Portland Maine Bucket List: 15 Cool Things to Do

From mouth-watering restaurants to epic lighthouses to a booming craft brew scene, Maine’s main coastal city of Portland just may have it all. It’s casual, yet trendy. It’s impressive, yet doesn’t try too hard. It is a city of many layers—it’s a seaport, historical hub and cultural hotspot all rolled into one.

No matter what you come here for, or when you arrive, the list of things to do in Portland is pleasantly long. Here is a guide to what to see and the best ways to explore the city.

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The Best Attractions & Things to Do in Portland, Maine

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1. ✦ Eat a Holy Donut

There could not be a better name than Holy Donut for this establishment as the taste of their specialty donuts is simply divine. Created with real Maine potatoes mixed with wheat flour, the donuts are made fresh with all-natural ingredients.

You can go to any of their three locations–Park Avenue, Exchange Street and Scarborough–for your dose of donuts. There’s almost always a line out the door, so for the best selections arrive right at opening!

Of course, everyone will have their favorite flavors of the 18 different ones offered, but a clear frontrunner is the Dark Chocolate with Sea Salt, followed by the Maple Bacon, Fresh Lemon and Toasted Coconut. Mmm!

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2. ✦ Take the Ferry to Peaks Island

A 20-minute journey from Portland via the Casco Bay Lines ferry will have you end up on Peaks Island where the laidback lifestyle will surely encompass you. The quaint island has a population of under 1,000, but it is packed with something for everyone. Spend your time here eating fresh seafood at one of the local cafes, relaxing on one of the many beautiful beachfronts or renting a golf cart to tour the entire island’s attractions, like the World War II history museum.

If you are up for a little more activity, opt to pop into a kayak to tool around the bay or take a bike ride along the scenic pathways. Whatever you do, don’t miss the quirky Umbrella Cover Museum with its assortment of umbrella covers displayed with various themes (including an X-rated section!).

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3. ✦ Spend an Afternoon at the Old Port

Cobblestone streets, red-bricked buildings, charming boutiques, trendy restaurants and fishing piers—that’s what you’ll find in Portland’s Old Port. It’s a quaint historic district that overlooks the Fore River. Many folks head there in early June for the Old Port Festival or in December for Merry Madness. But, it is fun to explore anytime of the year!

If you are a fashionista, don’t miss a stop by Rough & Tumble to ogle their handmade handbags, Aristelle for some luxurious intimate apparel and Zane that has a beautifully curated collection of designer labels.

The shopping scene can get overwhelming in Portland, but In the Know Shopping can take you on a tour to many of their favorites.

For all the home chefs out there, don’t miss a stop at Salt Cellar who carries a full line of gourmet flavors, or pop into Skordo who specializes in freshly ground spices, herbs, blends and rubs.

For eats, grab some thoughtful small plates at Central Provisions or indulge in the chef’s tasting menu at Miyake. And if you are a French fries lover like myself, you have to book a seat at Duck Fat. Or just take a culinary walking tour in Old Port to get a sampling of local food. 

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4. ✦ Sail the Casco Bay with Calendar Islands Sailing

Can you just imagine basking in the sun onboard a beautiful sailing boat with the wind in your hair and a glass of champagne in your hand? You don’t have to, because this can be your reality.  There’s no better bucket list worthy way to explore Casco Bay and its islands than on a sailing trip, and I had an incredible time doing so with Calendar Islands Sailing Co.

One of the most popular tours is their two-hour coastal sightseeing excursion, but they also offer island-to-island day cruises or personally customized trips. If you are up for more of an experience than opt for one of their overnight adventures. Either way, you will get a chance to discover the breath-taking scenery of the coast, the sights along the way and the islands.

Secrets of Casco Bay from GLP Films on Vimeo.

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5. ✦ See the Lighthouses

If you are the kind who just can’t resist historical lighthouses there a handful in the Portland area, each with its own charm. The Portland Breakwater Lighthouse (aka: Bug Light) is a small lighthouse that sits at the end of the breaker and is unique because it was designed to look like a 4^th century Greek monument.

