Hello! It’s me! I’m back again with a blog post! I’ve quite missed writing, but over the past months I’ve found myself to have quite a lack of focus for pretty much anything, which has been troubling in more ways than one. I thought I would ease myself back into blogging by chatting about the trip to Portland, Maine I went on nearly a year ago with my buddy Kristen (aka @kristen_m_young over on ye olde Twitter). I’ve been feeling antsy and wanting to travel with no real opportunities to do so for a little while, and I’m hoping that writing this trip up will ease my restlessness at least a little.
This trip came about when my boss let me schedule a week off of work in September. I considered just doing a staycation, but decided instead to try actually going somewhere. So I hit up my college buddy Kristen and asked if I could come visit her in Massachusetts during that time. I thought I’d maybe explore the area where she lives during times she was at work and then we could hang while she was free — I never want to be a burden and didn’t want her to feel obligated to entertain me. I was pleasantly surprised when she responded by basically saying, “I can take time off that week too! Do you want to travel somewhere? Maybe Portland?” She had been there very briefly a couple of years before and while I had been to Maine on a family trip when I was in high school we skipped over Portland to visit relatives further north. It was set to be a fresh fun adventure for both of us!
When September rolled around I first spent the better part of a day driving up to Kristen’s town and then the next day we set off for Maine. We stayed at the Portland Ramada. Not #spon, obviously, but I’m mentioning it by name because it turned out to actually be a nice place to stay. It’s a small drive from the actual downtown area and is surrounded by strip malls (some of which contain some…questionable…businesses, see picture below), but it was in our price range, it was clean, the staff we interacted with were nice, the attached restaurants were surprisingly decent, and it has a large pool and a gym. (Kristen used the gym every day, so the quality of it must have been fine.)
Neither of us had done very much research about the area before we set out, so after checking in we rested for a little bit and looked up local hotspots on our phones before heading into the Old Port section of downtown Portland. Several websites had recommended this area as one with a ton of little shops to poke through and restaurants to choose from. This is an area that we would accidentally keep returning to on our little walking adventures in the city throughout the weekend, but we liked it there so that wasn’t necessarily a bad thing.
But something that excited me a lot was the actual port itself because, as I like to put it, this bitch loves a water feature.
We had dinner at a restaurant called J’s Oyster that was very small and tucked away near the end of the pier area, but it was absolutely packed so we knew it had to be good. It had a local dive kind of feel, but not in a shady way. I had lobster because, well, not having lobster in Maine would be like not getting a bagel from a mom and pop shop if you visited New Jersey! The food was pretty good — we were overall pleased with our dinner choice.
Having looked up more tourism stuff when we got back to the hotel, we decided that our big goal on our second day would be to go on a tour of a famous old house called Victoria Mansion. We couldn’t take pictures inside, but it was fascinating to get a look inside such an old home. Much of the house still needs restoring, but a lot of the trompe l’oeil painting on the walls was still very impressive and I loved the library.
After that we strolled through downtown for awhile. Kristen is a book lover, so she made sure we popped into a few different independent bookstores along the way. I don’t know any of their names, but we went to several. It’s definitely a good town for supporting local business! We also stopped for some excellent potato doughnuts along the way when we accidentally wound up at the Old Port. They were more dense than regular doughnuts, but still very nice. There was quite a line in the store too — I’m not sure if they’re locally popular or popular with tourists or both, but this place is apparently a popular choice.
We eventually found a comic shop that Kristen knew about called Coast City Comics. I don’t really feel comfortable in comic shops because I don’t know shit about comics and I feel self-conscious that the (usually all male) employees can somehow tell and are judging me. (Why should I care? I don’t know, but I do, oops.) When I found a bunch of pinball machines in the back, I was instantly at ease while Kristen browsed the comics.
For dinner that night we tried the restaurant inside our hotel, partly because we had been given coupons at check in, partly because we were curious about it. It wasn’t bad, despite this weird ominous sign on the way there!
On day three we pursued a crazy ambitious plan from a guide we found on a Portland tourism website. Maine has tons of lighthouses and apparently Portland has six(!) within easy driving distance of the city/each other. This is a separate post, because six lighthouses would be a lot to cover in this already super long write up! But here is a preview picture of Kristen looking at one of those lighthouses from afar to whet your whistle for nautical adventure.
After this big adventure we popped into downtown to grab lunch (in, you guessed it, the Old Port area) and then went back to the hotel to try out the pool and hot tub. I’d never been in a hot tub before and it was so hot it felt like my skin/blood were tingling! Between swimming in the pool and relaxing in the hot tub I found nearly a dozen lost hotel room keycards, lol. Dinner was lowkey — we went to the Chipotle near the hotel and picked out ice cream at the nearby grocery store.
On the way back down to Kristen’s house the next day, we stopped off in Portsmouth, New Hampshire, another waterfront New England town full of old looking brick and cute little shops. I’m probably wrong about this, but I have this general impression of New Jersey as a place that really doesn’t give a crap about most of its cool old buildings and just wants to tear them down to build luxury apartment complexes for people who work in NYC (or maybe that’s just my area?) so I’m super jealous of New England’s respect for its old stuff.
It’s also home to a kitschy looking little diner Kristen loves called The Friendly Toast. I don’t remember what I ate and I’m a terrible millenial for not memorializing it with a photo, but I remember the food was good!
Once we arrived in Massachusetts I spent one final night on Kristen’s sofa. This last night of my trip is actually one of the overall highlights for me because Kristen and I went to dinner with Kristen’s sibling and another local friend that Kristen and I went to college with. I rarely get to see or talk to either of them, so hanging out with them was a real treat! We drove out to this tiny beach area nearby and had a pretty good dinner in a bar before walking across the street to get ice cream. There was fog coming in off the sea and the area was basically deserted apart from the people at the bar. We spent a good chunk of time just chatting outside, catching up and having a laugh, and I dunno, it was just really nice! It really made me wish I could see them more and hang out like that all the time. But, alas, geography. (Why do we not yet have the power of teleportation? Or at least an equivalent of the Japanese Shinkansen for the United States so I can see all the people I love more often?)
And that was sadly the end of my trip. The next day I had to get up and make the long drive home. As if to rub in the fact how much of a bummer it was to return to my daily life, and in contrast to my smooth ride north, I got caught in a major traffic snafu near NYC just an hour or so from home and added a whole extra hour to my trip because of it.
Someday I will get to have fun travels again, but until then I will always have my memories of this trip to Maine with Kristen.
If you want to read about our visit to six lighthouses in one day on the last full day of our trip, you can click here!
I hope you’re all doing well.
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