A Weekend for 20-Somethings in Portland, Maine: Breweries, Shops & More!

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Want to visit a hipster capital city that boasts a vibrant art community, tons of adorable shops and a killer beer scene? Then we’ve got the perfect destination for you! In addition to the oft-visited Portland, Maine breweries, there are so many things to do in this historical and charming city.

As a New Englander, I have been wanting to take a weekend trip to Portland for a long time now. I can’t believe I had never been before! The city has so much to offer. There are tons of art galleries and a great museum, lots of bookstores, boutique shops, and most importantly for me, amazing food. I didn’t have a single meal I didn’t like!

I certainly recommend visiting Portland when the weather is nice, as you’ll want to walk by the waterfront and spend tons of time exploring outside. Visiting in mid-May was perfect for us. We were lucky enough to have mostly 70 degree weather for our trip!

If you’re thinking of stopping by Maine for a weekend getaway, read on for a Portland weekend itinerary.

Where to Stay

We went back and forth a bit about booking a hotel or a rental space, and ultimately decided to go with Airbnb. We stayed at the Skofield Inn, which was very charming and quaint. There were five rooms on the property, and luckily it was pretty quiet the weekend we were there.

Ultimately, we were happy to have a bit more space than a typical hotel room for a comparable price. Plus, it was a 10-minute walk to downtown!

If a hotel works better for your plans, below are some of the popular spots:

• Portland Harbor Hotel: Great central location, free WiFi, a gym, a restaurant & other amenities
• The Press Hotel: Historic and charming hotel located at the former home of Maine’s biggest newspaper
• The Francis: Modern and cozy inn with friendly staff, and incredibly close to downtown

Day 1: A Museum Visit & Some Foodie Fun! 

We took the day off of work on Friday to really maximize our weekend in Maine. This turned out to be a great move, because the Portland Museum of Art offers free admission on Fridays! We signed up for a one-hour time slot in advance, and got to peruse with limited crowds.

After visiting the museum and beginning to take in all that downtown had to offer, we were ready for lunch. Quality seafood was high on our list of priorities for the trip, so we headed over to Highroller Lobster Co. for lobster rolls. The space is funky with a retro diner vibe, and the food came out SO quickly! We got classic lobster rolls with butter and garlic mayonnaise, plus french fries with Old Bay seasoning (the best!)

I had never had lobster in such a comfortable, casual restaurant vibe before, but it was a great experience. I would 100% go back!

After lunch and popping into a couple of shops, we headed back to the inn to settle in and get ready to go to the waterfront for dinner. There are a bunch of great restaurants near the water, but in my opinion, your best bet is Solo Italiano. They are famous for their Pesto Genovese, and after indulging in the dish, I can tell you it’s for good reason! It was the lightest, creamiest pesto I’ve ever had, and the pasta was super fresh.

We sat indoors, but they offer patio seating as well. If you visit on a nice day, I’d recommend taking advantage of the outdoor seating to enjoy the waterfront ambiance.

Day 2: Retail Therapy and Some Portland, Maine Breweries

While we puttered around downtown a bit on Friday, we really got in the shop-til-you-drop mindset on Saturday. As a bonafide bookworm, one of my goals was to hit as many bookshops as possible. I would say that we succeeded!

Longfellow Books had a great collection of both new and used books in a spacious and inviting setting. We also visited Yes Books, a massive secondhand bookshop with rare titles, and Sherman Books and Stationery, which I went into twice because I loved it so much!

If you prefer to shop for clothes rather than books, you’re still in luck. There were a surprising amount of vintage and resale stores that peaked my interest, including Haberdashery, where I got a couple of brand name items in perfect condition.

All this shopping made us thirsty (and tired), so we went to go chill in the sun on the patio of The Thirsty Pig. Of the many Portland Maine breweries, this one is super relaxed, located right in the thick of the shopping action. The outdoor seating was exactly what we were looking for.

Chances are, if you are planning a trip to Portland, Maine, breweries are high on your priority list. Taking in all of the different brewery vibes is a must, so we didn’t stop here! A short Uber ride took us to South Portland for a reservation at Foulmouthed Brewing. While there wasn’t much else in this area to explore, the brewery was great. We had delicious appetizers to munch on while enjoying our beer (plus, we indulged in a couple of their unique cocktails).

Our dinner Saturday night was a little less classic Maine, and a little more eclectic. We ended up ordering a charcuterie board and paella from Local 188, which offered up a variety of Spanish and Mediterranean dishes. The restaurant was a short walk from our accommodations, which we appreciated after a busy day!

Day 3: Mimosas at Brunch, A Java Jolt & Portland Head Lighthouse

To kick off the last day of our trip, we grabbed brunch at Marcy’s Diner. It was so fun to build our own mimosas! The food offerings are pretty classic diner fare at reasonable prices. I got their veggie omelet, which was just the thing I needed to start the day off right.

Then, we had a tricky time deciding between all of the hip coffee shops. We ended up grabbing lattes from Speckled Axe, which is tiny but full of character. Their wood roasted coffee is pretty spectacular!

Last but certainly not least, we checked out the Portland Head Light and Fort Williams Park to get those classic Portland photos. We were incredibly lucky to have such a gorgeous day to visit. It was a blast walking around and taking in all the sights. If we’d had more time, we would have grabbed a picnic blanket to sit outside and relax with a good book.

What We’ll Do Next Time

After such an incredible spring weekend in Portland, I will definitely be going back soon! There are still a bunch of places we didn’t have time to visit, so here’s a brief list of what we’ll prioritize on the next go around:

HiFi Donuts

These donuts looked absolutely scrumptious, and it seemed to be a very popular spot to check out. They serve us made from scratch, old world style donuts with sustainable coffee. Need we say more?

Coffee By Design

This craft-roasted coffee spot looked adorable, but was unfortunately closed when we passed by in need of caffeine. Though there were many coffee shops in the area, I made sure to jot this one down for future trips!

Sunset Cruise

Our Airbnb guide actually recommended a sunset cruise, but the dates we were visiting had already been booked up. Cruising around the Casco Bay Islands at sunset in the spring or summer sounds pretty unbeatable, though…so next time!

The Honey Paw

We were recommended The Honey Paw just as we were on our way out of town, but the menu made us practically salivate. It’s a contemporary bistro with Asian-inspired noodles and other delicious bites.

Allagash Brewing Company

Allagash is one of the Portland, Maine breweries that I had heard great things about. I was bummed to find out Allagash hadn’t reopened for in-person visits when we were planning our trip. They are reopened now, and you won’t need a reservation to go after May 29. Allagash is an independent craft brewery serving up their signature Allagash white, plus a number of wild, sour, barrel-aged, and spontaneously fermented beers.

Do you have a favorite New England destination?