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

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

Describing someplace as the perfect weekend destination seems like an overreach. But Portland, Maine, definitely 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. I drove up from Beantown in about 2 hours in a fully charged, fully electric Chevy Bolt EV to eat, shop and explore Maine’s foodie city by the sea.

I was a little nervous about road tripping in an electric car. What happens if the juice runs out? The car’s graphic display features a large battery icon. I monitored it nervously for the first 10 minutes, but then relaxed, tuned into one of my favorite playlists via the Bolt EV’s Bluetooth and settled back, enjoying the car’s quiet ride.

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.

• Get out on the water

• Eat a lobster roll (or two!)

• Get a birds’ eye view of the city

• Taste a potato donut

• Dream about owning the art

• Buy a piece of Portland

Take a Seaside Ramble

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.

Read More: The Best FREE Things to Do in Portland, Maine

When I needed a little more exertion and some salty air, I hopped into my Chevy Bolt EV and 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. Finding the lot was a breeze, thanks to the Bolt EV’s OnStar feature. Simply pressing a button connected me to a friendly rep who downloaded the point by point navigation to the car.

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.

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.

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 bay islands.

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.

From the Ocean to My Belly – The Life of a Lobster

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.

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.

The Best Restaurants 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 of which – Fore Street, Back Bay Grill and Hugo’s – have been perennial favorites for decades. I plan to go back with some of my foodie friends to check out some of the fancier places. For this trip though, I asked friends familiar with the city to recommend their must-eats that won’t break the bank. What I learned is that compiling a list of the best restaurants in Portland is impossible but it’s definitely a quest worth pursuing.

Here are some of the ones I recommend checking out when you’re visiting Portland. Be prepared to wait for a table on weekends, unless you’re traveling solo and can snag a single.

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. But it’s also a super dinner destination. The evening menu features southern comfort foods like fried green tomatoes, shrimp and grits, and a spicy cornmeal crusted catfish filet called the Hot Cat. Entrees hover below $20.

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. Dinner entrees are under $25.

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 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 good. Sit at the bar if you want to watch the shuckers do their thing. Sitting at the bar, I had a great view of the shuckers at work. If you’re on a budget, stop here for some oysters ($16/half dozen) and a draft from Allagash, one of Portland’s many breweries.

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 drawn butter over the top. It was perfect. If the $19 price makes your wallet squawk, head down to Commercial Street and look for one of the pushcart vendors peddling $10 rolls.

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 shop on Park Avenue while toodling around in my Chevy Bolt EV. Street parking in Portland, even outside of the touristy Old Port district, is hard to find. The Bolt EV’s compact size though made it the perfect car for my urban explorations. I found it a dream to park, thanks to Chevy Surround Vision. Images from 4 cameras are blended together to provide a 360 degree view of your car, offering both convenience and safety.

Buy Something Uniquely Portland

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. Some of the ones I “enjoyed” (my credit card might not agree) include Folly 101 (wonderful housewares), Motifs (clothing, jewelry) and Gus and Ruby Letterpress (whimsical stationery). 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.

Climb Up Through History

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.

Do a Little Art Appreciation

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.

Where to Stay in Portland Maine

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. Mid-week rates for a double start at $314.

I stayed at the Courtyard Marriott on Commercial Street. The hotel feels brand new and features a thoroughly modern interior that makes this budget-friendly property (midweek doubles start at $164) feel luxe. Adding to its appeal is an extra-friendly staff. The front desk clerk was extremely helpful with restaurant recommendations. And, every time I returned with my Chevy Bolt EV, the valet attendants offered to fill ‘er up – the hotel has a complimentary charging station for guests’ use.

Notes About the Chevy Bolt EV

My ride for the Portland weekend was a Bolt EV, Chevrolet’s first all-electric vehicle. As I mentioned, I got over my nervousness about running out of power pretty quickly. With a 238-mile range at full charge, it’s capable of taking you there and back, wherever there might be.

The ride was smooth with a surprising amount of zip on the highway. The only hiccup I had was using cruise control. The first few times I hit resume after braking, the acceleration felt lurchy. Then I tried easing back closer to my cruise control set speed before hitting resume and the transition was seamless.

I always assumed that owners of electric cars needed some type of special panel installed at home to power up their cars. Not so with the Bolt; you simply plug your car in at night just as you do your cell phone. And if you’re in need of a charge during the day, PlugShare and ChargePoint are downloadable apps that help drivers locate stations. I gave it a try at a Portland bank branch; while I made a ATM withdrawal, I plugged in and topped off my battery. It was easy as filling a traditional fuel tank but it was FREE – that’s a huge perk!

I’ll be returning to Portland soon. I have some 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.

What’s Your Favorite Restaurant City? Why?