Bridge is the main landmark here. It’s quite a fun thing to watch when it lifts to let the boats pass.
Make sure to walk up Main Street and explore the side streets as there are loads of shops, restaurants and bars.
Don’t miss a slice at the famous Mystic Pizza (yes, the one from the movie!), and head to the quieter Gravel Street for a gorgeous sunset (that’s a bit of a hidden spot so you won’t find that on other guides but I liked it because you get nice water views and if you are in luck, the bridge will lift up then).
🌾 13. Route 169 up to Woodstock
To finish this road trip, you’ll head back to Hartford but inland via Route 169, a National Scenic Byway through the peaceful Quiet Corner.
This is a part of Connecticut that most people skip but I think it’s well worth doing as it doesn’t take that long and there are some real gems here!
You’ll drive north through Canterbury and Pomfret first.
You can then go to Putnam which I would highly recommend as it’s great for antiques. There are loads of shops and it’s quite a small town so it’s very easy to walk around.
Finally, head to Woodstock, which has a beautiful pink Gothic Roseland Cottage and orchards.
This road is great in summer and absolutely beautiful in the fall with the colors.
🗺️ Map of this Connecticut Road Trip
💡 A few practical tips
- Fly into Hartford (Bradley) and hire a car, this loop brings you right back to the start.
- Allow around 7 days to enjoy it without rushing.
- Fall is spectacular for the Litchfield Hills and Route 169 foliage; summer is best for the beaches.
- Check tide times at Silver Sands, and book Yale tours and Mystic attractions ahead in peak season.
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