The BEST things to do in Portland, Maine (+ a two day itinerary option!)

Portland, Maine is one of our favorite cities in the United States and in this guide we’re sharing the best things to do in Portland, Maine, plus a two day itinerary!

For our final stop on our big month long New England road trip we headed to Portland, Maine, which is a city we had been looking forward to visiting for so long. And it was basically love at first sight!

With a historic downtown area, gorgeous waterfront views, an amazing restaurant scene, and unique activities, Portland had a vibe that we meshed with so perfectly and during our few days in the city, we had the best time trying delicious local foods, wandering around town, and even catching lobster. It quickly became one of our favorite cities we have been to!

Check out our time in Portland, Maine, including exploring the city and going lobstering!

Ready to experience this beautiful city for yourself? In this guide we’re sharing the best things to do in Portland, Maine, as well as all of our insight from our visit to this city, including where to stay, when to visit, how to get around, and a two day Portland, Maine itinerary to help you prioritize your time. We hope you fall in love with Portland like we did!

Looking for more things to do in Maine and New England? 

Note: this guide contains affiliate links, which means that if you use the links provided and make a purchase, we get a small commission at no extra cost to you. We will only ever recommend products we truly love, actually use during our adventures, and think you can benefit from too!

About Portland, Maine

Portland is the largest city in the state of Maine, with 40% of Maine’s residents living in the general area. But despite this, it still retains a small city feel, with historic buildings and no giant skyscrapers (the tallest building will soon be an 18 story building). 

The city was established in 1786 and was originally the state capital of Maine, until Augusta took the title in 1832.

Because of its location on the water, Portland became a booming center of trade, as it was the closest U.S. port to Europe. The city continued to grow when the railroad came to Portland in 1832, even overcoming a fire that destroyed much of the city in 1866, but around the 1960s, the area now known as Old Port began to deteriorate.

Portland, Maine

In the 1980s, the waterfront experienced a rebirth and today the Old Port neighborhood is one of the best preserved east coast historic waterfronts and has maintained much of its historic charm from the 1800s, with brick sidewalks and ornate buildings. 

While the city itself is beautiful to look at, what we loved about Portland is that it has a little something for everyone. Whether you’re a fine dining foodie or prefer a good food truck (like us!), enjoy museums and art, love to walk around parks and experience history, or prefer to be out on the water, there is no shortage of things to do in Portland, Maine for any type of traveler.  

When to visit Portland, Maine

You can visit Portland, Maine year round, but your experience will vary depending on the season. Here’s a quick rundown of what to expect!

Winter

As you can imagine, winter is bitterly cold in Maine. The lows in December, January, and February are well below freezing, with highs barely above freezing. If you enjoy snow, there are lots of snow activities to partake in near the city, including skiing, plus some great coffee shops and bars to warm you up afterwards. 

Note: Some activities and restaurants close in the winter, so you may not get the true Portland experience, but you will be able to see the city in a way many tourists do not and have less crowds.

Spring

The spring time will still be pretty cold, so you’ll want to pack layers for your visit, as the warmer temperatures don’t really come around until May. But the springtime will bring less crowds and flowers in bloom, with many outdoor activities becoming more accessible again. 

Summer

Summer is the best time to visit if you want the perfect weather and most activity options. You’ll have temperatures that rarely go above 80 and the lowest chances of rain all year. However,  this pleasant weather does bring the summer vacation crowds, so you’ll want to book activities and lodging early. There are also quite a few fun festivals and events in the summertime to enjoy!

Old Port | Best things do to in Portland, Maine

Fall

If you’re looking for crisp, cool temperatures, fall foliage, slightly cheaper accommodations, and less crowds then fall is your season in Portland. We visited in the fall and LOVED it!

Our visit was during mid to late October, around peak fall foliage time, and we were treated to sunny, warmer days. We may have just gotten lucky though, as typically October and November are rainier months, so make sure to bring a rain jacket and some layers just in case!

Getting to + around Portland, Maine

Portland is located in the southern part of Maine and is close to other major cities in New England and out East, which makes it pretty easy to get to no matter your mode of transportation. 

Flying to Portland, Maine

The closest airport to fly into will be the Portland International Jetport, which is located very close to downtown Portland and is Maine’s largest airport. It is served by several major airlines including American Airlines, Delta, jetBlue, Southwest, and United. 

