Road Trip Love: Take a Look at 25 of the Prettiest Little Towns in America

From coastal towns to southern gems, these idylls are worth a visit

I am always dreaming of taking a road trip, somewhere, anywhere. Do you ever find yourself staring out the window and wishing you could hop in the RV and drive away?

When you find yourself having moments like this, where do you imagine yourself driving? Do you envision a desert town or a beachfront campground? Or maybe it’s the drive itself you’re most jazzed about.

One of my favorite road trip destinations is traveling to pretty small towns that offer a unique experience in a lovely setting without necessarily having to brave a gazillion people once I get there.

If that is something to which you can relate, I’ve done a little research on some of the prettiest little towns in America. Let’s take a quick photographic tour. Cuz hey, even if you can’t head out on the open road immediately, you can at least make some travel plans so you’re ready to launch when you are.

And research shows that even just PLANNING a trip can be a mood booster. Isn’t that an encouraging thought? I think so! And while many others could be added to this list, let’s simply start with these.

OK, here are 25 of the prettiest little towns you ever did see.

Berea © Rex Vogel, all rights reserved

1. Berea, Kentucky

Known as the Folk Arts and Crafts Capital of Kentucky, Berea is a dynamic spot for creators and craftspeople working across a variety of media. Many sell their wares at galleries along Chestnut Street and in both the Artisan Village and the Kentucky Artisan Center. 

Wetumpka © Rex Vogel, all rights reserved

 2. Wetumpka, Alabama

Put your finger on the middle of a map of Alabama and you’re likely to land on Wetumpka. Just north of Montgomery, this town is known as the The City of Natural Beauty and it’s easy to see why: Visitors love canoeing and kayaking on the nearby Coosa River and enjoying the green spaces on walks and picnics. Don’t miss Swayback Bridge Trail (for hiking), Corn Creek Park (for birding, fishing, and waterfall watching), and William Bartram Arboretum (to see local flora and fauna).

To learn more about Wetumpka, read The Inspirational Transformation of Wetumpka, Alabama

Aztec Ruins National Monument © Rex Vogel, all rights reserved

3. Aztec, New Mexico

Known by the Navajo as Kinteel (wide horse), this town’s names come from Escalante’s misguided notion during his visit to the San Juan Basin. He stumbled across the ruins of the Aztec National Monument and thought it was built by the Aztec Indians (though they were built by the Anasazi). 

History lives here at Aztec, especially along its downtown core which is complete with a host of historical buildings listed on the National Register of Historic Places. Otherwise, this San Juan County community is packed with natural wonders and historical monuments, perfect for activities such as fishing, mountain biking, or hiking.

To learn more about Aztec National Monument, you can read The Ultimate Guide to Aztec Ruins National Monument

Schulenburg © Rex Vogel, all rights reserved

4. Schulenburg, Texas

Known as the town that’s halfway to everywhere, Schulenberg is a great small town between Houston and San Antonio. This quiet, cozy spot of just over 2,600 people is usually used as a stopover for those long road trips in Texas but it deserves more time on any itinerary.

Schulenberg was founded by Czech, Austrian, and German settlers in the mid-nineteenth century making it the perfect home for the Texas Polka Museum and a great place to try Czech kolaches (I recommend Kountry Bakery) or German schnitzel.

Downtown, you can dance the night away at Sengelmann Hall, a fully restored Texas dance hall that still has its original pinewood floors from 1894!

One of the local highlights is a stunning series of Painted Churches that some say rival the cathedrals of Europe.

To learn more about Schulenburg, read Halfway to Everywhere: Schulenburg

Murphys © Rex Vogel, all rights reserved

 5. Murphys, California

In California’s historic Gold Country, Murphys is nestled in the foothills of the Sierra Nevada Mountains and boasts a historic Main Street lined with wine bars and tasting rooms, restaurants, and boutiques. The picturesque town park is a popular place to have a creekside picnic after visiting several of the town’s historic sites where you can delve into the history of the Gold Rush. Don’t miss the Murphys Hotel whose famous guests have included writer Mark Twain. 

Bisbee © Rex Vogel, all rights reserved

6. Bisbee, Arizona

Bisbee is a funky artist haven with copper mining town roots. It sits nearly a mile high in the Mule Mountains which means it’s 10 to 20 degrees Fahrenheit cooler in the summer here than it is in Arizona’s major cities. Victorian homes and buildings are perched precariously on the town’s steep mountainside which has over 350 staircases carved right into it for access.  

