North America’s coolest downtowns

Experiencing signature cool in cities across the continent

You know the feeling—when you arrive in a new destination and immediately fall in step with a great groove. That’s the way every getaway should begin. It’s hard to describe a city’s special je ne sais quoi and awesome ambiance. So, we’ve put together a list of the best downtowns in North America. What’s our criteria for coolest downtowns? One-of-a-kind dining options, local arts venues, unique shopping experiences, fascinating historical sites, and access to urban greenspace. You’ll find some of your favorites and a few unexpected gems, and a locally loved place to hit “refresh,” so pack your fabbest street style and get ready to visit some hot cities with cool downtowns.

Cancun, Mexico

With the coastline close at hand and palm trees swaying everywhere you look, downtown Cancun is instantly swoon-worthy. We love the open-air food court and ample people watching at Parque de las Palapas, and the energy and colorful handmade treasures you’ll find—and haggle for—at Mercado 28.

Find your chill: After collecting amazing art, keep the good times going with an evening of live music, chic cocktails and candlelit vibes at Roots Jazz Club.

Downtown Boston, Massachusetts
Boston has been “lit” ever since Paul Revere looked for lantern light in the tower of the Old North Church way back in 1775. Old meets new at Modern Theatre, which first opened in 1876 and underwent a rebuilding in 2010, keeping the original façade. In the warmer months, enjoy your theater experience outdoors at the summer Shakespeare series on the Common.

Find your chill: Within walking distance to Modern Theatre and Boston Common, jm Curley is a quirky vintage bar where craft cocktails are served with an ample side of sass. Order the original Sister Abigail for a pear gin delight, and read the “law & order” dos and don’ts, which comes down to “Just don’t be a douchebag.”

Downtown Tacoma, Washington

You don’t have to spend too much time on social media to see that downtown Tacoma is the talk of the town. From world-renowned glass art to popular downtown bars, the waterfront area along Pacific Avenue has vacation vibes and photo opp-ready scenery. Walk the Chihuly Bridge of Glass—a pedestrian overpass with art installations including the Seaform Pavilion and Venetian Wall—for a unique ocean-inspired experience.

Find your chill: Just between us, Tacoma is the hottest city in the Puget Sound, and that’s because contemporary classics like Savor Tacoma Creperie keep the waterfront fresh with flavorful fusion cuisine. Sweet or savory, you’ll find a new favorite here. Need some help? The fresh strawberries crepe is topped with brown sugar pecan crumbs. Yum.

Downtown Boise, Idaho

There’s a buzz in Boise, and it sounds a lot like Instagram shutters snapping from Freak Alley Gallery. This outdoor venue is all about building a creative community in the heart of Boise, and it’s playing its part in making Idaho’s capital more colorful with murals and events. Boise GreenBike makes it easy to embrace the neighborhood’s open-air way of life with convenient bike sharing. How cool is that?

Find your chill: Craving some amazing craft beer? Visit downtown Boise in early October for the annual Hoptober Freshtival, hosted by Boise Brewing.

Old Town Alexandria, Virginia

Old Town Alexandria reminds us that historic landmarks have their own quirky character. Walk among colonial architecture now painted in a rainbow of color, including Christ Church, built in 1773. George Washington sang a few hymns inside those walls—no big deal. Old Town earns extra artistic points for Torpedo Factory Art Center, which houses interactive galleries in a renovated torpedo factory.

Find your chill: Downtown Alexandria is brimming with waterfront restaurants and pubs, and Pizzeria Paradiso is one of our favorites. Where else can you and your crew order delicious slices and sample dozens of international brews right on the Potomac?

Downtown Evanston, Illinois

The home of renowned Northwestern University, downtown Evanston is always on the go with world-class culture and college-town shenanigans. Even after the students go home for spring break and summer vacation, this waterfront city stays busy. Shop the world over at Ten Thousand Villages, a fair-trade retailer selling goods from 130 artisan groups around the globe.

Find your chill: Wander along Lake Michigan for beautiful views and check out Evanston’s green cuisine. Located south of the city center, Blind Faith Café is green-certified and serves up vegan and vegetarian eats. You can’t get much fresher than this, unless you buy the produce at Downtown Farmers Market yourself!

