Things to do in Connecticut

In October of 2024 I planned a road trip from PA to Maine. I ended up only going halfway to Connecticut as my time and budget allowed. Even though I did not make it all of the way to Maine, I am so glad I went! I hope this may inspire you to get out and explore as well!

Day 1

I checked into my Airbnb, which was an adorable lakeside tiny house. It was perfect for a solo traveler or to share with a loved one. Staying in a tiny house was very cozy. It was refreshing to live simplistically! I had a beautiful view of the lake during the day and the stars at night.

📍The Book Barn

The Book Barn is one of my new favorite places in the world. Any place that celebrates books is an instant winner in my heart. This is a unique used and rare bookshop that actually spans several different locations. There are cats, goats, and adorable decorations. It’s a sprawling, magical place. If you love books like I do, I would definitely recommend checking it out!

I arrived late in the evening on day one, so I wrapped it up with some pizza from 📍Family Pizza and retreated back to my Airbnb.

Day 2

I began day two by grabbing a coffee and croissant at 📍The Sift. I then hiked the red trail at Devil's Hopyard State Park. This trail is a nice loop that will take you to the scenic view of the falls. I highly recommend packing a sweet treat for your hike and saving it for when you arrive at the waterfall. I chose the hazelnut praline croissant. It was a nice reward to enjoy while I sat back and took in the the view of the waterfalls. Sunlight danced on the water and I saw dragonflies glittering across its surface. I've been told that dragonflies are a sign of dreams coming true, and I thought happily of that as I munched on my croissant.

The Sift

Devil's Hopyard State Park

I spent the evening exploring Mystic's shops and enjoying the views from the drawbridge while savoring an ice cream cone from 📍 Mystic Drawbridge Ice Cream. I'm a big fan of thrifting so after hopping around Mystic I explored a local Goodwill where I found a nice Nike shirt before calling it a day.

Day 3

I spent day three in New Haven. I will plan to make a separate post about New Haven, as there is so much to do there, and so much to write about! I recommend simply walking around the Yale Campus and enjoying the views. There will be more to come on New Haven. Once I write that blog post, I will return to link it here.

Day 4

I began the final day by exploring 📍Pandemonium Thrift Shop and walking along the beach at 📍Rocky Neck State Park. Pandemonium Thrift was full of charm. I found books and scored some second-hand Teva sandals. I love thrifting because of the thrill of the chase! You never know when you are going to find a hidden gem. It also feels good to shop used rather than give into fast fashion trends.

Pandemonium Thrift

Rocky Neck State Park

Even though I did not make it to Maine, I thoroughly enjoyed my road trip to Connecticut. Maine is there waiting for me and I'm looking forward to visiting Acadia National Park one day. I felt so refreshed and happy during this excursion! It was a peaceful and spirit-lifting time. Because I went in October, it was the perfect opportunity to take in all nature's beautiful colors. Plus, I enjoyed all of the cute Halloween decorations. I hope someone can follow this itinerary and have a wonderful solo trip or getaway with a friend to Connecticut!

Yale Campus

There is something so soul-soothing about a walk along a shore. Because it was off-season, there weren't many others to share the beach with. I had a very peaceful time at Rocky Neck, watching the waves, collecting shells, and listening to the gulls.

*It's important to note if you have an out-of-state license plate, you'll have to pay for parking at the state parks in CT!

The Book Barn

Mystic