TRIP IDEAS

The 9 Cutest Small Towns in

America
Every year, America’s small towns draw tourists—and new residents—to their streets
in droves. They are, after all, reminders of a simpler way of life, where mom-and-pop
shops are the norm, everybody knows your name, and the pace is slower than the
speed of tweets. To help you get away from the breakneck tempo of your daily routine,
we rounded up nine of the cutest small towns for an easy weekend escape, from a
picturesque New England coastal haven to a romantic Southern getaway that feels
untouched by time.

By Jennifer Fernandez December 28, 2018

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 1

Carmel-by-the-Sea, CA
With its local wineries (https://www.carmelcalifornia.com/things-to-do-wine-tasting-
in-carmel.htm) and Pacific Coast Highway views, the Northern California town of
Carmel-by-the-Sea is as idyllic as its name suggests. Come for the beach, a mile-long
swath of white sand from which you can view dolphins and sea lions, then wander
around town to shop quirky independent boutiques and see whimsical cottages that
look like they came straight out of a fairytale. The atmospheric gardens and chapels
at Spanish-colonial Carmel Mission (https://carmelmission.org/), founded in 1770 and
designated a National Historic Landmark, offer worthy spots for reflection, though
you'll find just as much tranquility after a stay in one of the intimate suites at L'Auberge
Carmel (https://www.jetsetter.com/hotels/carmel-by-the-
sea/california/506/l-auberge-carmel?
occupancy=%5B%7B%22adults%22%3A2%2C%22children%22%3A%5B%5D%7D%5D).
For dinner, nab a table at Cultura Comida y Bebida (http://www.culturacarmel.com/),
where chef Michelle Estigoy serves standout chicken tinga tacos and epazote
quesadillas inspired by her family's Mexican heritage.

Check Prices for L Auberge Carmel in Carmel, CA

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Sitka, AK
Accessible only by air and sea, the fishing village of Sitka is a remote beauty that anyone
who has watched the 2009 Sandra Bullock film The Proposal is sure to recognize
(filming took place in Rockport (http://rockport.com), Massachusetts, but sets were
built to resemble this port town). Here, you can indulge in the natural pursuits Alaska is
known for, from whale watching and kayaking
(http://www.sitkawildlifetours.com/sitka-alaska-whale-watching-tours/) to hiking
(http://www.alaska.org/destination/sitka/trails) up a dormant volcano or strolling
through towering spruce trees—spotting bald eagles and totem poles along the way—at
Sitka National Historic Park (https://www.nps.gov/sitk/index.htm).

Book Hotels In Alaska (https://www.jetsetter.com/hotels/alaska/)

 3

Taos, NM
It’s easy to see why this high-desert town in the Sangre de Christo Mountains has
become a haven for artists, writers, and other creative types. The UNESCO World
Heritage Site is a feast for the senses thanks to its striking adobe architecture, red-rock
canyons, and snow-tipped peaks. Feeling inspired? View works by the likes of Agnes
Martin and other local painters at the Harwood Museum of Art
(http://www.harwoodmuseum.org/) and more than 80 other galleries. There are also
plenty of activities to keep adrenaline junkies engaged year ‘round. Summer brings
hiking and hot air ballooning, (http://www.taosskivalley.com/play/summer-
activities/hiking) while winter offers some of the best skiing
(https://www.skitaos.com/) in the country.

RELATED: The Most Affordable Ski Destinations to Check Out This Year
(https://www.jetsetter.com/magazine/affordable-ski-destinations/)

Book Hotels in New Mexico (https://www.jetsetter.com/hotels/new-mexico/)

 4

Marfa, TX
As art meccas go, Marfa is an unlikely one. Founded in 1883, the tiny Texas
town—population under 2,000—has served as a railway headquarters and military
training base, but it wasn’t until the 1970s, when artist Donald Judd moved there, that it
became a cultural destination for the aesthetically informed. View some of his most
iconic concrete sculptures on a sunrise tour of the Chinati Foundation
(https://chinati.org/programs/sunrise-at-chinati), or make like the Insta glitterati and
take a selfie in front of Elmgreen and Dragset’s now-famous Prada Marfa
(https://www.tripadvisor.com/Attraction_Review-g56804-d5557195-Reviews-
Prada_Marfa-Valentine_Texas.html?m=58334)installation, off Highway 90.

