16 Reasons to Visit Portland, Maine Now

Portland, Maine has come quite a long way since I grew up there in my early childhood and teens. What was once a looked-over New England town has now become an East Coast gem with award-winning restaurants, design hotels, and tons of coastal charm.

Just in the last decade, Portland saw the opening of the city’s first lifestyle boutique hotel and others have followed suit.

Portland may be my former home, but all biases aside, this charming town should definitely be on your must-visit list. Here’s why.

Why You Should Visit Portland, Maine Now

1. Portland’s Hotel Scene is Catching Up With Other Cities 

The city’s first lifestyle boutique hotel, the Press Hotel opened in 2015 and it continues to bring a unique style to the hotel landscape in Portland.

As one in a curated selection of Autograph Collection properties in the United States, the Press Hotel is housed in the historic former office of the Portland Press Herald, which provided inspiration for design elements that run throughout the space.

You’ll find a typewriter installation in the main lobby, wallpaper featuring text that spills off the wall onto each floor’s corridor and vintage-style journalist’s desks in every room.

For other beautiful spaces to stay during your trip to Portland, Maine, check out The Longfellow, Blind Tiger, and these luxury Maine rental properties here.

2. The City is Changing Rapidly

With major development projects in process that promise to reshape the waterfront landscape of Portland over the next decade, now is the time to visit before Portland steps into its next iteration as a city.

One of the biggest projects underway is the Portland Foreside development, which aims to extend the Old Port by turning one of Portland’s more industrial waterfront sections into a 10-acre hub of retail, residential and office spaces.

It’s unclear when the project with come to completion, but changes are already underway.

3. It’s Super Walkable

The downtown area of Portland, dubbed The Old Port, is extremely walkable with restaurants, bars, shops, movie theaters and the Portland Museum of Art within manageable walking distances.

If your accommodation is located downtown, there’s really no reason to rent a car as Uber and your own two feet can easily take you everywhere you need to go.

4. It’s Got Small Town Charm with Big City Foodie Culture

The Old Port maintains a specific level of East Coast charm that hasn’t been tainted by tourism. Yet the foodie scene rivals that of any major U.S. metropolis.

Just ask any local and they’ll tell you they can’t keep up with the number of new restaurants popping up monthly. We’re talking award-winning, James Beard nominated restaurants.

Some old tried and true Portland classics you can’t miss are Fore Street, Eventide Oyster and the Honey Paw, to name some of the most notable.

I would also recommend Empire Chinese Kitchen for modern Asian eats, Duckfat (some of the best fries I’ve had in my life), and EVO Kitchen + Bar for a casual plate-sharing atmosphere.

Some newer spots worth booking reservations at are Twelve, Công Tử Bột for Vietnamese (which reopened with an expanded menu since shuttering during the pandemic), and Bar Futo.

5. People Are Unstuffy

The truth is, Mainers aren’t fancy—and I mean that in the best way possible as someone who grew up there.

Of course you may want to dress up a bit for a nicer dinner reservation, but you’ll never feel looked up and down on the streets of Portland if you’re not wearing the latest trends.

Casual and comfortable rules in this town, so you can visit Portland, Maine knowing you can just relax and let go of the stress of being or looking any “certain way.”

6. You’ll Eat the Best Lobster of Your Life

You won’t get better lobster than in Maine, and there are places that do it so differently here that you could eat it every day and have a wide range of experiences.

My favorites? For a classic, no-frills lobster roll of epic proportions head to dive J’s Oyster, located right on the waterfront.

For more atmosphere and a brown butter lobster roll that will melt in your mouth (and change your life) head to Eventide. Don’t forget to book a reservation here as they book out fast.

Lastly, don’t miss Bite Into Maine, a food cart located in Fort Williams Park that was listed on Yelp’s Top 100 Places to Eat in the U.S. Just note that it’s only open during the high season from May to October.

7. It’s a Coastal Decor Lover’s Dream

If you go gaga over coastal decor or just want that authentic Maine gift to bring home to friends, the Old Port is a gold mine. It has yet to become totally overrun by chain brands, so there are a lot of independent shops to explore.

I also personally find the stores here less traditionally tacky as far as souvenir shops go—if you know where to look. Here are a few of my recs for great Old Port shopping:

• Lisa Marie’s Made in Maine: This is my go-to for classic Maine gifts and items for your home. You’ll find everything from buoys, Maine shaped cheese boards, and balsam pillows, to a whole selection of food products made in state.
• Sea Bags: This brand produces nautical tote bags and accessories repurposed from old sails, making them a quintessential Maine gift.
• Maine Potters Market: For pottery lovers, this is a must stop located right in the heart of the Old Port on Fore Street that features handmade wares from Maine-based artisans.
• Blanche + Mimi: A mix of new and vintage treasures worth bringing home in your luggage.
• Asia West: An upscale and zen-inducing selection of treasures brought back from the owner’s own travels in Asia. Not necessarily very Maine, but I love it nonetheless.

