Travel Guide: Portland, Maine in 72 Hours

Portland, Maine. 

When you first think of this small northeastern coastal city, you may conjure up images of summer beach days and sleepy nights on a porch swing under the stars. And that's totally valid. Maine is full of gorgeous beaches and cozy cottages with wrap-around porches. 

But the East Coast Portland can claim some other stellar accolades like being named one of GQ's Coolest Small Cities in America.

And though the jury is out on whether or not Portland actually has the most restaurants per capita than any city in the U.S., it has earned a reputation as one of the foodie-destinations in America - being named Bon Appetit Magazine's "America's Foodiest Small Town" in 2009 and being named one of the top twenty on The Huffington Post's list of "Americas Best Food Cities" in 2014. 

And HELLO, Matador Network named Portland, Maine the best craft beer city in the WORLD. The WORLD! 

Picturesque foliage, small-town vibes, cute shops, restaurants galore, craft breweries and a strong coffee culture - Portland, Maine was the absolute PERFECT place to spend a Halloween Weekend out of crazy NYC. 

3 days in Portland was the perfect mini-getaway and the long weekend was packed with SO MUCH FOOD and fall happiness. Keep on reading for tips on making the most of your 48-72 hours in this perfect little place! 

Long Weekend in Portland Maine


Boda | very thai kitchen and bar 
671 Congress

Upon arrival in Portland we immediately set out from our Airbnb for a quick walk up the block to Boda, a restaurant on Congress St. with a late night menu. 

Despite it being 10:30 p.m., there were tons of folks eating in the mood-lit, rustic space with an open kitchen. 

We grabbed a seat at the bar next to a very Maine-looking-lumber-man who was very friendly. Many people at Boda seemed like regulars, which is always a good sign. 

The price was certainly right for Boda's late night menu, with plates ranging in price from just $4-$10! Abby, I don't think we're in Manhattan anymore!


We each tried one of Boda's creative cocktails. I wish I could remember which I ordered, but my memory is failing me. I do remember that Abby got the Thai Basil Tom Collins, because it was super basil-y! And what I also know is that the bartender at Boda really did "craft" our cocktail. There was zesting happening. 


The special "chips" of the night were pumpkin flavored, instead of their usual lobster chips. However, Abby and I were a little confused by them. They were satisfyingly crispy and crunchy, but the flavor was certainly not pumpkiny. I didn't like the taste much at all, though I kept finding myself reaching for more anyway.


boda portland

Kanon-Krok are a traditional Thai dessert - essentially coconut-rice pancakes. They're made in a specific indented frying pan called a khanom krok pan- which is where the name comes from for this Quail Eggs dish. Each individual egg comes served in one of the pan's indented sections. 

These eggs were DELICIOUS though the concept of eating an entire egg in one swift bite took some getting used to. 

The whites were perfectly crispy and the yolk was just the right amount of creamy-drippy. Paired with scallions and soy sauce, these Quail Eggs had the perfect Thai flair to taste far from "just eggs."


Fried and seasoned, these were delectable. However, a lot of places do a similar serving of sprouts.


Our unanimous decision was that these shrimp skewers, served with a spicy garlic lime dipping sauce, were the most flavorful dish of the bunch. I could have easily eaten 10 more skewers.


The last part of our Late Night Eats on Night #1 was a trip to the nearby gas station for a pint of Talenti . This was a fabulous decision despite needing to interact with some extremely inebriated locals. 


Portland Maine Travel Guide
Running in Portland Maine

We headed out early for an 8 mile run and despite a few wrong turns at the start, ended up looping the scenic Back Cove.

At the end of our run we took a little break to check out an adorable farmer's market before a pretty brutal uphill climb to our Airbnb. We were short a few tenths of a mile, which, as Type A runners, meant looping the block a couple of times until we hit a nice even 8!

Portland Maine Farmer's Market


40 washington ave.

Silly's Portland Brunch

With my appetite worked up (let's be real, I wake up with an appetite fully worked up regardless) we headed toward Silly's Restaurant for a good old fashioned brunch.

This place was an absolute hit with the group - the food was just greasy/diner-y enough to prepare for a day of brewery and bar-hopping but not too over-the-top for a group of girls who try to remain somewhat healthy.

The eclectic decorations perfectly toed the line between kitschy, cute and odd - hello Gingerbread man and woman salt and pepper shakers!

Though we passed on imbibing at Silly's they had killer Bloody Mary and Mimosa options. The weather was crummy, but on nice days they have an adorable outside seating area too. 

