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Connecticut is somewhere I’ve been dreaming about for years. In fact, if I had my way I’d spend a couple of months driving around all of New England. So, when I was invited to spend 3 days in Connecticut I grabbed it with both hands. Here’s what my Connecticut 3 day itinerary looked like. Have no fear, it was every bit as spectacularly #GilmoreGoals as I thought it would be. It definitely deserves to be added to my list of the most Instagrammable locations in the USA

3 Days in Connecticut

How to get there

3 days in connecticut 3 day itinerary flights

Cheers to Connecticut!

Getting to Connecticut is easy with the direct flights from Dublin to Bradley International airport in Hartford with Aer Lingus. The flight time is around 7hrs 15mins on the way over and around 6hrs on the way back. Fares start from €169 each way including taxes and charges. This includes complimentary meals and soft drinks.

With the USA pre-clearance in Dublin airport it makes arriving in America incredibly smooth. Just make sure you’re at Dublin airport at least 3 hours before your flight; the queues for immigration can be quite long. 

Bradley airport (Hartford) is compact but still has everything you need. It’s a great entry point from which to explore Connecticut and greater New England. It’s also located between Boston and New York, making it perfect for exploring either or both cities. To get from Bradley airport to downtown Hartford you can either rent a car, organise a transfer (we used Joshua’s Limousine Services) or get the 30-Bradley Flyer bus which goes to the Connecticut Convention Centre and Union Station in Hartford.


Simsbury was our first stop on our 3 day Connecticut trip. The first thing I noticed about Simsbury were the 32 bronze statues by Seward Johnson dotted around the town. The statues just look like normal people going about their business. I thought I saw a man mowing the lawn, but when I looked closer I realised it was a statue. They’re whimsically beautiful!

In Simsbury we stayed in the Simsbury Inn, which reminded me of Lauralei’s inn from the Gilmore Girls TV show. They had put on a beautiful cheese and fruit spread for us upon arrival. The rooms were cosy, comfortable and full of New England charm. All of the staff were incredibly helpful and proud of the Inn. It’s the kind of place I’d love to revisit with family.

3 days in connecticut 3 day itinerary patch

The pumpkin patch we accidentally came across.

For dinner we visited Millwright’s Restaurant and Tavern for dinner and drinks. This beautiful property used to be a working mill and has been part of Simsbury’s history since the 17th century. I ordered hummus for starters and it was a GIANT bowl of chickpea deliciousness. They didn’t have many vegetarian offerings, but there were lots of options for the meat eaters. 

There are plenty of lovely pumpkin patches around the town around this time of year (October) and they’re all picture perfect. I wanted to stop at all of them. You know I LOVE Halloween and Autumn in general. In the end we stopped on the road just outside Simsbury at The Pickin’ Patch. They sold all shapes and sizes of pumpkins and gourds as well as hot cider and more. I took about a hundred photos (example above, many many more available on my Instagram).

You can read more about the town of Simsbury here.


3 days in connecticut 3 day itinerary madison beach

Nothing like a New England beach.

Next stop on our Connecticut itinerary was Madison. We stayed in the adorable Homestead Inn. I don’t think it’s possible to be more taken with a place upon arrival than our group was with The Homestead. From the festive decorations to the vintage collectibles dotted around the living/dining spaces, the inn is beautifully decorated.

Each room has its own vinyl record player, which is a lovely touch. According to the owners they had several travel writers stay in the inn and critique it before they finally opened their doors to the public. One of my favourite touches was the black face cloth in the bathroom with a note saying “Use this to take off your make up”.

3 days in connecticut 3 day itinerary beach

The view from our dinner venue, the Madison Beach Hotel.

While in Madison we visited the Madison Beach Hotel for dinner. The views over the beach from the hotel are spectacular. It’s a typical Connecticut beach with dunes and New England beach houses lined up photogenically along the shore. We had dinner in The Wharf restaurant. There were no vegetarian options on the menu but our lovely waiter made sure I was looked after.  He also made sure I had the perfect hot whiskey, honey and lemon due to the fact that I was dying with a fever at that stage.

3 days in connecticut 3 day itinerary essex

All aboard the Essex steam train.

One of my favourite stops while we were in Madison were the Clinton Crossing Premium Outlets. You could easily spend a few hours there but we were on a tight schedule so we had 1.5hrs, which is adequate if you map out which shops to hit first. I got some great bargains, including two pairs of Adidas runners for $50. I got a couple of bits in American Eagle and a Wildfox jumper in Saks 5th Avenue Outlet Store as well. If you’re after bags there’s a Coach and a Calvin Klein outlet and lots of bargains to be had in Saks.

3 days in connecticut 3 day itinerary train

It was not my first train ride, but I took the sticker anyway.

On our way out of Madison we stopped at the Essex Steam Train. It’s only about 17 mins out. We had seats in the first class carriage with luxury arm chairs. The conductors mixed us some incredibly strong cocktails. The views along the way were lovely. It was very cute experience overall. Because we were there in October there were Halloween displays on local greens and the platform was decorated with pumpkins and hay bales.

You can read more about Madison here.


3 days in connecticut 3 day itinerary mystic p


Mystic is a MUST VISIT on any trip to Connecticut no matter what time of year. It’s a cute little town with colourful shopfronts and souvenirs by the bucket-load. There’s even a fortune teller with a shop on the main street that I’m sorely disappointed I didn’t have enough time to visit. Mystic Pizza is the town’s famous landmark thanks to the Mystic Pizza movie, featuring Julia Roberts. We made sure to stop by for a photo. Unfortunately, according to my sources, the pizza isn’t worth writing home about. But then again, how bad can pizza really be?!

