Portland’s Pearl District called one of the coolest neighbourhoods in North America
Low crime rate, great schools, accessibility to medical services, and pride of ownership are some of the characteristics that make a neighbourhood great. But what makes a neighbourhood cool? The following neighbourhoods all have a few things in common, including: good food, plenty of arts and culture, a vibrant nightlife scene, and, perhaps most importantly, a distinct lifestyle.
Here are the coolest neighbourhoods in North America.
Boston – Fenway-Kenmore
The Green Monster. Pesky’s Pole. Jersey Street. The aura of some of the game’s all-time greatest players, from Jimmie Foxx and Teddy Ballgame to Carl Yastrzemski and Carlton “Pudge” Fisk. Seriously, what’s cooler than Fenway Park, the country’s most beloved sports venue, on a warm summer’s night?
Windsor – Walkerville
Famous for its connection with entrepreneur Hiram Walker, founder of Canadian Club whisky, in recent years Walkerville, described as “the perfect blend of hip and historic,” has enjoyed a renaissance of sorts after suffering a recession. One of the area’s main attractions is the historic Willistead Manor, built between 1904 and 1906 and designed by famous Detroit architect Albert Kahn.
Chicago – Pilsen
Believe it or not, some of the best Mexican food in the country comes from the Windy City. Chicago’s Pilsen district is known for its large Mexican-American population, which has spawned places like Carnitas Uruapan, Taqueria Los Comales, and El Chubasco Mexican, just to name a few. But more than just carnitas and tacos, the neighbourhood also has great Italian and Vietnamese cuisine.
Halifax – North End
The North End’s biggest attraction is its food scene. This neighbourhood in the capital of Nova Scotia doesn’t specialize in just one type of cuisine, but instead excels at a variety of different styles, including French, Italian, Eastern European, Middle Eastern, Japanese, Chinese, vegan, and of course seafood. The North End is also characterized by its colourful row houses on Agricola Street.
Venice – Abbot Kinney
What makes Venice’s Abbot Kinney Boulevard the coolest street in America? As Forbes explains: “It’s where hipster meets bohemian. Where LA meets NYC, Portland and Chicago. Where cool meets urbane.” More specifically, Abbot Kinney, located in the heart of Venice, is filled with beach boutiques, vintage shops, and quite possibly the highest concentration of amazing restaurants on any one block in America, with eateries such as Felix, Gjelina, and the Tasting Kitchen.
Toronto – Kensington Market
Parkdale is probably the first place that comes to mind when you think of hip Toronto spots, but Kensington Market is where you will find a bit of something for everyone, from quaint coffee shops and restaurants to vintage clothing stores and grocers selling fresh foods from around the world.
Vancouver – South Main
Vancouver is made up of one hip neighbourhood after another, from Gastown, with its fine dining and cobblestone streets; to “The Drive,” with its boutique shops and small restaurants; to Yaletown, with its bustling nightlife and stunning view of the water. But if we had to pick just one place to spend the day it would be South Main, the area between East 2nd and East 33rd Avenues, which, after undergoing a transformation that saw the opening of galleries, breweries and boutiques, has been described as “Vancouver’s answer to New York’s Brooklyn.”
Nashville – East Nashville
With a “quirky vibe and a buzzing food and nightlife scene,” East Nashville, located right next to the Cumberland River, has established itself as one of Music City’s trendiest neighbourhoods. Popular things to do include exploring nature in Shelby Bottoms Park, grabbing a bite to eat at the Nashville Biscuit House, and taking in a show while grabbing a cup of joe at the Family Wash/Garage Coffee.
Boise – North End
With a youthful culture not unlike that of Portland’s, Boise, Idaho, is something of a hidden Northwest gem, with no shortage of microbreweries, lively bars, farm-to-table dining options, and an influx of young people from all over the country. In the North End, you’ll find some of the city’s older homes as well as one of its most popular parks, Camel’s Back Park (pictured), offering panoramic views of downtown.
Montreal – Little Italy
Between the cobblestone streets and colonial architecture of Old Montreal, and the vibrant nightlife of Downtown, Montreal has a strong case for being the coolest city in Canada, if not all of North America—and no, we’re not talking about the weather. But what makes the MTL so great is that it’s one of the most culturally diverse cities in the world, one example of which is its large Italian population, second only in Canada to Toronto.
Portland – Pearl District
Portland’s popular Pearl District is made up largely of reclaimed warehouses that now house some of the best bars, restaurants, craft breweries, and coffee shops in the Pacific Northwest. After you’ve filled up on food and drink, you’ll want to check out the amazing art on display in the neighbourhood’s many galleries. And if you’re a bookworm, you can’t miss out on Powell’s, the world’s largest independent bookstore. With roughly a million books to choose from, you can easily spend an entire day scouring the shelves.
