Exploring Portland, Maine in 3 Hours

If you’re in Maine, eat lobsta.

That’s what my friend and I were determined to do, and her research for the best lobster roll in Portland Maine led us to a little white cottage shack with an outdoor bar on the pier called the Portland Lobster Company. An Australian-accented Google Maps guide (did you know you could change the voice?) delivered us straight to the restaurant, but did not find us a parking spot. For that, we had to drive around until we found a paid parking lot with empty spots.

Downtown Portland was hopping with outdoorsy-clad ladies, tourists in t-shirts, and kids holding on to parents’ hands walking up the boutiques in vintage brick buildings and waterfront eateries. According to History of Portland on MaineGuide.com, Portland was settled in 1633 and though it grew to be a city, four fires destroyed it, so most buildings you see today were constructed in the 1800s. The place has a cool, historic vibe and laid-back energy that made me wish I had extended my stay to explore.

Back to the grub. Portland Lobster Co.’s counter service style is efficient: diners can order inside or place their order at the bar and are given a lobster-shaped buzzer. If you want to sit on the deck, a greeter with an iPad will put you on the waiting list. Everything is made to order and takes about 30 minutes, so we happily sat on the pier in the sunshine with a view of the tour boats, which float vacationers around the river to gaze at lighthouses and watch the seals.

On one side of the dock, the gate was filled with locks. Maine Magazine explains that one couple added a lock to the fence after a cocktail-filled evening, and others added to create a collection. “The result is a tribute to Maine and a visual catalogue of individual love stories,” the author writes, and continues, “Locks are printed with names, decorated with paint, and attached to the fence. Custom dictates that you should throw the key into a nearby body of water, and it seems highly likely that many couples have done just that.”

The best kind of lobster roll, in my opinion, is one that isn’t muddled in mayonnaise.

Portland Lovster Co. nailed it. Toasted bun, a pile of lobster, and lettuce.

If I were to go back to this town, I would head straight for the Portland Lobster Co. The menu stars lobster, but is remarkably extensive given the size of the restaurant.

After our late lobster lunch, we journeyed to the Mecca of prep, the signature L.L. Bean store, about 20 minutes away from downtown Portland in the charming Freeport. This shopping center resembles an Americana Main Street, rather than an outdoor mall, with cottages and brick buildings along a sidewalk-lined road that house retailers such as Sperry, Banana Republic, and Ann Taylor Loft. Parking was not a problem here: situated behind the shops lies a convenient and gigantic parking lot.

From a distance we could see the two-story tall Bean Boot, which beckons shoppers to the entrance. “Teenagers have jacked up the price of Bean boots,” my friend commented with a laugh, which we both agreed is perplexing since the boots have been around for ages. To be precise: Bean boots have been around since 1912, and in recent years have had a surge in popularity, creating a wait list. The Popular Mechanic article,”The never-ending greatness of L.L. Bean’s Boots,” states the wait list was recently as high as a 100,000 and since it takes 45 minutes to make a pair of boots, my assumption is it will probably keep growing.

“You’re the lamest business traveler ever,” says my husband, because I am often tempted to hole up in my hotel room and relax. Pajamas! Quiet! Wifi! Lots of pillows! It’s just so much work to figure out something non-work related to do on a work trip… But now, I’m committed: when traveling, do the touristy thing. My three non-work hours were a mini vacation to a place I’d never been – I’m pleased I tried a lobster in Maine and went shopping to boot.

Read next

Other food travel reading: the best brunch in Myrtle Beach and a lesson learned at Farmstead in Napa: How to eat an artichoke

Also all photos were taken with my Fuji x100s, my favorite all-around camera I take with me everyplace, and is excellent for travel photography.

Leave a comment


  1. 7.7.16
    Pamela Cordell said:

    Great review of a wonderfully charming city!