47 Cool Things to Do in Portland, Maine

Portland is a gateway city to all the wonder Maine offers. The city sits on a peninsula and is only three miles long! But it is three miles full of things to do!

Portland has a lot to offer– outdoor activities, World War 2 history, lighthouses, a working port, and some of the best food and drinks in the United States.

It was voted Best Restaurant City of 2018 by Bon Appétit. You will have a harder time deciding which restaurants you must miss on your weekend in Portland than deciding where to go. The food is so good!

Portland is a city full of people hoping to build themselves a bright future. You can see that entrepreneurial spirit in Portland’s thriving brewery and spirit scene, as well as the tours it offers.

I combine lots of sights, too much food and drink with some outdoor activities to burn off the calories. So read on and enjoy planning your long weekend getaway to Portland, Maine.

1. When you first come into town, get an overview by taking a city tour. I took mine with The Real Portland Tour. The owner Derek led this van tour. A real local with a thick Maine accent, he is a smart, funny guy who drove us all around town, even into the surrounding Cape Elizabeth and South Portland. Book your Real Portland Tour. (This post contains affiliate links such as this that don’t cost you more but support this site if you book through them. You can read more about that in the footer.)
2. See Portland from across the bay. You can do this in many ways. We got some great views of the city from our Real Portland Tour, including the straight-on view from Bug Light Park. While looking at Portland, notice that almost all the buildings are made of brick. Do you have an idea why that would be so? Portland has burned down at least twice, so brick buildings became a requirement.
3. To learn more about the fires, visit the Portland Fire Museum.
4. Take a walking tour with the Maine Historical Society or do a self-guided Maine Freedom Trail Walking Tour.
5. Take a bicycle ride through South Portland and Cape Elizabeth with Summer Feet Cycling on their Five Lighthouse Tour. I had the opportunity to do this tour, and they took such great care of us. It is the longest bike ride (around 10 miles) I have taken in many years but is mainly flat.
6. Take a ferry over to Peaks Island and do a self-guided bike or golf cart tour. Read on for my experience.
7. Summer Feet Cycling also offers a bike tour of Peaks Island off Portland’s coast. Book your Peaks Island tour.
8. Explore Portland Breakwater Lighthouse in Bug Light Park. This diminutive lighthouse is Grecian-styled. It was placed on the breakwater after a storm destroyed much of the harbor in 1831. Big work for a small light, locally called “Bug Light.”
9. Portland is still a boat-making town. It was very active in World War 2, making Liberty Ships. See where 274 ships were made at the Liberty Ship Memorial in Bug Light Park.
10. In season, take a tour inside the Spring Point Ledge Light, the only caisson-style lighthouse to which you can walk. Read more about all of Portland’s Lighthouses.
11. Picnic on a lobster roll, while listening to the foghorn of the Portland Head Light in Fort Williams Park.
12. After lunch, take the easy .4-mile cliff-side walk in Fort Williams Park.
13. Speaking of lobster rolls, try the incredible Brown Butter Lobster Roll at Eventide Oyster Co.
14. While there, try the lobster stew, creamy with sweet potatoes.
15. Now that we are on the topic of Portland and its incredible food scene, this is the perfect city for a food tour! I love food tours since you get to try a sampling of what a place has to offer. Not only that, but you usually get a sense of geography from the walking and history from the guide. Our tour with Maine Foodie Tours provided all that! Book your Maine Foodie Tour here. 
16. Visit Monjoy Hill and walk the Eastern Promenade, a 2-mile crushed gravel walk along Casco Bay. This neighborhood has an arty, eclectic vibe.
17. While in Monjoy, walk through the East Cemetery– the oldest historical site in town. Especially impressive (at least for those of us that think cemeteries are very cool), is the Dead House, a building used to hold bodies in the winter waiting for the spring thaw. It sounds like the perfect set-up for a horror movie to me, and Steven King doesn’t live that far away. If you like cemeteries, have you visited the ones in New Orleans?
18. Climb the Portland Observatory, America’s last standing maritime signal tower.
19. Have a wicked good pulled pork breakfast taco at Terlingua because Portland has excellent food from all over the world.
20. Decide if you are a Lillian or a Bob at Bob’s Clam Hut.
21. Take a picture with the bronze statue of the poet and native Portlander, Henry Wadsworth Longfellow. You can also visit his house.
22. Visit the Portland Museum of Art. Maine’s largest art museum contains art from around the world and an extensive collection of local works from artists such as Winslow Homer and Andrew Wyeth. Literary Inspiration for your visit to Maine: A Piece of the World: A Novel by Christina Baker Kline, historical fiction about Wyeth’s painting, Christina’s World.
23. Walk the 4.2-mile loop, Back Cove Trail, dreaming of buying one of the large waterfront homes. When you get to the bridge, look across at the B&M Baked Beans factory.
24. Start your day off with an incredibly smooth and flavorful French omelet at the Southern Hot Suppa.
