Adventures in Portland, Maine

I mentioned in my last weekend wrap-up that I spent this past weekend gallivanting around Portland, Maine with Drew and Colin. We were in town for the Shipyard Old Port 5K (also a half marathon) and, unlike last year, we had an extra day to spend gallivanting due to Airbnb arrangements. (This extra day kind of made this post extra rambly… brace yourselves, readers! Or feel free to abandon ship now!)

Last year, we arrived early Saturday afternoon after fighting traffic on I-95. We stayed at the La Quinta hotel, which was 2.5 miles away from not only the race location but also the fun areas of downtown. After picking up our race packets at the Maine Running Company [now a Fleet Feet], we wanted to have lunch at Duckfat but there was a wait of at least an hour, so we settled for a brewpub down the street. After wandering Commercial St (the main drag by the ocean) and trying not to melt in the heat, we had a delicious sushi dinner at Benkay, and then went to Trader Joe’s by our hotel to pick up provisions like bananas and bottled water and a cart full of local beer. We awoke super early the next morning, arrived at the starting line about an hour before gun time, ran our race, drank some beer at the post-race party (before 9am!), showered, then hit the road home, stopping for brunch at the Maine Diner and hitting up the Kittery Outlets on the way. It was a lot crammed into two short days, and we were really looking forward to the extra time this year to relax and explore the city.

Drew and I took Friday off and used that precious free time to do some yard- and housework and get things in order before we left to pick up Colin at work. He was able to leave early as well so we were on the road to Portland by 3 and thus were able to beat pretty much all the summer weekend traffic – huzzah! (We did hit a bit of rush hour traffic once we neared Portland, but still made it to our Airbnb place by our check-in time.)

I had splurged a bit on a GPS watch the weekend earlier, and was giving it a trial run during the trip. After a lot of research, I opted for a Garmin Forerunner 15. It seems really similar to the Forerunner 10, except it supposedly has a battery life of 8 hours while in GPS mode, as opposed to the Forerunner 10’s GPS life of 5 hours. My reasoning: if I ever run a marathon, I’ll likely take longer than 5 hours to finish and I’d hate for my watch to crap out before I cross the finish line. Also, the 15 has a built-in fitness tracker and counts your steps each day. After trying out the Breeze app and ultimately deciding it wasn’t useful because I don’t have my phone on me 24/7, I thought having a tracker that I wear would be more accurate and informative.

The fitness tracker part of my phone started getting bossy during our road trip.

The fitness tracker part of my phone started getting bossy during our road trip. (I kept answering, “YOU move!”)

I noticed from reading her blog that the Attempted Runner named her GPS watch Garfield, and I really liked the idea of naming my new digital running buddy. So, stealing Attempted Runner’s idea and also her “Gar,” I decided to name my watch Simon Garfunkel. Garfunkel because it was the only other “Gar” name I could think of at the time, and Simon because the fitness tracker part of it reminds me a little of Simon Says. Plus, it goes well with Garfunkel. My watch will be called Simon for short. (Thanks for the idea, Attempted Runner! … I hope you don’t mind that I borrowed it!)

Where was I before I went on that gearhead tangent? Oh right. Portland. We arrived around 5.30 and took our time driving up Munjoy Hill to where our Airbnb was.


Drew’s mom is a big supporter of Airbnb, and I had been curious to try it out. Like last year, the hotels around the Old Port neighborhood filled up super fast after race registration opened, and the closest we’d be able to get to the East End starting line was the same La Quinta as last year… about 3 miles away. Just for yucks I started browsing Airbnb and found a cute little place just steps from the starting line at the top of Munjoy Hill.

Approximate locations of race starting line, Airbnb house, and La Quinta

Approximate locations of race starting line, Airbnb house, and La Quinta

It ended up costing a little more than La Quinta would have, but it was cozy, clean, and relaxing; saved us so much hassle with getting to and from the race; was within walking distance of downtown and all sorts of awesome things in the city so we didn’t have to pay for parking; included 2 bedrooms, a little sitting room, and a private bathroom; and had a gorgeous view of Casco Bay instead of a parking lot:

One of the bedrooms. SO much nicer than the hotel!

One of the bedrooms. SO much nicer than the hotel!

