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A Weekend in Portland Maine

I recently spent a weekend in Portland Maine around the Women in Travel Summit (WITS) travel conference. It was actually my very first visit to Portland!

Shockingly, I grew up just down the road in Massachusetts and had spent years visiting Bar Harbor and Acadia National Park. But, in all that time, I never stopped into Portland.

Known as “the other Portland” to some, this East Coast Portland does have quite a lot in common with its West Coast cousin. Both are known for their hipster culture, their outdoor activity options, and their dining and drinking scenes.

City Hall in Portland Maine with flowering tree in front

My Weekend in Portland Maine

I spent a week in Portland mostly inside a conference hotel, with lots of food and drinks mixed in. With some time around the WITS conference, however, I squeezed in two full days of tours and wandering to make sure I took advantage of being in a new city.

I also loved checking out some of Portland’s cool and quirky bars. I prefer to support locally owned and operated businesses everywhere I live and visit, so finding some local spots was important to me.

Luckily, I met a few lovely local ladies at the WITS conference who gave me insider tips!

Local insight cannot be overstated. I’ve said it before and I’ll say it again:

Travel blogs are great for sharing experiences and telling stories, but expat and local bloggers can actually help you plan a trip.

Seek out the locals to get real-time, comparative information!

If you’re doing a weekend in Portland Maine, check out these local bloggers to help you plan the best things to do:

Why Visit Portland Maine?

Portland offers quite a bit for such a small city! Based on Maine’s southern coast, Portland has a fascinating history over the centuries, including being a primary port for the new United States and also suffering through multiple disasters.

The city has been built and rebuilt several times, which is reflected in its architecture. Much of the old port is a rather monotonous Federalist style of plain brick, but it’s an understandably practical design given the multiple fires that tore through this area over time.

Portland Maine architecture is mostly plain brick federalist style

Today’s Portland is thriving, with the beer and food scene leading the way in putting Portland on the map for more and more tourists. It’s also well-known for its coastal views, with iconic Maine lighthouses readily available for your viewing pleasure.

To be fair, driving into Portland off the highway into what my friends and family called such a “cute city” was a real disconnect!

It’s not very attractive through that part. But, once you’re in the downtown area, it becomes very walkable and you’ll find lots of quirky little parts that make Portland fun.

Tours in Portland Maine

I took several tours around my time at the WITS conference. Before I even talk about them, know that they were all offered to me for free.

I also only did these tours, so I (obviously) can’t compare them to other similar tours! I won’t call them “the best” or “must-do” or whatever.

But I can honestly tell you how much I enjoyed the tours I took!

Historical Walking Tour with Maine Foodie Tours

That’s an awfully confusing title, isn’t it?

Yes, Maine Foodie Tours has branched out and now also offers a history tour! That’s because the history tour guide, Mike, was a foodie tour guide with a history problem.

For the record, my dad was a math teacher with a history problem, so I get it! I’ve also inherited quite a condition called “Did you know…” #sorrynotsorry

Mike is super passionate about Portland and that passion offers you a chance to learn while being very entertained.

Maine Historical Walking Tours group led by tour guide Mike
Small lighthouse statue in a pedestrian area of Portland Maine

Mike is like me: He’s a transplant!

He moved to Portland a few years ago and has made it his home. As I always say, expats are the best tourists (ok, he’s not a real expat, but he’s a transplant nonetheless!).

Mike’s interest in the city and its history is completely contagious. It was a cold, wet, and fairly miserable weather day for our tour, but he powered through with such enthusiasm!

Church door with a flowering tree beside it in Portland ME
Gate to Eastern Cemetery with a small plaque - Portland Maine walking tour

Some quick facts I learned on this history walking tour of Portland:

  • Portland used to be called Falmouth
  • Maine handles 90% of United States lobster production and this is a $500 Billion business
  • The city has burned three times! It’s been rebuilt and rebuilt again, making the city’s motto even more poignant: Resergam (I shall rise again).
  • The coast used to be farther back. If you go, check out Commercial Street, which used to be the actual water line with the US Custom House along the shore itself. They filled in that bit of land to extend the coast.
  • You can visit the Henry Wadsworth Longfellow House, which was the first all-brick structure in Portland. The Maine Historical Society manages it now. (Note that it is only open during the high summer season.)
Henry Wadsworth Longfellow house with an informational panel out front in Portland ME
Portland Freedom Trail plaque

If you’re doing a weekend in Portland, I highly recommend you book a tour with Mike to learn all the layers of this city.