Silly's Portland


We considered the "bowl of bacon" but the "serious commitment" menu description discouraged us. The smaller portion was still plenty and it was SO crispy without being burnt. 


This was a breakfast flat bread smothered in Peanut Butter and topped with sliced bananas, warm berries and pumpkin pie spiced granola. I don't think I need to say more. 

As a group, we agreed on the impossibility of deciding between sweet & savory at breakfast time - so this dish served as satisfaction for our sweet teeth!


3 eggs scrambled with Silly's apple wood smoked pork, cheddar cheese, fresh tomato, bbq sauce, jalapenos and bacon with home fries. 

The best move of the brunch, in my humble opinion, was ordering a side of honey mustard for the home fries, which were more like beautifully crisped potato wedges. I pretty much drank an entire cup of honey mustard by the end of the meal. 


The vegan version of scrambled eggs, this scrambled tofu was loaded with veggies like onions, peppers, mushrooms and broccoli along with more home fries, salsa and vegan spicy sauce. 

Silly's Brunch


We walked around a little to work off our brunch, stopping into some cute stores and bakeries as we we ambled around. Shoutout to Lori's Natural Market Place, for indulging these city-dwelling health food freaks who went up and down the aisles talking about different products without actually purchasing anything. 

Two Fat Cats Bakery
47 India Street 

We stopped in this shop that specializes in pies pies pies and ate with our eyes. 

Two Fat Cats Bakery Portland Maine

Standard Baking Co. 
75 Commercial Street 

This was an impressive bakery - they had TONS of different breads, pastries, cookies, etc. and it was packed with people. The best part? Free samples! 


As I mentioned before, Portland is PACKED with breweries both big and small. There were a few that we managed to check out on Saturday - and while we could have spent dayssss brewery crawling, I think the amount that we fit into our schedule was perfection! 

Foundation Brewing Company
1 Industrial Way #5

Foundation Brewing Company

Foundation was my type of brewery! Flights, tons of IPAs and picnic tables - we happily posted up here for awhile and played a few card games while enjoying our brews. 

My favorite part was that to order your flight, everyone gets a cute little dry erase board and then your flight is filled in that order, so you always know which you're sampling!

Naturally, I chose 4 IPAs - the Epiphany, Venture, Afterglow and Wanderlust. It was interesting to see if I could tell the difference between a Maine IPA, American IPA and a "Hoppy Farmhouse." 

While I would have liked Foundation to have some board games, had the weather been nicer, it looked like they had a fun outdoor area with a food truck and corn hole. 

Foundation Brewing Company is open to the public Wednesday - Saturday from 12:00PM - 7:00PM, Sunday from 12:00PM-5:00PM and Monday from 12:00PM-7:00PM. They offer tastes ($2/4 oz sample and $4/10 oz sample), flights ($8/4x4oz flight), tours and growler fills. 

Foundation Brewing Company

Allagash Brewing Company
50 Industrial Way

Allagash Brewery Tour

Allagash Brewing Company is one of the largest brewing companies in Maine and specializes in wheat beers. Unlike the tasting room at Foundation, Allagash offers the full-on tour experience - for FREE! (They recommend reserving a tour ahead of time, which you can do on their website). 

Tours tend to fill up, so be sure to book yours in advance on their website. 

I really enjoyed this tour (although that could have had something to do with the fact that I had already enjoyed an entire flight of IPAs). 

Since it was Halloween weekend, there were candy buckets along the tour route along with a free sample of their top selling beer - Allagash White. 

I was pleasantly surprised by how much I enjoyed the Belgian-style wheat beer, which usually isn't my preference. 

The one thing that really excited me during the tour was our guides explanation of an experimental beer using CARROT SUGAR. I was a few beers deep, and audibly gasped while using my outdoor voice to announce, "I LOVE CARROTS!" I interpreted everyone's look of confusion as, "They must not have heard me," and again exclaimed, "Sorry, I just really love carrots!" 

Sadly, there was no carrot-sugar beer on the tour, and I spent the remaining half hour drafting a note in my phone with all of the beer-related puns I could come up with for future Instagram captions. I was absolutely cracking myself up with gems like

Sitting on the dock of the IPA 
Sippin' on Belgian and juice 
Yeast Mode 
Hoppy Campers

At the end of the tour we found ourselves in a room FILLED with barrels of beer. We got to try another 5 or so - but just a heads up - if you go on the tour, you won't be able to buy beer in the tasting room afterwards. Some law about how much they're allowed to serve you. 