Discover Bisbee’s past by visiting the Bisbee Mining and Historical Museum and taking the Queen Mine Tour. The tour will bring visitors underground to explore the mine on an ore ride while they learn more about the stories of the miners who worked here. Those who have an interest in the paranormal can book one of several ghost tours in Bisbee to hear the eerily fascinating reports of unexplained happenings and even sightings of spirits donning Victorian attire. Public art features prominently throughout town, from colorful murals and mosaic walls to cars that have been transformed into unique works of art.

Roswell © Rex Vogel, all rights reserved

7. Roswell, New Mexico

Chaves County’s community of Roswell is known among tourists for the reported site of an extraterrestrial sighting and spacecraft crash in 1947. Believers of the extraterrestrial flock to Roswell every July for the UFO Encounter Festival.

Visitors can admire the extensive UFO memorabilia and related activities at Roswell including exhibits at the International UFO Museum and Research Center and the souvenirs at the Invasion Station Gift Shop. 

Besides being famous as an alien town, Roswell is also a hub of cultural activities and local history given it was once the original homeland of the Mescalero Apaches and the Comanche’s hunting grounds.

To learn more about Roswell and the UFO Festival you can read What Really Happened at Roswell? and A Giant UFO Festival with All the Outer Space Vibes.

Mesilla © Rex Vogel, all rights reserved

8. Mesilla, New Mexico

While Mesilla exists as a small New Mexico town today, it was once a major stop for traveling between San Antonio and San Diego. Once visitors step into Mesilla they will feel like they stepped in time as the town remains mostly unchanged since its heyday in the 1800s! 

Explore the San Albino Church in the town plaza, which stands as Mesilla Valley’s oldest (and still active) church. This town is also lively thanks to its offerings of unique boutiques, galleries, wineries, and specialty eateries!

To learn more about Mesilla, read La Mesilla: Where History and Culture Become an Experience and Old Mesilla: Where Time Stood Still.

Mount Dora © Rex Vogel, all rights reserved

9. Mount Dora, Florida

Once a haven for hunting and fishing enthusiasts arriving by steamboat to escape chilly northern winters, today’s visitors flock to Mount Dora just 40 minutes northeast of bustling Orlando to play on 4,500-acre Lake Dora and see wildlife but also to shop for antiques, soak up the vibrant art scene, and stroll the historic downtown. 

With its live oaks, lovely inns, and quaint shops, Mount Dora offers a nostalgic taste of Old Florida. Head to Palm Island Park to stroll a boardwalk surrounded by old-growth trees and lush foliage or spend an afternoon hitting the many nearby antique shops. 

Just a bit north of Palm Island Boardwalk is Grantham Point Park, home to one of Florida’s few freshwater lighthouses. The 35-foot-tall lighthouse is one of the city’s most prominent landmarks and a great place to watch boaters and enjoy the sunset.

Fairhope © Rex Vogel, all rights reserved

10. Fairhope, Alabama

When Otis Redding sat down to pen The Dock of the Bay he may have been dreaming about Fairhope. The bayside spot is populated by ethereal live oaks, brilliant azalea bushes, pastel-colored bungalows, and brick sidewalks traversing a lively downtown. 

There are many reasons to visit Fairhope, especially in the off-season. If you love the Gulf Coast, there are few places more scenic with historic homes on streets lined with live oaks and a charming, walkable downtown. Fairhope sits on bluffs that overlook Mobile Bay, so you’re never far from a view of the water. 

Gatlinburg © Rex Vogel, all rights reserved

11. Gatlinburg, Tennessee

Given the millions of people who visit this area every year, the actual size of Gatlinburg which comes in at fewer than 4,000 residents escapes many travelers. Despite the high-season influxes, it’s the area’s homey Appalachian charm that helps draw all of the visitors here in the first place. The village has continued to evolve with a variety of new attractions joining the perennially popular pancake houses, candy shops, and craft galleries. 

To learn more on Gatlinburg and the Smoky Mountains, read Smoky Mountain Day Trips from Gatlinburg and Springtime in the Smokies.

Helen © Rex Vogel, all rights reserved

12. Helen, Georgia

The South holds its own in terms of small towns packing more than their weight in charm—but Helen, Georgia, really hammers that point home. With around 550 residents and only 2.1 square miles, it’s undoubtedly tiny. But the steeply pitched roofs, quaint cross-gables, and colorful half-timbering make the authentic Bavarian village enchanting. It looks straight out of fairytale dreams but sits in the mountains of Georgia.

Helen’s Oktoberfest celebrations have been going on for more than 50 years involving multiple weeks of traditional dancing, food, and beer from September through October. Held in the city’s riverside Festhalle, the permanent home of the festivities, the celebration is the longest-running of its kind in the United States. Helen’s Oktoberfest runs from Thursday to Sunday through September and daily from September 28 to October 29, 2023.

