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16 Reasons to Visit Portland, Maine Now

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Voted the #1 Coziest City in America last year, Portland, Maine is only getting more and more popular amongst out-of-state visitors. It’s come quite a long way since I lived there 10 years ago, with new award-winning restaurants popping up at a quickening pace. Now as of last year, Portland saw the opening of the city’s first and only lifestyle boutique hotel. It may be my former home, but all biases aside, this charming town should definitely be on your must-visit list. Here’s why.

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1. Portland Accommodation 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 of 55 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 — 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 Maine, check out these luxury Maine rental properties here.

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2. It’s Still Affordable (But Won’t Be For Long)

Room rates for the Press Hotel start in the mid $200/night range during off season and rise to the low $300s during the summer when temperatures are more pleasant. For a stay in the most stylish hotel in Portland, the prices really can’t be beat. Plus you can easily find entire homes for rent on Airbnb within the $250 range. I only anticipate these prices to trend up as the Old Port expands, so now is the time to go.

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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 get you everywhere you need to go.

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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 weekly. We’re talking award-winning, James Beard nominated restaurants. Fore Street, Eventide Oyster and the Honey Paw are probably some of the most notable, but I would also recommend Empire Grill for modern Asian eats, Duckfat (some of the best fries I’ve had in my life), The Corner Room for brunch, Union (the restaurant inside the Press Hotel), and EVO Kitchen + Bar for a casual plate-sharing atmosphere.

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5. People Are Unstuffy

The truth is, Mainers aren’t fancy — and I mean that in the best way possible. 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 and I love that. Casual rules in this town.

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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 head to Eventide (a must). Lastly, don’t miss Bite Into Maine, a food cart located at Portland Headlight 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.

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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 overrun by chain brands, with a few exceptions like Urban Outfitters. 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.
  • K Colette: Parisian charm meets seaside chic in this boutique’s perfectly curated selection of home goods, gifts and beauty products. Everything is so beautifully packaged that you’ll want to pick up each item, feel it, smell it and inspect the artistry of it.

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  • Maine Potters Market: For pottery lovers, this is must stop located right in the heart of the Old Port on Fore Street.
  • Blanche + Mimi: A mix of new and vintage treasures.
  • 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.

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  • Folly 101: Scandinavian meets country-chic home goods, all organized by color.
  • Motifs: Like stepping into your favorite French flea.
  • 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.

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8. An Island Getaway is Just a Short Ferry Away

Chebeague and Peaks Island are both two 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, although accommodation for the summer books fast. Visit Casco Bay Lines for ferry schedules.

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9. You Don’t Have to Go to Paris to Lock Your Love

Can’t make it all the way to Paris to put your own mark on the Love Locks bridge? Head to Portland instead, where locals started up their own version back in 2013 on a fence on Commercial Street right next to the Portland Lobster Co.

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10. Drinks Are a Fraction of the Price

After living in New York and LA for a combined 6 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. Portland also boasts some pretty awesome happy hour deals. My favorites are the The Front Room ($2 glasses of red or white weekdays from 4-6 pm) and Vignola Cinque Terre (pictured above) where they offer half price on all wines by the glass AND cheese plates, 5-6 pm weekdays.

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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.
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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. Tickets are $15 for adults and $10 with a student ID.

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13. Potato Donuts: Need I Say More?

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 their deliciousness? Well, it’s not so secret. They’re made with Maine potatoes (they offer sweet potato varieties as well), giving them a hearty yet healthy taste. Just make sure to stop by earlier in the day as the shop closes when they’ve sold out for the day.

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14. 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 (free admission) 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. Don’t forget to stop by the Bite of Maine lobster roll cart on your way out!

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 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 important. 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.

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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 last year, 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 drink to ease any nerves before your flight.

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  • Reply Jeanette Matlock January 2, 2017 at 10:32 pm

    Great article. I love Portland. Maine as well. So many good places to eat with a variety of cuisines to choose from. Love the historical aspect as well as the mix of modern things – like the art scene.

    • Reply Michelle Halpern January 7, 2017 at 10:25 pm

      It is seriously the best foodie town! Thanks for your comment 🙂

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