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I have a goal to visit all 50 states and got to cross off Maine as number 31 last weekend. Maine is a popular summertime destination, especially for those in New England. We visited at the start of fall just as the leaves were changing and the colors of the foliage were absolutely stunning, especially along the rocky coastline. The only downside of waiting until this late in the season is that the weather can be a bit more biting, as we experienced on our 2^nd day.

After a full day of work on Friday, we flew to Boston and spent the night. We would have flown directly to Portland, but the flight times didn’t work for us. Gotta do what you gotta do.

Day 1

Breakfast at Dutch’s

To maximize our time in Portland, we woke up early, picked up our rental car, and drove 2 hours from Boston to Portland. Our first stop was breakfast at Dutch’s, a cute national park-themed diner. I ordered the Not So Traditional breakfast sandwich (egg white, cheese, and chimichurri on an English muffin) which was really good. Thomas ordered the Portland Breakfast and we split a side of the grilled banana bread, which tasted like a delicious cross between regular banana bread and French toast. I’d seen people raving about it online and I totally understand why!

Tandem Coffee

After breakfast, we headed to Tandem Coffee, which is located in an old gas station that was then transformed into a laundromat before finally becoming a coffee shop. Tandem Coffee is clearly very popular, as evidenced by the line out the door. My black coffee was great and Thomas’s hot chocolate was rich and delicious. Had we not just eaten breakfast, we would have ordered from the large assortment of pastries they offered – everything looked amazing.

Lobstering

I love lobster, so when I found out you could take a tour to learn how lobstering works, I booked it immediately. About a dozen of us boarded a Lucky Catch Cruise s boat and headed out to Casco Bay where we got to get our hands dirty cleaning out traps, refilling bait bags, measuring lobsters, and pushing traps back into the water. We learned that it takes lobsters 7 years to grow to legal size and if a female lobster is caught covered in eggs, her tail is notched to indicate to future fishermen that she can reproduce. It is then required that she is thrown back for the rest of her life (and she can live up 100+ years!).

There is no commercial lobstering industry in Maine. Instead, it is all self-regulated by individual lobsterers and it is usually a multi-generational operation with parents passing boats on to their children. The people in this industry take their work seriously and are proud of what they do.

While it’s never guaranteed that you’ll catch any lobsters, we were fortunate to be able to keep a few. At the end of tour, we were able to buy a lobster for $10 (cash-only) and pick our favorite right out of the tank.

The tour took us around Casco Bay and between pulling up traps, we were shown amazing views of the Maine coastline, including Portland Head Light and Bug Light. The former is the most photographed lighthouse in the United States and the latter is the only lighthouse of Greek architecture in the country.

Note: there are no restrooms available on the tour or at the dock. The nearest restrooms are in The Holy Donut or Starbucks down the street, but you’ll likely need to make a purchase to get access.

Lunch at Portland Lobster Co.

Fresh caught lobster lunch in Portland Maine

Right next to the pier is Portland Lobster Co, where we were able to take our lobster and have them cook it for us for $14 with sides of a baked potato, corn on the cob, and coleslaw. We named our lobster Lisa and she was delicious! The restaurant has limited indoor dining space but it has a large heated outdoor eating area.

Buzz Coffee

Waking up early started to take its toll, so we made a quick pitstop at Buzz Coffee, a cute local coffee shop located in a basement. Thomas grabbed a maple cold brew and we were on our way.

Food Tour

While the food on this tour was fine, we ended up enjoying the other parts of the tour even more. Our guide, Brent, was very knowledgeable about the history of Portland and explained how much the city has been revitalized in the past few decades after falling on hard times for about 50 years in the 20^th century. He also let us know that the fire engine tour is the best tour in Portland because it explains the history of the 4 fires that burned Portland to the ground and hits all the major sites in a short time. If we’d had more time we would have gone.

The tour took us to 4 stops, but the guide said they go to different restaurants on each tour:

Andy’s Old Port Pub for clam chowder and Maine Root root beer
Rigby Yard Wharf St for half a lobster roll and bourbon sangria – apparently this is Anna Kendrick’s favorite restaurant in Portland (where she’s originally from)
The North Point for a meat/cheese board and cucumber martini
N to Tail for Korean chicken and a sake bomb

All of the food was just ok but the drinks were great and we lucked out and had a really great tour group. Everyone was super friendly and it really made for an awesome time. One of the people on the tour asked Brent about the hidden speakeasies she’d read about online and at the end of tour, he helped us find them.

Bar Hopping & Speakeasies

The first speakeasy we found was Lincoln’s, where every drink is $5 (thus the name). In the spirit of the hidden speakeasy, I will not give away how to find it and ruin the fun of it. The other speakeasy is less of a secret and is hidden inside the bar Blyth and Burrows. Several of us from the food tour stuck together to find them and celebrate with a drink. Afterwards, we tagged along with one other couple we met on the tour and went bar hopping. Portland has a vibrant nightlife and we went to Bar of Chocolate, Bonfire Country Bar, and Bubba’s Sulky Lounge.

Day 2

The Holy Donut

We started off day 2 by visiting The Holy Donut, where we ordered chocolate sea salt, maple, and apple cinnamon sugar donuts. These donuts are unique because they are made with potato flour sourced from Maine potatoes which results in a much more cake-like consistency than a traditional donut. Both of us agreed that the maple was the best flavor of the three.

The Holy Donut has 2 locations in Portland, but the location on Commercial Street has a much longer line and tends to sell out every day because it’s located in the more touristy part of town. We went to the Park Avenue location to avoid the crowds.

