Whether they have over-the-top American charm (we’re looking at you, Woodstock, Vermont) or proximity to some of the loveliest landscapes on earth (hello, Big Sur), these 20 idylls are worth a stopover. And while there’s something to be said about big city living, downsizing sure has its perks—think local boutiques, tons of outdoor activities, and restaurant-to-people ratios that lean way in your favor. Here, 20 of the prettiest towns in America.
This gallery was originally published in 2016. It has been updated with new information.
From streets filled with Victorian-era homes to classic rocky coastlines, the scenery of Portland is truly unparalleled—and you can’t visit without stopping by the Portland Head Light (pictured), which affords some of the best ocean views around. The town also entices you to extend your stay with accommodations like the Press Hotel, housed in the former Portland Press Herald building. Let’s not ignore the fact, either, that Portland’s ratio of restaurants to people is insane (in a good way), so take advantage: We recommend Eventide Oyster, Honey Paw, Central Provisions, and Portland Lobster Company—you know, just to get you started.
Harpers Ferry, West Virginia
Harpers Ferry has a lot going on, geographically speaking. After all, it’s where West Virginia, Virginia, and Maryland meet, and where the Potomac and Shenandoah Rivers combine. The scenic junction and surrounding Harpers Ferry National Historical Park make for one very picturesque townscape, especially during those leafy autumn months. Meanwhile, the town offers constant historical tours (it was the site of John Brown’s raid) and the occasional ghost tour. There’s more than enough here for adventurers, as well, like kayaking, rafting, zip lining, rock climbing, and hiking on the Appalachian Trail.
Asheville, North Carolina
Asheville is well-established as a food destination—for proof, head to farm-to-table Rhubarb, or Cúrate and Nightbell, both helmed by James Beard-nominated chef Katie Button. But the city offers more than just restaurants. You could spend all day exploring the North Carolina Arboretum (pictured), impossibly dignified Biltmore Estate, and grand dame Omni Grove Park Inn. Plus, when a town has the Blue Ridge Mountains as its neighbor, it already has a leg up on most other places in the country.
Long known as a quintessential summer getaway, travelers come to Nantucket every year to walk among the narrow rows of wood-paneled houses and bike out to the lighthouses that ring the island. Although crescent-shaped Nantucket may be small, it has room for terrains ranging from sand dunes to salt marshes to craggy bluffs. It’s nearly impossible to take a bad photograph here.
Lake Placid, New York
This small village in the Adirondacks is stunning pretty much year round, thanks to its combination of rolling mountains and the clear, spring-fed, 2,173-acre lake. Home to just over 2,500 people, it is a rustic getaway that’s popular with hikers, fishermen, and skiers (it was home to two Winter Olympics, in 1932 and 1980). But it also excels on the luxury front, and three of Lake Placid’s hotels have previously landed on Condé Nast Traveler’s Readers’ Choice Awards list of the top resorts in the region: Whiteface Lodge, Lake Placid Lodge, and Mirror Lake Inn Resort and Spa.
For a dose of absurdly quaint New England charm, it’s tough to do better than this town in the Green Mountains. Complete with a perfect village green with a white steepled church, this is just the destination for antique shoppers and B&B fans—some lodging even dates back to the 1750s. Almost all of the town’s buildings are on the National Register of Historic Places; be sure to drop in at the 1886-era general store F.H. Gillingham & Sons for some souvenir maple candy.
St. Augustine, Florida
You’ll quickly forget the Florida you think you know when you enter this Spanish-founded seaside city that dates back to 1565. In fact, St. Augustine is the oldest permanent European settlement in the continental U.S., home to some of the country’s first Spanish colonial architecture and many historic buildings constructed in the centuries since. St. Augustine also played a pivotal role in the Civil Rights Movement of the 1960s, and there is a Freedom Trail where you can walk in the footsteps of Rev. Martin Luther King, Jr. Don’t miss the Castillo de San Marcos, a 17th-century fortress complete with drawbridges and daily cannon fire.
Big Sur, California
Set atop windswept cliffs hugging the Santa Lucia Mountains to the east, and the Pacific Ocean to the west, Big Sur is breathtakingly beautiful. Though the town is sparsely populated, it has two top hotels: the five-star Post Ranch Inn and the four-star Ventana Big Sur. Fans of counterculture literature will also enjoy the fact that Jack Kerouac, Hunter S. Thompson, and Henry Miller all have ties to Big Sur—and the latter left behind a museum filled with Beat-era books and memorabilia. If your time is short, at the very least, take a drive through the town on Route 1.
This charming town, with brick-lined streets and structures that date back centuries, was founded in the mid-1600s. Set on the Chesapeake Bay, Annapolis went on to become a pivotal port for Civil War munitions, then was a fishing city (though, nowadays most of the trawlers have now been replaced by pleasure boats). Today, it’s home to the U.S. Naval Academy, and visitors are able to take tours of the vast, Beaux Arts campus, after which a visit to O’Learys Seafood Restaurant for crab cakes is essential.