The samples were delicious, though very rushed. 

On our way out, we noticed some signs saying  "Hot Chocolate" and "Donuts" - pointing the way to a creepy door. We naturally followed them, snuck into the door, and found ourselves in a haunted house-esque scenario. But despite the creepy mannequins and people dressed up like zombies, the promised donuts and hot chocolate were provided. 

We stocked up and made our way to the tasting room/entrance and the fact that we weren't allowed to purchase any more beer was A-OK with us considering we had a feast of donuts to enjoy. 

(Also, I couldn't figure out how exactly the bartenders in the tasting room would know we had been on the tour - I think you would be fine to buy a beer post-tour!) 

Shipyard Brewing Company
86 Newbury Road

Shipyard Brewing Company

We entered the Shipyard Brewing Company via the store and were immediately sucked in to their many glasses, stickers, koozies, bottle openers, etc. I ended up getting a glass that I absolutely love! 

Next we hit up the tasting room where I enjoyed a flight of fun-flavored beers with some fruity notes along with a super barrel-aged boozy beer. My favorite was the Little Horror of Hops. The place was hoppin', but I was sad that there were no board games! Luckily, I had come prepared with my own deck of cards.

If you're in town mid-week, Shipyard offers full brewery tours fo FREE and they include a flight and 10 oz beer. You should reserve ahead of time on their website.

Urban Farm Fermentory
200 Anderson Street 

Urban Farm Fermentory

When we'd had our share of beer, the tasting tour didn't have to come to an end because Portland is also home to a tasting room for kombucha, cider, mead and gruit (a beer style using little to no hops). 

The space was super cute, with couches that we got nice and cozy on. 

I absolutely LOVE kombucha, so it was fun to get to try inventive flavors. It was also my first time trying mead, which I didn't love. I did like some of the ciders, though! 


Eventide Oyster Co. 
86 Middle Street

Eventide Oyster Co.

This is one of the most popular spots in Portland, and from my research, I knew to expect a wait no matter when we tried to get in. 

We opted for a very late lunch in the hopes that wait times would be lower, and it was somewhat successful. We waited around 25-30 minutes for a seat at the counter by the bar.

The reason I had insisted on waiting to eat here was for a taste of their famous lobster roll - a unique brown butter version served on a pillowy, buttery bao bun that melts in your mouth. 

Girls Weekend in Portland, Maine

I sort of expected to be disappointed by the hype, but was blown away by the flavor. Luckily, we had only ordered 2 to split among the four of us, otherwise I would have been tempted to eat 5. 

We also sampled the fried oysters with thai apple slaw, mint and tumeric but the lobster rolls were definitely the stars! 

Where To Go in Portland, Maine

I would say it was worth the wait, and recommend going during non-peak hours.

Union Restaurant
390 Congress Street

Sweet Potato Dessert

The great thing about being in Portland, was that we could afford a ~fancier~ dinner experience without breaking the bank. 

We were in love with Union Portland from the first time we saw their food on Instagram - and from the second Abby read about their sweet potato based dessert. 

Housed in the Press Hotel, Union Restaurant offers innovative American dishes using fresh local ingredients. 

Shaved Butternut Squash Salad 

Chopped Kale | Frisee | Pumpkin Seed Sorghum | Smoked Maple

Tasted just like fall! 

Crispy Brussels Sprouts 

Walnut Aioli | Charred Lemon | Extra Virgin Olive Oil

I've had better, but these were pretty flavorful.

Cast Iron Spoon Bread 

Pork Rillette | End of Season Tomato Jam Thyme

This was my first time trying spoon bread, and I was a big fan! Not really shocking considering the fact that I love cornbread! 

The rillette I was a little more iffy about. I don't particularly like my meat in paste form. 

Pork Loin Chop 

Cider Brine | Celery Root Fondue Brussels Sprouts | Chestnut Honey

Though we loaded up on appetizers and sides, we did split one of the entrees. We chose the pork because it didn't include any ingredients that people were opposed to. 


Bok Choy | BlackVinegar | Soy Caramel

This was a little strange to us. 


Molasses Cremeux | Brown Butter Powder Pate Brisee | Burnt Marshmallow

Abby, the sweet potato queen, was more than excited to find this on the menu. It didn't taste overwhelmingly of sweet potato, but it was deliciously sweet! 


Orange Fritter | Hazelnut Mexican Hot Chocolate Sauce Orange Powder

Union Portland Review

Chocolate overload in the best way possible! 

