Last summer, I drove through Connecticut on my way to Boston and almost skipped it entirely.
Big mistake.
I pulled off at a random exit near the coast, grabbed a lobster roll, and stumbled onto this castle perched on a hillside that looked like it belonged in medieval England, not New England.
That moment changed everything.
Connecticut isn’t the state people talk about when planning road trips, but man, that’s exactly why I’m obsessed with it now.
It’s got this quiet magic—waterfalls nobody’s heard of, historic towns that feel frozen in time, and coastal views that rival anything you’ll find up north.
And here’s the thing: people are finally catching on fast.
Heublein Tower Will Blow Your Mind
There’s this 165-foot fairytale tower sitting atop Talcott Mountain, and the views from the observation deck are mind-blowing—you can see the Hartford skyline, the Farmington River Valley, the Long Island Sound, and even mountains in New Hampshire.
Sounds wild, right?
But it’s real, and it’s one of my favorite hikes in the state.
You’ll need to hike through serene woodlands to reach it, but trust me, it’s worth every step.
The historic stone structure was once the residence of a wealthy businessman named Gilbert Heublein and now serves as a museum.
When I finally made it to the top after huffing up those stairs, I just stood there for twenty minutes.
The whole state spread out below me like some kind of New England painting.
If you’re planning a Connecticut trip and you skip this, you’re doing it wrong.
Gillette Castle Is Like Nothing You’ve Ever Seen
Gillette Castle is well known among Connecticut attractions and is listed on the National Register of Historic Places—actor William Gillette commissioned this home, and it was built in 1914, and Gillette was most famous for portraying Sherlock Holmes.
So yeah, basically a Sherlock Holmes actor built himself a stone castle on a cliff.
And it’s not just any castle.
The 24-room mansion looks like a medieval stronghold from the outside, but the eccentricities certainly don’t stop there.
I’m talking hand-carved wooden doors, intricate locks, hidden spy windows, and secret passageways.
This guy was living out some serious fantasy vibes.
The surrounding park is incredible too—forested trails, rocky overlooks, and river views that make you feel like you’ve left Connecticut entirely.
Honestly, if I could go back and explore one place in the state all over again, this would be it.
Saville Dam Is Crazy Photogenic
On the 6-mile Lake McDonough Scenic Drive, be prepared to be inspired by views of the Farmington River, Lake McDonough, and the highlight: Saville Dam—as one of the prettiest and most photographed spots in Connecticut, the dam alone is worth the drive.
I wasn’t expecting much when I drove out there.
But then I rounded a corner and there it was—this massive, elegant dam framed by rolling hills and crystal-clear water.
It’s one of the most picturesque spots and this massive dam is the main water source for Hartford, CT and home to some of the most beautiful views around.
Pro tip from my experience: pack a lunch because there aren’t any restaurants nearby.
Just you, the dam, and nature.
It’s the kind of place that makes you slow down and actually breathe.
Mystic Seaport Takes You Back In Time
The very last whaling ship, The Charles W.
Morgan, can be seen at the Mystic Seaport Museum—it’s actually the largest maritime museum in the United States, and the ship, built in 1841, has the distinction of being the only wooden whale ship still afloat.
Walking around Mystic Seaport feels like stepping into the 1800s.
There are historically restored buildings, sailing ships, and exhibits that show you what life was really like back then.
I spent hours wandering around, learning about the whaling industry and just soaking it all in.
And yeah, if you’re a Julia Roberts fan, you gotta hit up Mystic Pizza in town.
It’s touristy, sure, but it’s also kinda fun and the pizza’s actually good.
The whole Mystic area has this charm that’s hard to describe—you just have to experience it.
Kent Falls Is Connecticut’s Tallest Waterfall
Kent Falls via Kent Falls State Park is a must-visit for any resident or visitor in Connecticut—who doesn’t want to check the tallest (at 250 feet) waterfall off their CT bucket list?
When I first saw Kent Falls, I couldn’t believe something this impressive was hiding in Connecticut.
