Portland, Maine- A Long Weekend on the Ocean

I lived in Connecticut for the better part of my life, all told, 28 years. Throughout that entire time, I made approximately one trip to Maine. And it was only to Kennebunkport, for like a single Saturday. I remember that it was a long drive (Google Maps tells me that it's only a little over three hours one way, but it seemed at least twice that when I was 8) and that that's how I had my first lobster. Neither of these details were enough to place this location in my brain as a place to continually return to. When I left Connecticut, I didn't think that Maine would be a place I felt a pull towards.
And yet, when Guster announced that they would be doing another weekend of concerts in Portland, ME, I immediately texted my best friends. We've made nearly an annual habit of seeing Guster together since we were in college. I've fixed it in my brain as a tradition, the same way Thanksgiving and Christmas are. When we miss a show over the course of a year, it's a noticeable void. This time, I was brave enough to even suggest that this would be the weekend to introduce my long-term boyfriend to my the oldest of my inner circle gang. I should clarify, this would be the first time they met in person. Everyone knows him already, but Connecticut and North Carolina are a bit far, so online likes and retweets are easier, but I wanted to make sure that my friends knew that he was real and that I haven't been living a secret life for the last three years. Trust me, there was a point in my life where my invention of a person as wonderful as he, and claiming I was running away to be with him, just to escape their insistence that I get on an online dating app was all too entirely possible.
And so we did. Tickets were bought, eventually hotels were booked, cars were rented, my summer procrastination in full swing, and we began planning our Portland getaway.
Apparently, I've been underselling Maine for a very long time. Or maybe it's just that Maine is a place some can't truly appreciate until they're older. It's full of history and charm and nature, and that wasn't quite my bag as a child. When I was 8, the idea of going to the L.L.Bean factory and consuming crustaceans was extremely underwhelming when compared to MY proposed vacation ideas, most of which included places I could buy stuffed animals with the possibility of barfing because of over-indulging on ice cream (this combination only happened once as far as I can recall).
By the time I was 30, I had absolutely had it with New England Winters, which aren't really winters but are an interminable stretch of time. I began to view the onset of September as a slow descent down a black hole filled with the prospects of shoveling and ice storms and the packing on of hibernation pounds and the idea of MAINE in winter seemed, well, nearly vile. However, time away and a change in seasons does wonders for the prospect and Maine in Summer, I am here to say, is quite enjoyable, although still a bit soggier than anticipated. Below is a quick rundown of our visit, places we ate, places we shopped, places we stopped by for a nice, Instagrammable photo op. Our trip was short (Wednesday Night through Sunday Morning) but we packed quite a bit in. 
We arrived too late on Wednesday night to see anything other than the tarmac and our hotel. We stayed at the Clarion Hotel throughout the whole trip, so I can't speak to other lodgings in Portland. As for the Clarion, it was fine. Perhaps priced a bit high for what we got, but it was a summer weekend, booked pretty late, so I only have myself to blame for falling into the peak season trap. The elevator didn't work while we were there, and there seemed to always be something fascinating happening in the hallways (secret doors left open, late cleaning carts, food trays, divorces occurring right before your eyes) but the hotel room itself was fine. Perhaps in need of a bit of an update, but I mean they're in a prime location and I'm sure they have no need to do too much to bring people in. They were booked the entire time we were there, literally turning people away.
Thursday:

Waking up the morning after traveling is rough enough. Waking up at 6:00 am the morning after traveling is slightly more rough. On this trip, there was only one thing that could make that easier, and it was also the bargaining chip I used to help lure my significant other to the Eastern-most state: a visit to Stephen King's town, Bangor, ME. Bangor is about an hour and a half drive from Portland, and it's a very easy drive, especially on the toll road.
There, a lovely man named Stu Tinker, who's known Mr. King for over 30 years, has set up an all-inclusive tour around Bangor, allowing you and any family member that may have begrudgingly agreed to sit in a tour van, the chance to see locations that have not only inspired Stephen King's stories and characters but also the home of the author himself. The tour takes a little over three hours, but is a must for any King fan visiting Maine. If you happen to be visiting the area and would like to check out how to book a tour, you can find more information here. Stu is wonderful, knowledgeable and instantly puts everyone at ease. He has stories, answers and a deep connection with this surprisingly quirky town. I don't know if it's because of the circumstances under which we were visiting or an actual fact, but Bangor feels like a place out of time, and it's worth a walk around the downtown area, even after the tour is over. 
After the tour we stuck around Bangor for just about another hour or so, as we had found Nicky's Diner online and decided we definitely needed to try it for our lunch option. And it did not disappoint. Everything from seafood to shakes is on their extensive menu and everything is exactly what the great American diner should offer.

