what to do with 16 hrs in Portland, ME

Let me tell you now — I am NOT a spontaneous getaway person. I plan my trips out far, far in advance, with color-coded Excel spreadsheets. I book everything ahead of time. I take immense joy in planning and organizing trips, so much so that sometimes I wonder if I should've just been a travel agent (as obscure as they now are).

This trip to Portland was as spur-of-the-moment as I could get. I waffled between spending the 4th of July in the city catching up on work, and heading to Portland, where I'd always wanted to go.

It was on my 18 for 2018 list to take a trip by myself. Contrary to how many people feel, I actually love traveling by myself. It allows me to do whatever I want, on my schedule. It allows you to meet new people, forces you to be a little uncomfortable, and really gives you time to hear your own thoughts.

I decided I needed to get out of the city and be with my thoughts for a bit. I hadn't traveled, not really traveled, since my 2016 trip to Southeast Asia. And before that, not really since my 2014 two-month backpacking trip through Europe. Sure, I'd taken some small domestic trips (Seattle, New Orleans, Florida, Toronto, Palm Springs), but it didn't feel the same. Wanderlust seems to be ingrained in me, and it really hurt that I was so bogged down by the day-to-day necessities like work, teaching classes, etc. etc. to leave this city.

Portland is by no means a large or scary or impressive trip, but it was a first step in the right direction.

I spent a little less than 16 hours there, but honestly I think anywhere from 1-3 days is perfect. Keep reading to see the highlights!

Day 1

Travel to Portland

Downeaster to Portland

Amtrak is one of my favorite things on the planet. I take it when I go to NYC — I've taken the bus before and it's not as reliable. I also get pretty carsick, so I love the speed, convenience, and wifi!! on the train. It allows me to get work done, take in the countryside, and read without feeling nauseous.

Plus, it reminds me of the trains I used to take through the Italian countryside (and basically everywhere) when I backpacked through Europe, which is kind of nice.

The Downeaster was only $24 each way (I use Wanderu to book and check prices!). They have a ton of times available. I chose a 9 AM train, but you can also do a 6 AM one to maximize your time in Portland; the train takes almost exactly 2.5 hours.

8:45 AM: Arrive at the train station.

9:05 AM: Depart from North Station.

11:35 AM: Arrive at 100 Thompsons Point, Portland ME.

12 PM: Check into my hotel. Drop my stuff off, grab water, and practically run to get food, because I just had a protein bar on the train.

Note: I stayed at the Inn on St. John, a 10-minute walk from the train station. The walk does involve going under a highway, but I've played accidental Frogger across a highway in Rome, so I wasn't too annoyed. The service there is great, and it's small and intimate.

First Stop: The Holy Donut

The Holy Donut, arguably Maine's most famous donut shop, has an assortment of donuts made of potato flour. They have two locations — one is downtown and the other is on Park, ~5 minutes walking distance from my hotel.

12:30 PM: There's almost no line and plenty of selection, probably because this location isn't as touristy. I get a gluten-free dark chocolate sea salt donut and a small cold brew to cut the sweetness (I can't eat donuts without coffee!), and sit inside to savor the combo.

Note: The gluten free donut is made of an assortment of flours, including garbanzo flour. It's not Paleo and also not dairy free (it has buttermilk), but I took some Lact-aid and I was fine.

Next Stop: Vintage Shopping + Book Browsing

1 PM: Surprisingly, the donut fills me up, and I feel more alive with the combination of sugar and caffeine, so I began to wander through the park, and then down Congress St. I marvel at how quiet it is compared to Boston.

I find a ton of vintage shops, which I'm super pumped about. I have a strange sense of style — I like unique pieces but have an almost "hippie/boho" vibe (think Free People meets a secondhand store). Consequently, I've found some of my favorite pieces at secondhand stores.

P.S. You can shop my closet on Poshmark for great deals or shop my Amazon favs here.

I stop in with the intention of just browsing (like looking at the awesome Meow dress above!), but end up purchasing a couple of things: a velvet-trimmed tank and high-waisted cotton shorts for just $15 total from Material Objects.

