Portland, Maine

Ladies and gentlemen.

What I bring to you this month is the trip that gave me the final push I needed to start my blog, presented in a four part series: Portland, Acadia, Cape Breton and Halifax.

I was inspired to write about my trip through Maine and Nova Scotia because I am a couponing queen who can help others save money while traveling, and I was super anxious about this being the first vacation I planned on my own. I will say, vacations are a lot more fun when they’re on my parents’ dime.

For pre-travel research, I followed @TheMaineMag on Instagram and texted around to see if any friends had must-see recommendations. Us millennials are currently in the process of infiltrating Maine, specifically the Portland and Acadia areas. After visiting, I understand the hype. The city may be small and cold, but it was SO CLEAN! If I was a seagull, I would definitely want to live in Portland, Maine.

Len Libby
If you think I’m only dating Connor for his calves, you are right.

Connor and I left Queens at 9am, after I was appropriately reprimanded for overpacking, and set off for Len Libby Candies, located just outside of Portland in Scarborough. A five hour drive through aggressive Bronx and Boston traffic was the perfect way to see how my brakes were holding up before starting our long journey.

Len Libby had passable chocolate, but nothing close to the league of Malley’s Chocolates in Cleveland. I went to Len Libby because I was told I should bear witness to this 1,700 pound chocolate moose named Lenny. Pictured above is a recently awoken Connor, dragged out of the car and forced to enjoy an American landmark.

We bought saltwater taffy (equally mediocre), a few squares of fudge and several kitschy chocolate lobsters for our office coworkers. I also got a prelude to Maine’s blueberry obsession and was hornswoggled into buying some blueberry tea, one of the cheaper items in this over-priced tourist shop. If you go through Maine and don’t stop at Len Libby, I don’t think it will make a difference in the quality of your trip. But feel free to do it for the ‘gram.

On the plus side, Len Libby is conveniently located caddy corner from one of the three Holy Donuts in the Portland area! I expected Portland to be more bustling and hectic, so I went to this Holy Donut rather than drive around the city getting cut off by taxis and hunting for hours to find street parking. (Portland was not like that at all. New York City has scarred me.)


For a full review on Holy Donut, follow the link! And read my baby blogging voice in my first post ever! To summarize, these potato based donuts were tasty, thick, chewy and a donut connoisseur’s dream to critique.

Above are some photos of our exploring. We found free parking next to Eastern Cemetery on the ‘outskirts of town’, which was fine because Portland is so small everything is walkable. The cemetery is 350 years old as of 2018! Connor and I found some wicked headstones dating back to the early 1800s. Really makes you think about the concept of time being a continuous and everlasting force, you know?

We ate a cheap dinner at Becky’s Diner because it was the first place we saw, but had we splurged for the Portland Lobster Company, we could have eaten on the water. If/when I go back, I would like to eat at Duckfat. I have heard good reviews about the restaurant from both friends and strangers on the MetroNorth.

As it was getting late, Connor and I took to wandering the streets, arm in arm, step in step, happy to breathe in the salty fresh air. On the waterfront, we walked the Maine State Pier where I took this picture of Casco Bay, and then up and down random wharfs speckled with rotting fish and seagulls eating french fries. A gift shop employee recommended we stroll down cobblestone Milk Street to check out the bar scene, so we did, and then we sauntered down Middle Street, wandering in and out of Salt Cellar, Bull Moose thrift media, West Elm, and finally Print: A Bookstore, because I love supporting independent bookstores. If I had another day, I would have liked to see the lighthouses! But I’ve seen many a lighthouse in my day so it wasn’t a priority.

Tired and stale, we arrived at our Airbnb in Gorham, not far from Portland and cheaper than anything local. My sister had sent me a referral coupon for $40 off my first Airbnb booking, but it could only be used for stays $70 and up, and this one was $40, so I saved it for when we went to Nova Scotia. It was both mine and Connor’s first times using Airbnb, but we are happy to report our host Wanda provided us with an excellent selection of soaps!

I could do an entire blog post on what it’s like to have matching boots with your boyfriend, given that I take a picture of our feet every time it rains.

By 10am the next day we were off on a 40 minute drive to Freeport to see the L.L.Bean mothership! It was so nice to be in a town as obsessed with this company as Connor and I are. The entire downtown economy was clearly supported by the massive L.L.Bean, plus L.L.Bean Hunting & Fishing; Bike, Boat and Ski; Home; and an Outlet, where Connor and I stocked up on raincoats, lunch boxes, pocket knives, backpacks, and tote bags but definitely not jeans because sweet Jesus those looked horrible on my figure. If I wasn’t on a budget I would have walked out of this place with more goodies than I could fit in my car. And I live in New York City, what would I even do with 3 kayaks, a machete and a monogramed camping tent?

Right down the street was Maine Beer Company, a brewery serving American-style ales, so basically small-batch artisanal. I got the stout-y Mean Old Tom and Connor got the fruity Zoe.

I have mixed feelings about how to review the Maine Beer Co. On one hand, the place was loud and crowded and the server was a jerk. On the other hand, the beer was actually really freaking tasty. On a third hand, it was pretty over priced, even for a craft brew.

I wanted to get a couple of beers to take to BYOB Young’s Lobster Pound, but after getting yelled at for drinking out of the bottle and not a cup and seeing the ~$7 price tag (varies per flavor), I decided to pass. Also I was stumbling drunk off of one beer, so that too.

We made our way up the coastline (Connor driving, not me, don’t worry) for another hour and a half until we arrived at Young’s Lobster Pound in Belfast, a restaurant and fishery raved about by a Maine obsessed coworker. As the sun set, the weather became cold and windy, typical of Northern US weather in mid October. We were still able to eat outside, so long as paper items were weighted down.

This was our fancy dinner of the trip; I got a whole lobster and Connor got lobster tail and steak tips. They cook it fresh right in front of you, and the workers are super friendly! I’ve never eaten a whole lobster before, so I received a step-by-step instruction placemat for kids. It did not prepare me for the gnarly green stuff smeared all over the insides…

After dinner, we drove one more hour to Colonial Inn in Ellsworth, just outside of Acadia National Park.


Our first two days were a lot of driving and shopping, but it felt great to be surrounded by open space and smiling faces! The worst tolls were New York bridges, but there are tolls all throughout Massachusetts, the New Hampshire bridge, and several Maine roads. Not all are tolls, so I checked my GPS to avoid them. The North East loves charging people to drive.



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