Set in the shadow of red-rock monoliths, Sedona benefits from its striking location—visitors often beeline for its buttes, canyons, and spires. On clear nights, take in the region’s light-pollution-free sky’s dazzling display of stars. A must-stay here is L’Auberge de Sedona, our readers’ top-rated hotel in the Southwest. The hotel is set in the heart of Red Rock Country, which means beauty abounds everywhere you look.
Set in a lovely pastoral region known as “The Valley of the Flowers,” Bozeman is incredibly scenic. It sits at an elevation of 4,820 feet and is surrounded by mountains—the Bridger Mountains to the north-northeast and the Tobacco Root Mountains to the west-southwest—on all sides. Look familiar? That’s probably because it was a location of the fly-fishing-centric film A River Runs Through It. And if we may be so bold, Brad Pitt nearly (nearly) paled in comparison to the beautiful setting.
Newport, Rhode Island
Newport is practically synonymous with tony New England, where sailboats dot the harbor and the well-heeled explore the cobbled shopping wharves. Every summer, visitors flock to Fort Adams, a lush green expanse at the mouth of the Narragansett Bay, for the Newport Jazz Festival and Newport Folk Festival. In the colder months, stay indoors and tour some of the town’s famous estates—most notably Doris Duke’s former home, Rough Point.
Friday Harbor, Washington
This beautiful hamlet sits in the farthest northwest reaches of Washington, with a marina at Roche Harbor that serves as a jumping-off point for cruising around small, uninhabited islands. Friday Harbor was once a major produce provider for the state, but these days, the economy is centered around tourism—sea kayaking and orca whale-watching are the biggest draws. Year-round ferries from Anacortes (on the mainland) make it easy to visit in every season.
Santa Barbara, California
This coastal town is a classic Golden State beauty: It offers both incredible south-facing ocean frontage and views of the Santa Ynez Mountains. And it’s not just a looker—its Franciscan Mission and other colonial buildings give Santa Barbara historical interest. The town also happens to be a surfer’s paradise, and many legends of the sport (like Tom Curren) live here. Go to locals’ favorite shop Surf-N-Wear’s Beach House to rent gear and find talented instructors.
Sitka is widely considered the most beautiful town in Alaska—mountains known as the “Sisters” serve as a backdrop, and spruce trees grow almost down to the sea. The harborside town is quaint and compact, with the look of a Wild West enclave, complete with flat-fronted wooden buildings that wouldn’t look out of place in a John Wayne film. The natural beauty and remote location of Sitka makes it a beloved destination for hikers, climbers, hunters, and fishermen; head just a few miles out of town and you’ll feel like you are in the middle of nowhere, in the best possible sense.
Taos, New Mexico
The lovely high-desert town of Taos has a long and fascinating history. The Taos Pueblo, which is three miles from the center of town, has been home to native peoples for nearly a millennium, making the community one of the oldest continually occupied places in the U.S. (it is also an UNESCO World Heritage site). Today, the town is known for its culture: Painters, sculptors, and writers began to come here in 1899, and Taos now has a thriving artists’ colony. The town’s natural beauty—with red-rock canyons, clear blue desert skies, and snow-capped mountains on the horizon—is both reflected in and inspires creative people of all palates.
It’s all about indulging your castaway fantasies in this small village on Maui’s North Coast. Sure, the town center is sweet, even a little hip: It boasts a too-cool tattoo parlor and boutiques selling stylish, locally made beachwear. However, insiders know that Paia is all about the beach—namely, Ho’okipa Beach Park, beloved by locals for its white sand and by surfers, wind-surfers, and kite-surfers for its near-perfect breaks. Tip: Grab a plate lunch at the Paia Fish Market to fortify you before a big day on the water.
Telluride sure seems to be on everyone’s radar these days: Not only was it voted one of the best small cities in the U.S. in last year’s Readers’ Choice Awards, but it was also dubbed the tenth-friendliest city in this year’s survey. And we totally get the appeal: The funky ski town looks like some sort of movie set (think: charming storefronts, stunning mountain views, etc.), and is filled with travel-worthy restaurants and hotels. Another option? The 76 vacation rentals available through Exceptional Stays, ranging from condos directly under ski lifts to remote mountain cabins.
Traverse City, Michigan
If it’s an untrammeled lakeside escape you seek, then head straight to Traverse City. So named for its port at the very south of the Grand Traverse Bay, it is a popular summertime getaway for city-dwellers in the Midwest, though four-season outdoor activities beckon. But just because it’s pretty much the epitome of “Pure Michigan” (the state’s tourism motto) doesn’t mean that Traverse City lacks sophistication. Foodies should particularly take note: eateries like S2S|Sugar 2 Salt and Grand Traverse Pie Company are more than worthy pit stops; plus, the region produces the tartest cherries in the country (the annual July National Cherry Festival is a real treat).
This classic New England seaside town is so picture-perfect, it was the primary filming location for the 1957 movie Peyton Place (a film about—surprise!—a seemingly idyllic town.) The motto of Camden has long been “Where the mountains meet the sea,” and indeed, Mount Battie and Bald Mountain rise up above the harbor and the village; a hike to the top of the former will reward you with a stellar view. Though most of the village’s commerce is aimed squarely at tourists, there are some gems, like boutique hotel Whitehall, a white-clapboard beauty.