View of the bay from our bedroom

View of the bay from our bedroom

Plus, as a bonus, the Airbnb came with the friendliest cat I’ve ever met – Rudy:


Our host told us about Rudy when we checked in, and said that if we were allergic or didn’t want his company just to close the door to the hallway and he wouldn’t bother us. Drew and I both love cats, and Colin seemed to have a good time playing with Rudy using his dangly bookmark, so I think I can safely say that we all enjoyed our furry co-host.

Rudy loved having his belly rubbed

Rudy loved having his belly rubbed

After getting settled, we set out to find some dinner. Remembering the trip-that-never-was to Duckfat last year, we tried there first in hopes we’d get in. Luckily, Duckfat is more known as a lunch place, so there were free seats at the usually packed bar just for us. Drew and Colin opted for panini and, since I had eaten a late lunch on the ride up, I chose a small basket of fries with lemon-herb mayo (yum!). Their fries are pretty delicious, especially the poutine that we also decided to get and share. We all sampled local brews, too – Colin an Allagash stout, Drew a Bunker Machine pilsner, and me the U.F.F. Sour Cidah:

Duckfat is more than a little hipster and serves all their beverages in mason jars

Duckfat is just a tad hipster and serves all beverages in mason jars

Unable to resist their dessert menu, we added an order of doughnut holes to share. They were incredible… soft and lovely with just a hint of citrus and topped with powdered sugar. They were good enough that we seriously discussed going back again just to get dessert!

After dinner we figured we’d wander the city a little and maybe stop by a bar. Whereas last year we spent most of our time on Commercial St by the water, this year we stuck to more “inland” streets (in quotes because we were still only a few blocks from the ocean). Having recently been in town for a friend’s bachelorette party, I remembered a really good bar/dessert place we’d visited nearby called The Bar of Chocolate. The lads heartily agreed that they liked the name and off we went.

A sign in The Bar of Chocolate that made me smile

A sign in The Bar of Chocolate that made me smile

It wasn’t too busy when we got there so we situated ourselves at the bar and drooled over the menus placed in front of us. It was unfortunate that we had eaten so much at Duckfat because their dessert specials for the day looked incredible! Especially the strawberry-rhubarb crumble. We were all way too full, so we opted for drinks and decided we’d see if we were any hungrier after.

Left to right: Drew's sazerac martini, my espresso martini, and Colin's Irish Coffee martini

Left to right: Drew’s sazerac martini, my espresso martini, and Colin’s Irish Coffee martini

Sadly our stomachs didn’t cooperate and no room was created for extra dessert, but we did spend a good two hours at the bar just chatting and laughing and, in Colin’s case, talking with the bartender about Ireland. It was close to 10pm when we left and the streets were alive, at least in that downtown area. Bands were playing in beer gardens, buskers were performing on corners, and we could easily see what a young, vibrant city Portland is.

Even though our Airbnb room was cozy and nice, a refreshing night of sleep was not to be had. There was some kind of party going on nearby and loud music and laughter made it hard to fall asleep until much later than we hoped. To top it off, our room faced the sea so the sun rose directly into our eyes at the crack of 5am. Drew and I were zombies in the morning, but Colin – who had slept in the other room that had no view and thus no direct sunrise – was bright-eyed and bushy tailed. We knew we wanted to hit up a local diner for breakfast and, after looking at menus online, decided on the Miss Portland:

Miss Portland Diner, featuring an original Worcester diner car

Miss Portland Diner, featuring an original Worcester diner car

For a Saturday morning there wasn’t much of a wait and we were browsing menus in our booth within 10 minutes of arriving. Apart from our hostess who looked like she hated life, all the other staff were friendly and helpful and our food came pretty quickly after ordering.

A history of the diner

A history of the diner

Since we were in Maine, I felt it only right to order something with blueberries. I went with the (giant!) blueberry pancake with real maple syrup, plus a scrambled egg on the side because I thought protein would be a good call before the race.

When it arrived, Drew exclaimed that the pancake was bigger than my face. And indeed it was!

When it arrived, Drew exclaimed that the pancake was bigger than my face. And indeed it was!

It might just have been the best blueberry pancake I’ve ever had. Colin’s breakfast came with two smaller versions and he thought the crust tasted sweeter than usual, even without the syrup. I don’t know how they make them, but they’re delicious! The only part of my breakfast that was disappointing was the iced coffee. The lads loved their food, and the hot coffee they both ordered seemed up to snuff.

