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One of my favorite places to visit in Maine is Portland. This small yet charming city has so many amazing things to do. Not only is it a foodie destination, but it’s also a hot spot for lobster rolls, high-end cocktail bars, and so much more. As somebody who visits the coastal city at least once a month, here are my choices for the best things to do in Portland, Maine.

The Best Things To Do In Portland, Maine

1. Try A Lobster Roll (Or 3)

One of my favorite things to do in Maine is eat as many lobster rolls as I can in one weekend.

It’s true, you can even check out my Local’s Guide To The Best Lobster Rolls In Maine.

Portland has so many options when it comes to Lobster Rolls!

Eat a fresh mini roll at The Highroller Lobster Co., which is open year-round.

You should also try the white truffle lobster roll at Luke’s Lobsters, which is located right on the pier.

I love this spot because you can enjoy the relaxing water views while chowing down.

2. Ferry to the Casco Bay Islands

Maine has over 4,600 islands, and the Casco Bay Islands are just a short ferry ride away from Portland.

It is easy to take a day trip on the Casco Bay Ferry since the terminal is right in the middle of the city.

The ferry tickets are also really cheap, about $7 each way. You can review the rates and schedule here.

But please note that you can only purchase tickets at the terminal, not online.

I recommend taking a day trip to Diamond Cove to grab some dinner and drinks.

You can also visit Peak’s Island, but I will get to that in a bit.

Interested in visiting Diamond Cove? Diamond Cove: Your Guide To The Ultimate Maine Day Trip.

3. Sip Creative Cocktails

In addition to amazing food, Portland is also home to some of Maine’s best cocktails.

My favorite cocktail bar is Blyth and Burrows, located in the heart of Old Port.

Everything about Blyth & Burrows is impressive, from its vintage-inspired style to its dimly lit rooms.

They also have a speakeasy hidden away from downtown Portland’s chaos. Whichever area you choose, you will not be disappointed.

Make sure to try some of their tasty food. I tried the Brandade Toast, sourdough bread, Smoked Haddock, Creamy Potatoes, XO Crumble, Pickled Husk Cherries, and Herbs.

Their entire menu is so delicious. Don’t leave without trying the Duck deviled eggs either!

There are so many amazing cocktail bars in Portland, Maine!

If you want to check out more cocktail bars in Maine, read my guide. The Best Cocktail Bars In Maine: A Local’s Guide!

4. Stroll Through Old Port

If you love shopping you should walk through Old Port along Commercial Street.

The Old Port District is known for its cobblestone streets, boutiques, and eateries.

Visit the local boutiques, selling Maine-themed decor, and wine and cheese shops.

I love strolling down the street in the summer, people-watching while enjoying an ice cream.

Winter is just as charming; the streets are quieter, but businesses are open all year round.

5. Brewery Hop

Portland, Maine, has over twenty breweries, and they all have their own vibe.

My absolute favorite is Shipyard Brewing, where I sip on Pumpkinhead every fall!

In the summer, I like to visit all of the breweries in the northern part of the city.

Some of my favorites are:

• Rising Tide
• Belleflower Brewing
• Austin Street Brewing
• Orange Bike (They offer Gluten Free beer)
• Root Wild (Hard Komubcha)

Don’t forget to check out the local food trucks, which are often set up at almost all of these breweries.

Here is a delicious fried chicken sandwich I got at Black Salt.

6. Enjoy The Eastern Promenade

The Eastern Promenade in Portland sits along Casco Bay and is a great place for running tennis, and bike riding.

I love biking along the Eastern Promenade, which offers stunning water views all around.

This area is also a popular spot for laying out a blanket and watching the sunset over the water.

In the summer, you’ll find a variety of food trucks here, so be sure to sit back, relax, and enjoy the scenery.

7. Attend Reggae Sunday On Peaks Island

Like I said, I love island hopping from Portland! But did you know one of the best islands to visit is Peaks Island on Sunday?

In the summer the island is home to Reggae Sunday.

Enjoy live performances from local and visiting reggae bands.

Make sure to try the Rum Punch! You can enjoy the lawn outside, pack a blanket to lie out on!

8. Try One of Portland’s Restaurants

There is no way around it, the best thing to do in Portland, Maine, is to eat!

One of my favorite restaurants in Portland is Via Vecchia. They offer a small plate Italian-inspired dining experience.

Located in the heart of the Old Port in an iconic brick and ivy-covered building overlooking cobblestone streets.

The menu features a variety of pasta, fresh seafood, and handcrafted cocktails.

I was lucky enough to visit them for The Feast Of The Seven Fishes last December! It was a bucket list item for me, if you have the chance to do it next year, go!

9. Visit Thompson’s Point

On the west side of Portland is Thompson Point!

You an come here all summer long to attend concerts and festivals.

In the winter you can go ice skating as they turn the grounds into a rink.

Make sure to stop by Bissell Brothers Brewery which has tasty beer and delicious food.

Bissell Brothers Brewing is located right next to Thompsons Point, so you can walk right there!

10. Have A Beach Day

There is enough to do in Portland, to last you an entire week, maybe even two.

But, if you want to take a day trip to Maines Beaches you can!

Old Orchard Beach is a favorite thanks to it’s boardwalk and nightlife.

For a calmer option, spend the day at Scarborough State Park.

Head to Old Orchard Beach, which is one of the best beach towns in Maine. Read my guide on The Best Beaches In Maine For A Beach Day

You can even take the train right to the beach from Portland’s Train Station if you don’t have a car.

Explore More Of Maine!

I also recommend reading my guide on The Best Cocktail Bars In Maine: A Local’s Guide!

Want more Maine foodie hotspots? Check out all my favorite Maine Foodie Locations.

If traveling around Maine, block some time to visit one of the many State Parks.

Visiting Acadia National Park? Here are 20 Exciting Things To Do In Acadia National Park this summer. Don’t forget to try the weird yet delicious Lobster Ice Cream in Bar Harbor.

You can also hike the Beech Mountain Trail and the Ship Harbor Trail before cozying up in one of these 13 Great Places To Stay Near Acadia National Park.

I love Portland, and I visit the city all year long! If you want more guides on Maine, check them out below.