3 days in connecticut 3 day itinerary pumpkin

Visiting Sift Bakery.

Instead, we headed to Sift bakery which came highly recommended by locals. I had a maple iced latte and an apple bourbon macaron – PERFECTION! Definitely worth a visit if you have a sweet tooth, and my opinion was in no way influenced by the fact that they were playing B*Witched when I first walked in. It’s the kind of place that I could picture Rory and Lauralei having coffee, you know, if Luke’s wasn’t open.

3 days in Connecticut 3 day itinerary

DELICIOUS – Sift Bakery.

If you like a bit of history and culture then head to the Mystic Seaport Museum. Admittedly I was not excited about this when I saw it on the itinerary, but when I arrived the museum quickly changed my mind. Mainly because it’s not really a traditional museum. It is spread across a large area and includes plenty of practical, interactive exhibits. You can learn how barrels are made, visit an old world pharmacy, climb aboard a real wooden whaleship and plenty more. It’s the kind of place that you could easily spend half a day in, or more.

You can read more about Mystic here.

New Haven

3 days in connecticut 3 day itinerary bus

The party bike!!

Holy hot pumpkin spiced latte, I’m in Gilmore Girls HEAVEN. I finally made it to New Haven, the home of Yale University, where, as we all know, Rory was an English major. But my first stop wasn’t the academic mecca, it was, in fact, an Elm City Party Bike food tour. If you don’t know what a party bike is it’s basically a giant bar with wheels that you cycle while sitting on a bar stool. We cycled our way, slowly, around New Haven, stopping at various restaurants and drinking as we went.

3 days in Connecticut 3 day itinerary pizza

The famous Pepe’s pizza! It was divine.

We stopped at Frank Pepe’s for pizza which was deliciously thin with the perfect amount of toppings. We tried the “plain” pizza too which has no cheese and is smothered in tomato and garlic. VERY different from the decadent deep dish pizza I tried in Lou Malnati’s in Chicago last month!!

Next up was Bar, a pizza place/night club. Then it was onto Louis’s, a pokey little fast food place that plays by its own rules. It might not always be open when it says its going to be on the sign, but the food is worth the wait. They serve great burgers and only accept cash.

Our final stop was Miya’s, a sustainable sushi place. This was an EXPERIENCE. The brother and sister duo behind Miya’s are endlessly entertaining, creative and ethical. I LOVE the idea that they use invasive species and make them into something delicious, from lion fish to Japanese knotweed (SO GOOD!).

3 days in connecticut 3 day itinerary yale

YALE/Gilmore Girls vibes!!

Now, finally, it was time to visit Yale. We were given a guided tour by an impossibly perfect student who made me feel like I was incredibly lazy in my youth. The Yale campus was absolutely beautiful, just like the Gilmore Girls. Unfortunately, no one on campus even vaguely resembled Logan Huntzberger. The Beinecke Library, a rare book and manuscript library, was one of the most stunning, more modern, buildings on the tour. If you’ve watched American Animals, the book they attempted to steal, The Birds of America, is on display in the Beinecke Library.

I’m fairly sure there’s an awful lot more to New Haven than I saw. You can read more about it here.


3 days in connecticut 3 day itinerary Hotel Delamar

Loving the room at the Delamar Hotel.

Hartford, the capital of Connecticut, was our final stop of our trip. We stayed in the beautiful Delamar Hotel in West Hartford. It’s a stunning design hotel with chairs made from coins and rich fabrics everywhere. It’s also pet-friendly if you’re travelling with your pooch. Location-wise it’s in a great spot with plenty of places to eat and cute boutiques nearby.

ARTISAN, the restaurant attached to the hotel also serves delicious food. They have a beautiful outdoor seating area with a garden. Farm to table local produce is the corner stone of their menu. The roasted tomato soup was delicious. There are plenty of vegan, veggie and coeliac options as well as traditional New England fare. 

3 days in connecticut 3 day itinerary mark twain house

The Mark Twain House

Of all the things that there are to do in Hartford, The Mark Twain House has got to me the most popular. It is an imposing building. It looks like something from an old horror movie, or an episode of Sabrina the Teenage Witch. I absolutely loved it.

Mark Twain (Samuel Langhorne Clemens) was a American writer, famous for Tom Sawyer and Huckleberry Finn. “Travel is fatal to prejudice, bigotry, and narrow-mindedness..” is a famous Mark Twain travel quote, so, of course I’m a fan. Inside, the house in incredibly well preserved. You can only visit by guided tour. The guides are full of wonderful insights and quirky facts. Keep an eye out for the wall paper, it’s fantastic.

You can read more about what there is to do in Hartford here.


Foxwoods is a resort Casino about an hour outside of Hartford. But it’s not JUST a casino, it’s a sort of destination. It’s home to the Tanger Outlets, a massive shopping destination. There’s restaurants galore, a hotel, a spa, and even bowling. If you fancy something a bit more exciting then check out their zip line, racing simulator or the Thrill Tower. For something a bit more informative and cultural make sure to visit the Pequot museum. It’s a very impressive museum full of interesting exhibits with incredibly life-like wax figures depicting the native people.

You can read more about Foxwoods here.

Connecticut may be one of the smallest states in America, but there is SO much to do there. We crammed A LOT into our 3 days in Connecticut, but there’s still plenty more to see and do. I highly recommend a visit! 

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