If you’re looking for the perfect weekend getaway I have just the place for you: Portland, Maine. Portland is a historic coastal town with an artistic, flannel vibe loaded with restaurants, galleries, and breweries. When you think of an iconic New England town, you’re picturing Portland. Ideal for a laidback, foodie weekend or a romantic, seaside retreat, I promise you will not be disappointed!
My husband and I spent our 2nd anniversary weekend in Portland and despite having lived just 2 hours south our entire lives we had never been! Our weekend was filled with food, drinks, walking tours, and a quick ferry to a nearby island. If you’re thinking of heading over to Portland and don’t know where to start, try out our itinerary:
Day 1:
We stayed at the Holiday Inn Portland-by-the-Bay which was just a short walk downtown but there are many other accommodation options to choose from! When we arrived in Portland, we knew we wouldn’t be able to check-in yet, so we stopped at one of the two iconic donut shops Portland has to offer: Eighty8 Donuts. They serve the cutest mini donuts that come in a box of 6, the flavors are so unique and they’re served right out of the oven so they melt in your mouth. We ordered the 007, which is maple dipped with bourbon cream and candied bacon on top, and the Bamm Bamm which is topped with fruity pebbles.
After this we drove around a bit to get our bearings before stopping at Terilingua to split a BBQ board. We did have to wait for a table so we put our name in and walked across the street to Oxbow Blending and grabbed drinks. They actually have a Duckfat Frites Shack right outside this brewery and I had read so many people recommending their poutine that we knew we had to try it. I’ve only had poutine one other time in Canada so I’m not an expert but I can tell you this was delicious. The drink I had was also out of this world, it’s made by Maine Craft Distilling and is a blueberry lemonade drink called Blueshine. It was so good we grabbed some to bring home! After finishing up here we walked back over to Terilingua. When I tell you I left this trip feeling like I’d never be hungry again, I mean it! There are so many amazing restaurants to try out I can definitely see why foodie’s flock here.
After checking into our hotel, we walked around downtown and stopped at all the boutique shops we passed. Portland has such a laidback vibe to it and the view from downtown is gorgeous. We stopped into a vintage-inspired cocktail bar called Blythe & Burrows on Exchange Street and this was one of my favorite places in all of Portland. The hostess said they didn’t have any tables but we could sit at the bar which was fine with us as we were still full from everything we had that morning. Little did we know the “bar” she was taking us to was actually behind a bookcase and down some hidden stairs at the back of the restaurant. They were playing an old-timey movie from a projector onto the brick wall and my espresso martini, called the “loose cannon”, came with a coffee bean cannonball and disintegrating paper cannon. The whole experience was 10/10.
We ended the night at Gross Confection Bar with chocolate martinis and their chocolate peanut butter torte. The couple next to us had ordered the Entourage Board which includes four of their desserts and everything looked so incredible. Highly recommend!
Day 2:
We woke up the second day and had a historic walking tour scheduled that morning. As we made our way downtown, we walked by a coffee shop called Bread & Friends that we decided to pop into and I’m so glad we did! They had the best pastries and freshly made bread. I had the pop tart and my husband ordered a baguette with butter and jam, both were so delicious and paired so well with our lattes that they serve in ceramic mugs made by a small shop around the corner.
The walking tour was super informative and gave us a better feel for the layout and hidden streets we had missed the previous day. We learned all about the four fires that have destroyed Portland over the years and how the city has risen from the ashes and rebuilt each time. We were also able to stop into a fish market and learn a little about Portland’s fishing industry in the past and present. If you’re looking to sprinkle in some activity and history to your foodie tour this was a great way to do so!
After the tour, it was time for our first lobster roll. The jury was out in my research over which restaurant housed the best, so we decided to try Luke’s Lobster first. Although we only ordered one, they do offer a lobster roll flight so you can try their different kinds. The views were amazing as well, for those who don’t love lobster (like me), you can still sit and enjoy a true Maine waterfront experience.
After we ate, we drove over to Baston River Brewing and grabbed beers while we played some cornhole. They also had a live jazz band which I believe still plays every Sunday. I absolutely loved it here, the atmosphere, the music, and the games just elevated the experience for me, we will definitely be returning!
Our dinner reservation that night was at Leeward, which was recommended to us by our tour guide earlier that day. If you eat here, please order the house-made focaccia, IT’S SO GOOD. We also had the cacio e pepe and the rigatoni beef & pork ragù Bolognese. My mouth is watering thinking about how delicious and fresh this pasta was. I’m telling you Portland just understands good food.
Day 3:
Our third and final full day in Portland we took the ferry over to Peaks Island. On the walk to the ferry, we had some time to kill and saw the line for The Holy Donut wasn’t as long as previous days so we grabbed some. The Holy Donut is famous for its potato donuts made from scratch daily. They have so many different and seasonal flavors, but we decided on the gluten-free dark chocolate sea salt and the maple. Both were so good and so completely different than Eighty8 so I would recommend trying both if you have the time! The ferry to Peaks Island was short and once we got over there, we ended up renting golf carts in lieu of bikes. Peaks Island is small, you can definitely spend a day here and feel like you were able to see everything. We spent the day on the beach and driving along the coast. We also came across a food truck called The Greeks of Peaks that had the most amazing gyros (we are such suckers for Greek food). The weather was great and the views around the island were even better. While waiting for the return ferry we stopped at Jones Landing for a drink which has a great deck with views of Portland across the bay. They also have live music during reggae Sundays which seems like it would be fun.
For dinner that night we had reservations at Via Vecchia. This was easily in my top 3 of the weekend. Our waiter was incredible, one of the friendliest people I have ever met and the atmosphere and décor of the restaurant was top notch. They even had a “Happy Anniversary” handwritten card waiting for us on our table which gave the whole experience such a personal touch. After dinner, we found another speakeasy called Lincolns. Finding the entrance was super fun and the bar had such a dive-y feel, which we love. It was cash only though, just a heads up! We actually arrived just in time for their rock, paper, scissors tournament. It was $5 to buy in and basically everyone in the small bar played and rooted for each other it turned out to be hilarious and such a good time; my husband almost won!
To finish the night we stopped by Luna Rooftop bar for a nightcap with stunning views overlooking the Portland waterfront. It was a great end to an even better trip.
The last morning of our trip we made one final food stop at Tandem Coffee. The line was crazy and we soon found out why. We ordered their breakfast sandwich that comes on their famous buttermilk biscuit with paprika mayo and It was out of this world. We took them to the Eastern Promenade so we could dine with a view. There is also a food truck park here if you want a quick lunch off the bike path! Before we got on the highway we made one more stop at Portland Head Light at Fort Williams Park. Next time we visit Portland we will definitely be spending more time here; it’s gorgeous on a sunny day and the perfect place to picnic!
Portland surprised us in the best way. We didn’t originally go to Portland with food in mind, but we absolutely left there thinking about it. The restaurants in Portland really outdo themselves and the people who work and live here are so friendly and accommodating. We are already looking forward to making a return trip this summer!