Another positive thing about Union was their cocktail menu! Delicious sounding drinks using some of my favorite flavor combinations like tequila, lime and ginger. 

The food at Union was solid and fresh and the atmosphere was nice. I will say that we were definitely the youngest clientele in the restaurant. 

Bonus? Before our reservation we got to watch a pretty crazy fire show outside city hall! 

Portland Maine Halloween


The Snug 
223 Congress Street

Each booth at this perfectly-homey-divey-feeling bar creates a private little nook which was a perfect way to end the night. This isn't a fancy place, but its a great place to low-key chill. 

And the beer list got a thumbs up from me - love Long Trail


Bard Coffee
185 Middle Street

Bard Coffee Portland Maine

Portland is packed with coffee destinations, and while it's not my specialty, I appreciated the tasty Americano and the vibe inside of Bard Coffee. It was bustling on a Sunday morning, the staff was friendly, and their espresso machines were just the right amount of intimidating to give them some serious coffee cred. 

Blake Orchard Juicery
19 Exchange Street

Blake Orchard Juicery

What better way to tell your body, "Sorry for all the beer" than a fresh smoothie bowl? None. 

We were so excited to find this spot and when we walked down the stairs into the somewhat hidden shop, we were greeted by an impossibly delicious sounding menu. How does one choose between so many options? 

There are tons of add-ins including housemade peanut butter, shredded coconut, bee pollen, grain-free-granola, hemp seeds, etc. 

The space was small but cute, with tons of little Polaroids and a couch to sit on while we waited for our smoothies. 

It took quite awhile to make the smoothie bowls, but when they were finally ready all was forgiven because they were beautiful and delicious. They were just the right consistency, filled with goodness like homemade almond milk and fresh fruit, and beautiful to boot. 

I also have an obsession with letter boards like the ones from Letterfolk that I included on my Holiday Gift Guide and thoroughly enjoyed using the one at Blake Orchard for a quick little smoothie bowl photo shoot. 

The Holy Donut
7 Exchange street, 194 park avenue 

Holy Donut Portland Maine

It's no surprise that I needed to make a stop at The Holy Donut to try their potato-based donuts. 

The line was out the door on a Sunday morning and the smell was heavenly. There were tons of choices, and luckily most flavors were still available by the time we arrived around 10:30 a.m. 

We tried a variety of flavors, including the one made with sweet potatoes! The sweet potato ginger glazed was unique but for the most part, you couldn't tell that the batter for these doughnuts used Maine potatoes! 

I thought they were delicious - not to mention really photogenic! We snagged a space along the counter and dug in! 

I was surprised at how delicious the dark chocolate Maine Potato cake tasted - especially topped with coconut! The Holy Cannoli filled doughnut was a sugar bomb in the best way, but the Chai was disappointingly bland. 

Overall, this donut shop impressed me- I would definitely make a return trip! 

Holy Donut Maine


You've had your caffeine, you've gotten some nutrients, and you've had your fair share of sugar - what's next? SHOPPING in the stupid-cute shops on Exchange and Market streets. Below are just a few that we stopped in - but you could spend hours wandering the shops! 


I got the world's prettiest avocado ornament here. I think Christmas ornaments are a great thing to collect on your travels. When you decorate your tree every winter, you can reminisce about all the places you've been. 

I might have failed at buying a Maine-related ornament, but I will certainly love my glittery avocado ornament for years to come! 

21 Exchange Street

Pretty paper, pretty cards, pretty journals. 

41 Exchange Street

Some cute women's clothes and accessories for decent prices. 

43 Exchange street

SO MANY FLAVORS! And free samples, too! Of course, I had to buy myself a bag! I fell in love with the rosemary & thyme! 


Portland Head Light and Fort Williams Park
1000 Shore road 

Portland Travel Guide

I remember this being a particularly pleasant Uber ride - though everyone we encountered in Maine was super friendly. 

We were like kids in a candy shop as we oohed and ahhed at the fall foliage. When we pulled up to Fort Williams Park and the Porland Head Light, we were beyond excited to get out and explore. We walked around the cliff, took tons of pictures, and eventually settled onto picnic tables where we were completely content to sit and stare out at the water - agreeing that all of our favorite places were near the water. For me, watching a sunset at Cedar Beach will always be my happy place. But looking out at Portland Harbor on a brisk but sunny fall day with friends was pretty high up on the contentment scale. 

bite into maine 
Various locations 

Bite Into Maine Lobster Roll

The satisfaction only grew when we stopped by the Bite Into Maine food truck - which we happened to catch on their last day of the season. Their lobster rolls are highly regarded one of the best in Maine, and we decided that even though we were full - we could manage to split one, New England Style of course. 