If the Portland airport doesn’t offer a good flight option for you, the Boston Logan International Airport (BOS) is about 2 hours away and is a massive airport that is serviced by all major airlines and offers nonstop flights from many destinations in the United States.

Portland Head Light | Best things to do in Portland, Maine

Driving to Portland, Maine

Driving to Portland instead? Here is how far the city is from nearby popular destinations:

  • Boston, MA: 2 hours (112 miles)
  • Providence, RI: 2.5 hours (163 miles)
  • Bar Harbor, ME: 3 hours (175 miles)
  • Burlington, VT: 4 hours (257 miles)
  • New York, NY: 5 hours (316 miles)
  • Montreal, Quebec, CA: 5.5 hours (277 miles)
  • Buffalo, NY: 8.5 hours (556 miles)

Note: These times are estimates based on no traffic, but plan to spend longer on the road. Also, some of the times above include driving tolls. If you want to avoid paying for tolls, make sure to turn off tolls on your Google Maps settings.

Getting around Portland, Maine

During our time in Portland, we did a combination of walking and driving to get around the city. 

The Old Port area is very walkable, but to get between neighborhoods and to explore some of the spots a bit out of town, you’ll either need to drive or rent a car, take a Lyft/Uber, or take public transportation

For Uber and Lyft, we’d highly recommend looking at their fare estimator tools (Uber, Lyft) to see how much you’d expect to spend when getting around town. While it would likely be affordable around town, it may get pricey to visit some of the spots outside of the downtown and main city area. We still think it would be cheaper than renting a car, but if you plan to explore more of Maine, having a car is worth it!

Old Port in Portland, Maine

Where to park in downtown Portland

Since we were staying in our van while visiting Portland and were sleeping outside of town, we had to drive into town any time we wanted to explore. And while we mostly explored by foot once in town, we still had to find parking for our van.

Our van is 22.5 feet long, so it’s longer than a normal vehicle, but we were able to find parking both times we drove into town. The first time was in the afternoon and we needed parking for about 5 hours, so we parked in this lot, which was $20 for all day parking. It was definitely pricier than street parking, but was a safe spot to leave the van.

The second day we arrived in town very early and parked here at a meter, which only cost a few dollars for a few hours. It was a great spot!

Note: RV parking (trailers or anything over 23 feet) is basically non-existent in the city, so if you have an RV, we suggest staying at a campground and either driving your vehicle or taking a Lyft around.

Where to Stay in Portland, Maine

To truly experience Portland, we suggest staying in the downtown area, where you can walk to coffee shops, restaurants, and bars, as well as the waterfront. Below are some of our top suggestions for Airbnbs (our preferred way to stay when not in our van!) and hotels, all convenient to the best things to do in this Portland guide.

Hotels 

Portland has almost any hotel chain you can think of right in the downtown/Old Port area. 

Airbnbs

Staying in an Airbnb would be a great way to experience the downtown/Old Port area of Portland like a local.

East End, Walk to the Old Port (1 bedroom, 1 bathroom): This Airbnb is located in the charming East End area, which has a more neighborhood feel than Old Port, but is still close by to enjoy all of the popular sights. It also includes parking, which is a big perk!

Bright & Spacious Apartment with Amazing Shower (1 bedroom, 1 bathroom): This bright and airy apartment is located on the western side of downtown, north of West End. It has all the amenities you’d need in an Airbnb stay including a washer and dryer and very nice bathroom and shower. 

Extraordinary Architectural Masterpiece Downtown (1 bedroom, 1 bathroom): This beautiful penthouse rental is located on top of the Old Port area. You have great views of the surrounding area through the big windows and can even enjoy them outside in your own private courtyard. It has a fully stocked kitchen with a gas range, but is also walking distance from many of the delicious restaurants we mention in this guide.

Quiet, Sunny 3 Br 2 Bath with Deck and Views (3 bedrooms, 2 bathrooms): This second floor rental can sleep up to 6, has beautiful bedrooms, and a deck with gorgeous views of the water, as well as a grill so you can cook and enjoy the outdoor space!

Camping

If you’re like us and traveling in a van or RV, here are some options close to Portland, but still a drive away. 

Bayley’s Camping Resort 
This campground is a 21 minute drive to Portland and has all the camping options you can think of. Along with loads of amenities, there is even live music on the weekends! 

Saco / Old Orchard Beach KOA Holiday
This KOA is also located about a 25 minute drive southwest of Portland and has all the camping amenities you’ll need.