Check Prices for Cibolo Creek Ranch in Marfa, TX

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 5

Beaufort, SC
If this Lowcountry fishing village looks straight out of a movie set, that’s because it is:
Beaufort was the backdrop for such films as Forrest Gump and The Big Chill thanks to
its sprawling antebellum mansions, moss-draped oaks, and picturesque downtown
streets. Located on Port Royal Island in South Carolina’s Sea Island chain, the town
makes an ideal base for enjoying simple pleasures and all manner of aquatic diversions
(http://www.beaufortsc.org/50-things-to-do/), including paddle boarding, kayaking,
dolphin watching, and crabbing.

Book Hotels in South Carolina (https://www.jetsetter.com/hotels/south-carolina/)

 6

Galena, IL
The romantic ideal of Main Street is alive and well in this mining town on Illinois’s
northwestern border—think of it as the Midwest’s version of Stars Hollow. Trolley cars
still cruise down the historic lane, which is lined with 19th-century brick buildings and
cute galleries, boutiques, and craft shops that give it a distinctly small-town feel.
American history fanatics, however, will be more impressed with Galena’s status as the
home of Civil War hero Ulysses S. Grant, a fact illuminated at the U.S. president’s
namesake museum.

Check Prices for Eagle Ridge Resort and Spa in Galena, IL

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BOOK NOW
 7

Edgartown, MA
On the southeast tip of Martha’s Vineyard, Edgartown
(https://www.tripadvisor.com/Tourism-g41558-
Edgartown_Martha_s_Vineyard_Massachusetts-Vacations.html?m=58334) is the
quintessential New England seaside getaway with classic shingle-style buildings,
windswept dunes, and a scenic lighthouse. Though the beaches are the draw, the
onetime whaling port brims with storybook charm. Tour the 18th-century homes of
whaling captains on foot or bike, then try your hand at sailing
(http://www.madmaxmarina.com/)like a local. All it takes is a short ferry ride
(http://chappyferry.com/) to explore neighboring Chappaquiddick Island, where,
during the summer, you can play a round of night golf by the light of the full moon.

RELATED: 10 Trips to Take If You’re An Introvert

(https://www.jetsetter.com/magazine/10-best-trips-to-take-if-youre-an-introvert/)

Book Hotels in Edgartown, MA (https://www.jetsetter.com/hotels/edgartown-ma/)

 8

Stowe, VT
This impossibly quaint Green Mountain town has all the makings of a Norman Rockwell
painting—right down to the general store (http://www.shawsgeneralstore.com/). But
there’s more to Stowe than simple pleasures. Not only does Stowe have Vermont’s
tallest peak, making it one of the East Coast’s most popular (and powder-friendly) ski
destinations (https://www.stowe.com/), it’s also home to the Trapp Family Lodge
(https://www.jetsetter.com/hotels/stowe/vermont/2583/trapp-family-lodge), an
Austrian-style chalet owned by the family immortalized in The Sound of Music, as well
as a stellar culinary scene. Don't miss the grilled cauliflower steak with quinoa at our
favorite dinner spot, Plate (http://www.platestowe.com/). Have a sweet tooth? The Ben
& Jerry’s Ice Cream Factory (http://www.benjerry.com/about-us/factory-tours)is
nearby in Waterbury.

Check Prices for Trapp Family Lodge in Stowe, VT

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 9

St. Augustine, FL
The cobblestone streets of St. Augustine are steeped in history. Founded in 1565 by
Spanish conquistadors, the northern Atlantic coast town is studded with colonial
architecture, from the 17th-century Castillo de San Marcos
(https://www.nps.gov/casa/index.htm) fortress to the Victorian antiques–filled
Lightner Museum, (http://lightnermuseum.org/?gclid=Cj0KEQjwo-
XIBRCOycL7hsuI_NoBEiQAuS6HtBTNb0GEHqipPEZAxF0zt6_2iXT9-wuYg-
oNaKPse_8aAs9l8P8HAQ) housed in an 1887 Spanish Renaissance Revival building
commissioned by Rockefeller business associate and Florida real estate magnate Henry
Flagler. If sun and sand is what you seek, there’s plenty of that, too: Anastasia State
Park (https://www.floridastateparks.org/park/anastasia)comprises four miles of
wildlife-dotted beach and maritime forests.

Book Hotels in St. Augustine, FL (https://www.jetsetter.com/hotels/st-augustine-fl/)

Want more?
• The Coolest Beach Hotels in America
(https://www.jetsetter.com/magazine/coolest-beach-hotels-in-the-usa/)
• 30 Trips to Take in Your 30s (https://www.jetsetter.com/magazine/thirty-trips-to-
take-in-your-thirties/)
• The Best Long Weekend Winter Getaways in (and Near) the U.S.
(https://www.jetsetter.com/magazine/americas-best-long-weekend-winter-
getaways/)

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