The Best Things to Do in Portland, Maine for First-Timers

The city of Portland in Maine is a vibe.

Picture it.  It’s a sunny fall day. After strolling the cobblestone streets in the Old Port, you relax at a waterside pub on a fishing pier (truly one of the best things to do in Portland, Maine).  Beverage in hand, you watch boats come and go as their reflections play on the water.  Live music starts up.  Life is good.  That’s the feeling I had in Portland.

I visited Portland as part of small group tour of coastal Maine with Collette Tours.  With the help of Collette’s expert guide, I explored Portland’s best attractions and a few hidden gems.

If you’re wondering what to do in Portland, Maine on your first visit, read on.

And, here’s a hint, your inner foodie is going to love this city.

Quick facts about Portland, Maine:

What is Portland, Maine known for?  Lots of things, actually.

Located on the southern coast, it’s the biggest city in Maine.  It’s been destroyed four times by things like war and a fire caused by an errant July 4th firecracker.

Portland is known for a delicious food scene (yes, lobster), active waterfront and walkable downtown.

And it’s the birthplace of poet Henry Wadsworth Longfellow and author Stephen King.

So, it’s an eclectic mix.

Getting to Portland, Maine:

You can fly, drive or take the train to Portland.

The Portland International Jetport (their word for airport) is less than 10 minutes by taxi to the historical district (I paid $20).  The city’s route #5 bus takes around half an hour and the adult fare is $2.  (Pay exact cash if you don’t plan to buy a pass, which you probably don’t need).

Best time to visit Portland, Maine:

The most popular time to visit is June, July and August.  This is when the weather is warmest, but also when things get busy.

I prefer the shoulder season of September and October because it’s quieter and the fall colours are gorgeous.

How many days do I need in Portland, Maine?

You can see the most popular attractions in two to three days.  A long weekend in Portland, Maine would be perfect. Stay longer if you want to explore outside the city.

About Collette Tours

Collette is a family-owned company that’s been organizing tours for over 100 years.  Its small group, explorations tours are designed to dive deeper into a destination.

I spent two days in Portland on the Roaming Coastal Maine tour.  A good chunk of that was free time to explore on our own, with a list of helpful suggestions from our guide.  The easygoing tour included local experiences, like lobster fishing, and visits to Bar Harbor, Acadia National Park, Camden, Freeport and the Coastal Maine Botanical Gardens.

Things to do in Portland Maine:

Soak in the vibe on the waterfront in the Old Port

What is the “Old Port”?  It’s a district of the city that includes the fishing piers, cobblestone streets and 19th-century brick buildings.  You’ll find many artisanal shops, restaurants and bars here.

The fishing port is a real working port.  It has all the classics from stacks of lobster traps to fishing nets and seagulls.  My favourite thing to do in Portland was to wander up and down the fishing piers and breathe in the salty air.

There are quite a few waterside pubs and restaurants to choose from here.   I liked the live music at The Porthole seafood restaurant on the Custom House Wharf.    I also enjoyed a tasty wood-fired oven pizza with a handcrafted Maine root beer at the Flatbread Company.

Wander the prettiest streets in the Old Port

As you move away from the waterfront, you’ll come across the cobblestone streets in the Old Port.

You’ll probably feel like you’re stepping back in time on Wharf Street – – one of the must-sees in Portland, Maine.  The street has been developed more recently as a pedestrian-only hub for bars and restaurants.

One of the most popular spots on the street is the upscale, seafood restaurant Street and Company (make a reservation).  It’s considered one of the best restaurants in Portland, Maine.   Anthony Bourdain reportedly enjoyed steamed clams, mussels and oysters there.

Be sure to explore Commercial (parallel to the waterfront), Fore and Exchange streets in Portland.  These streets are prime real estate for cute shops, bars, restaurants and bakeries.

Exchange Street was my favourite in the area.  I came across a Dixieland band and what seemed like an ongoing street party.

I also found this Longfellow poem on a wall of a lane way off Exchange Street, just opposite to Milk Street.

Portland, Maine shopping – Old Port

Browsing in the boutique shops is among the popular activities in Portland, Maine.

I’ll admit that I’m not a big shopper, but I couldn’t resist a look inside these charming stores:

• Sea Bags  This Maine company makes tote bags out of boat sails.  The totes are cute, but pricey. The flagship store is at 123 Commercial Street and there’s a factory outlet at 25 Custom House Wharf.

• Lisa-Marie’s Made in Maine showcases the work of the state’s finest artisans. (Think chocolate-covered blueberries)  It’s at 35 Exchange Street.

• Sherman’s Maine Coast Book Shop at 49 Exchange Street.  It’s billed as Maine’s oldest bookstore.

• Bliss Boutique at 42 Exchange Street.  Great name, don’t you think?  The store sells unique, high quality women’s clothes.

Take a Portland trolley tour

A trolley tour is a great way to cover the must-sees in Portland, Maine and its storied history.

Collette arranged a tour for us with Portland Discovery Tours.  Our guide, Wendy regaled us with entertaining tales of her home town and even shared her restaurant recommendations.

The tour lasts 105 minutes, and it runs from April 27 to October 27.

See the famous Portland Head Light

The Portland Head Light is an absolute must-do in Portland, Maine.  It’s the most photographed lighthouse in America and the oldest in Maine (completed in 1791.)