Full of tasty breakfast we set out on our day of adventures, beginning with a trip up the highway to Freeport. Freeport has been the home of L.L. Bean for as long as I can remember (quite possibly always), and in the past decade or so Bean has expanded into a giant retail extravaganza, with multiple stores, a cafe, an outdoor entertainment area, and even a giant version of their famous winter boot:


Look out, Colin!

Look out, Colin!

We poked around in some outlet shops (there’s an “outlet village” across the street from Bean) and introduced Colin to the wonder that is Orange Julius. (Since when does Dairy Queen own Orange Julius?! Whatever… I was happy that I could have one… it had been years since my last!) By total serendipity, we also stumbled on a sign advertising that night’s performance in Bean’s little outdoor concert area – Josh Ritter. Colin is a big fan and he was completely blown away that one of his favorite artists was doing a free show that night. Bonus!

We all felt pretty shopped-out after having only gone in 3 stores, so we hopped back in the car and returned to Portland. The Old Port race was hosting a Summer Festival all afternoon, with live music, food trucks, a health and wellness expo, and – most importantly – bib pickup. We decided to walk the scenic route from our Airbnb, partly to scope out where the starting line would be, and partly to enjoy the glorious weather. The Airbnb was right near the Eastern Promenade, a big park on a hill overlooking the bay. Across the street from the park are a bunch of gorgeous, huge Victorian-era houses that we enjoyed gaping at and pretending we could afford. This was one of our favorites:


We wandered around the park for a bit and Colin and I reminisced about running up the giant hill during the 5K last year. We were both so glad we wouldn’t have to do it again this time around!


We were also glad we didn’t have to tackle the Stairs of Doom again – the stone steps that lead from the Eastern Promenade Trail up to the park through the woods:

The bottleneck on these stairs last year was incredible

The bottleneck on these stairs during last year’s race was incredible

We eventually made it down to the festival, Colin and I picked up our bibs, and we wandered around the pier for a few minutes, scoping out the vendor tents. The band that was playing was okay, nothing we really wanted to stick around to see, especially since it was getting to be uncomfortably warm out. Plus, we were nearing kickoff of the Netherlands v Brazil third place World Cup game! (Priorities!)

Even though there was still about an hour before kickoff, we meandered our way off the pier and over to the Sebago Brewing Company, the brewpub we had settled on for lunch last year after Duckfat was too crowded. We had enjoyed sampling their beers on their little patio last year, and vaguely remembered TVs inside, so we figured it would be a safe bet for the game. We nabbed seats at the bar right by a TV and settled in. I was really intrigued by their specialty cocktails menu, but Drew forced the “mocktail” menu into my hands with a look on his face that said “You need to hydrate!” Sigh. Water and a raspberry lime rickey it was. By that point, Colin had pretty much decided that he wasn’t going to run with me the next day, since his ankle was was still bruised and tender from his fall on Thursday, so he didn’t hesitate to order a sampler flight. The lads enjoyed their beers (especially the doppelbock), I loved the lime rickey… as well as a cheeky dragonberry mojito, and the sweet potato fries were lovely, even though it did take us more than 30 minutes to get them after we ordered (they weren’t busy at all). And, to top it all off, the Netherlands won! Oranje!!

By the time the game was over it was just about 6, and Colin wanted to go back up to Freeport to see Josh Ritter, who was going onstage at 7. However, we were still full of beer/cocktails and sweet potato fries – and absolutely freezing after sitting in the air-conditioned bar for so long – so we plopped down in a sunny spot on some grass to thaw out and give our stomachs time to catch up. (SO much food was consumed on this trip!) Then it was time for our return trip to Benkay, the sushi restaurant we had enjoyed so much last year. We were still cold so Drew ordered hot sake and Colin and I both got hot tea (Colin was waffling again about whether or not to run). I don’t know if Benkay had changed their menu or sushi chefs or what, but I was really disappointed by both the selection and the food this time around. The edamame was soggy, the selection of maki didn’t really tempt me even though I remembered last year’s being awesome, and the rolls I did get had overly chewy seaweed wrappers. The lads didn’t seem disappointed though, so maybe I was just being too picky.