Maine Brew Bus Tour in Portland

I LOVED the Maine Brew Bus Tour! Extra bonus: They also offer Brew Bus tours in Boston and in Providence. So, yeah, you know what I’ll be up to on my next family visit!

A small bus with a tour guide who shares history and culture, plus stops at various breweries, wineries, or distilleries…plus snacks?! It was ideal.

Maine Brew Bus is lime green and ready to board
beer samples at Rising Tide Brewery on the Maine Brew Bus tour of Portland
Visit Portland Maine for Rising Tide Brewery and other Brew Bus tour stops

They also gave us swag bags that included some valuable discounts at other local establishments, fun stickers, and a coozie.

Said coozie has since made appearances in Boston, DC, and in Scotland. Good advertising, Brew Bus!

Pro tip: They included a plastic water bottle in the swag bag. It’s for good reason (hydrate while drinking, people!), but PLEASE bring your own reusable water literally everywhere you go! You just need to develop the habit. Once you’re used to it, you’ll never need another plastic water bottle.

Samples at Stroudwater Distillery Maine Brew Bus

What I really love about the Brew Bus is their motto: Driving You to Drink Local.

Supporting local businesses helps tourists to delve deeper into the place. And, of course, taking the Brew Bus tour also means you have a Designated Driver!

I took a tour with Nate and Zach, while Don was in the other bus with Doyle. These guys love their jobs and it shows!

We had such a blast chatting, learning, and sipping all afternoon.

Cellar Door Winery Maine
Maine Brew Bus Cellar Door Winery sample setup

Our two buses stopped at the following locations:

The Maine Brew Bus goes to different spots all the time, however, so you could actually do several tours if you wanted.

Cellar Door Maine Winery Portland
GOT Quote I drink wine and I know things outside of Cellar Door Winery in Portland Maine

Portland Maine Custom House Tour

The United States Custom House in Portland was the busiest in the country for many years. It is also one of very few Custom Houses still in use as a federal office building today.

Portland US Custom House

One of its current employees, Jeffrey Porter, offers tours of the building just because he’s so interested in its history.

He walked us around, pointed out interesting features, and offered comparative photographs so we could see what it looked like previously.

While I loved learning the history of the building and of the area, what I loved most about this tour was Jeffrey’s genuine passion for sharing his insights.

He does these tours for free in his own spare time – just because he loves history and wants to share that love with others.

That is amazing!

US Custom House tour with Jeffrey in Maine
Information on the US Custom House in Portland Maine

This space can also be used for events. Looking for a cool networking happy hour spot, anyone?!

Where I Ate & Drank in Portland

Where I ate and drank in Portland was just where I ended up while bouncing around with new friends from WITS.

I’m no foodie blogger and I certainly wasn’t taking notes between sips of cocktails around town – I was just enjoying them!

But I can recommend a few spots…


I really enjoyed the poutine at Duckfat! It was my first taste of poutine, but, really, what’s not to love?!

The staff there was also super accommodating.

We mentioned we wanted to try several things as a group so they carefully split portions up for us into separate plates/bowls/cups.

Having waited many tables in my day, that’s above and beyond!

Eventide Oyster Co.

I also loved the oysters at Eventide Oyster Co. and especially the vibe sitting up at the bar watching the crew shuck them so efficiently.

I often defer to the experts in spaces like that.

I asked the server for recommendations for the best local oysters to try…he did not let me down!

Poutine at Duckfat in Portland ME
Oysters at Eventide in Portland ME

On the seafood note: I just picked up a handy seafood guide from a local conservation organization here in Scotland. You can usually find these details online or in person so you know what you can sustainably eat and what you should try to avoid.

Nosh Kitchen

I can also recommend Nosh Kitchen for burgers and beers.

I had about 2 hours between events and it was on the way back to my hotel, so I popped in with my laptop and thoroughly enjoyed it.

