Must-try places in Portland, Maine

If you spend even a short amount of time wandering around the streets of Portland, Maine you will notice that it’s a food lover’s paradise—or maybe just mine. There are so many unique cafes and restaurants intricately woven into this amazing city. I’m trying to explore at least a couple of new places a week and still have many, many more to go but here are some of my favorites so far!

  • The Holy Donut – Possibly 50% of the reason I moved to Maine. These amazing potato donuts are simply out of this world. Plus they use natural flavors and local ingredients so it’s a snack you can feel less guilty about.

Holy Donut, Portland, Maine

  • b. good – It’s actually a chain here in New England, but doesn’t have the feel of your average run-of-the-mill chain. They have excellent salads, quinoa bowls, and burgers. What I like most about them is that they only use local and seasonal ingredients. They pride themselves on being able to tell you which farms they get every individual ingredient from. It’s a great, healthy option…I just wish it wasn’t next door to the Holy Donut—always makes my lunchtime decision 10x harder than it needs to be.
  • Bard Coffee – For the serious coffee drinkers who want more than just a quick jolt. These baristas seriously know coffee. The proof is in the pudding…and being named Portland’s Best Single Location Coffee House.
  • Portland Lobster Company – This mostly outdoor venue has the best in-town lobster rolls. It has a fantastic deck right on the water which is perfect for listening to the live music they have most nights.

Portland Lobster Company

  • The Crooked Mile Cafe – Tucked away on the little, inconspicuous Milk Street in the Old Port this café is well worth finding. They have an extensive breakfast and lunch menu and great, funky décor. It’s the perfect place for a leisurely lunch or a quick to-go breakfast sandwich.
  • Tandem Coffee Roasters – I have a soft spot for this place because their West End location is right by my apartment. They also have excellent coffee, tasty pastry options, and a large outdoor seating area.
  • Five Fifty-Five – Hands-down the best truffled lobster mac & cheese I’ve ever had. It’s a guaranteed food coma experience, but with the great wine and romantic ambiance it’s totally worth it. The reason for the name? It’s located at 555 Congress Street.

Five Fifty-Five, Portland, Maine

  • Rosemont Bakery and Café – This place has a little bit of everything! They have your regular café staples, but it’s also a great place to pick up some local produce, snacks, and some prepared meals—perfect for those nights when you just cannot eat leftovers again but don’t want to go out to a restaurant.

I’m still exploring this incredible city so stay tuned for more great finds!

Hiking: Pushing yourself to your breaking point in the best way possible

This past weekend I went on a hiking adventure that nearly pushed me to my breaking point. I like to think that I’m pretty healthy. I walk about three miles a day, I eat a lot of fruits and vegetables, and I do yoga. Overall that’s pretty good, but when you’re climbing your first 2,000 foot mountain it means diddly-squat.

Pleasant Mountain, Maine

Having lived in the flatland of Illinois my entire life up until recently I have been ill-equipped to deal with any kind of elevation. Hills? What are those? Mountains? You’ve got to be kidding. For me part of Maine’s allure is that it’s so different from Illinois. Drive an hour outside of Portland, ME and you’ll be in the mountains. Drive an hour outside of Chicago, IL and you’ll see nothing but flat farmland.


That’s why I was so excited to meet up with about twenty women of the Alpine Women Collective to hike Pleasant Mountain in Bridgton, ME. It was 72 degrees out and sunny—perfect weather for a hike. I got to talk to a lot of amazing women—a couple of whom are from the Midwest, too! It’s pretty cool how much people will open up when they’re engaging in an activity. I was doing pretty well for the first three miles since it was more of a gradual incline. However, the last half mile was at such a steep incline that I was panting like crazy and my legs felt like they were on fire.

“Am I dying? Is this what dying feels like? Everything hurts!”

I was pretty sure I wasn’t dying, but decided to wait until I got to the top of the mountain to be sure. I pushed myself harder than I ever have before. Since I was on a mountain and not a treadmill I couldn’t just stop if it got too hard. I was out in the wilderness. I HAD to make it to the top…and I did.

