The Maine Land: A Weekend Away

“The way life should be.” That is Maine in one succinct phrase. Maine offers so much, from hiking in the White Mountains, water sports on the lakes, spending time near the ocean, or exploring historic Portland.  The first permanent settlement in Maine was founded in 1633, as a fishing and trading village.  This village would later be name Portland.  The common theory of how Maine came to be named Maine, was that the fishermen would constantly have to distinguish “the main land” from the many islands off the coast of Maine. “Main land” eventually became “Maine.”  There are a million ways to structure a weekend in Maine, but here is one itinerary.

Saturday Morning: Breakfast in Portland


Grab Breakfast in Portland and spend some time getting a feel for the city.  The downtown area is small and very walkable.  The cobblestone streets and brick buildings bring a time warped personality to the small city. The architecture is old, but the city vibe is very youthful, even a little hipster.


After Breakfast: Hit the Beach

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We spent the first half of the day on Crescent Beach, which is in Crescent Beach State Park.  The sea gulls were surprisingly massive in Maine, but the beach was quiet and scenic.


Maine Sea Gulls are the size of small dogs


Afternoon: Shipyard Brewery Tour

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So you can’t actually tour the Shipyard Brewery (apparently you used to be able to, but I guess the tourists were getting in the way of things), but you can watch a short video about how they make the beer and then taste test different Shipyard, and Sea Dog brews.

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Fun fact: Shipyard makes their beer using the water from Sebago lake – the second largest lake in Maine, not far from Portland.

Brewery tours are becoming very popular in Portland now that a few successful craft breweries are based Portland.  Shipyard and Allagash are just a couple.

Dinner: DiMillo’s

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DiMillo’s is is a tourist classic in Portland.  The Restaurant is on a yacht docked in the harbor.  You can eat in the indoor dining room or on the balcony outdoors.  Of course, the lobster is the classic, but if you aren’t a fan of lobster, they have other options.

Sunday Morning: The Cliff Walk at Prouts Neck

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One of my favorite hiking/not really having to be active activities in Maine is the Cliff Walk around the end of the peninsula at Prouts Neck.  The views of the ocean and beaches are so cliché that you will finally know what all the fuss over Maine is about.  It’s not surprising that Winslow Homer found so much inspiration here – speaking of which, you can tour the Winslow Homer Studio in Prout’s Neck, located near the Cliff Walk.

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We finished off the weekend with sandwiches from The Carry All while over looking Old Orchard beach.

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