The staff were all really lovely and I stuffed my face while cramming some work in, too. #Winning

Portland Lobster Co.

Finally, I had a fabulous time at Portland Lobster Co. with several ladies from the WITS conference.

We sat outside, listened to live music, chowed down on lobster rolls (obviously), and had a fantastic conversation.

What more could you possibly want?!

Nosh burger and beer in Portland ME
WITS ladies at a table at Portland Lobster Co

Speakeasies in Portland

My favorite spots to drink were the two speakeasies we ended up at! Blyth & Burrows was really cool.

If you can find this spot, just knock on the door.

Portland speakeasy bar

Fun background:

Blyth and Burrows were the two captains, English and American respectively, who fought in a significant sea battle during the War of 1812.

They were both killed, but the victorious American sailors escorted their British counterparts ashore in Portland after the battle so both captains could be buried in a full military ceremony.

After they fought each other to the death, they were then laid next to each other for eternity.

It was a beautifully told story by Mike during our history walking tour, so I was extra pleased to end up at their eponymous speakeasy later that weekend!

The other speakeasy was next to Pat’s Pizza…and the pizza guys got a kick out of our struggle to find the right door. But we finally did and it was absolutely worthwhile!

Hint: Everything costs $5, which is reflected in the name of the bar.

Portland Maine to Boston

Getting from Boston to Portland Maine is such an easy trip, you’ll wonder why you never did it before!

You can take the Downeaster train from Boston to Portland Maine and back to see both cities in a single visit.

Boston to Maine by road is also super easy.

You’ll just hop on Route 95 and won’t get off until you hit Portland.

Whether by train or car, you can get between the cities in about 2 or 2.5 hours.

Unfortunately, you can’t take the Brew Bus the whole way. (New tour idea, guys??)

Maine Brew Bus in Portland

The train from Boston to Portland Maine is an excellent way to get between the two hubs without renting a car.

I had the luxury of borrowing my parents’ car for the week, but you may not share that option!

The Downeaster train is the Amtrak train from Boston to Portland. Check the details here and book yours to enjoy a relaxing train journey.

I’m still optimistic that trains will grow in popularity in the US soon! They are my favorite way to travel, and I can only hope more Americans start realizing their potential.

I’ve been spoiled rotten living in Scotland and I love it.

Fun Tidbits From My Trip to Portland

I had several interesting Uber drivers while in Portland!

First, there was Spencer from Kansas who moved to Portland with his wife as she completes her residency at the hospital.

He sang Portland’s praises in his southern drawl and it made me think that he is just like me in Scotland.

We speak the same language as our new neighbors, but it certainly sounds different.

marine with boats in Portland ME
Visit Portland Maine for a weekend trip

Another Uber driver I had was Glenn, a local Mainer.

He offered great insights into local life, but I was reminded of how infrequently locals act like tourists at home.

I think expats are the best tourists because we are so interested in our new homes, while locals tend to overlook and avoid anything deemed “touristy.” And tourists simply cannot do it all.

Chatting with Glenn reminded me how much we often overlook at home!

Eastern Cemetery in Portland ME looking eerie with pink flowering trees but a low fog

My other Uber driver was Dahir from Somalia.

His sister lives in Portland, so he followed her to Maine, but he can’t afford prices in the city.

He drives 45 minutes to be an Uber driver most days, on top of his other jobs.

His other sister lives in Minnesota, but his mom is still in Somalia because she felt she was too old to leave.

Sadly, he is not allowed to go to Somalia to see her; otherwise, he can lose his immigration status in the US.

So his best hope for seeing his mom is to travel to one of the neighboring countries and then also get his family to travel to the border to meet him there.

As that’s not easy or cheap, he hasn’t been able to see his mom in years.

But, despite all that, he said how welcomed he felt in the Portland area. Given that Maine is the oldest and whitest state in the US, I was thrilled to hear he felt like a part of the community there.

I have to say, I also felt welcomed in Portland quite heartily by all the locals I had the pleasure of meeting!

I was impressed with the diversity and inclusivity of the city, and I thoroughly enjoyed learning about the past, present, and potential future of this thriving area.

Thanks for a fabulous time, Portland!

Quick Links for a Weekend in Portland Maine



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