Last weekend we headed north for our first visit to the great state of Maine. According to my mom, this was not actually my first visit, having been on a trip once when I was very young, but since I can’t remember that I’ll count this as my first official trip to Maine. We decided to stay in Portland. Only an hour and a half from Boston, it seemed like the perfect spot to choose for our first trip to Vacationland.

As always (it seems), we did not have the greatest weather for our trip, with a deluge of rain for most of the day Saturday, but we still managed to check off most of our must-sees/must-dos and had a lot of fun getting to know the city. We were also able to visit nearby Freeport and Cape Elizabeth.

Filled with art, delectable food, great shopping, and historic architecture, Portland offers something for everyone. We were impressed by the historic charm and eccentricities of the city. There was too much to see and do for just one weekend, so I guess we’ll have to go back! I’m thinking a summer trip is in order.

My Top Picks for a Winter Trip to Portland, ME:

1. Tandem Coffee

If you know me, you know that I love coffee and may even border on being a coffee snob. So, when I visit a new place, I do my research. In my research, I found Tandem Coffee, which had great reviews not only for its coffee, but for its pastries as well, and just so happened to be a short walk from our Airbnb – bonus! That was our first stop on Saturday morning, and we enjoyed it so much that we decided to go back on Sunday morning as well. I highly recommend trying their biscuits and unique scones (Sandro tried an amazing kimchi scone) – I don’t think you can go wrong there though.

2. Snowshoeing in Freeport

Ok, so not in Portland, but certainly worth the drive. Freeport is L.L.Bean's headquarters. If you have ever seen photos of their giant Bean Boot – this is where you can find it. We took an L.L.Bean Snowshoeing Discovery Course – luckily before the snow turned to rain on Saturday – and it was so much fun! They provided all of the equipment and guides for our course. We learned a lot about snowshoeing and explored the beautiful L.L.Bean property. After our adventure, we headed to the L.L.Bean flagship store to get an obligatory photo with the bean boot and did a little shopping.

3. Food & Drinks

As I mentioned at the start, Portland is certainly not lacking in tasty food or drinks. Being there just for the weekend, there was only so much we could eat and drink, but we thoroughly enjoyed everything that we got to try! Beyond the downtown area, where I would recommend Novare Res Bier Cafe and Evo Kitchen + Bar, I would also recommend checking out Washington Avenue. We shopped at The Cheese Shop of Portland, tried delicious kombucha from Root Wild Kombucha and ate insanely large sandwiches from A&C Grocery, but we’ll be back to try Ramona’s, and Forage Market’s bagels. There are so many great options on one street! Pro tip: order your food early, Ramona’s sold out of sandwiches, and Forage Market ran out of bagels.

If you like beer, there is also plenty of that! Many breweries are takeout/pick-up only right now, but there are also quite a few open offering outdoor seating. We enjoyed a tasty brew at Rising Tide. They had plenty of outdoor seating and even had bubbles that you could reserve. On the way out of town, we also picked up some brews to-go from Bissell Brothers on recommendation from a friend, these were also awesome and I look forward to visiting when they open back up for in-person service. This site has a great list of all the Portland breweries.

4. Lovely Lighthouses

As with any seaport town, Portland and the surrounding areas boast many beautiful lighthouses. Across from the Portland Waterfront sits South Portland’s Bug Light Park. From the park, you can get a phenomenal view of Portland, the Bug Light Lighthouse, as well as a distant view of Fort Gorges.

On our way home, we drove to Cape Elizabeth (about 20 minutes from Portland) to see Fort Williams and Portland Head Light. We almost skipped this stop, but that would have been such a mistake! Completed in 1791, Portland Head Light is the oldest lighthouse in Maine. It is also one of the most beautiful I have ever been to!

Unique Finds & Facts

1. Valentine Bandit

It was abundantly clear that the city of Portland has a lot of heart. No really, there were hearts everywhere! Since 1976 the "Valentine Bandit/Valentine Phantom" has been plastering the town with paper hearts every Valentine’s Day. Even though our trip was two weeks after the holiday, the paper hearts were still posted everywhere - including some more permanent heart banners. It makes Portland a special spot to spend your Valentine's weekend. Or, if you’re not a big fan of hearts and love, you’ll know when to stay away. 😉

2. Eartha

Just outside of Freeport, you’ll find “Eartha” the largest rotating and revolving globe in the world! I’m not sure how we found out about this eccentric stop, but I’m so happy we did. We could not go inside, but the floor-to-ceiling windows allow visitors to gain a great view of it from the outside. At 5,600 pounds, it is quite a sight to behold. Granted, I am a big map/GIS nerd so I may be a bit biased. Definitely worth a stop – especially if you’re traveling with little ones. 😊

A Winter Weekend in Portland, Maine