Whether you are here for the weekend or just 24 hours, here are the top activities you must cross off your Portland, Maine Bucket List, coming from someone who lives there!
1. Start your day off at the Holy Donut
You can't visit Portland without getting a donut, or a dozen, from this local shop. Made from Maine potatoes, the Holy Donut makes fresh and unique flavors every morning, and they tend to sell out before the day is done. The shop will close when they run out of donuts so it's better to get your fix earlier in the day. The main location on Exchange Street is conveniently located in downtown, but is always more crowded, especially when a cruise ship is in town. However the location on Park Ave offers the same selection of donuts with half the crowd.
2.Walk around the Old Port
Portland's Old Port is not only home to various restaurants but tons of local shops as well. Souvenir shops are littered among specialty and vintage stores. For tourists, its always a surprise to see what is around the corner. You can even see a piece of the Berlin Wall and remnants of Portland's lock bridge down on the working waterfront.
3. Head over to the Eastern Promenade and the Portland Observatory
Located on the outskirts of downtown, many tourists neglect visiting the East End. Well too bad for them, because they are missing a beautiful view! You can simply drive along the coast or make your way down to the park. Enjoy a picnic at the cozy East End Beach, the only sand beach in Portland, while you watch the sailboats on the water. Then take a short drive to Sumner Park on North Street where you will find the best view of the city of Portland, for free.
Continue down North Street and you will come across the Portland Observatory! If you are traveling in the summer time, a tour of the observatory is a must. An adult admission ticket costs $10 and gives you the history of the observatory as Portland's signal tower, and offers breathtaking views of the city from the top.
4. Grab lunch on the water
One of the things that makes Portland such an attractive place to visit is that it's a city on the water. Not many places offer the downtown feel only blocks away from the Atlantic Ocean. If you are in Maine, you most likely have an urge for lobster. There are tons of options to fill your seafood fix right on Commercial Street. Dimillos on the Water is one of the most popular destinations because the restaurant was built on a real life boat. If you get sea-sick easily this destination may not be for you. But there are plenty other options to dine by the water. The Portland Lobster Company and the Porthole are two of my favorites. They both offer deck seating and live music all summer long.
There are also plenty of raw bars located on the water if that's more your thing. Although I have never had oysters, friends of mine speak highly of Eventide Oyster Co, and J's Oysters.
5. Head to a brewery, or at least try a craft beer!
There are just shy of 100 breweries in the state of Maine, and Portland is known for its vast selection of beers and breweries. Names like Seadog Brewing Company or Allagash are known around the U.S., but there are so many other brews you can't get anywhere else. If you are looking for a brewery tour head over to Allagash on Industrial Way...you can get a tour of the factory with a beer tasting for only $5! Or hop on the Maine Brew Bus to get a tour of Portland's best breweries. If you really aren't a beer person, but want to try something local, I suggest Allagash White or Seadog Raspberry Ale.
6. Catch a game
What most people may not know is that Portland is home to three different minor league sports teams: The Portland Seadogs (baseball), the Maine Red Claws (basketball), and the Maine Mariners (hockey). So no matter what season you visit Portland, there is always a game to see!
The Portland Seadogs are a Red Sox affiliate and have seen many famous players come through their team. Hadlock Field features the Maine Monster, its own version of the Green Monster, and Slugger the Seadog is arguably one of the most energetic mascots in the entire minor league. If you do find yourself at a game this summer, treat yourself to a Seadog Biscuit.
The Maine Red Claws, a Celtics affiliate, and Maine Mariners, a Rangers affiliate, also feature two of the most Maine mascots out there: Crusher the lobster and Beacon the Puffin.
7. Take a sunset cruise around Casco Bay
There are various harbor cruises to choose from, but the sunset cruise was amazing! Not only do you get a beautiful view of the sunset over the cityscape but you get a wonderful history lesson of Portland and famous people who lived there.
8. Take the ferry to Peaks Island
This is still something on my Portland to do list that I am hoping to tackle this summer. Honestly there is not a lot of "attractions" at Peaks Island, but the quaintness of the island is something to be enjoyed. Walk the 3.7 mile loop around the island, or rent a golf cart if you are feeling ambitious, and enjoy a relaxing day with gorgeous ocean views. There is only one public bathroom on the island so make sure you take note of it when you hop off the ferry!
9. Grab dinner somewhere new
Portland was named the 2018 Restaurant City of the Year by Bon Appeit, so no matter what you are craving there is a great local option for you. Here are some of the favorite restaurants in downtown, but make sure you make a reservation...especially if you are visiting on a weekend! There really is no bad choice when it comes to dining in Portland, so do NOT go to a chain!!
Duckfat: arguably the best french fries in Portland
Empire Chinese Kitchen: The best authentic Chinese food, even if you don't like authentic Chinese food
Flatbread Pizza Company: specialty pizzas with a beautiful view of the harbor
Taco Escobar: You can't go wrong with a mexican restaurant that infuses their own tequila
Central Provisions: offers a creative menu (still on my restaurant bucket list!)
10. Enjoy the nightlife of Wharf Street
One of the perks of a small city is that the best nightlife is located right next to each other and it is a rarity to pay a cover charge. Start your night off at Lincoln's prohibition themed bar, if you can find it that is, but make sure you have cash! Then head on down to Wharf Street where you can bar hop as you please. Enjoy a bacon happy hour in a tire swing at Bonfire Country Bar while you wait for the lowest price of the night on well drinks at the Drink Exchange right next door. Across the street, Oasis offers two floors of dancing, giant connect four, and Mario Kart.
If you're willing to venture out of downtown and pay a $5 cover, Bubba's Silky Lounge offers a light up dance floor, 5 levels to explore, and antiques everywhere you look. You have to see it to believe it.
Bonus:
11. First Friday Art Walks
The first Friday of every month hosts the Portland Art Walk. Stroll down Congress Street and see hundreds of local artists displaying their work, including photography, pottery, clothes, paintings, and more. Then head inside the Portland Museum of Art FOR FREE, one of the perks of First Fridays. The night offers great opportunities to explore local art, food, museums, and music at no cost (unless you choose to buy something).
12. Visit the Portland Headlight
This is the sight that most people envision when they think of Maine. However the disappointing thing about the Portland Headlight, is that it's actually in Cape Elizabeth. But if you have the chance to visit you absolutely should. The park is free to enter and has a carry in carry out policy. There is a massive grassy area to picnic on, walking trails, and the ruins of Fort Williams to explore. And of course you must snap a picture of the oldest lighthouse in Maine!
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