Best Things to do in Portland Maine

Not to be confused with Portland Oregon Portland Maine is the coastal town you didn’t know you needed to visit. If you’re road-tripping New England or exploring Maine you’ll want to spend at least a weekend in Portland. With the help of a few travel blogger friends, I’ve gathered together this list of the best things to do in Portland Maine to help you make the most of your trip.

Best Things to do in Portland Maine

Go Sailing with the Portland Schooner Company

I grew up in a coastal town right off of Cape Cod in Massachusetts, but never got the chance to go sailing (#poorkidproblems). So when I had the opportunity to step foot on one of Portland Schooner Company‘s ships I was thrilled!

Located on the Maine State Pier off of Commercial Street in Old Town Portland, Portland Schooner Company has 3 Windjammers, the Bagheera, Wendameen, and Timberwind. All three of these ships where made and refurbished in Maine and date back to 1920s and 30s.

They do public and privates sails, as well as special events where guests can bring drinks and snacks to enjoy during their sail around Casco Bay.

During my 2 hours public sail we saw seals and plenty of coastal birds. I even got a little lesson on how to coil the lines after we set off. However, it’s safe to say I don’t have a future as part of a crew.

Read More: A 3 Day Weekend in Portland Maine

Best Things to do in Portland Maine: Visit Portland Head Light

Submitted by Moshe Huberman

The historical lighthouse at Cape Elizabeth is only 15 minutes’ drive from Downtown Portland, and it is one of the interesting sites to visit while in Portland. Its name, Portland Head Light, signifies the importance of this place in the history of the region.

The Lighthouse is located on a head of land at the south side of Casco Bay. It helped ships avoid the rocky shores on their way to Portland’s harbor. The construction completed in 1791 which makes it the oldest lighthouse in Maine. Not only the oldest, but it is also the most photographed lighthouse in the US and a must-visit landmark for everyone traveling in New England.

Today, Portland Head Light is part of Fort Williams Park. People who come to the area can visit the lighthouse and the museum (what used to be the lighthouse keepers’ house) and enjoy a fun day at the park.

There are several trails along the coastline to walk on, with amazing views of the bay and the lighthouse itself, both from the north and south sides. The park has a few other historical sites, like the Goddard Mansion and Battery Keyes, and the Children’s Garden, where kids can explore their relationship with nature. Alternatively, you can just come to picnic on the wide green lawns of the park. Parking is available at no cost.

Portland Head Light is a great place for taking a break from the city and enjoying the outdoors with a
touch of history and gorgeous views.

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If you're road-tripping New England or exploring Maine you'll want to experience some of the best things to do in Portland Maine.

Drinks and Appetizers at Solo Italiano

During a weekend trip to Portland to visit my dear friend Kate she surprised me with drinks and appetizers at Solo Italiano. We sat at the bar for a couple of hours catching up, enjoying the ambiance, and eating some tasty treats.

Solo Italiano has an extensive wine list, and a collection of signature cocktails that is always being updated and refreshed. In fact, we made friends with one of the bartenders and they gave us a little taste of a new cocktail he was creating. I’m usually not a big fan of hard alcohol, but this concoction was spectacular!

best things to do in portland Maine

I’m not a foodie, but Kate is and she says it’s one of the best restaurants in town. From a local, that’s a pretty big compliment. She always gets, and that night we did too, the Gonfietti con Prosciutto e Burrata. The meat was so smooth and buttery, and the cheese was perfection. I highly recommend it!

Kayak to Fort Gorges

Submitted By Ryan Victor

The Casco Bay islands are rife with fascinating historical sites, but none are quite as impressive as the enigmatic Fort Gorges. The six-acre military outpost sits on the Hog Island Ledge. It is roughly a one-mile paddle from Bug Light Park or East End Beach.

