After my adventures throughout the Midwest, I jetted off to New England to explore the area for the first time. I spent the majority of the week driving throughout Connecticut. Towards the end of the week, I also had a day filled of driving in Western Massachusetts. As a newbie to these areas, it was a lot of fun for me to explore – and I’ve got many insights to share. Read on for a deep dive into my explorations in New England.
Southeast CT: New London
A late arrival from my flight and crashing as soon as I got to the hotel made for a busy start to the week. I was up relatively early the next morning to begin the adventure, with my first destination being New London. After a work event for a couple of hours, I decided to check out the area. I went to what I think was the downtown area, but there wasn’t a ton to see. I got a real coffee, much needed – I definitely felt off, which was likely due to being really tired. This may have contributed to the weird vibe I got from New London, so I didn’t stay downtown very long. Take my vibes with a grain of salt, but it wasn’t my favourite place.
Northwest CT: New Milford, Kent, Cornwall, and Lakeville
For the next few days, I spent the majority of my time in northwest Connecticut. This area of the state was much more rural than I had expected. It is surrounded by a lot of forests and has limited cell service. The first area I really visited was Kent. I stopped at Kent Falls, a cute viewing spot with a waterfall, before getting into the town of Kent itself. It’s a tiny cute town that gave Stars Hollow vibes. They had a cute bookstore I really liked, and I wish I had a bit more time to spend there.
I worked my way even more north towards Lakeville and Salisbury. The service was even more sketchy in this area, pretty much non-existent. I recommend bringing a physical map if possible to make sure you’re prepared! (Shoutout to the bed and breakfast that gave me one, which helped a lot.) Salisbury is a very tiny town, but they did have a great little coffee shop – I enjoyed my latte immensely. Lakeville is small as well, but their highlight was a cute bookstore with fun stationary supplies.
In this area, I stayed at the Cornwall Inn, a local bed and breakfast. Staying there was such a highlight, I couldn’t recommend it enough! I don’t think I’ve ever stayed at a proper BnB before, and it was so lovely. The room was super cute and I had a great start to my morning with a nice hot shower and a delicious breakfast. I wish I could have stayed longer! Next time, I’ll try to book for more than one night to enjoy the experience even more.
I travelled a bit further south to visit New Milford, the town that apparently was the inspiration for Stars Hollow in Gilmore Girls. It was so cool, they had the gazebo in the middle of the town square and everything! Apparently they had a festival on the weekend which I missed, but they still had some cute stuff around the town like signs and merch. I wandered around the town for a couple of hours, thoroughly enjoying the cute vibes. I got many Gilmore Girls souvenirs. If you’re a GG fan like myself, I definitely recommend visiting New Milford!
I saw a few other Gilmore Girls-esque places later in the week in this area as well. I visited the Mayflower Inn, which is apparently the inspiration for the Dragonfly Inn in Gilmore Girls. It was very fancy. Then I went to a nearby town to scope out the Hickory Stick Bookshop, the inspiration for the Stars Hollow bookstore. I got a book about Gilmore Girls and writing, that I can’t wait to dive into! This area of the state was one of my favourites, and despite the limited service, I still recommend checking it out.
South CT: New Haven
Later in the week, I went to New Haven and lucked out with a very nice day of weather! I wanted to check out Yale and a nearby bookstore, and I actually had the time to enjoy both. Atticus Books was super cool, filled with great books, merchandise, and a cafe. The weather was amazing, which made it the perfect time to scope out the Yale campus afterwards! I enjoyed walking around to see the buildings, and stopped in at their very cool rare books library. There was one quad absolutely filled with students enjoying the sun and hanging out, which was awesome. I had to leave New Haven sooner than I would have liked, but in my short time there, I really did enjoy it.
Central CT: Wallingford to Torrington
The more central area of Connecticut was a mixed bag for me. I was in most areas for a very brief time, so take my observations with a grain of salt! At the beginning of the week, I stopped in Torrington and went to a yoga class, which was more of a sound bath/reiki session. It was much needed after travelling so much, and was very relaxing. Another day brought another café, and I joined a group of colleagues for a hangout at Cheshire Coffee. We enjoyed some coffee and goodies while working together, and had so much fun.
I drove out to Litchfield and wound up at a really cute store that I spent forever in. The owner recommended that I should visit nearby Topsmead State Forest, so I decided to check it out. In the 1900s, a woman built a Cotswold-style cottage on the land, and she didn’t want it to be destroyed or to lose any of the land when she passed. So, she donated the cottage and the many acres of land to the state, who turned it into a state park. It was really nice to get out in some green space, but it was very windy so I didn’t stay out there very long. Still, if you’re looking for a vast green space to enjoy in central Connecticut, Topsmead State Forest is definitely it.
Western Massachusetts
At the end of the week, I headed out to Massachusetts, and had a whirlwind of a day exploring throughout the western end of the state. I drove from Windsor, CT all the way up to Northfield, MA – definitely quite the drive! After getting some work done, I decided to swing by the Yankee Candle Village in Deerfield, that someone had recommended to me. I wound up spending hours in the village! They obviously have candles everywhere, but also fun themed rooms like a country store, a Christmas section, Harry Potter section, a forest, a castle, a toy store, a candy store, a home store and more – all connected within one building! It was very unexpected but really fun to check out.
After that, I had some more work to do, and in the evening I drove back throughout the state all the way to Springfield, MA. I crossed into Connecticut and stayed overnight right near the border. The next morning, I was flying out of Hartford, with the whirlwind of my explorations of New England coming to a close. My travels leaving the state went fairly smooth, and before I knew it, I had landed back home in Toronto.
Recommendations
Exploring New England was definitely a whirlwind of a trip, but overall I really enjoyed it! Some areas felt more my vibe than others, so I’ll share a few of my recommendations. My favourite, and most unexpected, area of Connecticut was the northwest area of the state. It is very rural so don’t expect your phone to always work, and bring a physical map – but despite that, it is really beautiful and features many quaint small towns. If you’re a Gilmore Girls fan, I definitely recommend visiting New Milford and the nearby Mayflower Inn and Hickory Stick Bookshop. Lakeville, Salisbury, and Kent are quaint small towns to scope out as well. I strongly recommend staying at the Cornwall Inn or a similar BnB in the area – they are super cute and it’s worthwhile to stay nearby!
Another area of Connecticut I really enjoyed was New Haven. I don’t think I spent enough time there, and I’d love to go back. Topsmead State Forest is another cool spot if you’re itching to enjoy some green space! I wouldn’t recommend visiting New London or the central CT area, I wasn’t drawn to them as much as other areas of the state. The western area of Massachussets that I visited didn’t capture me much either, but I was there for such a short time, it’s really tough to share an accurate picture of the area. All in all, it was an eye-opening journey of exploring New England. I hope to return and enjoy the area even more in the future.
If you’ve visited New England before, drop your thoughts in the comments – I’d love to hear your take! Safe travels on your own explorations in New England ❤