Maine in May - 5 Days in Maine 2023 - Day 3

Worth the Visit

May 20, 2026

Day 3

Hey, y’all! 

Here we are on Day 3 of Maine in May. If you are just now seeing this, please go back and read through Day 2 to catch up!

Today, we got to see more of Freeport that was not L.L. Bean, visit a famous lighthouse and add New Hampshire to our list of 50 states visited :)

Day 3 overview:

•  Freeport to Portland

•  Explore Portland Head Light

•  Kittery to York

•  Portsmouth, NH


Let’s get into it!


Freeport to Portland

We enjoyed a delicious breakfast at the Freeport Café. It has some history, serving food since 1952 :) While we had breakfast, they also serve lunch and dinner.


Location: 29 US-1 N

After breakfast, we did a bit of window shopping and took in the town. There are a lot of shops in the area if you are looking to shop.

It was time for our friends to leave, so we dropped them at the airport in Portland and continued on.

Portland Head Light

Lighthouses are well known, and I had a hard time trying to decide which ones to see on this trip. Given our plan, Portland Head Light was a logical choice since we were leaving the airport and heading south. This lighthouse is the oldest in Maine, dating back to 1791 for the original structure (the time it was first lit). 

The lighthouse is located in Fort Williams Park in the town of Cape Elizabeth. The history here is something to behold. The park is 90 acres and absolutely a visit to make. If you are debating-don’t! We enjoyed all that it had to offer - lighthouse, the cliff walk and talking with locals. 

To learn more, click on this link:  Portland Head Light and Fort Williams Park

Kittery

Since I was fairly new to the coffee house scene, I was pretty focused on visiting some cool places on this trip. Granted, I am not a coffee lover, but thankfully, Joy and her sister introduced me to chai latte. 
I was excited to go to Lil’s, but it wound up being so much more than expected! It was situated on a corner in the lovely (yes, I said it) town of Kittery. Lil’s was just extra cool because it embraced the building history as a former bank, kept key elements and then made it a beautiful café. 
Did you notice the old school former safety deposit boxes under the cash register? What about re-purposing the original vault to a vinyl vault? 
All of these notes on Lil’s and I have yet to talk about the chai or the baked goods. What can I say? The pictures speak for themselves. The chai was perfectly spiced (not too much or too little), the baked goods were perfect. They are known for their cruller and I had never had one before. OOOOOOOOH, I can attest they should be known for them!

Check them out: Lil's Cafe

York

After Lil’s we went to see the Nubble Lighthouse, our second of the day and of the trip. This picture gives a snapshot of the history:

We had a great talk with the super friendly people that work in the gift shop. It was great to just learn some additional tidbits and to share some laughs.

While we enjoyed the park, the highlight was seeing the couple out on the rock in their chairs. It was so sweet to watch them enjoy the view, talk and hold hands at times. It touched our hearts :)

To learn more: Nubble Light House

Welcome to New Hampshire!

Yay! We crossed a bridge and entered right into a new state (for us). It’s always exciting to add a new state to our 50-state challenge.

Portsmouth is a beautiful town situated on the coast. It was clean, had so many food options and many things to do. 
It is a very patriotic town; the bridge we crossed was just one example of many. We met many people out and about with flags near the water just enjoying the weather and beautiful day. Here are a few of my favorite pictures from our first night there (those flowers!!!!):

Let’s talk dinner. OK, I was super excited to have dinner because it was going to be my first time having cacio e pepe. It was everything I had dreamed it would be :) I remember sitting outside, dining al fresco, enjoying great conversation with Alex and watching the day come to an end. I still smile when I think of that night…