Between Lobster Rolls: The Best Things to Do in Portland Maine

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Portland Head Light in Fort Williams Park is one of the best things to see in Portland Maine
Fort Williams Park is worth visiting to check out Portland Head Light. Photo credit: Cathy Bennett Kopf

Portland, the coastal jewel of southern Maine, is an epic destination for couples, friends or families. Include a stop on your way to or from Acadia National Park. You’ll find a very walkable city with historic 19th century brick buildings, cobblestone streets, funky boutiques and tempting aromas drifting out of the city’s famous restaurants.

Describing someplace as the perfect weekend getaway seems like an overreach. But Portland, Maine, comes pretty close to achieving that distinction. Easily accessible by flights into its local airport, the city’s also within road trip distance of the NYC tri-state area and Boston. And, if your ultimate destination is Acadia National Park in Bar Harbor, it’s a welcome pit stop for sightseeing.

What’s there to do? Portland, dubbed Restaurant City of the Year by Bon Appetit magazine, has a food scene you’ll definitely want to check out. After eating your way through town, you’ll be tempted to pronounce the local dishes like a native. Repeat after me. Lob-stah. Chow-dah. Between meals, you’ll find plenty of fun things to do. Here’s where to get a bird’s eye view of Portland, see it from the sea and more.

Read More: Is a Maine Windjammer Cruise for Kids?

Things to Do in Portland Maine

Portland has tons of great restaurants to provide sustenance as you check out the fun things to do: take a seaside ramble, get out on the Atlantic, step back in history, check out the arts or do some shopping. If none of that’s appealing, then Portland might not be for you. And that’s okay. It’ll make those waits to get a table at one of Restaurant City’s hot spots just a little bit shorter.

Visit the Casco Bay harbor, one the the things to do in portland maine
The Portland harbor is still one of the busiest in the U.S. Photo credit: Cathy Bennett Kopf

Get Out on the Water in Portland

Portland is located on a peninsula that juts out into Casco Bay. Originally settled during the early 1600’s, Portland developed into one of the largest commercial ports in the U.S.. You’ll catch glimpses of the Atlantic as you explore the city. But the best place to appreciate the dramatic geography is by getting out on the water.

casco bay ferry ship at dusk in portland maine one of the fun things to do
Take a ferry ride in early evening to catch a sunset on Casco Bay in Portland. Photo credit: Cathy Bennett Kopf

Ferry to the Islands

Portland has an extensive ferry system that connects the islands of Casco Bay with the city. Operating for over 150 years, the Casco Bay Lines ferry service is based in a terminal in the Old Port District on Commercial Street.

A popular option for visitors is to hop a ferry and take a day trip to explore Peaks Island, the most populated of the bay islands. The best way to get oriented is a 75-minute Spirit of Peaks golf cart tour.

Rent a Boat or Kayak

If you’re more of a DIYer, boat rentals are available from a number of different companies, including Sail Maine, a community sailing center offering hourly rentals to certified skippers.

Want to get up close and personal with the waters of Casco Bay? Then head out in a kayak. Rentals, sea kayaking instructions and tours are available through Portland Paddle.

If you’re traveling with your own kayak and looking for places to put in, check out this list of favorite spots from the folks at Portland Paddle.

Read More: When’s the Best Time to Visit Maine?

Captain and lobster on a lobster boat tour, one of the fun things to do in portland maine
Gucky. Slimey. Delicious. Lobsters are vital to Maine’s economy. Photo credit: Cathy Bennett Kopf

Take a Lobster Boat Tour

For my water adventure, I hopped onboard a lobster boat to learn the art of lobstering. Lucky Catch Cruises offers daily lobster boat cruises. Captain Tom and his crew motored us out into Casco Bay and let us try our hand at lobstering. From July to November, Portland area lobster boats fish in the bay; in the winter, they need to venture farther out into the Atlantic.

setting a lobster trap, one of the things to do in portland maine
Trap overboard! I got to try my hand at lobstering. Photo credit: Cathy Bennett Kopf

It really is all about luck with lobsters. You bait the traps and push them off the boat. Then you check them in a couple of days, before the bait gets old and stinky. When retrieved, you hope to get at least one lobster who meets size requirements; they can’t be too small or too big. You can’t keep female breeders either. Yes. There are boy lobsters and girl lobsters. We learned to tell the difference.

antique railroad car draped with patriotic bunting
Ride the rails along scenic Casco Bay when visiting Portland Maine. Photo credit: Cathy Bennett Kopf

All Aboard the Maine Narrow Gauge Railroad Co.

