Lobster rolls, fresh seafood and craft beer are for me the perfect ingredients for an ideal weekend getaway. For the past few years, Portland has paved its way to being a key player in the food and beer scene. And believe me, it will live up to your expectations. The city is perfect for a short weekend getaway of 2 or 3 days. So get ready to pack your bags and travel to Maine! Here is your Portland Maine itinerary.

Get ready to explore the seacoast and try some New England cuisine on this Portland itinerary. It doesn't take long to fall for the city and the New England city vibe. Portland will seduce you with its old red brick architectural buildings, cobblestone streets and the sea breeze along the harbour.

A little about Portland, Maine

Native Americans originally called the Portland peninsula Machigonne ("Great Neck"). The first European settler arrived in 1623 to found a settlement in Casco Bay. In 1820, Maine was established as a state with Portland as its capital. In 1832, the capital was moved north and east to Augusta, where it is now. 

Portland is a port city and the most populous city in the state of Maine. The city’s economy is historically tied to commercial shipping and the marine economy. Despite the economic shift towards the service economy, the Port of Portland is still the second-largest tonnage seaport in New England.

Things to do in Portland Maine

Old Port District

I would suggest starting your visit in the Old Port District as it is the most picturesque area overlooking the Fore River. This area is full of fishing piers with lots of action with all the boats leaving and arriving with their freshly caught fish and shells. This area of the city is listed on the National Register of Historic Places. Most of the boutiques, shops and cafes are located on the cobblestone Commercial Street. This street has a lot of independent stores so you don’t get to see the same redundant chain stores which add to the charm of the district. The street also has two of the oldest structures in Portland, Widgery Wharf and Union Wharf.

Arts District & museums

This is the artsy part of town. The Arts District is centred on Congress Street and is home to several art establishments. It hosts the Portland Museum of Art, Portland Stage Company, Maine Historical Society & Museum, Portland Public Library, Maine College of Art, SPACE Gallery, Children's Museum of Maine, Merrill Auditorium, the Kotzschmar Memorial Organ, and Portland Symphony Orchestra, as well as many smaller art galleries and studios.

The most important museum on the list is the Portland Museum of Art at Congress Square. It has interesting works of art from the American and European continents as well as some contemporary art pieces. The museum has 22,000 artworks dating from the 18th century to the present.

If you are an art lover, you can plan your trip to fit the first Friday of the month to take part in the First Friday Art Walk. This is a self-guided tour through the different galleries of the Arts District with music, dance and theatre.

Parks 

The city has several parks to visit. Baxter Boulevard around Back Cove, Deering Oaks Park, the Eastern Promenade, Western Promenade, Lincoln Park and Riverton Park are all historical parks within the city. Baxter Boulevard Parkway was designed by the firm Olmsted and Eliot in 1895. The same firm attributed to multiple parks in North America like the Central Park in NY and the Mount Royal in Montreal. Baxter Boulevard was listed on the National Register of Historic Places as a historic landscape district.

To have the best views of the water, you should head to the Eastern Promenade. In this historic public park, you can see the city harbour and Casco Bay. This is the perfect place for a walk, a picnic and relaxing by the water. 

East End Beach

A must-stop should be a stroll around East End Beach. Even though it wasn’t summer and the day was foggy, I always liked to walk in the sand and enjoy the salty ocean air. This only public beach in the city and it is a mix of sand and pebble-covered beach. You can have great views of Casco Bay and the nearby islands from here. In the summer, you can rent kayaks. You can continue wandering through Eastern Promenade and Munjoy Hill.

Portland Head Light 

In your Portland itinerary, you need to make sure to see the landmark of the city, the iconic Lighthouse, Portland Head Light in Fort Williams Park. The shores cut sharply to the cliffs and the rocky sea looked very dramatic with the dense fog (we had a very foggy day during our visit). The Portland Head Lighthouse is located within Fort Williams Park. The military fort was operational from the 1800s until the mid-1960s. After exploring the lighthouse, you can check out the old batteries nearby.

Victoria Mansion

If you like historical mansions, then you should head to the stunning, Italianate palace from the 1860s. This was the Summer home for hotelier Ruggles Sylvester Morse, the opulent decor shows the way of living of the 1% of the time. The interior has elaborate frescoes and furniture of the bygone era. 

Peaks Island & Casco Bay Islands

Taking a Ferry to explore the nearby islands is a must-do in the Summer. The Peaks Island is the most popular with its beaches, nature, history, and laid-back living, but you can also explore Little Diamond Island, Great Diamond Island, Long Island, Cliff Island, Chebeague Island, and Bailey Island to name a few.  Peaks Island is only 20-min away from Portland.

The Casco Bay Lines ferry terminal is conveniently located in the middle of the Old Port area and has a regular schedule. The islands will offer beautiful views of the ocean and you can visit restaurants, cafes and boutiques. This can be a good half a day trip.

Sadly, I did not get a chance to visit them since we went in spring and the fog was intense and we thought it wasn't worth it. 