25. As I said before, Portland is a city of young people hoping to build themselves a bright future. You can see that entrepreneurial spirit in Portland’s thriving brewery and spirit scene. We saw it on our food and Maine Brew Bus tours. On the brewery tour, a bus drove us to meet the faces behind some of Portland’s best alcohol products.  Book your Maine Brew Bus tour.
26. Try a rhubarb (yes, rhubarb) wine. Maine has long, harsh winters, resulting in a short growing season. Because of that, its plants need to be hardy. One of the most successful crops in Maine is rhubarb. Amanda at Eighteen Twenty Wines set out to make a rhubarb wine that even a wine connoisseur would appreciate, and she did a fabulous job.
27. Taste Gin at Hardshore Distilling Company. If you asked me before my Maine Brew Bus Tour, which my least favorite liquor is, my answer would be gin. It smells and tastes of Christmas trees. A pleasant smell at Christmas, but not in my cocktail. The founder, Jordan, adds other botanicals to his gin, giving it a more complex flavor and an excellent taste. Gin convert here.
28. Try Honey Mead at Maine Mead Works. I warned you that Portland, Maine’s cocktail game is strong, right? They also make excellent mead in varied flavors. I hadn’t tried mead before but loved it. My favorite was the HoneyMaker Lavender Mead.
29. Enjoy the food trucks at Allagash Brewing Company, Portland’s most famous brewery. Check their website to see what food trucks are set to be there, and then walk around to all the other spirit shops in the area, such as Foundation Brewing Company.
30. You have to try Duckfat french fries. Do you know those crops that thrive in cold weather? Potatoes are one of them, and Maine makes good use of them with super-crisp fries, cooked in duck fat and served with curried mustard or truffled ketchup. A small DuckFat kiosk (Duckfat Friteshack) is right next to OxBow Blending and Bottling.
31. They even use their potatoes to make unique donuts. Try a potato donut at The Holy Donut. They claim that the potato creates a lighter donut. I didn’t find that to be true, but the host of creative flavors make these donuts worth a taste. Our favorite was the sweet potato donut, and they have many gluten-free options. If you are crazy about donuts, be sure to read my Rhode Island Donut Road Trip.
32. A soda that is uniquely Maine is Moxie. It is a strange flavor, but one worth trying while here.
33. Get a cup of coffee and stroll through the West End neighborhood with its Victorian mansions and brownstones.
34. Watch a sunset from the Western Promenade.
35. Soak your feet in herbs while enjoying some exotic tea at Soakology.
36. Take time to stroll down the cobblestones of Commercial Street. It lies right along the working waterfront and is full of stores and restaurants.
37. You can see a small fort in the middle of Casco Bay, Fort Gorges (pronounced gorgeous), from Portland. You can kayak or take a water taxi to explore this fort, which was obsolete before it had a chance to be used.
38. The mail gets delivered to Portland’s islands by boat, and you can join in the delivery. Book passage on Portland’s Mail Boat tour.
39. Chew a piece of gum while ambling by the Hub Furniture building at 291 Fore Street. This location was the first chewing gum factory in the US, making spruce gum, State of Maine Pure Spruce Gum.
40. Try numerous flavors of kombucha at Root Wild, a kombuchery (the owner, Reid’s name for a kombucha bar). I am a fan of this fermented tea and liked it enough to bring some home. The open space is cool, too, with touches such as kombucha-stained wood on the bar. We visited as part of our food tour.
41. Locals are crazy about Otto’s pizza and its inventive thin-crust pies. Be sure to try the mashed potato, bacon and scallions, and the blue cheese, roasted pear, and arugula.
42. The theme of this blog is discovering the adventures in each day. That is also what the Umbrella Cover Museum is about- celebrating the mundane.
43. Cryptozoology is “the study of hidden animals.”  such as Big Foot and Nessie. And in Portland, you can visit the International Cryptozoology Museum!
44. Since you are exploring the creepy side of Portland, take part in a Haunted Walking Tour of the Old Port.
45. I have always been a fan of eating lobster, so getting out on a lobster boat has long been on my bucket list. You can do it in Portland on the Lucky Catch Cruise. It was so much fun, a way to see Casco Bay, and I got to set and pull up a lobster trap! Book your Lucky Catch Cruise.
46. After your cruise, you can buy your lobster and have it cooked to eat at the Portland Lobster Company restaurant. Farm to table, baby!
47. If you love sweets like me, you have to visit Gross Confection Bar! End your night in Portland with a drink and a dessert sampler. Each bite will transcend your expectations. Also, grab a taste of their house-made ice cream- the brown butter cider swirl was some of the best ice cream I have ever had. Like the discovery of Penicillin, this ice cream was made from a misstep.

Enjoy your time in Portland. If you are using Portland as a gateway to explore all that Maine has to offer, read all my Maine posts, including Exploring Acadia National Park.

I stayed in Portland, Maine, to attend the Woman in Travel Summit. For attendees, many tours are hosted. That is how I got to experience many of my Portland adventures. As always, I will only recommend something I really enjoyed.

While in Portland, Maine, I stayed at The Holiday Inn Portland by the Bay. The location was perfect, a walking distance from almost everything we did. They also had a shuttle to get us to points farther. Book a room at the Holiday Inn Portland by the Bay or search for your ideal Portland, Maine hotel here.

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