No longer confused with its counterpart in Oregon, Maine’s Portland is not only the state’s largest and most populous city (just over 68,000 folks call the Port City home), but The U.S. News and World Report named it as the eighth best place to live in 2022-2023.

downtown portland overlooking the bay
As a matter of fact, you’d be hard-pressed to come up with even a modest list of cons when considering a move to this beautiful city by the bay (Casco Bay, that is)—and after reviewing the abundance of pros (you’ll find 12 of them below), you’ll come to the same conclusion most folks do: Portland, Maine, is a great place to live.

1. Commuter-Friendly

In comparison to other large U.S. cities, Portland, Maine, is a small city, yes…but that doesn’t mean “you can’t get they-ah from he-yah.”

Not only does the city have its own jetport as well as a stop on Amtrak’s Downeaster route, but being only a 2-hour drive from Boston and with easy on-and-off access to Interstate 95 makes Portland very attractive to folks that travel elsewhere for business.

2. Welcoming, Youthful Vibe

Contrary to the popular belief that Maine is an “old” state, Portland’s median age is 36.5 years, thanks in due part to the city being so hospitable for people of all colors, nationalities, and lifestyles.

While still exuding classic New England charm and character, there is an inherent feeling of evolving vitality, close-knit community, and purposeful progress.

The city is also very attractive to startup ventures, and many millennials are taking advantage of that fact—especially in the hospitality industry—which occupies the next two items on this list.

3. Foodies, Rejoice!

If you’re considering moving from a sleepy bedroom town to the Portland area (as I did), you’re in for a treat. Gone are the days of needing to hop in the car and go elsewhere for a delicious dinner; Portland is a literal Shangri La for any self-respecting foodie.

No matter what your palate is craving, there’s a restaurant out there for you…and chances are you won’t need your car to get there.

4. Beer, Wine, and Cocktails, Oh My!

Regardless of what your tipple of choice is, you’ll find the perfect spot to raise a glass in Portland.

Wine bars, craft breweries, elegant cocktail lounges, dive bars, and even a speakeasy or two are liberally sprinkled throughout the city, perfect for drinks before a show, a raucous pub crawl, or just a couple of drinks and small plates with friends.

5. Four Seasons of Fun

While some people consider winter weather a negative aspect of moving to the New England area, I beg to differ.

Sure, it gets cold and snowy…but that’s what winter gear (looking at you, L.L. Bean) and snow removal professionals are for (of which there are literally dozens in the area).

Portland is a veritable winter wonderland come Christmastime, and residents enjoy a bit of breathing room from the tourists that visit the city during the spring, summer, and fall thanks to the many things to do in the area—including relaxing on the beach for the day. Which cues up our next item nicely…

6. From City Streets to Beach Bliss

While a fair amount of Portland’s coastline is devoted to other purposes (working waterfront, housing, and dining), the city does have its own beach.

Located at the foot of the Eastern Promenade’s expansive grassy hill, the ½-mile-long East End Beach is a great spot to spend a hot summer day, especially if you don’t mind the extra-chilly water. There are also plenty of other beaches in nearby towns if you don’t mind a short drive.

7. Activities for All Ages

No matter what you and yours like to do in your hard-earned downtime, Portland has something for every interest.

If outdoor activities like hiking, biking, or kayaking are among your favorite pastimes, you’ll have plenty of options here.

There are also all manner of walking and boat tours on offer, depending on your inclination, sea hardiness, and fitness level.

And as for culture, the offerings are myriad: the First Friday Art Walk, the city’s many museums, and the vibrant performing arts scene for live music and theater are just a few elements of note.

8. Shopping Options for Every Whim

Not only is Portland, Maine, a great city to do stuff in, but it’s also a fantastic area to buy stuff in.

Looking for a wardrobe refresher? There are oodles of both high-end and affordably-priced clothing stores in the city—including consignment and thrift stores.

On the hunt for that perfect gift for a special someone? Portland’s abundance of unique gift shops will scratch that off your to-do list in no time.

waterfront condominiums in portland maine

9. Comparatively Affordable City Living

When compared to the national cost-of-living averages for many major U.S. cities, Portland holds its own.

While certainly not inexpensive (Portland’s cost-of-living is 15% higher than the national average), its numbers don’t look nearly as bad as compared to Boston (50% higher), New York City (128% higher), Miami (21% higher), or Los Angeles (51% higher), for example.

It is notable, however, that despite a higher-than-average cost of living, Portland’s median household income ($66,109) is lower than the national median ($70,784).

10. Neighborhoods Galore

Home to a gamut of distinctly different neighborhoods, Portland is a city of many faces, each with its own appeal and unique characteristics.

For parks and other greenspaces, pack up the family and head to Parkside. Want to take in a show or browse a gallery? The Arts District is the place for you.

The West End is infinitely beautiful for strolling with its gorgeous Victorians and bowering trees; both East and West Bayside as well as the Old Port are burgeoning with eateries, breweries, and coffee shops.

The East End offers prolific views along with Munjoy Hill’s beautiful old homes, and while you may need your car to reach the off-peninsula areas from downtown, it’s well worth the drive…especially when considering buying a home.

11. Housing is Available (if you know where to look)

Much like the rest of the country these days, affordable housing can be nigh on impossible to get your hands on. As soon as something viable pops onto the market, it’s gone in the blink of an eye.

Portland is no different…but if you’re willing to consider living off-peninsula—particularly in the Stroudwater neighborhood—your budget will thank you.

With cost-of-living expenses at around 12% less than downtown Portland’s, Stroudwater is one of the oldest neighborhoods in the area and features many beautiful, historic homes.

Most residents here own their homes, and the school system is rated as above average. But if you want to buy, be quick—because homes are going to pending status in less than eight days.

12. Schools are Above Average, City-Wide

Portland’s 30 public schools (there are also nearly 60 private schools on offer) are ranked 11th on the state’s 2021 list of the top 100 school districts; not too shabby for an urban public school system.

The student body as well as the staff are very diverse, with 53 languages spoken and 27% being English language learners. The district also boasts an 85% graduation rate, with 75% going on to post-secondary curricular endeavors.