If your getaway group includes littles or the grands, I suggest taking a ride on the Maine Narrow Gauge Railroad. Kids love trains and grownups will enjoy the scenic views of Casco Bay as you travel 35 minutes on a 3 mile long round trip.

Trains leave every hour on the hour, beginning at 10 am, with the final trip at 3 pm. Planning your Portland trip around the holidays? Definitely check out their Polar Express event!

colorful art installation at the Portland Art Museum
I loved the bright primary colors of this outdoor installation at the Portland Art Museum. Photo credit: Cathy Bennett Kopf

Explore Portland’s Arts District

I get suckered in by art galleries everywhere I travel. While walking by, I’ll catch a glimpse of a painting or photo that I immediately fall desperately in love with. I wander in, saunter up to the object of my affection and, when I see the price, my heart breaks into a million pieces.

It happened to me again in Portland, but it didn’t stop me from popping into a number of galleries during my strolls. Art lovers should also check out the Portland Museum of Art.

farmers market sign advertising wild blueberries in portland maine
My market visit was one week too early for Maine’s famous wild blueberries. Photo credit: Cathy Bennett Kopf

Blueberries and More at the Farmers’ Market

If you’re staying in an Airbnb or VRBO rental and need to stock your kitchen, a trip to the Portland Farmers’ Market is a must. It’s held twice a week, on Wednesdays and Saturdays, in Deering Oaks Park.

Visiting Portland in late summer? You’re in for a treat. That’s wild blueberry season in Maine. They’re small, sweet and delicious.

SheBuysTravel Tip: Deering Oaks Park has a large, recently renovated playground for the kiddos and a small wading pool too.

Wash Down the Oysters with Craft Beer

If you drink beer, then you’re familiar with Allagash Brewing Company. Founded in Portland, their signature brew, Allagash White, is an easy-sippin’ Belgian-style wheat beer. Check out seasonal offerings in their beer garden. It’s located outside of town; depending on traffic, it can take you 45 minutes to get there, so plan accordingly.

Prefer to stay downtown? Head to the East End. You’ll find several craft breweries within walking distance of one another. Start at family-owned and operated Rising Tide. Their brews are created to pair with Maine’s cuisine. They suggest drinking their Daymark beer with local oysters. Then toddle over to Austin Street Brewery’s outdoor patio. Finish your tour at Belleflower Brewing, or, for a change of pace, try the rum at Three of Strong Spirits. Their small batch spirits use water from Maine’s Sebago Lake.

guide in the Portland Observatory taking a tour is one of the fun things to do in portland maine
Everyone on the docks would react with excitement when a ship approached flying this flag. It meant there was rum onboard! Photo credit: Cathy Bennett Kopf

Climb to the Top of the Portland Observatory

There are a number of house museums in Portland to visit, including the Wadsworth-Longfellow House, home of the American poet Henry Wadsworth Longfellow (“Paul Revere’s Ride”), and the Victoria Mansion. If you only have time for one peek back in time, though, head to the Portland Observatory and take one of the guided tours.

The docent for my tour was an engaging senior citizen, who led us up each of the 7 stories of the octagonal tower in the Munjoy Hill neighborhood. It was a journey the tower’s owner/operator Captain Moody made every day, including just before he died.

The Observatory functioned as a for-profit signal tower from 1807 to 1923. With a state of the art telescope, scouts scanned the sea and sent notifications about approaching ships so that dock preparations could begin for unloading cargo. It is the only remaining signal tower in the United States.

By stopping along the climb for brief Portland history lessons, you’re really able to appreciate the sweeping city views when you reach the top, instead of huffing and puffing.

things to do in portland maine include an oceanfront walk like the Prouts Neck Cliff Walk
Despite the ominous warning sign, the Prouts Neck Cliff Walk was an enjoyable and scenic ocean ramble. Photo credit: Cathy Bennett Kopf

Take a Seaside Hike

Each time I pushed away from a great meal in Portland, I felt the urge to walk it off. So I did, spending much of my weekend wandering the cobblestone streets that connect the city’s major thoroughfares, Commercial and Congress Streets. I wasn’t alone. Portland’s a city of walkers; the 2.1 mile Eastern Promenade is an especially popular trail, offering sweeping views of Casco Bay.

