In September of 2023, my girlfriend got married just outside of Portland, Maine. We had a few hours to explore Portland in the morning and afternoon before we had to report to the rehearsal dinner. I didn’t know where to start for exploring Portland so I figured I would share what we did with a few hours we had in addition to some other things that were suggested to us.

That morning, we drove up from Boston. Because we were coming from the south, we decided to head straight for Portland Head Light in Cape Elizabeth. We didn’t have too much time to explore, but we opted to walk a small loop trail instead of visiting the museum and gift shop which had some crowds.

We enjoyed stretching our legs while soaking in some breathtaking views of the coastline.

My girlfriend also suggested we stop at Bug Light Park to view another lighthouse, but we were running short on time and were growing hungry for lunch. Had we had time for Bug Light Park, we would have also stopped at the suggested Scratch Bakery nearby. We heard it was a must-stop and everything there is delicious.

We headed straight for downtown Portland and found parking in a parking garage. Portland is an adorable town to walk around in with tons of shops and eateries. According to several “Mainers” or “Maniacs,” we met over the weekend, Portland has experienced revitalization as a foodie city.

There are endless restaurants and cuisines to explore. But, because we don’t get it at home very often, we couldn’t turn down fresh lobster for our lunch option.

So we walked to Portland Lobster Company for lunch based on a suggestion from our friend. We loved the vibe with its waterfront location, outdoor seating, and live music.

We shared a lobster roll, clam chowder, and a crab cake sandwich with our friends. The food was amazing and the lobster was so fresh. I’m still dreaming about it. The lobster roll was actually quite different from the one we had in Boston at Quincy Market the day before. I probably liked the one in Portland better, but do I have to choose?

After lunch, we had a drink at The Porthole, another spot suggested to us.

According to the website, it opened in 1929 as a place that served breakfast to lobstermen and it felt like a very local spot to us. It also has waterfront views, outdoor seating, and a delicious-looking menu, but we just had a drink where we tasted some beverages local to Maine. This is when I learned Allagash Brewing Company started in Portland.

Next, we visited a unique shop across the street from The Porthall called Sea Bags which offers bags made of sails made right in Portland. What I enjoyed most about this store was that there was a small area in the store where you could observe the workers making the bags in the shop. My girlfriend gifted me a bag from here when I got married, so it was so neat to see where the bag came from.

We were running low on time so from there we headed back toward the parking garage, stopping in a few stores that caught our eye on the way around Commercial and Exchange streets. One of our favorite stops was the Portland Beer Hub where we snagged a few Maine craft drinks to have on hand for the wedding weekend. The selection was impressive and we enjoyed tasting local craft beverages.

We could have spent all day walking the adorable streets of Portland. I wish we had more time, but hopefully, this can serve as a starting point for some plans you might have for exploring Portland, Maine.

Other places that were suggested to us but we didn’t make it to:

After the wedding, we took a direct flight back home to Pittsburgh on an airline new to us Breeze Airways. The flight was about 1 hour 15 min and was relatively inexpensive, a flight I might even be tempted to try with my kids if the flight continues. I think Portland would make for a lovely getaway weekend without too much travel time. I’m tempted to combine a weekend in Portland with a bucket list trip to Acadia National Park.

Feel free to leave a comment with other suggestions. If you end up visiting Portland, be sure to tag me on Instagram (@adventureswkelly). I want to hear about your adventures in Portland.

Here are a few of my other travel itineraries:

And don’t forget to think about visiting where I live in southwestern Pennsylvania. There are tons of hidden gems, historical sites, and points of interest in the beautiful Laurel Highlands plus several recreation opportunities that I am in the process of highlighting on my website. Here are a few sample posts to explore:

Happy Travels!