25+ Fun Things to Do in Portland, Maine

If you’re looking for a fantastic and underrated city in the US, I will sing you the praises of Portland, Maine! This incredibly cool city is one of my favorite places in New England — yet it doesn’t get a fraction of the attention it deserves.

Why is that? I think it’s because so many people default to Portland, Oregon, in their minds. That and most Maine visitors seem set on beaches and the outdoors rather than a city getaway. But there are SO many great things to do in Portland, Maine — and I think this city might be the highlight of your Maine trip.

As a native New Englander, I’ve visited Portland many times, but I’ve been visiting more frequently since my close friends moved there a few years ago. Because of that, I’ve been able to explore Portland both through a tourist’s eyes and through a local’s eyes.

While it’s the largest city in Maine, Portland still has a small-town feel with a population of just under 70,000 people. There is so much rich history, everywhere you look, and it’s beautifully set on Casco Bay, overlooking dozens of islands.

But Portland has become increasingly known as a foodie city for those in the know. If you’re looking for cutting edge cuisine, this is a great spot to splurge — but if you’d rather keep it basic, the lobster rolls and donuts here are second to none.

And this might be anecdotal, but Portland is home to some of the nicest, friendliest, most welcoming people I have met, anywhere. (Honestly, I think it’s tied with Asheville for the nicest people in the US!) I’ve had so many great conversations with Portlanders, from ferry passengers to baristas and brewers.

So how should you spend your time in this delightful city? Let’s take a look at the best things to do in Portland, Maine!

This post was published in June 2025 and was co-written by Adventurous Kate and Dale Peterson.

Best Things to Do in Portland, Maine

Walk along the waterfront and Old Port

Start your visit to Portland with a stroll through the Old Port. This historic waterfront district is full of cobblestone streets and stately brick buildings. Commercial Street, which runs right along the waterfront, is the vibrant main thoroughfare here.

On Commercial Street, you’ll find plenty of shops,…