Old Orchard Beach Campground
This campground has 4 main areas with 3 of them being for campers and RVers. Reviewers say it is very clean, the staff is very friendly and is in a great location.

Boondocking

There aren’t very many boondocking spots in Portland, in nature or even in a parking lot. If you’re in a pinch or are just in for one night, the Falmouth Walmart allows overnight parking and the Freeport Village Station is a quiet place as well. We stayed at both of these and had a safe, quiet experience. 

How much time do you need in Portland, Maine?

Portland Head Light | Best things to do in Portland, Maine

Portland, Maine is what we like to call a “liveable city.” This is a title we give cities we visit that we could see ourselves living in and when visiting, you may spend a lot of time doing things that you would do at home, like visiting parks, going out to eat, checking out coffee shops or bars, and shopping. They may have tourist attractions, but the town doesn’t necessarily revolve around tourist sights and for the most part the things you do are relatively normal activities. 

And what that means for us is that we could spend tons of time in these cities just hopping around to different restaurants, going for walks, and just enjoy “living” there. So while you could spend weeks in Portland just experiencing life like a local, for a tourist trying to visit the most popular sights, we suggest having 2-3 days.

This timeframe will give you the chance to experience some of the best activities, explore the downtown area, plus try a handful of good restaurants. We’re including a two day Portland, Maine itinerary at the end of this guide to help you plan your time in the city!

The Best Things to do in Portland, Maine 

Ready to explore the city? Below are some of the best things to do in Portland, Maine, based on our experience, as well as spots that were high on our list and highly recommended, but we ran out of time to visit. If you’re overwhelmed by all there is to do, we’re including a two day itinerary below as well!

Watch our time in Portland, Maine, including exploring the city and going lobstering!

Drink Local Coffee

Tandem Coffee Portland, Maine

The best way to start our day in a new city is with a local coffee shop! And lucky for us, Portland has no shortage of solid options. We LOVED Tandem Coffee Roasters while in Portland, which not only roasts their own coffee, but also makes breakfast biscuits that we hear are solid (arrive early to snag one). This coffee shop is located in a converted 1960s gas station and you know it’s good when locals are lined up before it even opens.

Some other good coffee shops to check out are Bard Coffee, Yordprom, Speckled Ax, Burundi Star Coffee, Coffee By Design, Higher Grounds, and The Proper Cup.

Walk around Old Port

One of the best things to do in Portland, Maine is to just walk around the Old Port area, which goes from Commercial Street along the water up a few blocks. This area of Portland is extremely walkable and has so much of the historic charm we mentioned earlier in the guide. 

While in Old Port you can check out the different shops and boutiques, enjoy the different restaurants (more on that next!), walk along the water, and maybe see fishermen loading and unloading their daily catch. You could spend a whole afternoon just in this area and likely not see it all!

Eat your way through the city!

Portland was named Bon Appetit’s 2018 Restaurant City of the Year and there is NO shortage of delicious restaurants to enjoy while in the city. In fact, where to eat will likely be the toughest decision you’ll have to make during your visit, as there are just so many incredible options.

Where we ate

During our visit we visited a couple spots that we highly recommend, plus a few that we were dying to try, but ran out of time for. 

First up on our Portland food adventure we went to The Holy Donut for their famous Maine potato donuts, which have a unique texture from a regular donut, but are so hearty and delicious. We got three donuts total, including a Chocolate Sea Salt (this flavor is their most popular), Pumpkin Head, and Maple Bacon, which was hands down our favorite. They also have gluten free and vegan donuts too!

We also ate at Bite Into Maine, which was said to have one of the best lobster rolls in town. We were torn between the Maine style, which is cold and is tossed in mayo and has chives on top, or the Connecticut style which is hot and has melted butter that they pour on top right in front of you.

The Connecticut style sounded better to us, but we were in Maine afterall, so we had to try both. And to our surprise, they were both equally delicious and we couldn’t really pick a favorite. Both had incredibly tender lobster meat and were served on a heavenly, toasted New England style hot dog bun. 

At the time of our visit, each roll (we got the 4.5 oz) was $26, which is pricey, but we had heard that lobster was more expensive in 2021 due to demand and that this was a pretty standard price. We typically do not spend that much on food, but it was more than worth it to try this decadent delicacy! 

We also got a homemade Whoopie Pie from Bite Into Maine, which is Maine’s official state treat. It’s two chocolate cake-like rounds with a creamy filling between them and is said to have been popular in Maine since 1925. It was delicious! And we washed it all down with the state fruit of Maine, but in soda form, Blueberry soda.

