Living in one of America’s prettiest towns | Waccabuc Real Estate

There’s a good reason Presidents Eisenhower and Kennedy chose Newport, Rhode Island, for summer escapes by the water. First, consider the draw of one of the most enchanting stretches of shoreline on the East Coast, a seascape best viewed when traveling down the ten-mile twist of Ocean Drive.

Then there’s Newport’s time-traveling charm, its ability to whisk you away to other periods in American history by way of colonial-era homes and Vanderbilt mansions.

See full slideshow: America’s Prettiest Towns
See full slideshow: America's Prettiest Towns

To designate Newport and the rest of America’s most picturesque towns, we called on recommendations by experts from the Travel Channel, National Geographic, the author of a book about towns in the Northwest, and Fodor’s. Some locales have changed considerably in the last few decades, while others have remained the same for centuries. All offer not only aesthetic reward, but also memorable activities and destinations nearby.

Would you choose to live in one of America’s prettiest towns?

Newport, Rhode Island

Photo: Fraser Hall/Robert Harding/Newscom

Like a town stuck in time but with the occasional hole in the space-time continuum to allow for modern touches, Newport, with its stunning harbor and bevy of old homes, is the quintessential New England town. Newport’s fame began as a 19th century summertime visitors’ magnet of a town, and it still reliably draws in clusters of visitors, both for the daytime shopping, eating, and sightseeing options. At night, one of the town’s many music festivals or varied collection of bars draws in local students and stalwart party goers for good times that can run late and loud. But the town itself is chief among American small towns in the category of most well-preserved colonial homes and Gilded-Age mansions – a testimony to its tony residential reputation, and to its history as the summer destination of choice from 1953 until around 1963. It is also the location of an important collection of naval training centers.

Old San Juan, Puerto Rico

Photo: William Randall/istockphoto

Located on a small island just east of the main island, Old San Juan, while technically part of the Puerto Rican capital, is a small town all its own. Cross one of the three bridges that connect it to the mainland, and it’s as if you have stepped into a 16th-and 17th-century Spanish colony. European-style cobblestone streets – which were, of course, not built for cars, make navigation by any vehicles other than taxis difficult. Wander its quaint paths, stop into one of its boisterous bars, or visit any one of the restaurants collectively considered the vanguard of the Nuevo Latino food movement. The old fort that guarded the entrance into the original “Rich Port” still stands guard over a white-capped Caribbean, and glimpses of old Spain through an American lens are everywhere. Best of all, you don’t need a passport to visit what is arguably the Caribbean’s most enchanting capital city.

Key West, Florida

Photo: Matt Tilghman/istockphoto

Closer to Cuba than it is to the mainland United States, Key West exudes a laid-back and casual vibe that is different than almost any other town in the country. It’s a place that marches to its own (usually steel) drummer. Take the kids dolphin-spotting, charter a boat to snag a marlin, or just relax on the beach beside crystal blue waters. And getting there is half the fun: the 127-mile Overseas Highway is the only road in or out to the mainland, and there’s no road in the country like it. If that’s not enough, Key West is also home to the only National Park that is accessible only by boat, Dry Tortugas National Park, where the snorkeling, diving, or just exploring are unparalleled.

Tarrytown, New York

Photo: Philip Scalia/Alamy

Tarrytown’s rich history, including being a throughway on the Underground Railroad, name-dropped by Washington Irving in “The Legend of Sleepy Hollow,” and, later, one of the preferred Upstate getaways for New York’s rich and powerful, is visible wherever you go in this Hudson River-side town. Lyndhurst, the widely-regarded robber baron Jay Gould’s castle-like mansion in town, is toured by throngs of visitors every year. The town has played host to recreational and cultural options aplenty, including the famous (and former, running from 1971 to 2006) Tarrytown Film Festival, which was more of a film salon hosted by noted ‘70s and ‘80s film critic, Judith Crist.

Longview, Washington

Photo: Peter Horree/Alamy

Not even the port industry that clusters around the Lewis and Clark bridge can block the scenery of one of the Pacific Northwest’s most charming towns. “It is one of the only, if not the only planned community in the west at the time,” says Foster Church of “Discovering Main Street: Travel Adventures in Small Towns of the Northwest. “It was planned by a wealthy lumber magnate who decided to build two lumber mills in this location because it was close to the Columbia River.” He needed 14,000 workers to help run his two mills, so in 1921, he built a city that could house up to 50,000 people. Today, the town retains its old town lumber mill feel, and is home to the well-planned but serene beauty of Lake Sacajawea Park, which Foster says is “one of the most beautiful parks I’ve ever seen.”

See full slideshow: America’s Prettiest Towns

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