The fort occupies the entirety of the island, its stone walls seemingly rising straight up from the sea. Unlike many of the other islands in the area, Fort Gorges is not served by any public ferry. Your only options are to take a private tour boat or paddle a kayak across Casco Bay. Kayaks are available for rent from Portland Paddle at Eastern Promenade Park. Given the sometimes treacherous conditions in the bay, they ask that one person in your party be an experienced paddler. They should be capable of recovering a capsized boat.

Fort Gorges was built just prior to the Civil War as part of a string of forts between Boston Harbor and the Canadian Border. They intended to protect New England’s critical shipbuilding industry. In the nearly 100 years it was operational, the fort never saw any action and was primarily used for storage.

Today, Fort Gorges’s haunting parade ground and labyrinth of gun emplacements are a favorite of urban explorers. One of the original 10-inch diameter cannons can still be found lying on the vine-covered rim of the fort. Extreme caution should be used when exploring the fort, as some areas might not be stable. You should also bring a flashlight since the interior corridors don’t get much sunlight. That’s especially true on a cloudy day.

Read More: Explore the Maine Beaches Region

Learn about Lobstering with Lucky Catch Cruises

Maine is all about the lobster so why not learn about it when you visit Portland? When I was visiting Maine for a travel blogger conference I was lucky enough to get to experience and learn about lobstering with Lucky Catch Cruises.

Once we stepped on board, everyone was given bright orange bibs to wear to keep their clothes clean and mostly dry. I was singled out, as I usually am in these situations due to my extreme enthusiasm, and given a pair of orange overalls instead, this was a good call.

We baited traps, hauled them in and were taught how to hold a lobster without getting pinched. At one point, while tossing old bait overboard I made friends with a large flock of seagulls (no, not the band.).

This is a great activity for older children because they’ll get a bunch of hands on things to do. And if you just want a nice educational boast ride around Portland Harbor that works too!

Relax and Unplug at Soakology

Submitted by Brittany Quaglieri

If you’re seeking some self-care, set aside at least 2 hours one day to kick back, unplug, and relax at Soakology, a woman-owned spa and tea house right in downtown Portland. Soakology specializes in luxurious foot soaks, massages, and treatments.

Before the pampering even begins, you’re treated to a complimentary cup of tea while you decide on your treatments and snacks. Once you settle into a cushy armchair in a private curtain-lined stall (and turn off your phone and put it away for the remainder of your visit), your foot soak and a lavender-scented neck warmer are brought to you.

best things to do in portland maine

The treatment of your choice is mixed with hot water in a copper bowl full of river rocks. Then for the next 90 minutes, you will be treated to soft music, pleasant aromatherapy, and the delicious snacks you selected when you arrived – all distraction-free! The hot water in your copper bowl will remain piping hot for the entire duration – the water is replenished several times while you’re there.

There are treatments for recovery, uplift, replenishing, balance, and more – something to match all moods and needs. During my visit, which followed a travel blogger conference, I selected the Clarity of Mind Citrus Silk Bath. As an extra treat to myself, I ordered a Lavender London Fog and some Rosemary Shortbread cookies – both were delicious!

Make sure to call Soakology ahead of time to book an appointment. You’ll want to wear comfortable clothes including pants that can freely and easily roll up to your knees. You may get a little warm, so dress in layers that can be removed as needed. And finally, come prepared to relax!

Eat some Fresh Maine Seafood

If you’re on the coast you NEED to get some fresh caught seafood, and Portland is a great place to get some! Need I say more?

Check out the Maine Lobster Shack for amazing fish and chips and lobster rolls.

Taste Local Brews with the Maine Brew Bus

I love beer and I want to taste all of it no matter where in the world I go. Portland, Maine has around 30 breweries within the city limits and even more, in the surrounding area. With the help of the Maine Brew Bus, you can experience several breweries in a day on their mini-bus or walking tours.

Best Things to do in Portland Maine

At each stop we tasted 3-6 beers and at some locations got to go behind the scenes and see where they make the beer. At one place we where given the opportunity to taste a beer that haven’t been released yet!

Not into beer? No worries, they have tours to local wineries and distilleries too!

What do you think the Best Things to do in Portland Maine are? Let me know in the comments!

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