Traveller By Birth

An influencing photo travel blog where exploration is limitless

offbeat connecticut road trip

On our “The Ultimate New England Road Trip”, we decided to ditch the freeways and see the real, what is called as, Old America. Our road trip started from Connecticut and we drove through some gorgeous towns. Hence, I am going to share details about our offbeat Connecticut road trip and routes of the scenic drive.

New Milford

Our road trip started from Bensalem, Pennsylvania and New Milford was our first stop.

Offbeat Connecticut Road Trip

New Milford is a historic and pretty little town on the banks of River Housatonic. It is about 55 miles from Hartford, the capital city of Connecticut, and 85 miles from New York City. Therefore, it is quite easy to reach New Milford and begin the scenic drive.

The route of the scenic drive begins from New Milford, but before that we wanted to check out what New Milford had to offer. 

First we head our lunch at this wonderful restaurant called Tivoli.

Lovers Leap State Park

Later, we went to the Lovers Leap State Park. It is an impressive state park, most of which is left untouched. It is in its complete raw state. There are several hike trails here as well. Due to it being a less touristy place and in raw form, when we hiked there, it almost felt as if we were exploring something which has not been seen yet.


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Story behind the park

According to the legend, hundreds of years ago there was a Native American woman named Lillinonah, who was the daughter of a chief in Connecticut. She fell madly in love with an Englishman and married him, but he then needed to leave for business. When he hadn’t returned as he’d promised to do, Lillinonah decided to jump from the mountain into this river. When her husband did return and learned what she had done, he followed suit, diving down into the water to be with his love. Hence, the name, “Lovers Leap State Park”.

Offbeat Connecticut Road Trip

Scenic Drive Route

We took Route 7 from New Milford and drove towards Canaan, making sure to stay on Route 7 till Canaan. Then we took a right and caught Route 63 towards Litchfield.

Offbeat Connecticut Road Trip


We stopped in the middle at this town called Gaylordsville on the way. If you are into colourful stuff then you should definitely take a look at this town full of cute houses, shops, organic farms and kind people.


By the time we reached Litchfield, it was already evening. Hence, we decided to call it a day. Spent a little time in Litchfield, and stayed the night at Torrington, which is only 9 minutes from Litchfield.

New London

Next day, from Torrington, via the Old Norwich Road, we ended up at New London.

We parked and explored New London by foot and discovered that it is a splendid coastal town with stunning street art all around the city.

Subway Story of New London

(Read the caption of my this Instagram Post)

Harkness Memorial State Park

Later, a local suggested us to visit the Harkness Memorial State Park, which we did and loved it as it was a fun beach park. It was one beautiful evening that we spent there, first at the beach and then on a bench at the lush green park admiring the oceanic views.

Connecticut Road Trip Map

Our time in Connecticut ended here and from the park, we made a move towards Providence, Rhode Island. Do read my next post about our one day in Providence.

I am sure there is still a lot to experience in Connecticut but I am happy that we road tripped through these places and explored some really cool destinations.

Also, check out these YouTube videos about my offbeat Connecticut road trip experience, for a visual treat.

Have you been to/live in Connecticut? Where all did you go and tell me what I’ve missed, I’d really love to make a list for my another road trip.

Also, do react, share and comment below, if you liked my Connecticut travel story.

See you in Providence!


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