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Day 1

We started off our journey in Sandusky, OH headed to our pitstop of the night, The Sagamore Hotel in Lake George, NY. After a 9 hour car ride, loads of beef jerky and coffee, we finally arrived at our destination and it was absolutely breathtaking. We were looking for 1920’s style resorts to stay at on our way to and from Portland and this fit the bill. There are boats and jet ski’s available as rentals to the guests, your own private beach and boat tours as well as 3 delicious restaurants. While there we picked up a few bottles of Adirondack wine for ourselves and gifts, which turned out to be some of the better locally produced wine we have ever sampled! We loved the charm and coziness of this resort and hope we will be able to go back soon!

Day 2

We started off this day by heading into the town center of Lake George, NY. Unfortunately we were passing through before a lot of the outside adventures such as zip lining and kayak rentals opened but there seems to be endless amounts of such activities when in season. We packed back into the truck to make our drive to Portland, ME. If you have the chance to do this road trip, I highly recommend taking the scenic route up through New Hampshire and Vermont, the view is something out of a magazine and keeps you engaged on a long drive. We arrived in Portland finally! On extended trips we try to use airbnb for our housing choice. When you break down daily costs, its much less expensive and convenient to have your own apartment with everything you’ll need, plus, you get the real experience of the town you are visiting. In hindsight, I may have chosen a different apartment just because we did off-street parking which turned out to be a game every morning after 10am with the local parking nazi’s.

Within a matter of an hour, we immediately found our favorite bar in Portland, $3 Dewey’s. Apparently “back in the day”, this establishment was a brothel and the phrase “$1 for a Looky, $2 for a Feely and $3 for a Dewey” stuck. There are over 25 beers on draft and when I say beers, either imported beer or beers brewed in Maine. It’s shocking how many phenomenal breweries are located in Maine, that the rest of the United States doesn’t know about, they make some kickass beer people (Shipyard, Sea Dog & Maine Mead Works to name a few). After a few yummy libations, we strolled across the street the Portland Lobster Company where we indulged in what I personally consider the first real seafood I have ever had, lobster rolls, fresh mussels and fresh clam strips. This place is heaven with a side of melted butter, seriously, go!

Day 3

This trip was somewhat of a leisure/business/house-hunting trip for us so day 3 was spent entirely looking for property, with a night cap at $3 Deweys and the Portland Lobster Company.

Day 4

Longfellow Square

I was hoping to do some kayaking this day and ferry sightseeing but again we were too early for the “in season” activities and the weather was less than favorable. So on this day, we explored our neighborhood a bit. We stayed on Brackett St. in the West end which is also know as Longfellow Square, or as I like to refer to it as Hipster Hill. Portland is a strange mix of individuals which makes this city extremely interesting. If you’re looking for a hip night scene, Longfellow Square is the place to be, it really came alive at night, every night of the week.

Day 5

L.L. Bean Flagship Store

There was more house hunting on this day but I made a pitstop in Freeport, ME to visit the flagship store of L.L. Bean, which is the only one in the United States. To call it a store is an understatement, it’s more of a campus of stores, which is hard to believe because less than ten years ago, it was half the industry that it is today, thank you L.L. Bean boots. Across the street from the L.L. Bean campus is also an outlet mall filled with stores such as Vineyard Vines, Patagonia, The North Face and Hunter.

Day 6

Portland Flea-For-All

We ventured down to the Portland Flea-For-All, a local flea market in a 3 story old manufacturing building that was everything Pinterest had told me it would be and more. Not only were there endless record bins to search through but a plethora of mid-century furniture and upcycled pieces as well! Some vendors were even creating their own pieces right there in the market! Such a cool find! We spent this night with Ian’s friends who live in the area. We went to their home, grilled out and hung out for the night.

Day 7

DiMillo’s

On this day our lives changed, Ian proposed to me in our apartment!! We celebrated by heading down to DiMillo’s on the water which is actually an old ferry boat that has been docked and turned into a floating restaurant. Out of this world food, highly recommend if you aren’t afraid to eat your seafood while feeling the boat rock!

Day 8

Becky’s Diner

We waited all week to head to the local spot that everyone talks about for the dish only served on Sundays. We headed to Becky’s for their Lobster Eggs Benedict, well worth the 40 minute wait for a table for breakfast. Looking back on our stay in Portland, the food is to die for, the people are strange, interesting but strange, there are lots of drunks and if a local asks you how you like Portland, never ever tell them it’s “quaint”… I learned the hard way.

Day 9

We ended our last stay of our epic road trip with a night at the Hotel Hershey in Hershey, PA. Keeping with our 1920’s resort style, we chose this fantastic hotel! Upon check-in, your party receive a Hershey bar for every person! Most of the resort has been kept in it’s original art deco design. There is a Mediterranean courtyard in the middle of the hotel that opens up onto the second story patio. Perched high on a hill, the view from this patio is by far the best I have ever seen of the Appalachian mountains. There are gardens in the rear of the hotel along with botanical gardens in the front. It was a privilege to stay at such a lovely resort, we will be back! Upon leaving and heading back to Ohio, we exited Hershey on the chocolate colored roads, aptly name, The Hershey Highway. Fun little town, would love to see more if we hadn’t been strapped for time getting home.

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Portland, ME Road Trip

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