Portland Observatory & Munjoy Hill

The observatory is the only maritime signal tower still standing in the United States. The tower was built in 1807, by Captain Lemuel Moody, atop Munjoy Hill. At the time, the ships entering the harbour could not be seen from the docks of Portland so the merchants didn't know when the boats were going to arrive. With this tower and its telescope, the merchants could be notified and improve the harbour's efficiency. Now the observatory is a museum about the history of Portland, the maritime industry, and the octagon-shaped building. The views of the city are worth the visit. The tower is closed in the winter.

Munjoy Hill is the classic tragic story of a gentrified neighbourhood once working class now filled with art galleries, funky boutiques, and top of their game restaurants.

Portland Freedom Trail 

This is a free and self-guided tour through the Portland Freedom Trail. There are 13 stos highlighting the 19th-century Black Mainers who fought to end slavery. The places are around the Underground Railroad which was used to move slaves into Maine and then to Canada. The stops are varied, from the wharf to churches to private homes and businesses. 

Portland Farmers' Market

Support local producers by buying cheese, honey, fruits and more, The market is open twice a week in the Summer and Fall. On Saturdays, the market is located at the Deering Oaks Park location, and on Wednesdays, you will find it at Monument Square. The frequency in the Winter months is only once a week, on Saturdays on Stevens Avenue.

Festivals 

If festivals are your thing, then the city also has a few for you! Please note that a visit during this time might mean that your accommodation is more expensive. 

• Festival of Nations, is a one-day festival featuring family-oriented cultural activities to celebrate Maine’s ethnic diversity and traditions. It usually takes place in July in the Deering Oaks Park.

• Harvest on the Harbor, a multi-day festival takes place in October and highlights the state distillers, brewers, oyster farmers, and other members of the food hospitality. 

• Maine Brewers Festival. This is self-explanatory, it celebrates the state’s numerous beers and breweries. This event is held multiple times a year.

• Maine VegFest, highlights vegan food and takes place in October.

• Maine Restaurant Week is a beloved festival that takes place every March. The participating restaurants have special offers, menus, and different events. This is one of the most anticipated annual events and ad more than 50 restaurants participating.  

• Maine Seaweed Week takes place in the spring and highlights Maine seaweed at businesses across the state. If you were wondering what seaweed ice cream tastes like, this is your opportunity. 

Lighthouses

Besides the Portland Head Light, there are other lighthouses a few minutes away from each other. If you are like me and find that the lighthouses are photogenic and mysterious then take the car and head to these stops. You can also visit during the Maine Open Lighthouse Day to learn more about them. This event is in September. Maine Lighthouse Bike Tour or take one of the cruise options like the Harbor Lights and Sights Cruise.

Portland Breakwater Lighthouse (Bug Light) is small in size and was built in 1855.  It is the only lighthouse in the world shaped like a 4th-century Greek monument.

Spring Point Ledge Lighthouse is worth visiting because you can see the views of the Portland skyline from across the water. It is very close to the Bug Light.

Two Lights State Park -  This park has ocean and forest trails. If you are going in the summer, you can go to the nearby sandy beach of Crescent Beach State Park.

The food & beer scene in Portland, Maine

Due to my professed love for lobster rolls, I was on a mission to eat as many lobster rolls as I could during our 3-day trip. There is something about the combination of the sugary bread that goes perfectly with the lobster. The dish is so simple yet so delicious.

To top the immense variety of lobster rolls, Maine is the home of great craft beers. Indeed, you can enjoy and visit more than 50 breweries throughout the state. This was a jackpot for me, Lobster roll + Craft beer = Happy belly!

Joke aside, to my big surprise, the food and beer scene is delicious and vibrant. The lobster rolls are amazing and each restaurant added its own personal touch. Most of the places use local ingredients as you can taste the freshness of every bite. 

These culinary discoveries will make the visit to the city worth the road trip! In 2018, the famous Bon Appetit publication was named Portland Restaurant City of the Year!

There are places we did not get a chance to eat during our visit but that are highly popular, Holy Donut “Maine potato donuts” and Duck Fat, duck fat baked fries. I guess we will just have to go back another time. Or go to the Maine Brews cruise and visit the Allagash Brewing Company.

OUR PERSONAL RECOMMENDATIONS

Eventide Oyster Co. I will highly recommend it to everyone! The seafood selection lives up to the expectations of a port city, if you are an oyster fan, this is the place to go. Plus the lobster rolls are in steamed buns and the sauce comes with a twist, mayo, and brown butter vinaigrette or hollandaise. It was just delicious! The New England traditional food is served with a modern flair against a beautiful setting with bright colours and picnic tables.

Go to Gilbert Restaurant and Portland Lobster Company for classic but delicious clam chowder, seafood cakes and of course lobster rolls. All their seafood is fresh out of the sea. Gilbert Restaurant has been open for the last 28 years and offers an award for winning chowders. As for, the Portland Lobster Company, their Lobster Roll was voted Best of Portland 2021.

Liquid Riot Bottling Company, located at the waterfront deck, this place is a brewery, distillery and restaurant bar that will give you plenty of choices for your palate drink and food. Try their signature cocktails with their own spirits.