Breaking point

Getting to the top of Pleasant Mountain was incredible. I had never conquered anything as big or amazing as that in my life. The views were absolutely breath-taking and I felt such a high from accomplishing it and not giving up. There are many parallels that can be made for conquering a mountain and conquering life in general, but I’ll refrain since they’re pretty obvious and a bit cliché anyway.

Yay! We made it!
Yay! We made it!

If you ever have the opportunity to hike up a mountain I definitely recommend that you do it. Take as many breaks as you need, but you have to make it to the top. I promise you that you’ll be glad you did.

In what way have you pushed yourself to your physical or mental breaking point? What was the outcome?

Safety in Chicago vs. safety in Maine

Ever since I moved to Portland, Maine I’ve had several people talk to me about safety.

“Don’t walk alone in shady areas at night. If you have to walk at night don’t wear headphones. Always be aware of your surroundings. Don’t leave your doors unlocked.”

Safety in Chicago

I truly appreciate my new friends and coworkers looking out for me, but what they seem to forget is that I grew up in Chicago. Granted I lived in the suburbs for most of my life up until I moved to downtown Chicago last year, but the same basic, safety rules applied even in the suburbs. It’s just what you did. From a very young age my influencers taught me how to be safe almost to the point of paranoia:

  • Always wear your purse across your body, not just on one shoulder.
  • Always have the zippers of your purse facing towards you, not away from you.
  • Never hang your purse on the back of your chair at a restaurant.
  • If you’re walking home and you feel like someone MIGHT be following you, change direction so they don’t see where you live.
  • Walk with a purpose even when you’re a tourist.
  • Keep your windows and doors locked when you’re not at home.
  • Never advertise the fact that you live alone when you’re talking to strangers.

I admit some of these rules sound a little silly, but I’ve been following these rules for most of my life and have never been robbed, attacked, or had my purse stolen. Again it could just be the paranoia that was instilled in me at the age of 5.

Safety in Maine

Technically I now live in the Parkside neighborhood of Portland, and while the neighborhood has its characters I don’t consider any of them dangerous—just a little kooky. In fact I have a pretty good rapport with most of them. They usually ask how pup is doing, how I’m doing, etc. Most of my neighbors are pretty nice people who keep to themselves.

I like to think that I have a pretty good head on my shoulders, and while anyone can fall victim to a crime I do believe that if you use a little common sense (and perhaps a little paranoia) you can significantly cut down your chances. Moving to a new city is scary, but I’m glad that I moved from a truly scary, crime-filled city to a pretty calm one.

What safety habits have you picked up in your new city?

Bring your dog to work (every) day

One of the cool things about my whole moving to Maine thing is that I got a new job. It was about time anyway as I had been at my previous job for 2 years which seems to be enough time for me to learn my job and do it repetitively enough to get completely sick of it. I have changed jobs every 2-3 years for my entire working career which has given me quite a varied resume: retail, doctor’s office, more retail, ophthalmology office where I ended up having 3 different job titles, and most recently finance.


So it was a bit surprising for me to land into another finance position since I barely made it through high school math, and I’m more of a creative person anyway. However I’m really liking this job so far. I’m pretty much doing exactly what I was doing at my old job, but there are a few key differences: I get to wear jeans to work every day, there’s a constant supply of coffee and snacks, and it’s a dog-friendly office so I can bring my dog to work any/every day.

Since Carm is getting up there in age there are days that I really worry about leaving her alone all day. On those days especially it’s nice that I have the option of taking her to work with me. It also forces her to exercise a little more since she mostly paces around the office the entire day, other than the times she wanders into random executive offices and plops down in front of their windows. She’s a sucker for a good window, and I have to admit walking into to people’s offices under the pretense of looking for my dog is a pretty good ice-breaker.

Hanging out in the VP’s office

Some jobs are made better by the people you get to work with every day. It certainly helps if you have a good boss, or a friend you can vent to. In my case it’s made better by having my best friend with me. She has quickly become known around the office as the entitled pup who does what she wants when she wants. It’s her world and I’m just living in it. As long as she’s here with me every day putting up with my moods and schlepping across the country with me, she can pretty much have whatever she wants.