When I needed a little more exertion and some salty air, I headed to Scarborough Beach State Park, about 20 minutes south of Portland. Parking’s available in the beach lot; check the website for hours and fees.

The parking attendant gave me directions to the trail. He told me to walk down to the beach, make a right and stroll all the way to the end to the pumphouse on the right. You can end your walk here, but I highly recommend scrambling up the rocks and taking the Prouts Neck Cliff Walk.

I did the entire 4.3 mile loop trail. Half of the trail consists of an elevated, narrow cliff path, flanked by hardy foliage with drop dead gorgeous sea views. Then the trail emerges from the bushes and continues on paved streets in a wealthy neighborhood of traditional New England homes. I have a serious HGTV addiction, so I was in heaven.

If you’re looking for other rambles, Portland Trails, a nonprofit urban land trust located on Commercial Street, has trail maps available for $4.95. Or, for a gentler outdoor adventure, head to Fort Williams Park, home of the Portland Head Light, in nearby Cape Elizabeth.

New England shingled mansion seen on an ocean walk, one of the things to do in portland maine
One of the beautiful, shingled New Englandd mansions I drooled over on my ocean walk. Photo credit: Cathy Bennett Kopf

Where to Eat in Portland Maine

The Bon Appetit designation of Portland, Maine, as its Restaurant City of the Year is not surprising. The town is full of great restaurants. Some are destination restaurants, like perennial favorite Fore Street. But don’t limit yourself. Duck into a dive bar like Tomaso’s Canteen. I had a chicken sandwich served Vietnamese banh mi style that was delish.

Following are the must-eats recommended by my Portland friends. What I learned is that compiling a list of the best restaurants in Portland is impossible, but it’s definitely a quest worth pursuing.

Be prepared to wait for a table, unless you’re traveling solo and can snag a single. Alternatively, book a food tour. The three hour Old Port Culinary Walking Tour provides a taste of the city’s flavors.

closeup of fried scallop at Scales in Portland Maine
Looks good but tastes better! Everything was spot on at Scales in Portland. Photo credit: Cathy Bennett Kopf


My son and I checked out Scales based on a recommendation from one of the island residents we met while biking around Great Diamond Island off the coast of Portlan. He sails in once a week because it’s that good.

And it is. The large, bright dining room is located steps away from the ferry terminal. Start with fresh, local oysters. Check out the daily specials. We split a fried scallop appetizer that was as yummy as it was pretty. My lobster roll was the best of many I’d tried during our trip. And we were not disappointed when we chose what our waitress suggested for dessert: a butterscotch sundae with homemade frozen vanilla custard and a strawberry mousse made with the last of the season’s fresh berries.

Hot Suppa

Go for the chicken and waffles and thank me later. A popular brunch destination, Hot Suppa prepares the best Bloody Mary in Portland, according to my old college roommate.

Isa Bistro

My roomie says this is her go-to weeknight restaurant and I understood immediately after settling in at the bar. Family-owned and operated (the chef’s wife is the hostess and her brother’s the bartender), it felt like “Cheers”; everyone seemed to know each other and made this out of towner feel at home.

I tried my oysters with a side of Tabasco Ice, a crystallized form of the famous hot sauce. Photo credit: Cathy Bennett Kopf

Eventide Oyster Co.

Although it’s a tourist destination attracting large crowds, Eventide is worth a visit to sample the freshest oysters you’ll ever taste. The offerings change daily based on availability. Since I’m not an oyster connoisseur, I let my waitress pick my 1/2 dozen on each of my two visits. That’s right. Two visits in 3 days. They’re that fresh.

Sit at the bar if you want to watch the shuckers do their thing. Don’t come hungry. Your wait time (even for bar seats) will be over an hour.

This is everything you want in a lobster roll. Simple. Fresh. Delicious. Photo credit: Cathy Bennett Kopf

Highroller Lobster Co.

The lobster roll here features chunks of ocean fresh lobster meat piled into a split top roll. Choose a sauce, if you want to. They offer a number of flavored mayos. I chose to go old school and simply poured melted butter over the top. It was perfect.