Built in 1897, Spring Point Ledge Lighthouse is a caisson-style light station (the only one in the United States!), but what is special about this one is that you have the opportunity to tour it. But, the most impressive and the one that is best known is the Portland Head Light at Fort Williams Park. You can easily spend a couple of hours strolling along the pathways to check out Maine’s oldest lighthouse from every angle. For even more information read our article: 5 Epic Lighthouses in (& Around) Portland Maine

For an extra bucket list worthy experience try taking the Lighthouse Bike Tour that will take you to three lighthouses, and includes a lobster roll! 

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6. ✦ Visit the Historic Victoria Mansion

Built around 1860, this ornate summer mansion turned museum is impressive with its vintage look and captivating history. Everything about it is grand including the exterior that has balconies and verandas, and an interior décor of gilded areas, wall paintings, stained-glass skylight, beautiful draperies and splendid furniture.

Take a tour inside with knowledgeable guides who will tell you all about the mansion–from its origins as a summer residence for hotelier Ruggles Sylvester Morse to being bought by a resident of Maine who converted it into a museum. For its time, the mansion also had modern amenities such as hot and cold water and a central heating system.

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7. ✧ Explore Maine’s Historic Eastern Cemetery

This is not your typical activity for any itinerary, but when a cemetery has a long and riveting history, it makes for an interesting visit as is the case with Eastern Cemetery. Dating back to 1668, this cemetery with thousands of graves is a chronicle of the life and times of several people including Portland’s leaders and soldiers. It also offers a glimpse into the social divisions of the early times as the graves are divided into different locations.

You can venture there on your own or opt for a guided tour organized by the non-profit group Spirits Alive from June to October.

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8. ✦ Go on a Food tour

‘Live to eat’ should be your motto while in Portland as it has a vast variety of yummy food options and restaurants. You can easily set out to find your own delicious meal (which won’t be hard!) or unleash your inner foodie while learning about sustainability on a guided Maine Food for Thought tour.

The educational food tour will lead you on a walking path to eat your way through restaurants who feature locally sourced ingredients and a farm-to-table mindset. You will also get an understanding of the local food culture and delve even deeper with the stories behind the plate.

Though the stops and dishes can change, there was quite a delectable sampling on the day of my tour. For instance, the Union Restaurant dished up a bowl of locally sourced clam chowder with trout and Evo served a beet salad with a kalamata olive crumble and famous Maine blueberries. All the other stops were equally as delicious.

I can promise you that you will not leave this tour disappointed or hungry!

Take a peek behind-the-scenes:

GLP Films on Vimeo.

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9. ✧ Visit the Portland Observatory

An imposing seven-story structure, the Portland Observatory is the only maritime signal tower still standing in America. Back when it was built by Captain Lemuel Moody in 1807, it functioned as a communication tower for ships making their way to the docks. You can go on guided tours of this octagonal tower that stays open from late May to October.

Each floor has interesting displays related to Portland history, maritime traditions and the observatory. You can climb to the top of the tower’s lantern (cupola) and then arriving at the lantern’s balcony will reward you with tremendous 360-degree views over Portland and the bay.

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10. ✦ Enjoy the Craft Beer Scene

For all you beer lovers out there, Portland’s craft beer scene is booming! There’s nothing quite like drinking a ‘cold one’ in the open air while sitting at a picnic table with your pooch or playing a game of corn hole. Right? With a booming craft beer scene there is no shortage of good breweries to choose from.

Bunker Brewing Company is set inside a 1920s garage whose doors slide wide open. Novare Res Bier Café is a popular hidden beer garden that not only has a great food menu but also a nice international draft and bottle list. Of course, you can’t forget a visit to Allagash Brewery where you can take a classic tour then plop on their patio to indulge.

For a little more unique beer experience, pop onto a tour with the Maine Brew Bus whose expert guides (and bright green bus) will take you on a trip to discover the distilleries, breweries and wineries in the area. If being on a bus is not your thing, then take a walking beer tasting tour.

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11. ✧ Visit the Portland Museum of Art

If your perfect afternoon includes ogling famous works of art, then the Portland Museum of Art is one of the top things for you to do in the city. With a collection of over 18,000 pieces on rotation you are bound to see some notable names during your visit, like Claude Monet and Andy Warhol. But, that’s not all! Ranging from paintings to pottery and sketches to sculptures, the exhibits include American, European and even local Maine works.