Sebago Breweries has five locations throughout the state. Let their IPA delight you. Plus, you can enjoy their beers outside on their outdoor patios.

Maine Beer Company where every beer has its personal story written on the bottle. They are part of the 1% for the Planet Program which I think is pretty cool! This brewery is not technically in Portland but it's only a few miles away and is worth the detour.

Rising Tide is a tasty family-owned brewery in the East Bayside neighbourhood. The brewery supports farmers by using local ingredients. Plus, you can enjoy their beers along with their shareable bites and sausage sandwiches.

Maine Spirits. Their motto “A Farm to Flask Distillery” will impress you with their products. Maine being the largest producer of blueberry in the U.S., we tasted and loved the BLUESHINE, a blueberry moonshine. The shine goes perfectly with cocktails as we discovered back home.

The perfect Portland Maine itinerary for your weekend

Is 2 to 3 days enough to visit Portland? The answer is YES! I thought that this was the perfect amount of time. It is small enough for you to unwind and take your time to enjoy your vacation, you are not running from one place to the other to hit all of the main attractions. The city has enough delicious restaurants for more than a week and enough things to do in and around the city. Here is your itinerary for your 3-day weekend.

DAY 1

Arrive at your hotel and hit the streets. Here, you can walk downtown and do some shopping around Commercial Street. Then head to the Old Port area for the more historical side of the city which blends nicely with the working waterfront where you get to see the fishing boats arrive with the fresh fish.

Go for a beer at one of the city's many breweries and then book a night at a fancy restaurant like Eventide Oyster Co.

DAY 2

Have some brunch or breakfast and go South Portland and more specifically to the Portland Head Light which is around a 20-minute drive. Here you can choose to hang out at the beach hit another beach along the way or visit the other lighthouses in the area. In fact, there are 5 lighthouses within a reasonable driving distance from the city. If you have been following me for a while, you know that I love lighthouses!  The good thing about taking this day trip is that you can go to beaches along the coast or go to some museums along the way.

Another suggestion, if the weather allows it, go do a boat tour of the Casco Bay islands.

Whether you decide to go, be sure to have fresh Maine lobster for lunch.

DAY 3

You can do a food or brewery tour or decide to do other sea-related activities like visiting another island. In your itinerary, be sure to spend some time at the Eastern Promenade which is a coastal trail with a 68-acre historic landscape that offers great views of Casco Bay and Portland Harbor. This is the perfect place to do a picnic or watch the sunrise if you are an early bird.

Or just enjoy your time in the city and go see the museum or to the Portland observatory. The latter was built in 1807 and it is the only known surviving tower of its type in the United States. If you enjoy history, then you would like to dive deeper into the Maine Historical Society museum.

Beautiful discoveries in New Hampshire

On our way back to Montreal, we decided to spend the night in New Hampshire to make the drive more enjoyable. Sadly, New Hampshire looked very shaken by the economic crisis, with lots of trailer parks and closed stores. 

We rented a cabin which I must admit was a bit creepy as it was on the mountainside/ backyard of a house. It looked like the perfect setting for the next horror movie. After "enjoying" the night in The Cabin in the Woods, we hit the road and drove through The White National Forest. The road is beautiful as it zigzags through the Appalaches. 

The panorama was astonishing. Cutting through the mountains, you will drive by lakes, rivers, and dense forests, to name a few. Along the way, we stopped several times at observation points, hiking to explore the area. Note that the National Park offers different activities such as skiing, hiking, and camping throughout the seasons.

This was definitely one of the highlights of the trip!

Practical Information

GETTING AROUND

Portland is a fairly small city, you can do most of the activities walking around. However, I would suggest taking a car to visit the Portland Head Light and making other stops along the way. If you feel adventurous, you can also visit the other lighthouses nearby, they are around another 20-minute drive from the headlight.

WHEN TO GO?

Portland, Maine is located on the coast and gets a lot of humidity from the ocean. The Summers can be hot and the Winters are cold and snowy. I would suggest visiting during the Summer since much of the sea activities are at their peak. It is only in the summer when you can go to the beach and swim! However, Portland attracts a big crowd so be prepared to see lots of tourists and see the prices of your hotel go up. We visited in Spring and we did not have great weather and springs are always a little unpredictable. However, we enjoyed our visit and I liked seeing the trees in full blossom. In winter, while you can do a lot of activities, many establishments have reduced hours or closed during the winter. If you love leaf-peeping, the area is known for its Fall colours so it can also be perfect timing to visit.

GETTING IN AND OUT

Portland is fairly central to other big cities on the Northern East Coast. The city is a 5h 30 min drive from Montreal and New York, a 2h drive from Boston.

The city also has an international airport, Portland International Jetport but keep in mind that you might need to make a connection if you are coming from afar.

You can also easily take the Amtrak or a bus.

EXTENDING YOUR VISIT

Maine is a beautiful state full of beaches, sea activities and rug coastlines. I have been dying to visit the Acadia National Park. This can be a perfect day trip addition. Or you can take the ferry and head to one of the many islands to explore.

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