What are some perks about your job? Who makes your job better?

When you have a bad day in your new city

Bad days happen. Sometimes you get stuck at work longer than usual, the dog does her business in the house, the upstairs neighbors keep you up late blaring their music, you drop everything you pick up, you forget to pack a lunch, etc. This can even happen all in the same day…

Bad day

The point is that bad days happen no matter where you are. However when they happen soon after you move to a new city you may think it’s a sign from the universe that you shouldn’t have moved; you should’ve just stayed where you were.

“This wouldn’t have happened if I was still living in Chicago.”

Yes it would have, and it did! What got me through those tough days back home in Chicago was that I only had X-number of days before I could move to Maine…and now I’m here!

So here are some things I try to remember when I’m having a bad day in my new city:

  • Bad days happen everywhere. Not every day can be magical. If you’re staying anywhere longer than a week, you’re going to have a bad day here and there. That’s just how real life works.
  • Tomorrow will be better. It has to be, right?
  • At least I’m in my new city! When I’m having a bad day and it feels like nothing is going right I just remind myself that I’m in Portland, ME—this amazing city that has a rich history, the sea, and so much lobster! It’s hard to stay down when I remember how many great attributes this city has.

Lobster roll

  • If I can move across the state/country/ocean, I can handle anything. It’s easy to forget our biggest accomplishments. I moved across the country just a month ago and I constantly forget how amazing that is. If I can move across the country all by myself I can certainly handle a crappy day once in a while.

Pemaquid Lighthouse

Bottom line: It takes a lot of guts to pick up your life and move to a new city. Some days are going to be harder to adjust to than others, and that’s okay! It’s all part of the process. You take the good with the bad. If you can end the day saying, “Yeah, but at least I’m here,” then you know you’re in the right place.

What helps you get through a tough day? What helps you put things in perspective?

Comfortably pushing yourself outside of your comfort zone

This past weekend I ventured out of my comfort zone but still acted completely within my comfort zone. I’ll explain. Lately I’ve been feeling on edge about not having a strong friend circle here in Maine yet. I know, I know—it’s only been a month, but I got it in my head that I really need to come out of my shell and open up to people here and for some reason I felt like that wasn’t happening fast enough. I’ve met up with a few fabulous people already, but I started psyching myself out with thoughts like, “Is that enough? Should I be doing more? Should I attend every networking/social meetup I can find and just go all in?”

Comfort zone

The truth is I really like doing things by myself—and with my dog, preferably. I get such a sense of fulfillment when I’m curled up reading a good book or going to see some live music by myself. I am putting myself out there and trying to get to know people so I shouldn’t feel badly for wanting a balance between the two.

I am an introvert which means that I get my energy from within. Doing things by myself is how I recharge and prepare for big social interactions—like getting a cup of coffee with a new friend. It’s my “me time” and it’s equally important as my venturing out of my comfort zone time.

So this past weekend I found a way to do both: venture out of my comfort zone, but still do it in a way that was within my comfort zone—i.e. by myself. Friday night I went to see some live music at Port City Blue in Portland followed by a walk through the Portland Museum of Art. I loved how most of the artwork at the PMA was done by past and present Mainers along with people who just love the state of Maine. I definitely fell in love with a few paintings there along with their rich backstories.


On Saturday I went up to Bradbury Mountain State Park in Pownal, ME where I completed my first ever solo hike up a mountain! I’ve been hiking before, but never by myself. The experience was incredible. It was such an adrenaline rush, but at the same time I was more at peace than I’ve been in weeks. I may be becoming addicted to hiking because I joined two hiking meetup groups which is another great way for me put myself out there while still doing something I enjoy.

Bradbury Mountain, ME

It’s all about balance. It’s about pushing yourself outside of your comfort zone, but doing it in a way that’s comfortable for you.

How do you push yourself out of your comfort zone, but in a comfortable way?

