America's Best Downtowns

We located the country’s most alluring downtowns based on factors including attractiveness, accessibility, diversity of offerings, shops, restaurants, proximity of parks and cultural options.

Chicago, Ill.
Chicago, Ill.

Chicago, Ill.

Courtesy of UIC

We located the country’s most alluring downtowns with the help of travel experts from Frommer’s and Livability, a travel and analysis site that focuses on mid-sized or smaller towns. While Livability’s own list of best downtowns helped us narrow down the playing field, we ultimately considered a wide variety of factors including attractiveness, accessibility, diversity of offerings, shops, restaurants, proximity of parks and cultural options.


Some cities, like Santa Monica, made the list because they both offer a lively downtown and have the luck of being located in a beautiful setting. There are smaller towns on the list as well, and they often earn their spot due to easily navigable downtown areas and unparalleled attractiveness.


In Pictures: America's Best Downtowns


Chicago, Ill.


Of the country’s big city downtowns, Chicago’s relatively compact zone in and around what’s known as “The Loop,” wins hands down for being the most accessible, pedestrian-friendly and varied in its offerings. Within a two-mile radius, visitors and residents alike can visit some of the world’s best restaurants, lounge in a resplendently outfitted urban park, visit world-class art museums, shop their wallets dry on Chicago’s famous store-covered Magnificent Mile, examine some of the finest architecture on the planet, find boats to tour Lake Michigan, or wander around the waterfront tourist-friendly esplanade, Navy Pier.


Portland, Ore.
Portland, Ore.

Portland, Ore.

Thinkstock

Portland, Ore.


Although Portland is well known as a city that is friendly to bicyclists, it also has a walkable and attractive downtown that offers a wide variety of cultural options and commercial options. There’s a vibrant and active arts scene, great food on both the high and low ends, the country’s best selection of locally sourced craft beers, an attractive and popular riverside park, and Powell’s, the largest and one of the best independent bookstores in the country. And while you can, with some effort walk around much of Portland’s relatively small downtowns, its best to mike like a local and rent a bike – you’ll get around more effectively, see more of the area, and get a little exercise – all good things in the greenest of “America’s 50 Greenest Cities.”


Burlington, Vt.
Burlington, Vt.

Burlington, Vt.

Vermont Dept. of Tourism

Burlington, Vt.


Although it does have some famous ski destinations nearby, Burlington’s not only attractive when there’s snow on the ground. The city’s location on Lake Champlain provides a scenic backdrop to a lively and charming downtown full of shops, restaurants, and one of the country’s best craft breweries, the Magic Hat Brewing Company. “Downtown’s Church Street is the center of culture and students in this college town,” says Livability in its online ranking. This hopping pedestrian mall is home to all kinds of commerce and culture, including a wide array of street performers, and is a big part of why Burlington makes the list.


Indianapolis, Ind.
Indianapolis, Ind.

Indianapolis, Ind.

Thinkstock

Indianapolis, Ind.


Sure, there are museums, such as the Indianapolis Museum of Art, a large and important cultural locus that maintains a 54,000-piece collection. And yes, the Fountain Square district boasts a growing and productive bohemian vibe that is a big part of the city’s identity – many of the city’s downtown development efforts are focused on it. And of course, there are a number of well-regarded universities within the city and its surrounding areas that help instill downtown with a young and active character. But Indianapolis packs that and more into a six-square-mile downtown area. “For some, downtown paints a city scene: skyscrapers and taxis, nightlife, and takeout restaurants around every corner. If that's you, you're in luck. Indianapolis will give you the big-city experience, minus the actual big city,” says Livability in its listing.


San Antonio, Texas
San Antonio, Texas

San Antonio, Texas

Jo Ann Snover/istockphoto

San Antonio, Texas


For those who haven’t yet visited San Antonio, the city conjures up images of a tragic and bloody last stand at The Alamo. But for anyone who has visited, the city is more than just home to one of the most famous historical sites in the West. The San Antonio River Walk is perhaps the most beautiful part of the city, creating a verdant pathway lined with colorful café umbrellas that winds its way through downtown, offering up a bevy of shops, restaurants, and bars on the way. Tour downtown, follow the river by foot or tour it by boat, and save your visit to the Alamo for the late afternoon, when the sun is in retreat and you’ll have more to remember from your trip than just an historic and valiant defeat.