Downtown Denton, Texas

Looking for small-town peace and quiet and lots of indie charm? North of Fort Worth, the downtown area of Denton has both and then some! Anchored by a gorgeous and green central square, this city is sprinkled with vintage vendors like Beth Marie’s Old-Fashioned Ice Cream. With a double-scoop in hand, sway your way to the annual Denton Arts & Jazz Festival, which takes place each April.

Find your chill: Can you keep a secret? Come closer. Right off Downtown Square, look very closely for the simply marked entrance to Paschall Bar and follow the staircase up to this old-school haven of literature and libations.

Historic Downtown Fernandina Beach, Florida

You don’t have to be trendy to be cool. Want proof? Explore the historic downtown Fernandina Beach, where Victorian walkups and row houses line your path to the Atlantic seaport. Warm community spirit gives this small town its larger-than-life character, and each May you can join the locals downtown for the Isle of Eight Flags Shrimp Festival—don’t miss the boat races!

Find your chill: At Café Karibo, old things become new. This historical building is the home of an amazing turkey Cuban sandwich and a “famous” veggie burger.

Historic Downtown Gravenhurst, Ontario, Canada

There’s nothing cooler than being able to walk to a city’s top attractions, stopping for drinks and treasure hunting along the way. Well, in Gravenhurst, you can walk to four parks and beaches from downtown. In fact, you can walk anywhere in town and be near the water. For some culture on the coast, visit the birthplace of Canada’s summer theater at Gravenhurst Opera House and join the Spring into Summer Art Crawl.

Find your chill: Wet a parched palate at Sawdust City Brewing Company’s tap room. Order a tasting flight, or better yet, take those brews out for a tour of the town in the brewery’s beer bus.

Saskatoon City Center, Saskatchewan

In addition to being able to see the Northern Lights on a clear night (we love science), you’ll have plenty of waterfront views as you wander along the river. Prefer the gleam of chrome? Don your vintage wear and browse over 900 classic cars at the Rock 102 Show & Shine Weekend, which takes place each August.

Find your chill: What goes better with waterfront strolls and late summer festivals than chilling out with Canada’s top songwriters and musicians? Stop in for a spell at The Bassment and we dare you to name a better combination.

Old Pasadena, California

Pasadena may be located incredibly close to the busy streets of La La Land, but the historic city center moves to the breeze of its own palm trees. On a warm evening—which most of them are—walk under vintage market lights strung over Colorado Boulevard and stop to swoon at the red-brick buildings and intricate ironwork tucked away in quiet alleys.

Find your chill: Chow down on gorgeous SoCal comfort foods and sip innovative mixed drinks at White Horse, a popular “brown bar,” where you can expect your glass to glisten like amber.

Downtown Tarrytown, New York

Washington Irving fans know that Tarrytown, which once included the tiny glen to the north, is the true location of “The Legend of Sleepy Hollow.” If being the site of American mythology isn’t impressive enough, downtown boasts the Tarrytown Music Hall, one of the country’s oldest theaters. Before a show—or trip to the cemetery—indulge in some downtown shopping in galleries and boutiques along the Hudson river.

Find your chill: Warm up any New York morning with a hot cup of coffee from Coffee Labs. They source their beans from sustainable farms, so every sip makes a difference.

Downtown Prescott, Arizona

Welcome to the wild, Wild West. In the wide-open landscape of Northern Arizona, Prescott is home to old-timey saloons and an up-and-coming cuisine scene. Walk down Whiskey Row, officially Montezuma Street, the historic thoroughfare lined with saloons and unique shops. Each June through August, rock out with local bands at the Summer Concert Series at Yavapai County Courthouse Plaza.

Find your chill: Be sure to relax with a drink at quirky The Point Bar & Lounge. Rebuilt after a fire in 1901, it’s now a speakeasy. To taste history, enjoy a meal at The Palace, Arizona’s oldest restaurant and dinner theatre. For the best of both worlds, grab your friends for a saloon crawl.