1:30 PM: Further down the street is Longfellow Books. I'm drawn in by the carts of used books they have outside; similar to secondhand clothes, I love secondhand books even more. Not only are they cheaper, but I like the idea that someone else has read and loved the book (also why I like library books).

I buy three for $24 total: Harper Lee's Go Set a Watchman; Dr. Paul Hammerness and Margaret Moore's Organize Your Mind, Organize Your Life; Carl Jung's Modern Man in Search of a Soul.

They pretty accurately depict my interests — I love classic books that make me think (I didn't enjoy To Kill a Mockingbird per se, but it did make me think a lot) but also love psychology/self-help/productivity books.

Next Stop: LB Kitchen for a Late Lunch

LB Kitchen - Breakfast Bowl and GT's Kombucha

2 PM: I'm hungry again at this point. Actually, I'm surprised the donut held me over for so long.

I'd had my eye on LB Kitchen; their menu sounded so wonderful that I could envision myself eating there every day for a week and not get bored, so I walk over there.

I stick with the basics and get the breakfast bowl, which comes with a coconut fried egg, lightly-dressed organic mixed greens, and pickled veggies. I add avocado mash (it has truffle oil!) and beet-cured gravlax (smoked salmon), plus kombucha for extra gut-health.

It has a cute vibe, and I stay there for an hour and a half reading Go Set a Watchman.

A Break from the Heat: Nickelodeon Cinemas

Nickelodeon Cinemas

I had passed by this cute little movie theater on my way to LB Kitchen, and while I had planned to sunbathe at the East End Beach that afternoon, I decide, last-minute, to catch a movie instead since it's SO frickin' hot.

That's one of the perks of traveling solo — you can literally do whatever the F you want.

4 PM: I stop by the Portland Food Co-op for some snacks (cashews and an organic Fuji apple — I'm boring — for $5) and catch the 4:20 PM showing of Ocean's 8 at Nickelodeon Cinemas.

To my delight, it's only $5 because it's a Tuesday. Win!

The theater is small but there aren't a ton of people there. I grab a seat in the back and settle down to enjoy the cool air and the movie.

Last Stop: Getting R & R

6 PM: I had originally planned on going to Taco Escobarr per a friend's recommendations, but I wasn't too hungry yet and the place was completely full when I walked by.

Not wanting to deal with people (plus I was exhausted), I wander back to the hotel, taking a different route than I did before. I settle in to shower, do a face mask, lie about in my comfy robe, and watch TV.

8 PM: I'm starting to get hungry again. I embrace the weird eating schedule and order a gluten free / dairy free pizza from Otto's. I know they have it in Boston, but it's one of the few delivery options around here and I always wanted to eat pizza in bed!

9 PM: My pizza comes and I devour everything except one slice. Guess I was hungry! I contemplate seeing if they have Drizly because wine would make this complete, but I settle for drinking copious amounts of water and watching rom coms I love (Bride Wars and 27 Dresses, anyone?).

11 PM: I force myself to turn off 27 Dresses so I can go to sleep. I set my alarm for 7:30 AM so I can make the 8:15 AM spin class I booked, and turn off the lights. The benefits of an interior room and a king bed are that it's dark and I fall asleep immediately.

Day 2

Fourth of July Workout: Jibe Cycling Studio

Jibe Cycling Studio

It's pitch dark when I wake up since there are no windows in the room, but I suspect it's later than I think.

I roll over and check my phone. 7:15 AM. Good job, internal alarm clock! It feels like sleeping in for me, since I'm usually up between 5-6 AM.

7:20 AM: I go through my morning skincare routine, get dressed, pack, and check out, grabbing water and some fruit (they have nectarines and plums!) from the free continental breakfast spread. I also drop off my backpack, telling them I'll be back later to get it.

8 AM: I walk to Jibe Cycling Studio, regretting already drinking all the water I had grabbed (I left my reusable water bottle in my backpack and I feel lost without it). The studio is super cute and clean; I feel a little out of place since I'm quite obviously not a regular, but I'm excited for spin. It's something I try to do once or twice a month to balance out my other workouts, plus it's intense and way fun to dance to the beat.