Savannah, Ga.
Savannah, Ga.

Savannah, Ga.

worldsbestbeaches.com

Savannah, Ga.


There are carriage rides and riverboat cruises, a lively music scene, and famous restaurants such as Paula Deen’s The Lady and Sons, but let’s face it: if you’re visiting Savannah you’re here first and foremost for its historical architecture and beautifully maintained buildings and homes, all framed by the town’s famous Spanish moss-covered oak trees. There will be time to visit Forsyth Park, the city’s beautiful riverside stretch of greenspace, later, and the gallery shopping can wait. You want to see some of the best homes and architecture in the country, so you can either hop onto a trolley and explore the offerings one stop at a time, or go the unabashed tourist route and tour the city’s best architectural offerings by horse and carriage.


Kansas City, Mo.
Kansas City, Mo.

Kansas City, Mo.

Wikipedia

Kansas City, Mo.


Although there had already been a wide variety of artists living, working, and coalescing around downtown Kansas City, the brand new Kauffman Center for the Performing Arts just opened in September and quickly became central, and a visual monument to just how seriously Kansas City takes the arts. Combine that love of culture with a walkable and livable downtown, a wide variety of neighborhoods such as “The Plaza,” which is known for its upscale shopping and entertainment. Plus, everywhere you look in Kansas City, there’s another fountain dancing in front of you, “They were one of the first cities in the US to add a pedestrian mall back in the fifties,” says Jason Clampet, senior online editor for Frommers.com. “Plus you’ve got great barbecue there, and you can spend all day going from barbecue to barbecue joint – it’s that delicious.”


Winston-Salem, N.C.
Winston-Salem, N.C.

Winston-Salem, N.C.

City of Winston-Salem

Winston-Salem, N.C.


Although Winston-Salem has a lot to offer from an active arts and culture scene, it’s the downtown district of Old Salem that really earns the city a place on the list. Many of our cities boast historic downtowns, but Old Salem’s is different because of its focus on the town’s former Moravian settlers, and because there is a steadfast effort to keep parts of downtown in a time warp to the 18th century. It’s like a little slice of Old Williamsburg in the center of a mid-sized city. The whole district was declared a National Historic Landmark in 1966, and continues to draw in visitors with its quaint old shops, churches, and costumed reenactors.


Greenville, S.C.
Greenville, S.C.

Greenville, S.C.

Citydata.com

Greenville, S.C.


As recently as fifteen years ago, there would be no chance of Greenville making anybody’s list of top downtown areas. Suffering from decades worth of neglect losing business to the suburbs, the city engaged in an aggressive renewal project that has been enormously successful in transforming the downtown into a thriving cluster of new homes, shops, restaurants, and arts offerings. “There are pedestrian areas where people are walking around and shopping, and it’s really different from the other cities in South Carolina,” says Clampet. The addition of a BMW plant 30 miles outside the city has had a big impact on the workers coming in, and has changed it, in Clampet’s terms, “from a backwater to a really functioning and beautiful place.”


Santa Monica, Calif.
Santa Monica, Calif.

Santa Monica, Calif.

Panoramio

Santa Monica, Calif.


With its proximity to Los Angeles, its world-class beaches, and its mix of families, students, surfers and the very rich, Santa Monica earns its place both because of its commercial offerings and its stunningly beautiful natural settings. Clustered around some of the best beachfront acreage in Southern California, with the world-renowned Santa Monica Pier as the anchor, the city fans out into a lively and diverse set of surrounding areas. “You’ve got a great six blocks or so of shopping, with a mix of local stores, boutiques and chains,” says Clampet. “And unlike most of the rest of the region, you can really walk around and get by without a car.” A varied mix of smaller but interesting museums, galleries, and a busy nightlife scene also contribute to the reasons why Santa Monica earns a place on our list.


In Pictures: America's Best Downtowns