Once back in Portland, we had the rest of the evening to wander around downtown. Street parking, even down by the port area is plentiful, especially early on in the evening. We had already decided that Lobster, or Lobstah, the official state dinner, would also be our choice. Portland Lobster Company doesn't need any additional endorsement from me (when we were there, there was already about a half hour wait, on a Thursday night, at 5:30 pm) but that's because not only are they great at lobster, but they have prime real estate. Right on the water, as any good seafood shack should be, you have a built-in water view with your dinner. Mostly outdoor seating, it's worth a stop if you're in the mood for cooked or chilled crustacean. We both got the lobster roll (chilled lobster) which came with fries and coleslaw but there were full on bib-required dinners available. If you're truly adventurous (we didn't have much time to be too adventurous) you can go out on the boat and catch your own dinner. Myself, I am a culinary wimp and would be unable to face my food before the inevitable pot drop.
Dessert-wise, I've never met a summer night that ISN'T improved by ice cream and I've certainly never met a vacation evening that's not improved by a cone, so if you're in the mood, there's also a very good ice cream shop right up the road from the Portland Lobster Company, Captain Sam's
Just a quick ride away, we found a park that overlooked the water. Portland ended up seeming to me like the San Francisco of the East Coast. I was, perhaps silly, and surprised by the amount of hills and over one of those hills, once we crested, it seemed like we were looking out on a surprise beach. Of course, it's not a surprise, it's Portland; the land of ports, which implies water, but still, for a girl who's been away from the water for 2 years, this turned out to be a welcome sight:
Friday:
It is no small thing to be able to wake up on a Friday morning in a town you don't know. To be able to explore is the best way to begin a weekend. But first, you must fuel that wanderlust in the only way one should while on vacation: donuts.
Portland has their very own version of fried dough heaven, and it's called The Holy Donut. Yes, the pun is fantastic, but also fantastic are their crafted delights. In a world where everything is now crafted and artisinal, many have discovered that, most often, the item that does best "crafted" is the thing you can't really mess up. Beer, pizza, donuts, it would take a lot to truly mess these up, but adding a slight twist to the recipe never hurt anyone either. And The Holy Donut is THE spot for a proper sugar fix. Boasting donuts that use mashed potatoes as the secret ingredient, this shop's donuts do NOT mess around. They are heavy and rich and flavorful and kinda gigantic. If you go, be prepared to get their early. The line was already out the door by the time we got there around 9. This little shop and its potato donuts are certainly worthy of the hype you'll find online.
Once we had prepared ourselves to face the day, we headed to another Portland staple: the lighthouse. Well, I should clarify, because there are no less than 3,000 lighthouses in Portland, but only three that you'll be able to access as a regular human. Ok, that's an exaggeration, but there are at least 6 or 7 in the area that are all vying for the Leader of the Lighthouse Universal Belt. But, the one we were finally able to get to, janky directions and mistaken roads taken into account was Portland Head Lighthouse and we were not disappointed. The day was gorgeous, the sky an almost offensively pretty blue and there were flowers still blooming. It was hot, but at least a trip to the beach area meant that it wouldn't be quite so humid. Supposedly constructed at the request of George Washington, the husband of that hip, hip lady Martha Washington, and also the first leader of a free gaggle of colonies, the lighthouse stands as a guard for the East Coast. On our day it just looked really good as a background for some potential holiday photos, but it is quite a sight. The adjacent Fort Williams Park is worth a stop if you have the time. On the other side of the lighthouse, across a beautifully craggy beach area, the Fort won't take long to explore, but we did get some great views from that side as well. To vouch for the fact that it's at least worth an exploration, I will say that there was one child we were behind who was being convinced that the fort was, in fact, an old palace that a king had lived in. Man, it's so easy to fool toddlers.

But by the time we got done lighthousing or gaslighting, whichever your big take away is from the above passage, we were gross. It was hot and humid and the only thing I cared about in the world was a Peanut Butter Cup Sundae from Friendly's. Despite my best efforts to not miss anything from Connecticut, it turns out, along with some fantastic people, what I missed the most was, yes, a sundae from a restaurant that, for whatever reason, North Carolina just refuses to involve itself with. I mean, among the many political stances that I disagree with my residential state on, is, insult to injury, the serious lack of a Friendly's. Alright, I've built it up too much, but seriously, just look at this thing:
Anyway, as you can tell, I won the lunch battle and was satiated. My need for another Peanut Butter Cup sundae sent into hibernation for the next 4 years. Like my own personal dessert version of the cicada phenomenon.
We headed back into Portland for some downtown sightseeing and shop finding. Heading into Print and then down the road a piece, down some stairs and into the cool(ish) seclusion of one of the most comfortable record stores/used film shops I've been in a while (Bull Moose), which also happened to be right next to the equally delightful Casablanca Comics
It's odd because after all of that things really speed up a bit. We met my friends at their Air BnB, a quaint little New England home that most definitely could have been haunted by someone who was accidentally trapped in one of those weird little New England rooms, had some mashed potato pizza, and went to see Guster at the historic State Theater. Here, I must pause and remind everyone that when something is described as "historic", and it's August, best believe that what they really mean is "sweat hole". You're going to descend into a sweat hole and will only be pulled out by EMTs or the grace of god. You will be physically exhausted and dehydrated, but yes, you will also have seen a beautiful old theater, perfectly and accurately restored. Only you can decide if that was the right choice or not.
Saturday
After the kind of drawn out decision-making process that can only occur when 5 adults who haven't seen each other for four years are suddenly thrown back together and left to face both the most basic of life's needs and contemplate the existential nature of friendship, we decided that some of us would head to Miss Portland Diner, while others would venture to Mast Landing, a brewery that was making an extremely tasty pale ale, called On the Ocean, in collaboration with Guster. 
I was one of the diner-bound, and while brunch all over Portland seemed to be hopping, the wait at the diner wasn't so bad. And I certainly wasn't about to say no to my second diner in three days. 
The rest of Saturday was spent gearing up for and attending the second night of Guster shows at Thompson's Point, which is, while perhaps not directly on the ocean, in fact, on a very real body of water. It was gorgeous and rainy and muddy and wholly satisfying as an outdoor Portland concert venue. 
So that's it, the weekend was exhausting. We have plenty to go back to Portland to see, but for the moment, that was enough. We packed a whole lot of little adventures into a few tiny days and it was the perfect reason to head up to New England again. And even though it rained every single time we went to a show, I'm not sure if you can ask for a better picture of what summer concerts look like than this one:

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