The Best Small Cities In America

All have populations of under 100,000, and often as much to offer as cities ten times their size.
07/31/2015 08:49am ET | Updated December 6, 2017
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by Debbie Strong, Condé Nast Traveler

Ian G Dagnall / Alamy

Here are the small American charmers, as voted on by Condé Nast Traveler readers. All have populations of under 100,000, and often as much to offer as cities ten times their size.

30. Newport Beach, CA

Check out the legendary waves at beautiful Balboa Peninsula, where surfers reign and a nearby bustling boardwalk offers some of the best people-watching in all of sunny SoCal. Stay at The Resort at Pelican Hill, in an elegant, Palladian-inspired villa overlooking the Pacific.

Gary Crabbe / Alamy

29. Annapolis, MD

History buffs, take note: Maryland's capital city is home to the U.S. Naval Academy (and its bright copper-domed chapel, pictured) and more than 50 well-preserved buildings that predate the Revolutionary War. Stop in for crab cakes at the Middleton Tavern, which dates to 1750 and counts George Washington, Benjamin Franklin, and Thomas Jefferson as former famous patrons, among others.

Sean Pavone / Alamy

28. Palm Springs, CA

Soak up old Hollywood glamour mixed with breathtaking scenery in this ultra-hip desert oasis. Stay at the candy-colored Saguaro Palm Springs (pictured) and dine at Copley's on Palm Canyon, once Cary Grant's estate.

Courtesy Saguaro

27. Palm Beach, FL

The city is home to the largest croquet complex in the world, but it's the beachfront mega-mansions most visitors make sure to check out, either with a bike ride or a cruise on the Palm Beach Water Taxi. For the ultimate South Florida experience, stay at The Breakers, listed on the National Register of Historic Places.

Ian G Dagnall / Alamy

26. Eureka Springs, AK

In the middle of the Ozark Mountains, Eureka Springs is full of Victorian charm, and is affectionately known as 'The Little Switzerland of America.' Get in the mindset with a stay at The 1886 Crescent Hotel and Spa, whose velvet couches and crystal-filled ballroom will transport you back to the 19th century; but be on the lookout for ghosts (some claim this is the most haunted hotel in the country).

25. Hilo, HI

It's no secret that Hawaii is full of beautiful scenery. Hilo is home to dramatic waterfalls and sunsets, as well as the Pana'ewa Rainforest Zoo, the only U.S. zoo in a tropical rainforest. Spend the night at the charming, Victorian-era Shipman House Bed & Breakfast in the center of town.

24. Ashland, OR

At the base of the Siskiyou and Cascade mountain ranges, the scenery here is second to none--and the town's year-round mild weather doesn't disappoint, either. Despite being thousands of miles from England, the Oregon Shakespeare Festival draws major crowds, and the Ashland Springs Hotel has a distinctively European flair in its 70 rooms.


23. Healdsburg, CA

You don't need to be a lover of wine to relish the lush beauty and tranquility of this northern Sonoma County hamlet, just an hour's drive from San Francisco. Farm-fresh food at many local restaurants earned Healdsburg the no. 8 spot on Condé Nast Traveler's Readers' Choice list of America's best food cities and rooms at the Madrona Manor are unapologetically romantic.

22. Natchez, MS

History runs deep in this historic Southern city, the oldest settlement on the Mississippi River. Many of the town's antebellum homes are open for public tours; be sure to book a room at the Monmouth Historic Inn, surrounded by 26 acres of beautifully maintained gardens.

21. Monterey, CA

Take advantage of one of the most scenic drives in the world, along 17-miles from Pacific Grove to Pebble Beach, featuring jaw-dropping vistas and legendary natural treasures including The Lone Cypress and Stillwater Cove. Steer clear of the happening (but touristy) scene at Cannery Row and instead head for Restaurant 1833. Once the city's first pharmacy, the spot is now known for its James Beard-nominated cuisine and silver-spoon absinthe service.


20. Naples, FL

Among the country's best destinations for golf and sunshine, Naples is dotted with sleek hotels, top-notch shops, and restaurants. Two of our readers' favorite places to stay are the Ritz-Carlton (pictured) and LaPlaya Beach and Golf Resort.


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