August 17, 2011

Where To Go In Portland, Maine - If You're Single, Broke, And A Law Student

I leave tomorrow for my second weekend in Portland, Maine, so I thought it might be a good time to share some of my favorite spots in Portland. These are The Places To Go if you are a single, broke, sleep-deprived, law school student in Portland, Maine. (This means that none of the fabulous tourist places will make this list, but it also means that this list is even better. Promise.) Ready?

{note: most of these photos are not mine, but some are}



Holy amazing milk-shakes, Batman. And burritos. And slop bucket. (Which is what I had last Friday night and, oops, left in Nicole’s fridge. I’d bet my entire bank account that her boyfriend has already finished those left-overs, though. He knows the drill.) Silly’s is colorful and cozy – a combination hard to find – with creative, delicious food and wicked chill servers. Also, hot. I’ll let Nicole tell you about the time that she left my number for the waiter on a napkin… okay, one of the many times. She’s pretty much determined to single-handedly end my single-dom. Moving on…

Best breakfast sandwiches ever. That’s all I’ll say, and direct your attention here.

The Bar of Chocolate




They have amazing drink-able chocolate. It comes in tiny espresso cups and fills you before you reach the bottom. I think this bar is actually the first bar I ever went to in Portland. They also serve cake. See why I adore it? Chic mixed with rustic and a low-key atmosphere makes it a great place to actually hear the people you are hanging out with. They also have mini-bottles of champaign and flour-less chocolate tort. Not that I know from experience or anything. 

L.L. Bean at Midnight

Actually, 11pm on a Monday night was one of my favorite times to frequent L.L. Bean. Sure, it’s well-known that their mother-ship store has any Bean item you could possibly desire and it is open 24 hours a day, but do you know how amazing it is to wander around at 11pm on a Monday night? Hello, free therapy. That pretty much sums it up for me. I spent a lot of time there my last year of law school wandering aimlessly around the store and dodging the helpful associates who kindly asked me if I needed help. Um, no, but could I cry on your should for a while because I miss D.C. and hate negotiable instruments and am terrified that I am never, ever going to find a job and going to law school was the worst decision of my life and, and, and… Thankfully, my favorite bed on the third floor and maple syrup candy solved all problems.

The. Best. French. Fries. Ever. I guess they are fried in duck fat – hence the name – but they also come with unique dipping sauces. I’m not a big mayo fan, but the vinegar and mayo dipping sauce is amazing. Paired with a grilled cheese and tomato panini makes an awesome lunch. Frequent flyer tip: order to-go and then pick it up with a friend – parking is hard to find around there, so it helps if the car circles the block while you run in. Not sketchy at all. Ha.

Whole Foods

I have spent an embarrassing amount of time eating meals at Whole Foods. I have had study groups at whole foods. They have great sushi. And edemame. And soup. With corn bread. Seeing as they are technically a grocery store, I will refrain from naming all the food they carry, but let’s just say that they pretty much single-handedly fed me most of my time in Portland. And provided the backdrop for about 75% of my stories. Oh, also, they have a coffee bar. Just sayin’.


Gorgeous views of Portland and one of Portland’s swankier establishments – in a good way. We had our law school “ball” in the Eastland Hotel the first two years, so I’m quick to associate the building with pretty dresses, free wine, and general mayhem. Ah, good memories from the ballroom… upstairs, as in up fourteen flights of stairs, is the fabulous Top of the East bar area with areal views of Portland. I’m notorious for getting turned around up there (which direction is south?) but I could look out those windows forever. The bar area has leather couches, fireplaces, and martinis… actually, I’m not so sure about the fireplaces, they could be martini-induced, but I do know the Top of the East and Eastland hotel hold some of my favorite memories - martini and non-martini.



(this and other photos here)

Okay, so this is a bar, too. Are you noticing a pattern here? I’m pretty much the farthest thing from a foodie and, as I said, I was broke, single, and holed up in the law school library for most of my time in Portland. Bars were the preferred option. Grace is a church converted into a bar. No joke. Stained glass window, choir balcony, super classy, always warm (you know that means it’s really hot, right? ‘cause I’m the girl that’s always cold.), good music (recorded usually but sometimes live) and quiet enough to hold a conversation.


Nothing beats an everything bagel with vegetable cream cheese and a Green Mountain coffee on Thursday mornings after Biz Ass class. That’s Business Associations – but you knew that, right? This was the best ever reward for making it until Thursday morning at 11:00am. Trust me.


Touscan Scrambled Eggs. My stomach is growling just thinking of them. The wait is usually a few minutes, but they serve Coffee by Design coffee while you are waiting, so it’s almost like you’re not waiting at all. Coffee by Design does that. Chic and cozy – it’s my favorite place to go if I’m looking for a real, sit-down breakfast. Parking isn’t great, and the placement of the stop signs are a little weird (but not new, Nicole) but it’s totally worth the tour around the homeless shelter and the screeching from the back-seat. Also, they serve Vermont maple syrup. Now that is the way to my heart, one spoonful after another.


This is getting longer than I intended, so I’ll just combine the last two… and they’re another two bars – surprised?


The Armory is in the basement of a hotel and sports leather chairs and wallpaper that looks like old books lining wooden bookshelves. Brian Baru has live music and an outdoor porch and a bartender that gives me free shots. Which is pretty much the only time I do shots. He doesn’t take no for an answer. 

So, those are some of my favorite Portland, Maine places. At least off the top of my head. Who knows, maybe after this weekend, I'll have a few more to add to the list.

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