We rolled ourselves back up the hill to our Airbnb and while Colin waited for his phone to charge so he could use his GPS, he taught us how to play one of his favorite card games. I really loved having the little sitting room in our Airbnb; it was a relaxing, cozy place to hang out, and Rudy even came in to hang out with us. Colin eventually headed off to Freeport while Drew and I read and charged up Simon. The Summer Festival was still going strong and the wind was carrying the music right up into our windows so I knew it was probably going to be another night of difficult sleep. At least I was ready for it this time!

Not only did the sunrise wake us early the next morning, but the PA announcer at the race did as well. Registration started around 5:30, and so did announcements apparently. (Man, sound really travels up Munjoy Hill from the piers!) I do remember hearing PA man say “It’s probably a little cooler than most of you were expecting” which made me really happy; after last year’s heat fest, I was ready for an earlier, cooler race. Thanks to the excellent location of our Airbnb, we had a much less stressful morning getting ready and making our way to the starting line, a journey that took all of 3 minutes. A full recap of the race itself is coming soon!


Colin eventually decided not to run, so my pointing, posing self ran it solo.

After racing, showering, and checking out of the Airbnb, we drove across the city to try out a breakfast place that had come highly recommended from a friend – Bintliff’s. Unfortunately, the whole process of washing off sweat and sunscreen and squaring up with the Airbnb host meant we weren’t arriving until 10ish, and the line for Bintliff’s was out the door and down the block. Luckily we knew a place. Back to the Miss Portland we went!

We got to sit inside the original diner car this time! I love the Worcester Diner clocks the old cars have. (Wormtown represent!)

We got to sit inside the original diner car this time! I love the Worcester Diner clocks the old cars have. (Wormtown represent!)

The wait was a bit longer this time, but the hostess was a different woman who was bright and happy and she ushered us into a booth in the old diner car. (We sat in the newer addition the day before.) I’m never very hungry right after I run, and even after a delay of a few hours I still didn’t think I could polish off another amazing pancake despite really wanting one, so I tried to focus on recovery foods. When my breakfast was placed in front of me, all I could think was that it looked like a child’s meal:

Scrambled eggs with cheese, cinnamon-raisin toast, a cut-up banana, and chocolate milk

Scrambled eggs with cheese, cinnamon-raisin toast, a cut-up banana, and chocolate milk

A child’s meal, perhaps… a delicious meal, yes.

After breakfast and a trip to the Trader Joe’s across the street to stock up on some local beers, it was time to say goodbye to Portland. We did make a stop in Kittery again for some outlet shopping (sales at Under Armour and 50% off the entire Puma store – yes!) and a Starbucks stop, then it was Massachusetts ahoy for a viewing of the World Cup final in the comfort of our own living room and an early night in our own cozy bed, in our quiet room with the blackout curtains. Ahh, home.

Have you ever been to Portland? What are your favorite places to visit there?

Do you have a nearby(ish) city you like to road-trip to?


12 thoughts on “Adventures in Portland, Maine

    • As a New Englander who’s frequented Portland, Maine for years, I’ve always been curious about Portland, Oregon! Hopefully we can visit our “other” Portlands soon! πŸ™‚

  1. Sounds like you had an amazing weekend! I actually went to the University of Southern Maine for my first semester of college, and I have a lot of fond memories of the Portland area. Unfortunately, I wasn’t old enough to take advantage of the amazing bars and local beers 😦 I’ve been wanting to get back for an adult adventure for a while, but any time we’re in Maine our schedule is jam-packed because it’s usually for a family event.

    • It was pretty fun! Sounds like you’re due a Portland trip soon πŸ™‚ I hear you about family plans though… awesome to see them, but sometimes you want to do something a little different!

    • Thanks! πŸ™‚ I came *this close* to getting the black and green watch instead, but I think I’m digging the teal now that I have it in person.

    • Thanks! I like “Mr. Nike.” I used to refer to my MapMyRun app as “MapMyRun Lady” (usually to yell at her) but it was way too many syllables. It never occurred to me to give her a name until just now!

    • Thanks! I love Portland πŸ™‚ The good thing about getting to run alone was that I didn’t have to worry if I was holding Colin back, or feeling bad if I wanted to keep going if he had to stop. I was thankful to have Simon so I could keep better tabs of where I was at!

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