It was well worth the somewhat steep price for a few bites each because it was brimming with lobster and not overly doused in mayonnaise. 

Definitely the cherry on top of our trip to Cape Elizabeth. 

Bite Into Maine Portland


90 Congress street

Lolita Portland Maine

Our last group dinner was spent at a cozy little Mediterranean restaurant called Lolita, featuring a wood-fired grill that gives the entire space a warm, comfortable feeling. 

The menu was great for sharing and we got to taste a ton of different items. The lighting wasn't ideal for pictures, but was great for enjoying good food and good wine. 

Lolita takes pride on where they source their food from as well as simple preparation - letting the food speak for itself - my favorite part about the Mediterranean cuisine. 


We went for the 3 for $10 option on this portion of the menu, and I really enjoyed both the Tunisian Carrot Puree and the Roasted Eggplant. 


The Moroccan Lentil Soup with turmeric and cilantro impressed the group while the much anticipated Ricotta Gnocchi with poached carrots failed to live up to expectations. We also ate the Mezze Platter and I went HAM on the labneh. 


We also split the Grilled Game Hen served with Brussels Sprouts, sweet potatoes and chorizo and it was absolutely delicious! 

Portland Maine Travel Guide


This group of girls are never one to say no to dessert - and we ordered both the warm milk + house baked cookies and coconut pudding with pistachio which was, in my opinion, KILLER. 

To think, I used to hate coconut. 



Bramhall is just hidden enough to constitute as a speakeasy - though it's not too difficult to find. On our way there, we had a phenomenal Uber karaoke session before descending into this dimly lit space specializing in creative craft cocktails. 

While it took awhile for us to attract the attention of a custom-clad waitress (it was Halloween weekend, remember), the cocktails were flavorful and unique. I opted for the Satan's Lawn Chair - made with Tequila Blanco, Honeydew Melon, Genepy Des Alpes, Lava Tincture, Lime and Mint Garnish. 

Perhaps more impressive than the drinks are the daily homemade Rice Krispie Treat specials. They must have known I was coming, because the flavor of the night was peanut butter! We demolished this and I absolutely loved it - it was so light and somehow not overly sweet - while really tasting like peanut butter. 


REVE Cycling Studio 
559 Forest Ave. 

REVE Cycling Studio Portland Maine

From our Airbnb, I was able to run to REVE Cycling and enjoy a class in this beautiful, airy and sunny studio. 

While the bikes weren't the newest things I've seen, the rest of the amenities were wonderful, the staff were friendly, and the class was refreshing return to spinning without all the bells and whistles of studios like Flywheel, Swerve, etc. Just cycling - plain and simple, which I can appreciate every now and then. 

After class, I ran around since it's the best way to explore a new place! I stopped at a bunch of stores as I went, including CHART Metalworks, also featured in my Holiday Gift Guide

I had such a nice morning slowing meandering my way around the east end and eventually back to my Airbnb - taking pictures and enjoying the sights and stores along the way. 



Mi Sen Portland Review

I was on my own to explore on Monday, and after spinning and running around site seeing I had worked up quite an appetite. 

Not normally one for Thai food, I had a strange craving for noodles and made my way to Mi Sen on a whim. I ended up absolutely LOVING the Beef Khao Soi special that I ordered - a noodle bowl with the most tender meat I've ever had! [Slow-cooked beef in a rich and creamy curry served with egg noodle, garnished with crispy noodle, red onion, scallion, cilantro, lime and a side of pickled lettuce]. I ate every last bite along with the deep fried taro rolls which were delicious as well. 

Since eating at Mi Sen, I've had Thai about 6 or 7 times which is more Thai than I had ever previously eaten in my life. I definitely recommend a visit to Mi Sen, especially if you're in Maine during the colder months. It was so satisfying. 


Travel Guide Portland Maine

Before heading out, I wandered the shops on Congress Street and actually liked them more than the popular Exchange/Market Street area. 

There were fun second-hand clothing stores, a store full of socks, and a used bookstore that I could have wandered around in for hours. The area seemed young and hip, and I was glad that I stumbled upon it before heading home! 


I couldn't have asked for a more perfect weekend getaway from the city. There was great food, great drink and the great outdoors! 

I would definitely come back for another trip to this perfectly-sized city. 

What do I need to do next time I'm in town?? Leave your recommendations in the comments and let me know if you end up using any of my suggestions on your trip to Portland!