Other spots to check out

While we wish we could’ve eaten more in Maine, our time constraints and budget didn’t allow it, but there were some spots that came highly recommended to us that are high on our list for next time and we feel confident recommending.

Hifi Donuts for more traditional donuts, Standard Baking for delicious baked goods, Eventide Oyster Co. for oysters and other seafood, Duckfat for duck fat fries (they also have a frites shack in town), poutine, and sandwiches, The Highroller Lobster Co for lobster rolls and other lobster filled dishes, Terlingua for BBQ, and Hot Suppa for brunch.

There are obviously many more amazing local restaurants than this, but those are the spots that are pretty iconic to check out if it’s your first visit. 

Go on a food tour!

Can’t decide where to eat and want to experience a taste of many spots? Go on a food tour! Maine Day Adventures offers food tours in both the Old Port and East Side neighborhoods!

Go Lobstering! 

Lobstering in Portland, Maine

When you think of Maine, the top food item that comes to mind is likely lobster (or lobstahh!) and our absolute favorite thing we did in Portland, Maine was go lobstering with Lucky Catch Cruises!

On this lobstering tour you go to not only get out on the water and learn about how lobsters are caught, but you also get hands-on experience, from baiting and emptying traps, measuring lobsters, banding claws, learning the difference between males and females, and so much more. 

The crew really makes you feel like you’re a fisherman and puts you to work. It was one of the most fun and educational tours we have ever been on! (Watch our full experience here)

You can choose between different sailing locations and we did the Seal Watch tour, as it worked best with our schedule. We didn’t see any seals, but that didn’t matter, the views were still amazing and we were so focused and jazzed about catching lobsters! 

And at the end, you have the option to buy a lobster from the boat, which may be one that you just caught (don’t worry, they have extras from earlier cruises if you didn’t catch many, like our boat).

You buy this lobster at market price (ours was $10) and then can take it over to Portland Lobster Company, where they’ll steam it and provide some sides, like fries, corn, and coleslaw for only $12. While we definitely preferred our lobster in roll form, it was so fun to catch lobsters and eat one fresh right afterwards!

Tip: make sure to bring cash to buy a lobster AND for a tip!

Take a ferry to Peaks Island

Want to visit an island while in Portland? Take a ferry to Peaks Island, which is just a 17 minute ride away on the Casco Bay Ferry. While on the island you can walk around, kayak, rent bikes or a golf cart, and enjoy a couple public beaches. It’s a calm, relaxing getaway from the “big” city!

Visit the Portland Observatory

The Portland Observatory, which is located on the east side of town, is a historic maritime signal station and is the only one left in the United States! It was created in 1807 by order of Captain Lemuel Moody as a way to alert ship owners of their ships arriving, as you couldn’t see the ships entering the harbor until they were almost there. 

Moody charged a fee of $5 per year for ship owners to be alerted of their ships and used a telescope to identify vessels as far as 30 miles away. This maritime signal station ran until 1923, when two-way radios replaced its purpose. It has been renovated multiple times and is now open to the public to experience and costs $10 per adult for tours.

Unfortunately this spot was closed during our visit, but we would love to check it out next time!

Kayak to Fort Gorges

Portland, Maine

During our cruise with Lucky Catch Cruises, we went by this cool looking fort on an island on the Casco Bay called Fort Gorges. This fort was built in 1864 to protect Portland from foreign naval powers, but by the time it was completed, new technologies for artillery had emerged and it was already obsolete. It ended up being a storage facility in both World Wars and was then given to the city of Portland.

The only way to access this fort is by boat or kayak, which limits how many people actually get to experience it. If you don’t have your own method to get out there, we suggest going on a tour with Portland Paddle, who will ensure you cross the Casco Bay safely and take you all around the fort.

It is worth noting that the fort isn’t maintained very well, so it provides a very dark, rustic experience, which in our opinion, only makes it more fun and authentic to check out! 

Explore Fort Williams Park & the Portland Head Light

Another huge highlight for us in Portland was Fort Williams Park, which is a free park that was formerly a military fort. Construction of the fort began in 1873 and the fort became officially named Fort Williams in 1899. During World War 1 the fort was manned by artillery companies and National Guard troops and during WWII it served as the headquarters of the Harbor Defenses of Portland, before becoming more of a training site in 1951.

