Portland, Maine | The Best ‘Small Town’ Weekend Getaway


I’ll always remember a specific Christmas before becoming a teenager because of a gift my aunt gave to me. I viciously tore off the wrapping and opened up a cardboard box and inside lied a pen. Yes, it was only a pen, but for some reason I was in awe of how it cool it looked. I picked it up, examined it, and twirled it around in my hands. From then on, I was passionate about writing and became obsessed with reading Stephen King & watching movies based on his novels.

In the spring of 2016, I set off on an inspirational voyage to visit the friendly confines where he was born because I knew it would help motivate me to continue my writing hobby. That wonder of a place is Portland, Maine.

I hopped off the plane and grabbed an Uber (for 10 bucks) and headed into the city. As I drove throughout the city, the thought of camping consistently came to my mind. The city is spectacular with all of the trees, the Atlantic ocean, and the charming locals. Portland is a miniature forest and I truly felt that everyone’s backyard would be a perfect isolated campground.

My first stop was at Portland Lobster Company where you can chill on a dock while enjoying beers and delicious lobster. Of course, I got Maine’s ‘maine’ delicacy, the steamed lobster dinner, as I overlooked the Atlantic Ocean on a back patio filled with a few people and friendly pups. Everyone was very warm and didn’t hesitate to start a conversation.

The Midwest may have the reputation for being friendly, but I was very surprised by how charming everyone I spoke with was. In fact, although I was only there for a two-day weekend, on the second day, someone recognized me on the street from being out and about the day before. This is a testament to the small town, outgoing atmosphere Portland is able to maintain despite having a population of 2 million people.

In the afternoon, I ventured over to the Portland Discovery Tours area on the pier and felt compelled to capture Mr. King’s scenes from his novels on the ocean. The real treat on the pier is getting a glimpse of the Portland Head Light, which is truly a beautiful sight. Between the aroma of the Atlantic and the blue waters splashing across the rocks at shore beneath the lighthouse, it felt as if I was temporarily living inside one of King’s novels. Several of his passages include his home state of Maine, and the beautiful view of the lighthouses.

To polish off my final evening, I checked out J’s Oyster Bar where you sit at the bar and watch the staff work their magic preparing your oysters. They were absolutely incredible and I chatted with an elderly couple about how they had been coming to the place for years. The gentleman even bought me a beer as a thank you for moving to make room for his wife without being asked. Regarding nightlife in Portland, you need to remember that the city sleeps pretty early. Prohibition started in Portland, so curfew for the bars is set at 1 AM.

Before I headed to the airport, I took a brewery tour at Allagash. It’s about five to ten minutes outside the city. I was greeted by one of the managers who, like me, is also from the great land of Wisconsin, and he gave me a few beers before the tour. During the tour, you get to sample five different beers. The Golden Brett is especially good — if they sold it locally in the Midwest, it sure would be a treat. Per their website, the finished beer has fruity nose and flavors of citrus, apricot and bread crust.

I will definitely visit Maine again. For over two decades, I heard about the amazing scenery and wilderness in Portland. It wasn’t over-exaggerated. In my opinion, Portland is the best ‘small town’ weekend getaway destination in the U.S.



About the author

As an employee for a world-class airline, Matt is able to travel the world via free standby flights. Originally from Wisconsin, Matt now lives in the Logan Square neighborhood of Chicago and loves the Green Bay Packers. He's TravelSages' expert on how to navigate the top experiences a city has to offer in a limited time, on a limited budget.

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