Spring Point Ledge Lighthouse

We had some time to kill after getting donuts, so we drove out to the Spring Point Ledge Lighthouse, which is located on a rocky pier. You have to hop from one rock to the next to make it out to the lighthouse, but it’s really fun and a great spot for photos. It was much windier than it had been the day before, so we were glad we weren’t going out on a boat with rough waters and wind chill.

Victoria Mansion

Victoria Mansion is a beautiful pre-Civil war mansion that showcases a lot of different architectural styles and cultures throughout the house, from baroque to medieval revival to Turkish and Indian. It originally cost $120,000 to build, which is the equivalent of about $4.3 million today when adjusting for inflation. After falling into disrepair, the house has been restored to its former glory and now stands as a time capsule to the era it was built in and of the two families who called the mansion home.

You can only see the mansion via a guided tour. As of October 2022, masks were still required in the house and the gift shop, but they have extras on hand in case you forgot one. The tour lasted about 45 minutes.

Fort Williams Park

Next, we drove to Fort Williams Park and ate lunch at Bite Into Maine, a food truck located in the park. We each ordered a 4.5oz Connecticut-style lobster roll (which meant it just had warm butter on top of the lobster meat) and split a Maine Root blueberry soda and a whoopie pie. I love lobster rolls and this one completely lived up to my expectations for how amazing a lobster roll in Maine should be and worth the $28 that each roll cost. They offer 4.5 and 6 oz sizes (+$8 for the larger size), but I thought the smaller size had the perfect meat-to-bread ratio.

The blueberry soda was super interesting and really enjoyable to sip on. Whoopie pies are Maine’s state treat, so I felt it was only fair that we try one. It tastes very much like a cupcake, but with the frosting in the middle instead of on top. I’m glad I tried it, but I was satisfied after just a bite.

After lunch, we briefly warmed up in the car before exploring the Goddard Mansion, which is another pre-Civil War mansion. However, unlike the Victoria Mansion, this one was completely abandoned and now all that remains are the brick and stone walls. The roof is gone and plants are now growing where rooms used to be. The building is completely fenced off, so you can only walk around the outside, presumably for safety purposes.

If it has been warmer or less windy, we likely would have explored more of the park and seen the Portland Head Lighthouse again from land, but we were eager to get warm.

Portland Observatory

We didn’t spend as much time at Fort Williams Park as we’d originally planned, so we decided to check out the Portland Observatory, which our lobstering guide had told us about the day before. When we got there, we found that you can only go inside as part of a guided tour. I quickly bought tickets to the next tour on my phone which was taking place 15 minutes later.

I hadn’t known what to expect, but this tour ended up being fascinating. Our guide made sure we were clear that the observatory is not a lighthouse – it’s a marine signaling tower and actually the last of its kind in the United States as the rest were left to fall into disrepair or destroyed after the invention of two-way radio made these towers obsolete. This building is also likely the only ballasted building in the world. The earth under the building was too rocky to lay a regular foundation, so instead the building is weighted down with 22 tons of rocks in the basement.

Our guide led us up through the various levels and did a great job explaining the history of how the building came to be and the renovation efforts that have allowed it to become a museum today. From the top we had 360-degree views of Portland, the bay, and even Mount Washington 70 miles away in New Hampshire. The tallest building in Portland is only 16 stories, so not much the city is out of view.

The only downside of doing this tour was that instead of the stated 45 minutes, it lasted an hour, which caused us to miss the next tour we’d booked on the Maine Narrow Gauge Railway. This tour was so great we weren’t too upset (and it just means we have a reason to return to Portland one day!).

Mt Desert Island Ice Cream

Since we missed our railroad tour, we had an unexpected hour to kill, so we decided to go to the 2 places we’d originally intended to go on our first night. The first of these places was Mt Desert Island Ice Cream, even though it was cold outside. They don’t offer samples, which I didn’t realize until after I’d asked to try the plum sorbet, so that was what I ended up with. I struggle to even call it sorbet because that is rude to all the amazing sorbets in the world – this was an icy and largely flavorless. Thomas got the cookies & sweet cream ice cream and his was amazing, so if you come here, just avoid the sorbets.

Urban Farm Fermentory

The second spot we’d missed on Day 1 was Urban Farm Fermentory, which brews every kind of fermented drink, from non-alcoholic jun to kombucha to hard cider, gruit, beer, and mead (I’m not even sure all of those are real words). All the flavors they had on tap were fun and unique, perfectly in line with the funky atmosphere. We each ordered a tasting flight, where you can try 5 different drinks.

Otto Pizza

We had to head to the airport around dinner time, so we decided to pick up pizza from Otto Pizza and eat it after we got through security to avoid having to eat airport food. This turned out to be a really smart idea because the Portland airport (actually called a “jetport”) is small and all the restaurants close before 6PM. We ordered a tortellini pizza and a sausage pizza and thought both were pretty mediocre. The tortellini was the best part but the pizza didn’t have enough of them. Both pizzas probably would have been a lot better had we eaten them right out of the oven, but they did not travel well.

Overall, we had an amazing time in Portland and while we could have used one more day to explore, we were happy with how much were able to pack into a weekend. Our first impression of Maine was a good one, and I hope we get to come back and explore more of the state.

Quick tip: while I definitely recommend renting a car to explore Portland, parking can be expensive, so do your research ahead of time to avoid paying $75+ for parking like we did!