8:15 AM: The class starts and absolutely flies by. The energy in the room is great and the instructor (who's also the owner) was fabulous.

9 AM: Since I'm super sweaty, I shower at Jibe. The showers, towels, and amenities are so nice that I find myself wishing I could workout here every day...

Breakfast: Blake Orchard Juicery

Blake Orchard Juicery

9:30 AM: I walk down to Blake Orchard Juicery, praying that it's open since it's the 4th of July. It was recommended by a friend who's from Portland, and when I looked at their menu online, I was SO excited that they have grain-free granola and house-made almond milk.

It's open, super cute, and the bowls are even better than I expected. Almost as good as the ones in California and Hawaii, but you know I'm biased ;)

I get the green bowl (house made almond mylk, mango, banana, orange, seasonal greens, shredded coconut, and local raw honey; topped with Grandy Oats Oat & Honey gluten-free granola, fresh fruit, shredded coconut, and local raw honey drizzle), subbing grain-free granola for the normal one, and sit down on a bench in Post Office Park to eat it.

Caffeinate: Bard Coffee Shop

Bard Coffee - Cappuccino

9:45 AM: I have an obsession with cute coffee shops, and Bard Coffee Shop is right next to Blake Orchard. I head there, get a cold brew, and settle down to read, do my monthly and mid-year reflection in my Passion Planner, and work on this blog post.

The cold brew is one of the strongest I've tried and I'm a little shook (in a good way). I end up staying for almost four hours. Feeling guilty about sitting there for so long, I get an almond milk cappuccino before I leave.

Late Lunch: Isa

Isa - Portland

2 PM: My friends stop by Portland on their way back from Canada and swing by to pick me up for a late lunch at Isa.

It's small inside, but beautiful — a mix between modern and traditional. They have patio seating, but we opted for indoors since it's sweltering outside. The menu is small and carefully curated; I chose the tacos. Typically they're duck carnitas, but for the day they had braised veal.

With a lightly dressed salad, beautifully crunchy radishes, and rich veal, the tacos were small but satisfying. Would definitely recommend!

The Trip Back

3 PM: I had originally intended on taking the Amtrak back at 7 PM, but suddenly, I was ready to go home. There was no more I wanted to do in coffee shops, I didn't want to go through the hassle of finding dinner somewhere that was open yet close to the train station, and I needed to de-compress a little. So my friends drove me back, and it was a quick ride — just under 2 hours — since there was no traffic.

Places I meant to go but didn't make it to:

  • Duckfat: The place with the famous fries. I'm a huge fry lover, but honestly I think I'd go here in the fall/winter — it's too hot for heavy food!
  • Central Provisions: Tapas-style, Asian-fusion type dishes. I'd go with a group rather than by myself.

  • Maine Squeeze: The Juicery's sister smoothie shop. I only had time/room for one smoothie in my belly (sorry!).

  • Urban Farm Fermentory: I love their kombucha — I tried it at the Boston Public Market. Ran out of time for a tour/tasting.

  • Scales: Upscale seafood. Considered going for apps + drinks by myself, but again, ran out of time.

  • Tandem Coffee: Super sad I missed out on this one. Next time!

  • Taco Escobarr: Tacos! Margs! Again, would go with friends because tacos are best with good company (and also go when it wasn't packed).

  • Local Sprouts Cafe: This was similar to LB Kitchen, so I opted for that one.

  • Whole Foods: Don't hate! I love going to different states' Whole Foods... I'm a whole-hearted Whole Foods lover.

Bonus: Packing List

Weekend packing list

All my stuff fit into a backpack and my trusty Madewell Transport Tote. I ended up overpacking — I definitely didn't need all of this stuff (items italicized are ones I didn't use), but better safe than sorry!

Note: I've linked where I got the products from. Some of these are affiliate links; most of them aren't. Just in case you see something you like and want to buy!






And that's it! What're your favorite places for a quick weekend getaway? Any places in Portland you've been to that you've absolutely loved? What am I missing? Let me know below!

P.S. Huge thank you to everyone for their recommendations prior to this trip!

What to do, eat, see with 16 hours in Portland, ME
Weekend Packing List