Seattle – Downtown
Seattle’s legendary Pike Place Market, the country’s oldest continuously operating public market, is a requisite destination for any tourist visiting the Pacific Northwest city for the first time. SavorSeattle offers a two-hour Signature Food Tour that gives tourists an “insider’s look” at several market vendors with “entertaining stories of the Market’s rich history and culture.” But most importantly you will get to sample some of the amazing food with more than 14 tastings.
Brooklyn – Williamsburg
Despite its reputation as being full of hipsters and so trendy that it’s practically untrendy, Williamsburg is still the coolest neighbourhood in New York, at least according to Cathy Adams of The Independent, who said that the Brooklyn district has “morphed into a sort of relaxed, adult kind of cool, perfect for those in the upper millennial age bracket.”
Reno – Midtown
Best known for its neon-lit streets and monstrous casinos, Nevada is also home to some cool—and decidedly less gaudy—neighbourhoods, like Reno’s eclectic Midtown District, with its abundance of specialty shops (like Junkee Clothing Exchange and Antique) and well-reviewed restaurants, including the Korean fusion Arario Midtown.
Brooklyn – Greenpoint
Williamsburg has competition within its own borough for the title of coolest neighbourhood in NYC. Just how cool is Greenpoint? Well, it’s cool enough for Bill Murray, which means it’s cool enough for anyone. Back in 2016, the Ghostbusters star was spotted serving drinks at 21 Greenpoint, one of the neighbourhood’s many popular bars.
San Francisco – The Mission
San Francisco was named the coolest city in America by Forbes a couple of years ago, and a big reason for that is because of trendy neighbourhoods like the Mission District in the east-central region of the Northern California city. Aside from being famous for its food scene, and in particular its many great Mexican restaurants, the Mission is home to the oldest standing building in San Francisco, the Mission Dolores, founded in 1776.
Fort Myers – River District
Offering “a nod to the history of the City of Palms with a vision for the future,” the River District, with its historical walking tours and more than a dozen art galleries, attracts both older tourists and hip young travellers, which might explain why Fort Myers was named America’s fastest-growing city in 2018.
Austin – Downtown
With its laidback, hipster vibe, legendary music scene, and proudly “weird” persona, Austin, Texas, has a reputation for being one of America’s coolest cities, so it’s tough to pick just one neighbourhood. To be safe, let’s just go with the entire Downtown area, which includes Rainey Street, Red River Cultural District, Sixth Street, and Warehouse District.
Miami – Wynwood
The former warehouse district of Wynwood is now famous for its colourful outdoor murals, showcasing the work of some of the world’s greatest graffiti artists. The happening district was also named a “food mecca” by the Miami New Times thanks to restaurants such as Alter, Kyu, and R House.
Pittsburgh – Lawrenceville
Pittsburgh’s Lawrenceville neighbourhood is home to the oldest brewery in the city, Church Brew Works, which once served as a place of worship but now serves up pizza, pierogi, and bratwurst, which you can wash down with some delicious house-brewed beer.
Detroit – Corktown
Despite its reputation as a high-crime city, Detroit has seen young people flocking to its many cool neighbourhoods in recent years, and none are cooler than Corktown. The city’s oldest neighbourhood is home to some of the best bars and restaurants in the country, including Slows Bar, Mudgie’s, and Ottava Via.
Hamilton – James North
What makes Hamilton a perfect place to visit is that it’s made up of many distinct neighbourhoods, each great in its own ways, which means there’s something for everyone. James Street North in particular has been heralded for its growing arts and culture scene. The street hosts an art crawl on the second Friday of every month.
Calgary – Kensington
At just four blocks by four blocks, Calgary’s hip Kensington neighbourhood is small enough to explore in just a few hours, but when you see everything that it has to offer, including historic buildings, modern architecture, and roughly 270 shops, you will want to stay much longer.
Los Angeles – Silver Lake
Described by the Daily Hive as a “unique pocket of the city with great green spaces to explore,” Silver Lake is quickly earning a reputation as L.A.’s coolest district, especially popular among “hip Angelenos, artists and even celebrities.” Some of the famous figures who have called Silver Lake home include Rachel McAdams, James Franco, and Ryan Gosling.
Ottawa – ByWard Market
Known simply as “The Market” to locals, Ottawa’s ByWard Market consists of over 80 restaurants (by far the highest concentration in the city), an exciting outdoor street scene with vendors selling unique foods and products, and ongoing events throughout the summer. Plus, if it gets too humid in the summer, Ottawa’s largest mall, the four-level Rideau Centre, is just a short walk away.
Edmonton – Old Strathcona
One of the coolest streets in Canada—Whyte Avenue, with its “funky, bohemian spirit,” world-class restaurants, and one-of-a-kind shopping opportunities—resides in the famous Old Strathcona neighbourhood of Edmonton. Much of the city’s arts and culture scene, including its theatres and live-performance venues, can be found in this neighbourhood.