Today there are a couple batteries to check out, an old mansion, and one of the most iconic lighthouses in the US, called the Portland Head Light. This lighthouse was the first lighthouse completed and put into service by the government under the Lighthouse Act of 1789. 

Portland Head Light | Best things to do in Portland, Maine

It was first lit in 1791, using 16 whale oil lamps. The tower and keeper’s quarters have changed a bit over time and the tower now stands at 80 ft tall. And it is said to be the most photographed lighthouse in America, and also the oldest in Maine.

Tip: If you want to check out more lighthouses, Bug Light and the Spring Point Ledge Lighthouse are close by too!

Another perk of Fort Williams Park is that Bite Into Maine is located here, so you can enjoy history, views, and lobster rolls all in one spot!

Walk the Eastern Promenade

Located on the East Side of town is the Eastern Promenade, which is Portland’s largest developed park. Here you can walk the 2 mile trail that goes along the Casco Bay waterfront, hang out at a beach, and just soak up the views. If you’re looking for a nice, scenic stroll, this is a great stop!

Visit the Victoria Mansion

For architecture lovers, check out the Victoria Mansion, also known as the Morse-Libby House. This home is a perfect example of a 19th century Italian Villa style home, with a gorgeous exterior and interior to explore, with 90% of the interior being original. It was built as a summer home for Ruggles Sylvester Morse and his wife and completed in 1860. Once Ruggles died, his wife Olive sold the home to J.R. Libby, who kept it in almost the exact same condition and lived in the home until 1929. 

The house has been a public museum since 1941 and costs $16 per adult, with different rates for seniors, children, students, and families.

Go Brewery Hopping

Photo by Alice Donovan Rouse on Unsplash

Portland is home to an amazing craft brewery scene and while we don’t drink, if you do, you’ll be in beer heaven! Here are some top breweries in town:

If you want a safe way to check out multiple breweries around town and not worry about driving, go on a brewery tour with Maine Brews Cruise!

Check out the Portland Arts District & Museums

Portland is home to an arts district, which is located around Congress and High Streets and was created in 1995 to be the cultural and creative hub of the city, with different galleries. 

The Portland Museum of Art is the most popular attraction in this area and focuses on a mission called “Art for All,” which was created to ensure the museum is diverse, inclusive, and accessible for all. There are changing exhibits, as well as permanent collections to explore while in the museum. It costs $18 per adult (22 and up), $15 for seniors and students over 22 years old, and is FREE for anyone 21 or under.

If you visit the Arts District on the first Friday of the month you can take part in the First Friday Art Walk. During this event, all of the art institutions in the Arts District open their doors for free from 5 PM to 8 PM.

Two Day Portland Itinerary

Now that you know of some of the best things to do in Portland, Maine, here is our suggestion of how to combine some of these activities into two epic days in the city! While you won’t be able to see and eat it all in two days, these are our top suggestions to ensure you experience the best of Portland.

Day 1

  1. Grab coffee at Tandem Coffee Roasters and then donuts at The Holy Donut.
  2. Spend the morning and afternoon doing one or a combination of these activities:
    • Lobstering cruise with Lucky Catch Cruises (our TOP PICK!) and then enjoy steamed lobster at Portland Lobster Co.
    • Kayak to Fort Gorges 
    • Take a ferry to Peaks Island
    • Go on a food or brewery tour
    • Visit the Portland Art Museum or Victoria Mansion.
  3. Enjoy the rest of the day by walking around the Old Port area, going into different shops.
  4. For dinner, head to Eventide. We suggest trying to make a reservation in advance!

Day 2

  1. Start the day with breakfast at Hot Suppa or grab a pastry at Standard Baking. 
  2. Head to Fort Williams Park for the morning and afternoon. Explore the bunkers, outside of the mansion, and the Portland Head Light!
  3. Have lobster rolls and whoopie pies at Bite Into Maine.
  4. Spend the rest of the day doing any activities from day one that you didn’t have time for, or go up in the Portland Observatory and walk around the Eastern Promenade.
  5. Enjoy your final meal at Duckfat or Terlingua.

Ready to explore Portland, Maine?

Pin this guide with the best things to do in Portland, Maine to help plan your trip!

about us

Hi y’all! We’re Adam, Kathryn, and Kona, an adventurous married couple (+ pup!) living on the road in our self-converted sprinter van! You can often find us driving all around the US and Canada, scoping out the best coffee shops, eating tacos and ice cream (we’re a 5+ taco and 2+ scoop household), and enjoying nature.

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