Since living in Florida, I’ve noticed every winter I start itching for a cold-weather trip! Last year we went to New York City and this year we opted for a winter weekend getaway in Connecticut. Carter and I had never been to Connecticut, so we were excited to explore a new place. Plus I started watching Gilmore Girls this fall for the first time ever… I know crazy! So planning a trip to Connecticut was especially fun for me as I was inspired by the series!
I did do a lot of research on this trip, so I will be sharing everything we ended up doing while there! If you decide to take your own trip to Connecticut, I highly recommend you do a little of your own research as there were so many things to do in the area and we did not get to all of them!
Flying into Hartford
We started by getting on a nonstop flight with Breeze Airlines from Tampa to Hartford Connecticut. To my understanding, Breeze is a newer airline and they only fly on certain days, but our tickets were inexpensive and the flight was really pleasant!
When we landed in Hartford, I did see a couple of snow flurries, which was really fun! We rented a car through the Turo app and immediately made our way to the coast for a lobster roll!
Connecticut Lobster Roll
We were both starving, so the first place we stopped at was Lobster Landing in Clinton, Connecticut. The little shack on the water was absolutely adorable and I loved the Christmas lights.
We each ordered a lobster roll and shared a cup of clam chowder! I could not recommend this place enough. The food was amazing and the service was great. Since it was winter, they did have outdoor tents with heaters which helped keep us nice and warm while eating.
Where We Stayed
I really wanted to stay somewhere on the coast, so we landed on a little Connecticut beach town called Madison. We drove into town and walked up and down the quaint main strip of Madison, Boston Post Road, and did a little shopping.
Madison Connecticut a Sweet Little Town
We loved the popular RJ Julia Booksellers! They had so many amazing books and gifts. It was fun to walk through and see their curated store.
Madison, Connecticut isn’t very big and doesn’t have a ton to do during the winter, but was so charming and felt like we were in a Hallmark movie! We did get breakfast at a local place called Christy’s, famous for their blueberry and raspberry crunch pancakes! If you eat here… Know that the portions are huge, and absolutely delicious!
Madison Beach Hotel
We pulled up to the Madison Beach Hotel around 5 PM to check in and, can I just say, it’s absolutely stunning! The front was decorated for Christmas, and as you walk in the whole place feels so cozy! The staff were incredibly friendly and we loved our stay at this hotel.
The Madison Beach Hotel is a part of the Curio Collection by Hilton. If you aren’t familiar, there are Curio Collection hotels all over the world, and they are hand-picked for their character and location. The location in Madison is absolutely breathtaking and I love all of the details throughout the interior of the hotel. It immediately had me feeling like I was immersed in a small New England town!
Madison Beach Hotel Views
Our hotel room had a fireplace and an amazing view! Being from Florida, we were so cold when we first arrived and bundled up in our room with the fire on to warm up before heading down to The Wharf, which is the hotel restaurant.
Hotel Restaurant – The Wharf
We did not plan to eat at the hotel restaurant three nights in a row, but somehow found our way there every night. The first two nights we ate in the dining room, but the third night we opted for a more casual spot at the bar! The bartenders, Dave and Jeremy, were great at making you feel like you dine at The Wharf every weekend. By the end of our three night stay, the Madison Beach Hotel felt like home!
Everything on the menu looked amazing! And everything we ordered tasted amazing! On the first night at The Wharf, I ordered the Cioppino, which is a seafood stew in a tomato broth. It was to die for!! The following nights, we had clam chowder, short ribs, oysters, and desserts that will I will never forget! If you can’t tell by now… We love food! 😉
Day In Mystic Connecticut
After a good night’s sleep, we woke up and headed to Mystic, Connecticut. I read so many good things about this adorable New England town and just knew I had to see it for myself during our winter weekend getaway.
Downtown Mystic Shopping
We started by shopping downtown Mystic, really taking our time going into all of the adorable shops. Our favorite shop was called Trove, which was a very masculine shop with some fun antiques.
We snapped a picture at the famous Mystic Pizza but weren’t able to get a table! So we had a quick bite to eat at S&P Oyster Restaurant and Bar. We ordered a dozen oysters and split a crab grilled cheese. The view was amazing at the top of the restaurant, and we loved our experience.
Olde Mystic Village Shopping
We then hit up Olde Mistick Village to do some more shopping. We had read online that it was a must! While, I absolutely loved the Christmas store with every and any glass ornament you can think of. I personally wasn’t impressed by the rest of the shops. A lot of the other shops felt a little too touristy for me. However, if you have 30 minutes to check it out, I’d add it to your list!
Winter Connecticut Sites
We then ran over to Stonington, Connecticut to see the Lobster Trap Tree. This was one of my favorite things we did. The Lobster Trap Tree is made out of lobster traps and handpainted buoys by local businesses! They do such an amazing job and I loved seeing the tree lit up! Such a fun idea.
After leaving the Lobster Trap Tree, we were still pretty full from lunch, so we ran over to Noah’s Restaurant for a sweet pick me up. The restaurant was full, but we were lucky enough to snag two seats at the bar! I got a delicious apple crisp while Carter ordered his favorite dessert — crème brûlée. I would love to go back and eat at this restaurant! Based on our desserts and the menu, I’m sure dinner would be fabulous.
Jump over to Rhode Island
While there is still so much to do in Connecticut, like a pizza tour in New Haven, or exploring all the other small towns, we wanted to switch things up from shopping and do something more nature-oriented. So, we headed to Simmons Farm just outside Newport, Rhode Island to hike with goats!
Hiking with Goats
This was such a fun experience, and we learned so much about goats! Simmons Farm is a family owned farm in Rhode Island and the hike took about an hour and a half. If you love animals and nature, I highly recommend this unique experience!
Day in Newport
Since we were so close to Newport, Rhode Island, we decided to spend the rest of our afternoon there. We walked up and down the main streets of downtown Newport while we waited for our reservation at the Brick Alley Pub & Restaurant.
The Brick Alley is a cozy, iconic watering hole with a great variety of different food choices. We heard so many great things about this restaurant and I can confirm we were not disappointed! We were very hungry so we ordered beef nachos, lobster mac & cheese, and fish and chips, which all were so full of flavor, and I’ll be dreaming about for a while.
Newport Shops
The last stop on our winter weekend getaway was the Kiel James Patrick flagship store at Bowen’s Wharf. Kiel James Patrick is known for his amazing online photography highlighting the most cozy, detailed, dreamy…I could go on and on, but you can just see his Instagram here!
His storefront was everything and more! It was decked out for Christmas, and absolutely charming to see in person.
We had such a great time during our winter weekend getaway in Connecticut. We didn’t even touch the surface of things we could do, so just know we will be back! We would love to see Connecticut in the summer and visit more of the historic sites.