Take the short flat walk to the main fall or continue up the stairs and walk the less than half mile along the right side of Kent Falls where you can see all the different drops on the observation decks along the way.
Each level gives you a different perspective, and after heavy rain, this thing is absolutely roaring.
I went in July and the flow was insane.
Bring your camera, wear good shoes, and give yourself time to explore the whole trail.
It’s one of those spots that reminds you nature doesn’t need to be out West to be spectacular.
Hammonasset Beach Is A Shoreline Gem
This is actually the largest shoreline park in the state, and Hammonasset Beach State Park is an excellent CT destination if you’re interested in spectacular Long Island Sound views.
I’m a sucker for a good beach, and Hammonasset delivered.
There’s more than just sandy beach at Hammonasset, too, with camping sites, bicycle rentals, and Meigs Point Nature Center, where you’ll find educational programs like nature walks, touch-tank programs, and craft workshops.
I rented a bike and rode along the coast for a couple hours—best decision.
The sunset here is unreal, and the whole vibe is just chill and welcoming.
If you’re traveling with family, this is perfect because there’s something for everyone.
Even if you’re solo like I usually am, it’s a great place to unwind.
Louis’ Lunch Invented The Hamburger (Seriously)
Louis’ Lunch in New Haven has the true record: they are the birthplace of the hamburger sandwich and the Library of Congress says so—grab a classic burger in this small, cute restaurant, but know that they only offer tomato, onion, and cheese so you get the burger’s true flavor.
No ketchup allowed here, guys.
They’re serious about that.
When I walked in, I felt like I’d entered some kind of time capsule—the place has been around since 1895 and they still cook on the same vertical cast-iron grills.
The burger was simple, delicious, and honestly one of the best I’ve ever had.
It’s tiny inside, so expect a wait, but it’s worth it just to say you ate at the birthplace of the American hamburger.
Plus, New Haven has an amazing pizza scene, so make a day of it.
Lover’s Leap Trail Packs A Punch
When it comes to a short and sweet hike that is packed with adventure, the one-mile Lover’s Leap Trail delivers—along the way, you’ll cross an iconic 19th-century iron bridge, historical ruins, and an old spring house.
Only one mile, but it’s loaded with cool stuff.
What I enjoy about this trek is the views of the Housatonic River and the rolling hills, plus, there are several scenic spots, including the large rock formation from which the park gets its name.
The iron bridge alone is worth the trip—super photogenic and just beautiful.
This trail is perfect if you’re short on time but still want that outdoor Connecticut experience.
I hiked it on a weekday morning and had the whole place to myself.
Pure peace.
The Glass House Is Architectural Genius
The Glass House is located in a 200-acre park and is one of the most impressive pieces of architecture in Connecticut.
If you’re into design or architecture at all, this place will blow your mind.
It’s exactly what it sounds like—a house made almost entirely of glass, set in this sprawling, beautiful park.
The clean lines, the way it sits in the landscape, the whole concept—it’s just genius.
I’m not usually an architecture nerd, but walking through The Glass House made me appreciate how creative and bold design can be.
It’s modern, it’s striking, and it’s totally unique to Connecticut.
Book a tour in advance because spots fill up fast.
Essex Is A Perfect Sunday Escape
Essex is one of our favorite places to visit, especially on a Sunday—we love checking out the Essex Steam Train and never leave without doing some shopping down town, and our favorite spot to have lunch is, hands down, the Tap Room at the Griswold Inn.
Essex has this old-school New England charm that just feels right.
The Essex Steam Train and Riverboat tour begins at the historic 1892 Essex Station and makes a 2.5-hour round-trip journey into the Connecticut River Valley.
I took the train ride and it was honestly so relaxing—rolling through the countryside, watching the river, no rush.
Downtown Essex is filled with cute shops and great food spots.
The Griswold Inn has been around forever and the atmosphere is cozy and welcoming.
If you want a low-key, charming day trip, Essex is your spot.
