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A Day in New Haven Connecticut

Updated: Oct 8, 2022

At the beginning of March 2020 my sister did a road trip to New Haven, Connecticut. This gorgeous city hold a lot of history. At the center of the city is Yale University.

If you are a Gilmore Girls fan, this will be a day for you! When I say the Gilmore Girls fan, I’m talking OG peeps who watch the show weekly when it was live, and then watched repeats on ABC Family or whatever the network is named now.

Now! I came from New Jersey, it was about an hour and a half drive. My sister joined me for the day! We went over the Tappan Zee Bridge and 95 North and went till the Westport exit. You might be thinking why stop in Westport? Coffee!

If you're coming from New York City it's about an hour and a half train ride. Take the New Haven train from Grand Central. This will arrive at New Haven Union Station. If you're closer to Penn Station take the Acela Express to Boston South Station then transfer at the Stamford Station and head to New Haven Union Station. If coming from Boston, it's about a two and a half hour train ride via Acela Express to Northeast Regional to finish at New Haven Union Station.

Terrain Cafe

If you want an Instagrammable spot, go to Terrain Cafe. It is spacious and the staff does an amazing job making each space you enter so unique. Their space has 4 entrances, the garden, cafe, and two by the succulent area. The first spot I walked into was the succulent entrance.

There were birch logs wall and just seemed like such a welcoming spot. Once you enter, the beautiful array of succulents, glass display or arrangement they’ve made for hanging pieces that you can buy. Continue to walk through this space till you reach the entrance that you’re brought to the rest of the shop.

Terrain Cafe has amazing instagrammable stop. Visit Westport and get a plant from here.

To your left will be the register and even more spaces throughout the store. Each room is a new experience. Each spot calls for a photo to be taken! Now, the staff and marketing team work very hard to set up each display. Do not rearrange things and be respectful of how Terrain arrange their displays. You can buy items, so if you’re planning to buy anything, enjoy!

Terrain cafe has great displays throughout the cafe. Snag photos for the gram. Be respectful of the space. Snag a photo with coffee or plant from the garden.

After exploring the space, go to the espresso bar for a coffee and snack to go. If you really enjoy the cafe space, their food is wonderful! Since New Haven is about a 45-minute drive from Westport, we got ours to go. I got a vanilla latte and almond croissant. You know my go-to is almond milk. I forgot to say it so that was on me and why the latte tasted off to me.

The garden is beautiful display of plants. Each area I'm amazed more and more by the garden set up.

Lighthouse Point Park

This park is open all year round. A major perk if you’re not a resident, if you come between November 1 and April 1, it’s free! This made the decision easy for me taking a day trip from New Jersey, I had a deadline of traveling to this park before April 1.

I was surprised by how large the beach is. The sand was perfect for walking in my converse shoes. The parking lot we selected brought us to a paved walking path by a pier to our right, and we turned left to head down the path to the lighthouse.

Visit Lighthouse Point Park. There is a beautiful beach to walk. Walking path that will take you along the coast line. Bring coffee, lunch, a picnic, or just catch up with friends and family.

This path seemed a great spot to come and get in a good workout. I loved walking around the park. There was a carousel but was all locked up from it being the offseason. We got a gorgeous day which I think was a bit more quieter than normal due to knowledge of the Covid-19 outbreak.

While driving to Easy Rock Park, we passed the walking trail that looked like a great place to stop. We saw this walking trail that looked extremely appealing. This park is free to enter no matter the season. It has a nice walking path, long pier, and you’re able to walk on the beach as well.

From the beginning of the pier, you’re able to see the lighthouse at Lighthouse Point Park. Beautiful alternative if the park is full or if you want to walk from the lighthouse to this pier. It looked like the walking path connected here from Lighthouse Point Park.

Walking piers are the best way to relax. Get another view of the Lighthouse from Lighthouse. Get another walking alternative.