The price of restaurant lobster rolls in Portland might make your wallet squawk. If so, head down to Commercial Street and look for one of the pushcart vendors peddling rolls from pushcarts.

potato donuts at Holy Donuts, eating them is one of the best things to do in portland maine
I fell hard for the dark chocolate and sea salt Holy Donuts. Photo credit: Cathy Bennett Kopf

Holy Donuts

No visit to Portland is complete without a stop at Holy Donuts. The secret to the taste of these exquisite snacks? They’re made out of fresh Maine potatoes. The line to enter their Exchange Street location snaked around the block. I’ll wait for a lot of things, but donuts aren’t one of them. Luckily, I happened upon their location on Park Avenue which had no line.

shopping at sea bags is one of the best things to do in portland maine
So many bags. Not enough money. I liked all of the charming and waterproof offerings at Sea Bags. Photo credit: Cathy Bennett Kopf

Portland Maine’s Best Shopping

I love to window shop. It’s one of my quirks that confounds my hubby. He just doesn’t get the point. I’ve tried to explain the thrill of the hunt to him, but he just wags his head indicating that this is something he will never understand.

So, when left to my own devices in Portland, I had a blast weaving in and out of the boutiques located in the cobblestoned Commercial Street district.

My favorite, although my credit card might not agree, was Gus and Ruby Letterpress, a whimsical stationery store. If you’re seeking a legit “Made in Portland” souvenir, seek out the Sea Bags shop. The store’s tucked down a side alley on the harbor side of Commercial Street. They offer a variety of nautical waterproof bags, fashioned out of old sails.

vintage Royal typewriter in the lobby of the Press Hotel in Portland Maine
Wow! Loved seeing the vintage typewriters on display in the lobby of the Press Hotel. Photo credit: Cathy Bennett Kopf

Where to Stay in Portland Maine

Press Hotel

Marriott offers two lodging options at different price points in Portland. The writer in me was tickled by the lobby of the Press Hotel in Portland, one of Marriott’s Autograph Collection hotels. There are typewriters of all kinds on tables, desks and on the walls, an homage to the building’s history as a newspaper headquarters.

Courtyard by Marriott

On one visit, I stayed at the Courtyard by Marriott on Commercial Street. The hotel feels brand new and features a thoroughly modern interior that makes this budget-friendly property feel luxe. Adding to its appeal is an extra-friendly staff. The front desk clerk was extremely helpful with restaurant recommendations.

pool with deck chairs in front of exterior of inn at diamond cove portland maine
Spend the day in Portland then head back for a dip in the pool at the Inn at Diamond Cove. Photo credit: Cathy Bennett Kopf

Inn at Diamond Cove

Want to make your Portland vacay extra special? Book a room at the Inn at Diamond Cove. It’s located on one of the islands in Casco Bay. You’ll take one of the regularly scheduled Casco Bay Lines ferry rides or book a water taxi to come and go.

Read More: Inn at Diamond Cove Review: A World Away in Maine’s Casco Bay

I felt like I was a guest at a rich friend’s posh summer house. Rooms are large and well-appointed and there’s an outdoor pool, hot tub and tennis courts. Explore the island’s 100 acres by bike (available at the front desk). Stop at Seaglass Beach, the Moon Garden and end your day at Sunset Park.

There are lots of options for hotel stays near Portland, including vacation rentals. Use this interactive map to help you find a place to stay in the area.

I’ll be returning to Portland soon with friends who like to eat, shop and wander. Trying to taste everything Portland has to offer is probably impossible, but I’m willing to give it a try.

flower arrangement on table at Forage Market in Portland Maine
The food was great at Forage Market. So was this pretty flower arrangement. Photo credit: Cathy Bennett Kopf
Cathy Bennett Kopf serves as the Daily Editor of SheBuysTravel, reporting to Editor-in-Chief Cindy Richards. She began travel writing after serving as the unofficial (and unpaid) vacation coordinator for hundreds of family and friend trips. She launched her blog, The Open Suitcase, in 2012 and joined the SBT (formerly TravelingMom) team in 2016. A lifelong resident of New York, Cathy currently resides in the scenic Hudson River Valley. She’s a member of the Society of American Travel Writers, the International Travel Writers Alliance and TravMedia.
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