5 Things to do in Portland, Maine

5 Things to do in

Portland, Maine

Hello Dreamers! Our names are Crystal & Shane and we are Dates in the States! DatesintheStates.com is a blog chronicling the lives of a couple traveling the USA on a budget.

We blog about all of our special dates we take in each state. Recently, Crystal had the privilege of traveling to Portland, Maine for the Women in Travel Summit so she wanted to talk about a few of her favorite things she did while visiting this beautiful city. It was really tough to narrow it down to only 5 things, but we hope you have the opportunity to do one or more of these in order to experience Portland. 

5-Enjoy a Donut in Authentic Downtown

The most amazing donuts I’ve ever had can be found in Portland, Maine at The Holy Donut. My first morning in the city, I walked the streets of downtown and grabbed a bite to eat at this cute little cafe. Each of their donuts are made from potatoes and are fresh made daily. They have tons of unique flavors such as Maple Bacon (so good!), Margarita, and my ultimate favorite - Honey Lavender. After chowing down on some donuts, take a walk in historical and authentic downtown. Around Exchange Street you can find cute stores and boutiques. Each business in Portland is authentic meaning no chain stores allowed in the city! This helps the city maintain it’s authentic seaport center while offering options close by. 

Authentic Portland doughnut

Authentic Portland doughnut

U.S Customs House

U.S Customs House

4-Tour the U.S. Custom House

At the Corner of Fore St. and Pearl St. resides the beautiful Custom House that’s been closed to the public since 2001. Now used as an office space for some Federal employees, The Custom House stands in the middle of Downtown Portland serving as a beautiful landmark in Maine’s history. Inside you will find elaborate interior designs, hidden doors, and a dungeon! Some days it’s opened to the public for tours guided by a Federal employee himself. If you happen to walk by during the week, you can always ring the doorbell located on the outside of the front door. If he’s there, he will let you inside – but shh, you didn’t hear it from me!

3-Take a Bike Tour by SummerFeet

On my last day in Portland, I did a bike tour with SummerFeet Cycling where we took a ferry to Peaks Island and spent a few hours biking the island and learning the history. The only way to get to this island is by Ferry and it’s a quick 20 minute ride that happens every hour on the hour. The tour guides were so fun and informative and the island was so peaceful and remote. I had no idea Portland had so much World War 2 history. On the island you will see many sniper towers, old cannons, and military forts. Which brings me into something else you should explore…

Bike tour of Summerfeet

Bike tour of Summerfeet

Fort Gorges

Fort Gorges

2-Kayak to Fort Gorges

This is something I wish I had done, but didn’t know it was an option until the tour with SummerFeet Cycling when I asked the tour guides on the ferry what this place in the middle of the water was. Fort Gorges was a former military fort back in World War 2. It is only accessible by boat, kayak/canoe, or paddle boarding. You can go to the Fort on your own without a tour guide and have a picnic or to take photos. It’s fascinating to hear some of the history of World War 2 and how exciting the time of the war was in Portland, Maine.

There’s multiple forts like these in Casco Bay. Military protected Portland in a lot of ways because the city had many resources that people wanted. They had seafood, forests, ships, and so much more. Not only were these forts made for snipers to hide out in and keep watch, but they also had wires connecting different areas in the bay that would catch submarines that might try to sneak in. FASCINATING!

1-Walk the Eastern Promenade Trail

I know many if not all of the 5 things I am mentioning involve exercise. That’s because we talk a lot about, “How To Stay Fit While Traveling” on our blog and how some of the best ways to see a city involve walking. The Eastern Promenade Trail is a paved trail along the water. It’s a wonderful way to explore the outskirts of Portland, especially if you are just visiting for a day. The trail starts in downtown Old Port and is an easy walk along the seaside where you will see the forts in Casco Bay, trains, beautiful mansions, more World War 2 sights and cannons, and epic views of the coastline.

5 things to do in Porland blue pin.png
5 Things to do in Portland red pin.png

Thank you to Planetdreaming for letting us tell your readers 5 amazing things they should do when they visit Portland, Maine. It truly is a wonderful and beautiful city that we hope everyone can visit someday. We would love it if you can check out our blog and say Hi by visiting DatesintheStates.com and follow us on social media:

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