Easy Rock Park

So the pre-April 1 worked for getting into Lighthouse Point Park, however, April 1 is when the Summit drive is open. The day was perfect for an amazing hike and multiple walking trails. There are many parking spots around the park. Since I am recovering from my broken ankle we sadly couldn’t walk the trails. I highly recommend doing this though! It looked like so many people were enjoying the day.

Hillsborough Ave

This is said to be the prettiest street in America. Now, I’ve been to many streets. I was trying to see it through a different lens, but Yale and the campuses are gorgeous as a whole. It was hard to see this street standing out from the others. When I went, the Hillsborough Ave, the historic walking path was under construction so we weren't able to experience the prettiest street in America.

I saw a few blogs recommend visiting this street, my advice if this happens to you, go a street over to Prospect Ave. Actually, either way, check out Prospect Ave.

Visit Yale's campus on Prospect Ave. There is revival gothic style architecture.

Hillsborough is a block away from The Peabody Museum - get your photo with the brontosaurs and enjoy the gothic architecture of the building. Then walk one block down to Prospect street and see the modern revival of the gothic style.

Enter Yale's campus. Explore the beautiful architecture. There is so much this campus and area offers.

Atticus Bookstore

Instantly when walking into the building I was hit with the amazing aroma of bread and soup! Instantly made myself hungry. Unfortunately, we did got eat here just from being mindful of social distancing and the increasing cautions made for Covid-19.

Get lunch or a book from Atticus Cafe.

It is the best of both worlds here for book lovers or a student walking from the college dorm to get food and need to bunker down for school work. The bookshelves had a great varying selection for all different genres. If you saw my recent book recommendation blog spot, I saw a few on the shelves here!

Ice cream is a must! This was on the same street at Atticus Bookstore. Talk a walk to enjoy the fresh-made ice cream. I will say most ice cream bases are vanilla. My sister’s favorite ice cream and was hoping for cotton candy, but they do not have that kind of variety, If you love vanilla ice cream with different toppings, this is the place for you.

Arethusa Farm and Dairy ice cream is amazing! If you want fresh made ice cream, this is a place to come. Waffle cones are amazing.

I got the mint chip in a waffle cone and I recommend getting your ice cream in the waffle cone! It was honestly great! If you are a fellow waffle cone lover, isn’t the biggest struggle to button getting soft? That did not happen with this cone. Best waffle cone I have had in my life. If you go here and have their waffle cone, please let me know in the comment down below.

Louis Lunch

Now, who can know is this is true or not. According to Congress, this is where the hamburger was invented! How crazy is that? Since we have ice cream we weren’t hungry enough to get the burger but from the people we overheard coming out, they loved it!

Louis Lunch is where the hamburger was founded. Enjoy the food and embrace the history,

If you go from Chapel Street to Sherman’s Alley you’ll come right next to it. It is between High Street and College Street on Crown Street. Check out this historical spot that is on the border of Yale’s Old Campus and New Haven’s Theater District.

Notes I suggest parking on Chapel street to enjoy locations 6-8. If you walk down College street to get to Louis’ Lunch you’ll see Shubert Theater that has a long history to the area. An additional place I recommend going is Beinecke Rare Books and Yale Library. Both were closed because of thing that were 2020. Both are reasons worth returning for.

New Haven is know for having a competition for the best New Haven pizza. Coming from Northern NJ, this is a very big deal. With things being such an unknown, trying out the pizzerias did not happen. This is another reason to return!

I hope you enjoyed hearing about my trip to New Haven, Conneticut. If you have any questions about the area please email me at

Save the below Pin to keep this post for your New Haven Adventure!

New Haven has so much history, here is how I spent my day in New Haven. This small city will not disappoint a peaceful day away. If you're looking for different scenery or something in your backyard, this guide will help you plan out your day!
New Haven Connecticut is a great day trip from the Greater NYC area. Explore the gorgeous Yale campus and stone work of this great city.

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