The lighthouse sits on dramatic rocky shores, marking the entrance to Portland Harbor at Casco Bay.  I could watch the waves crash onshore for hours.

It’s located in a 90-acre park in Cape Elizabeth known as Fort Williams Park.

Climb to the top of the Portland Observatory

The Portland Observatory is the only remaining maritime signal station in the U.S.

Wendy explained that, from the top, the station keeper could see 26 miles into the harbour and would raise a flag to let the ship captain know where to dock.   Another flag would let the owner know his ship was coming in.

The Observatory, at 138 Congress Street,  is open for tours during high season from from 10 a.m. to 3:30 p.m.  Tours run every half an hour.  It’s 104 steps to the top of the Observatory.  Unfortunately, I missed this view as this didn’t fit into my two-day Portland, Maine itinerary.

Visit Victoria Mansion

A historic landmark, the Victoria Mansion is one of the top things to see in Portland, Maine.

It was built as a summer home around 1860 in the “Italian villa” style.  To this day, you can see the original wall paintings by an Italian artist.  Many are done in the trompe l’oeil style and make the walls look three-dimensional.

The museum, at 109 Danforth Street, is open from May 1 to October 31st.  It’s best to reserve tickets in advance.

Walk the Portland Freedom Trail

Did you know that Portland was one of the last stops in the U.S. on the Underground Railroad?

On a private historical tour arranged by Collette, we learned about the Portland Freedom Trail.  The trail includes safe houses and a meeting house where local African Americans worked to move former slaves to freedom in Canada.

The trail runs through downtown Portland for about two miles.  You’ll see markers along the trail, like this one at 47 India Street.

Portland Museums

Wondering what to see in Portland, Maine on a rainy day?

Although I didn’t have enough time (and the weather was gorgeous),  I was interested in a couple of the ones suggested by our Collette guide:

• The Portland Museum of Art at 7 Congress Square has an impressive collection of art dating from the 18th century.

• The Wadsworth-Longfellow House at 489 Congress Street.  All of the artifacts in the house are original to the time when Henry Wadsworth-Longfellow grew up there.

Enjoy a stroll along the Eastern Promenade

The Eastern Promenade Trail is a 2-mile walk that starts downtown and runs along the harbour.   It leads to the East End Beach and 68 acres of parkland.

While I’m not suggesting you go there at night, I couldn’t resist a shot of the fancy yachts in the harbour that you’ll see near the start of the trail downtown.

Take a ferry to Peaks Island

When the weather is good, it’s fun to take the ferry from Portland to Peaks Island.  The island has a small-town feel and fantastic ocean views.

When you arrive, head up the hill to Peaks Cafe for its famous cinnamon buns.  And, after exploring, the wood-fired oven pizza at Il Leone is a must.

You can catch the ferry like I did at the Casco Bay Lines Bay terminal at 56 Commercial Street.  It takes just under 20 minutes to get to the island.

Go sailing on a schooner

One of the most popular attractions in Portland, Maine is to go sailing on a famous schooner tall ship.  Breathe in the salty air on this two-hour cruise from Portland around Casco Bay.  Book your sailing experience here.

Where to eat in Portland, Maine

You may need extra time in Portland, Maine just to try more of its restaurants.  This is a thriving foodie scene. In fact, Portland was once called the restaurant city of the year by Bon Appetit.

Of course, there was lobster!  It was served on our first night at a delicious, privately catered dinner organized by Collette Tours.

On the second night, I couldn’t resist trying the fries at Duckfat at 43 Middle Street.  (Yes, it’s a meal!)  This cozy restaurant serves Belgian-style fries, fried twice in duck fat.  There are five dipping sauces to choose from.  I recommend the truffle ketchup.  I think these are the best fries I’ve ever had.    The restaurant doesn’t take reservations, so if you can’t get in, head over to the Duckfat Frites Shack at 43 Washington Avenue (open Thurs – Sunday).

Another iconic snack to try in Portland, Maine is a donut from the Holy Donut at 177 Commercial Street.   These donuts are made from Maine potatoes, which makes them healthier and heartier than your average donut.  I enjoyed a tasty apple cider donut.  People were lining up for these donuts when I was there.  Go early, because the shop closes once they sell out.

A few other restaurants that were recommended by locals:

• Luke’s Lobster, 60 Portland Pier
• Eventide Oyster Co at 86 Middle Street
• Central Provisions 414 Fore Street (small plates)

You should also know that Portland has a reputation for its craft brewery scene.  Check out this list of breweries to visit or consider a brewery and pub walking tour in the Old Port.

Where to stay in Portland, Maine

Collette Tours carefully selects its accommodations for comfort and to highlight the local experience.

I enjoyed my stay at the AC Hotel by Mariott Portland Waterfront.  As the name implies, it’s right across the street from the harbour, one of the best places to stay in Portland, Maine.  The room was spotless and comfortable, with a lovely rainshower.

This year, tour guests will stay at the Hyatt Place, Portland, Old Port, which is a little closer to downtown.

Plan your trip to Portland, Maine with Collette

I hope these tips help you make the most of your time in Portland, Maine.

The Roaming Coastal Maine tour made planning a breeze.  And, most importantly, I’ll always remember the special, local experiences organized by Collette that gave me a true feel for life on the coast of Maine.

Map of Portland, Maine highlights:

Click on the blue markers to see locations for Portland, Maine attractions.

 

I was a guest of Collette Tours on this trip, but my opinions are entirely my own.

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