Downtown Boca Raton, FloridaThings are different in Boca Raton. High rises are outlawed around here and Mediterranean-inspired architecture and palm trees compose the downtown skyline. After a day spent ankle-deep in the Atlantic, air-dry as you walk to Mizner Park, a shopping destination with an amphitheater, performing arts venues, and a museum.

Find your chill: For a beverage as cool and unique as Boca, stop for coffee or fresh juice at The Seed on Palmetto Park Road.

Downtown Bend, Oregon

Many people know Bend as a ski destination in Central Oregon. Well, that’s not the half of it. Set against the backdrop of gorgeous Deschutes National Forest and mighty Mt. Bachelor, Bend is a hub for arts and craft beer. Visit on the first Friday of the month to join the Art Walk and sample from regional vineyards, nearby breweries, and the best restaurants in downtown—all decorated with local artwork you can take back home.

Find your chill: Bend is home to lots of craft breweries with tasting rooms downtown, including Bend Brewing Company, Deschutes Brewery, Silver Moon Brewing, Boneyard Beer, Immersion Brewing, and more. Cycle Pub takes you on a pedal-powered trolley tour through local brews. Don’t worry—there’s a designated steerer.

Downtown Oaxaca, Mexico

Oaxaca is a city of markets, and you’ll find some of the most colorful shopping experiences downtown. Wander through Benito Juarez and the Mercado 20 de Noviembre to collect handmade leather goods, ponchos, and blankets. Vendors are always cooking up delicious dishes and drinks to fuel your treasure hunt, including fresh tortillas, chocolate, and unique soft drinks.

Find your chill: Each year the streets fill with fireworks, dances, parades, and radish-carving contents for the Fiesta de Rábanos. Yes, this party is all about refreshing, spicy radishes.

Downtown Grand Junction, Colorado

Beautiful fountains and public art installations make downtown Grand Junction a living art gallery. You don’t have to keep quiet around here, though. Follow the sound of street performers around town year-round, or plan a trip to Grand Junction during the Off-Road & Four Peaks Downtown Music Festival. For 29 years, the event has showcased free music from local and regional musicians.

Find your chill: Channel your inner artist at ARTBar. Painting classes come complete with “liquid inspiration,” in the form of mimosas, beer, and wine. That’s a masterpiece in the making.

Provo Downtown Historic District, Utah

With Utah Lake to the west, Y Mountain to the east, and Brigham Young University to the north, downtown Provo is both historic and eclectic. Students and travelers alike pore over the shelves in search of literary gems at Pioneer Book, and every Thursday the Provo Food Truck Roundup fills the streets with good eats.

Find your chill: Chocolate gets a bad rap as indulgent and “sinful,” but the Taste chocolate factory gives downtown Provo its heavenly scent. Follow your factory tour with a healthy drink from Ivie Juice Bar and go from naughty to nice.

Downtown Hanover, Pennsylvania

Hanover’s pairing of historic mansions and open-air markets gives the city its signature cool. Join a lavish party at the Warehime-Myers Mansion, built in 1911. To keep it casual, browse Hanover Market House; it’s a piece of living history, dating back 200 years. Today, you’ll find the freshest ingredients you crave, plus flowers and handmade art all in one place. Want to search for even more East Coast treasures? Explore the Hanover Geo Trail and join the hunt!

Find your chill: The perfect mix of academic and artsy, Reader’s Café is a library and café all in one. Sounds like paradise. Check the calendar for live music and open mic night opportunities.

What makes your hometown cool?

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Kohleun Adamson

Kohleun is a fan of high tea in Scottish villages and low tide on Coronado Beach, and she can’t get enough of rolling vineyard vistas. These days it’s no easy feat to pull her away from the California coast, but she can be wooed with Moroccan cous cous and ancient palace ruins. As a writer, Kohleun has a passion for sharing the intricate details of a journey well traveled, whether it involves crossing continents or exploring close to home.

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  • rbd171

    I guess you have never been to San Antonio, Tx.

  • Loren Kline

    From prescottonians: its not that cool, please go somewhere else tourists the roads are bad enough as it is there’s mostly just racists and drug addicts here