• Folly 101: Scandinavian meets country-chic home goods, all organized by color.
• Judith: Portland is admittedly not my favorite place when it comes to shopping for clothes, but this store is a unique diamond in the rough. I prefer their accessories but you can find some unique minimally chic finds here.
• Salt Cellar: A must visit for foodies and hosts; you’ll love sampling all of the salts in this hidden gem off of Middle Street.

8. An Island Getaway is Just a Short Ferry Away

Chebeague Island, Great Diamond Island, and Peaks Island are all popular destinations right in Casco Bay that are a quick ferry ride from downtown Portland and are ideal for a day trip or an overnight.

Keep in mind that accommodation in the summer books fast, so you’ll want to plan ahead if you’re looking to spend the night on one of these island getaways. I would recommend searching as soon as possible for availability in hotels or use Airbnb or VRBO to find local home rentals.

Visit Casco Bay Lines for ferry schedules.

9. Every Season Offers a Distinctly Unique Experience

While I highly recommend making your first visit to Portland, Maine in summer or fall, the beauty of Maine is in its very distinct seasons.

In summer you’ll experience the bustle of summer tourism with the waterfront, beaches and outdoor dining coming alive.

In fall, Portland is one of the most stunning places in the U.S. to experience fall foliage and enjoy the crisp fall air that I loved so much growing up here.

In winter, you can enjoy the coziness of a true Maine winter and explore cold-weather activities like skiing just a short drive away. Plus, dinner reservations at Portland’s hot spots are easier to come by during this time.

Spring starts to make way for warmer temperatures and is a great time to visit for outdoor adventures before it gets too hot.

Whenever you choose to visit Portland, Maine, you’ll find wonderful ways to enjoy the city. Plus, each experience will feel completely different so you can return again and again to make new memories.

10. Drinks Are a Fraction of the Price

After living in New York and LA for a combined 14 years, I’ve gotten used to paying a pretty penny for a cocktail or glass of vino.

So when I came back to Portland for the first time in many years, I was shocked that my same favorite class of red wine at an upscale eatery in Portland was $5 less than at my favorite LA spot.

Shocked in the best way possible, I should say.

Portland also boasts some pretty awesome happy hour deals. My favorite is at the The Front Room, which offers $3 on select glasses of red or white and draft beers daily from 4-6 pm.

11. The Fresh Air Actually Feels Fresh

In big cities where pollution is more prevalent, waterfront breezes don’t always equal the freshest air. Portland is a different story. If you go here you’ll see what I mean. The air here has a particular punch of freshness that is a rare find these days.

12. The Art Scene is No Joke

Yes, the Portland Museum of Art showcases a slew of Maine-based artists (some of my favorite pieces in the collection), but you’ll find many works from globally famous names as well.

Think Andy Warhol, Claude Monet, Jasper Johns, Robert Indiana, Alexander Calder and many more.

Plus, if you’re looking to expand your art explorations beyond the museum experience, Portland hosts a plethora of art galleries to choose from. Some worth checking out include Anderson Gallery, Portland Art Gallery and the Maine Art Collective.

13. You’ll Fall in Love With Potato Donuts

Sure, you’ve likely eaten dozens of donuts in your lifetime. But have you tried potato donuts?

The Holy Donut has become a Portland staple—in fact last time I was in, a local couple had just gotten engaged and made their first celebratory pit stop here.

Holy Donut was named one of the top 10 donut shops in the U.S. by Fodor’s Travel. So what’s their secret to such deliciousness? Well, it’s not so secret: they’re made with Maine potatoes.

This unique ingredient makes for a donut experience you won’t forget (plus, they offer sweet potato varieties as well, which make for a hearty yet healthy taste).

Pro tip: Make sure to stop by as early as possible as the shop closes when they’ve sold out for the day.

14. Visit the Most Photographed Lighthouse in the U.S.

This iconic lighthouse (it’s the most photographed lighthouse in the U.S.) dates back to the 1700s when it was used to protect the harbor and surrounding areas from British attacks.

Now, the structure and surrounding Fort Williams park are a beautiful landmark and tourist attraction.

I recommend taking a whirl through the small museum on site (admission is free) which gives some fascinating context to the history of the lighthouse. Make sure to check the hours on their site as the museum is not open every day.

And don’t forget to stop by the Bite of Maine lobster roll cart on your way out!

 15. It’s Easy to Get Outdoors

Eating and drinking in Portland may be an ever-growing aspect of the culture here, but exploring the outdoors is equally as exciting.

Portland Trails is a non-profit organization that is committed to keeping these green spaces alive, so whether you’re a biker, runner or just want to schedule in a casual stroll with incredible views, it’s easy to do so here.

16. PWM Might Be the Easiest Airport in America to Navigate

Voted as one of the top 10 airports in America by Condé Nast Traveler in recent years, Portland’s airport is a breeze to fly in and out of. They could do with more non-stop flight options, but if you can find a good flight, you’re in for a treat.

Staffers and security guards are friendly and you never have to deal with huge lines or elbowing your way through crowds to get to your gate on time.

Plus, it’s an easy 10-15 minute drive to downtown depending on traffic and has a plethora of craft beers on offer so you can enjoy that one last Maine brew to ease any nerves before your flight.

Did this post inspire you to visit Portland, Maine? Let me know in the comments!