Chicago – Wicker Park
Wicker Park’s food and drink scene is second to none in Chicago. Forget about deep dish and instead head to Piece Brewery and Pizzeria, which Anthony Bourdain identified as one of his favourite restaurants in the city, calling its ultra-thin crust pizza “very good, wood-fired, non-deep-dish pizza.”
Houston – Montrose
Austin isn’t the only city in Texas boasting a strong hipster vibe. In fact, with its endless row of tattoo parlours and dive bars, mixed in with cozy coffee shops and antique stores, Houston’s Montrose might be the weirdest, most delightfully diverse neighbourhood in the Lone Star State.
Minneapolis – North Loop
In recent years, Minneapolis has established itself as one of the U.S.’s premier food destinations, which is perfect, because you are bound to work up a strong appetite after spending the day biking around North Loop, regarded as one of the country’s most bike-friendly neighbourhoods.
Washington – Shaw
Washington, D.C., the coolest city in America? According to The Telegraph it is. It really shouldn’t come as a surprise, given the nation’s capital’s many trendy neighbourhoods, from Adams Morgan to Dupont Circle to Georgetown. But one neighbourhood that makes a strong case for being the coolest of the cool is Shaw. Not only does it boast great food and entertainment, but it also has the distinction of being the place where legendary jazz musician Duke Ellington was born and started his career—and what’s cooler than that?
Philadelphia – Society Hill
The best restaurant in America can be found in Philly’s historic Society Hill neighbourhood. Steven Cook and Michael Solomonov’s Israeli eatery Zahav, famous for its mouth-watering roasted lamb shoulder with pomegranate and chickpeas, won the prestigious James Beard Award for Outstanding Restaurant in 2019.
Denver – RiNo
Denver’s River North Art District, or RiNo for short, earned the title of “America’s most improbably cool neighborhood” by GQ thanks to its youthful punk-rock energy, and an ever-growing roster of bars, restaurants, craft breweries, and dispensaries. Mission Ballroom, a new concert venue with nearly 4,000 seats, opened in August.
Atlanta – East Atlanta Village
Once a key site in the Civil War, East Atlanta Village now welcomes people from all walks of life. Before picking up some fresh produce at the outdoor farmers’ market, get a boost of caffeine at the popular Hodgepodge Coffee. And then at night take in a live show at The Earl, where acts such as St. Vincent, The National, and the Avett Brothers have all performed.
San Diego – North Park
North Park started out as a modest lemon grove in the late 19th century but has evolved into one of California’s trendiest neighbourhoods. And just a short drive away is Balboa Park, a 1,200-acre urban cultural park complete with open-space areas, natural vegetation zones, green belts, gardens, walking paths, museums, theatres, and the San Diego Zoo.
New Orleans – Bywater
The French Quarter is wildly popular for a reason, but if it’s the cool factor you’re after, you can’t beat New Orleans’ Bywater neighbourhood, part of what became known as the “Sliver by the River” neighbourhoods after Hurricane Katrina. As Fodor’s put it, “If Bourbon Street is a sprint, the Bywater is a long, sauntering stroll,” full of charming restaurants, dive bars, and cozy bed-and-breakfasts.
Scottsdale – Old Town
Don’t let the name fool you. Located in the heart of downtown Scottsdale, Old Town is a vibrant neighbourhood largely tailored towards young people, with its many restaurants and drinking establishments. And let’s not forget the shopping, including Scottsdale Fashion Square, one of the largest malls in the Southwest, with more than 225 stores and restaurants.
Quebec City – Upper Town
When you think of Quebec City, chances are you think of the historic Château Frontenac, the Basilique Cathédrale Notre-Dame de Québec, and cobblestone streets. Basically, you think of Old Quebec’s Upper Town, or Haute-Ville, a neighbourhood as beautiful as it is rich with history.
Alexandria – Del Ray
As the hometown of the United States’ first president, George Washington, this independent city located just outside of downtown Washington, D.C., is steeped in history. According to Apartment Therapy, which named Alexandria one of the coolest suburbs in America in 2019, while most tourists think to visit Old Town, the true hidden-gem neighbourhood is Del Ray, which is “full of young families and dogs, and boasts its own main street of shops and restaurants on Mount Vernon Avenue.”
Louisville – East Market District
There’s Old Louisville, and then there’s the East Market District, known to locals as “NuLu” (or New Louisville) due to its re-emergence as one of Derby City’s trendiest, most sustainable neighbourhoods. NuLu is also where you’ll find some of the best grub—from Feast BBQ to Royals Hot Chicken to Grind Burger Kitchen—in what Thrillist once named one of the 18 Best Food Neighborhoods in America.
Toronto – West Queen West
It’s impossible to do a list of the coolest neighbourhoods in North America without mentioning Toronto’s West Queen West (not to be confused with the also cool—but slightly more commercialized—Queen Street West), located between Bathurst Street and Gladstone Avenue. Home to the largest concentration of art galleries in the city, it was once named the second-coolest neighbourhood in the entire world by Vogue.
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