My unwavering allegiance to Chicago-style pizza

Of all the things I love about Maine, there is one thing that I can’t get here and that is Chicago-style pizza. Having lived in the Chicagoland area my entire life up until now, I grew accustomed to (and love) deep-dish, cut it with a knife and fork, feel like you swallowed a brick kind of pizza pie. I’ve had a few arguments with Mainers about what the “right” kind of pizza is. Most prefer the thin, soggy, fold in half, New York style pizza. After much debate of Chicago style vs. New York style pizza we ultimately agreed to disagree. I’m severely outnumbered out here so I’m now known as the kooky Midwestern girl who likes deep-dish pizza–a title I wear proudly.


I’ve been to a couple of pizza places here in Maine — Otto Pizza and Portland Pie Company. Both places have very tasty “pizzas.” At the Portland Pie Company you can even select a beer-flavored crust! But to me, it still doesn’t compare to Lou Malnati’s or Giordano’s pizza. What I have learned to do when I’m going out for “pizza” is to think of it as going out for flatbread pizza which is basically what it is out here anyway. Once I stopped expecting to get my Midwestern version of pizza I was actually able to enjoy it.

Lobster salad
Easily one of the best salads I’ve ever had.

A good trade-off to not having Chicago-style pizza is how ubiquitous lobster is out here. Nearly every restaurant here in Maine has at least one lobster dish on their menu, and I’m well on my way to trying them all. I feel a bit like Bubba from Forrest Gump when I list all the different kinds of lobster dishes I’ve tried so far: lobster rolls (butter and mayo varieties), lobster bisque, steamed lobster, baked lobster, lobster mac & cheese, lobster tacos, lobster and pasta, and lobster salad. I love lobster so at least I’m in the right place for that. Now if only I can find a good substitute for another Chicagoland staple–Portillo’s, I’ll be all set!

What are some of your favorite dishes from your hometown? What’s been a good trade-off for you in your new city?

How to say YES more often

Some people are natural joiners: they say yes to any invitation, they’ll show up to events by themselves, and can strike up a conversation with anyone. I am not one of those people. For whatever reason my first instinct is to decline an invitation, even for things I’ve done before with great success. I really don’t know why my knee-jerk reaction to things is to say “no.” Perhaps it’s because my first word was “no” and has stuck with me ever since, or maybe I’m just afraid to try new things.


In these moments of doubt when I’m inclined to decline an invitation or walk into a new environment I try to remember the following things:

  • Saying “yes” is not as big of a deal as I make it out to be. Chances are the person who is inviting me to an event isn’t weighing the pros and cons of my answer so neither should I. Just say yes.
  • I can always leave if I’m not having fun. Somehow reminding myself that I’m in control helps tremendously.
  • I might actually have fun! Who would’ve thought, right?
  • If not, a book is always at home waiting for me. A good book can salvage any evening.
  • Talking to new people isn’t as scary as I think it is. In fact most people respect those who make the first move and speak first. Even if you’re just commenting on the venue or the event itself it shows that you’re open to conversation and usually helps put the other person at ease, too.


  • I don’t have to put myself out there every day. I’ve started making this deal with myself: If I go out 1-3 times a week for a networking event, meetup, coffee date with a friend, etc. then I can spend the rest of my nights that week doing whatever I want without feeling guilty or feeling like I “should” be doing something else.
  • It’s a learning experience no matter the outcome. Whether I walk away having made a few new connections, learned a new skill, or just had an okay time, I still took a chance and learned more about myself. I think that’s actually the coolest part—having come away from a new experience having learned new things about who I am and what I’m capable of.

It isn’t easy for us introverts to put ourselves out there. It’s scary, awkward, and completely out of our comfort zones but sometimes you just have to say yes, and do it. Over time it DOES get easier.

What thoughts put your mind at ease when you’re pushing yourself outside of your comfort zone?

Finally moving to Portland!