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12. ✦ Get Fries at Duckfat Friteshack

Do you love French fries as much as me? Then don’t walk, run to Duckfat Friteshack for some of the best made from hand-cut Maine potatoes and fried in—you guessed it— duck fat. The Friteshack is an offshoot of the well-known Duckfat restaurant in Portland, and a popular one at that.

The shack is a casual joint where you place your order at the walk-up window from the limited menu. Fries can totally be a meal (especially if they are in the form of duck poutine), but in case you need more add on some doughnut holes or an extra thick milkshake.

Tip: Though I deemed the truffle ketchup the best homemade dipping sauce they serve, you can order a flight of all the six and judge for yourself.

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13. ✦ Shop for Sea Bags

If you want to take home the ultimate Maine souvenir then don’t miss a stop at Sea Bags, where nautically inspired totes are made from recycled sails cloth. No two bags have the exact same markings! The magic happens in the heart of a working waterfront, where craftspeople meticulously design, sew and finish each piece.

You can shop right there in the front storeroom where hundreds are displayed, including their vintage collection that feature mainsail insignia logos. As each bag is unique, leave yourself some time to pick out the perfect one for you.

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14. ✦ Drink at a Secret Speakeasy

Before you actually get to drink at Lincoln’s, you’ll have to find it first, and know how to get in—two minor details that won’t be shared here. But, that’s half the fun! Once you’ve cracked the code to get into this chill underground bar you’ll be greeted with a packed house who have come for the low-key vibe and $5 drinks. Yep, all the drinks are just five bucks, hence the name. Get it?

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15. ✦ Eat Lots of Lobster

It doesn’t get more quintessential Maine then eating fresh lobster, and Portland has some of the best. You can start the indulgence with the well-known lobster roll. Typically, the famous rolls are simply made with fresh chunks of lobster meat, melted butter (and/or mayonnaise) served on a top-split New England hot dog roll. If you don’t want the carbs, then just opt for a whole lobster tail on a plate. You don’t have to complicate things to make them delicious!

There are plenty of places to get your lobster fix. Luke’s is one of the favorites amongst the tourists, but many of the locals also swear by Bob’s Clam Hut or Porthole. Warning: you may just have to do a lot of research (lobster sampling) to find your favorite.

A peek at where Maine’s lobster comes from:

Pete the Lobsterman from GLP Films on Vimeo

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From lobster to museums to a booming craft beer scene, the city of Portland is packed with the best things to do and attractions to see. Be it on the water or on land, Maine’s hub is the perfect blend of the best activities.

Essential Tips for Visiting Portland, Maine

Getting There: Portland International Jetport is a major hub and most airlines will fly into it. You can easily check for the best fare deals at Skyscanner, which also has the option to choose ‘cheapest month’ as the departure to find the lowest priced dates to fly to your destination. From the airport to the city center, you can use the subway, private car, limousine, shuttle or take a taxi.

Where to Stay in Portland, Maine: It’s best to stay near the city center, public transportation or the area that you will be spending the most time in. AC Hotel by Marriott is a great choice in the Portland district. For something on the less expensive side, try Inn at St John located in Portland. For a hotel with a little more extravagance, book a room at the Blind Tiger Guest House. Or search some great deals on hotels of your choice at Booking.com. If you’re looking for more of a home atmosphere (or are traveling with a group of people), head over to Airbnb that has houses, apartments and even just a room for rent in every price range. 

Getting Around: Driving in a new destination can be a bit of a challenge, but if you choose to rent a car, RentalCars.com has great deals. If you are not renting a car, there are plenty of other options. Taxis, Lyft and Uber are available all over the city. For a more budget friendly option, you can take the public bus or metro/subway. The DiriGo Pass Card is an all-in-one transit card offering rides on multiple forms of transportation (metro, train, bus) for one fee.

Best Tours in Portland, Maine: You can find some of the top tours at Get Your Guide or Viator, and here are some of the top ones. tours:

• Portland: Old Port Culinary Walking Tour
• Portland, Maine: 2-Hour History Tour with Sweet Treat
• The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

Insurance: It’s always a good idea to travel fully insured so you are protected in case of trip cancellations or medical emergencies. You can check out pricing at Travelex Insurance.

This post may contain affiliate links. If you make a purchase through my links, I earn a commission that helps to keep this blog running—at no extra cost to you. For more information read my full disclosure.

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