Now that I’ve been in Maine for three weeks, it’s time for me to make another change. I’m moving out of my Airbnb and into an apartment of my own in Portland! I’m a little sad to go because I’ve been very lucky with my Airbnb. The owners have been so friendly and helpful. They have gone above and beyond for me in so many ways and have always made clear that they are around should I need anything for myself or the dog! They are dog people who traveled cross-country with an elderly dog, too, so they know how difficult it can be…even without them getting hospitalized for three days like Carm was last weekend.

Enjoying our deck at the Airbnb
Enjoying our deck at the Airbnb

As nice as it has been to live in Freeport for a few weeks, I’m excited to finally be moving to Portland. It’s what I’ve been working towards for over a year. In fact this time last year I was just about to travel to Portland for my week-long solo excursion. It was during that vacation that I knew I had to move here. When I think back on it, it’s amazing how far I’ve come in just a year.

This weekend I’m moving to the West End neighborhood. It is my favorite neighborhood in all of Portland. I love the history, the old cobblestone, tree-lined streets, and the local pubs and restaurants. It’s also a quiet residential area and just a 25 minute walk to work! I couldn’t be more excited to call this place my home.


It still hits me in random bursts that I’m actually in Maine. I know it intellectually, of course, as I’m cruising down the 295 expressway past Back Cove Bay to get to work, or when I’m wandering the streets of the Old Port on my lunch break, but every so often it hits me that I really am here. I finally made it. I hope I always get that awestruck feeling from time to time no matter how long I stay in Maine.

Did you still have awestruck moments after you relocated?

Don’t settle for the first option

This week I learned an important lesson: don’t settle for the first option. It can seem alluring to choose whatever is behind door number one without looking to see what’s behind doors two and three. It’s the safe bet. It means not putting yourself through the additional anxiety of holding out for something that may or may not be better than the first option. What makes it more difficult is that life doesn’t tell you how many “doors” or options you have. That first door may be all that you get, or maybe you get a hundred doors. You just don’t know.

Don't settle
The view from my Airbnb, a.k.a. door number two

To give you a personal example, I have been freaking out about not having an apartment lined up yet since I have to be out of my Airbnb in two weeks. I knew that I had some “if all else fails” options like staying in a hotel or my cozy car, but I really wanted to have a secure, semi-permanent place to live. I found a couple of apartments that were a bit above my price range and not in the Portland neighborhood that I preferred. It would work, but it’s not what I wanted. Part of me thought I was acting crazy.

“I need a place to live! This seems fine; I could live here if I had to. Sign the lease! Sign it! Something better may not come along!”

However something was telling me to wait just a little longer. It was terrifying, and I was second-guessing myself right up until I was approved for a lovely, one-bedroom apartment in the West End that just so happened to be $100 less per month than the previous apartment I was looking at. Not only that, but I also didn’t have to put down a pet deposit or pay an additional pet rent per month. For any pet owner who has looked for an apartment, you know how rare that is.

Damariscotta River, Maine

The same lesson reiterated itself this weekend when I went shopping for a new bed. Since I only brought to Maine what could fit in my car, a bed was the first big-ticket item I had to get. I really dislike shopping. Shopping for books on Amazon for hours is one thing, but going into a store and having to deal with crowds and obnoxious salespeople just puts me on edge. I went to several, big-name stores and found a couple of options, but with delivery fees and pushy salespeople I just wasn’t feeling it. I decided to call it quits for the day and just enjoy wandering around downtown Portland.

Then I stumbled across a local furniture store in the Old Port called Hub Furniture Company. It’s third generation owned and has been running for 103 years. I loved the history already. When I walked through the door I was quickly greeted by one of the salesmen who I instantly took a liking to. He wasn’t pushy, he listened to my needs, and he was efficient—all the things that make up an ideal salesman in my book. I walked out of there having purchased a new bed for $200 less than the other places, and they are going to deliver and assemble it for me for free. It pays to shop local.

It also pays to hold out for the better option. It’s usually out there. You just have to listen to your gut, and do what feels right for you. If something isn’t sitting well with you for some unidentifiable reason, then move on. It wasn’t your door. Hold out for the door that’s right for you.