Alamogordo © Rex Vogel, all rights reserved

13. Alamogordo, New Mexico

Nestled in the high desert on the base of the Sacramento Mountains in Otero County, this southern New Mexico community gets an average of 287 days of sun giving visitors plenty of sunlight to enjoy a collection of thrilling activities.

Play a round of golf at the Desert Lake Golf Course, admire the mechanics of the F-117 Nighthawk at the Holloman Air Force Base, or feel the soft sands at the nearby White Sands National Park. This New Mexico destination is also home to several family-friendly attractions, including the Alameda Park Zoo and the New Mexico Museum of Space History. 

Before you leave Alamogordo, don’t forget to stop by the world’s largest pistachio which is located near the world’s largest gypsum dune.

Bardstown © Rex Vogel, all rights reserved

14. Bardstown, Kentucky

Rand McNally and USA Today called it the Most Beautiful Small Town in America. But Bardstown, Kentucky, is much more than just a pretty face. This Bourbon Capital of the World is home to six notable distilleries. Kentucky’s Official Outdoor Drama, one of the country’s most highly regarded Civil War museums, and one of the most recognized structures in the world is here at Federal Hill, better known as My Old Kentucky Home.

 If you’re looking to get away and take it easy for a couple of days or longer or for a home base for your pilgrimage along the Kentucky Bourbon Trail, this is the ideal location.

Learn more about Bardstown by reading Bardstown Sets the Stage for Spirited Memories and Step Back Into Time at My Old Kentucky Home.

Shiner © Rex Vogel, all rights reserved

15. Shiner, Texas

Speaking of beloved American beverages… Shiner, Texas is home to 2,069 people, Friday’s Fried Chicken, and—most famously—the Spoetzal Brewery where every drop of Shiner beer is brewed. Tours are offered throughout the week where visitors can see how every last drop of their popular brews gets made. 

Tours and samples are available for a small fee. Founded in 1909, the little brewery today sends more than 6 million cases of delicious Shiner beer to states across the country. Founder, Kosmos Spoetzal, would be pretty proud! To which we say “Prosit!”

To learn more about Shiner and Spoetzel Brewery, read A Toast to Texas History.

Bay St. Louis © Rex Vogel, all rights reserved

16. Bay St. Louis, Mississippi

Just 51 miles away from the one-of-a-kind hub that is New Orleans, Bay St. Louis couldn’t feel further from the hustle and bustle. The town’s prime spot on the Mississippi Sound, an embayment of the Gulf of Mexico, provides a glorious stretch of white-sanded beach with virtually no crowds. This strip of shoreline is known as Mississippi’s Secret Coast.

Just off of Beach Boulevard, you’ll find Old Town Bay St. Louis, a walkable area full of local shops and eateries. Spend an afternoon strolling through Old Town, browsing the beach boutiques and art galleries. Plan your trip to be in town on the second Saturday of each month when Old Town puts on a giant art walk complete with live music, local merchants, and other special events.

To learn more about this charming town, read Bay St. Louis: A Place Apart.

Marietta © Rex Vogel, all rights reserved

17. Marietta, Ohio

The oldest town in Ohio, Marrieta gets its name from the infamous Marie Antoinette, the Queen of France. Marietta was the first settlement of the Northwest Territory which was all of the land west of Pennsylvania, northwest of the Ohio River, and east of the Mississippi River. The end of the Revolutionary War saw the establishment of this territory in 1787.

A group of pioneers settled and founded Marietta in 1788. The town was easy to access by boat due to its placement on the banks of two major rivers. One of the early industries of the area was boat-building. Boats built in Marietta made their way down to New Orleans and often into the Gulf of Mexico. The town also made steamboats and furniture but much of their industry began to focus on brickmaking, sawmills, iron mills, and, eventually foundries.

Port Aransas © Rex Vogel, all rights reserved

18. Port Aransas, Texas

Hurricane Harvey caused major damage here in 2017, but nothing can keep this resilient coastal town down. Port A remains one of the state’s main spots for deep-sea fishing and dolphin watching and its 18 miles of beautiful beaches continue to attract returning visitors and new residents.

Stowe © Rex Vogel, all rights reserved

19. Stowe, Vermont

This impossibly quaint Green Mountain town has all the makings of a Norman Rockwell painting—right down to the general store. 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, but it’s also home to the Trapp Family Lodge, an Austrian-style chalet owned by the family immortalized in The Sound of Music.

Have a sweet tooth? The Ben & Jerry’s Ice Cream Factory is nearby in Waterbury. Be sure to book a maple syrup tasting at one of the local sugar farms to get a real sense of Vermont’s long and storied maple sugaring industry.

Breaux Bridge © Rex Vogel, all rights reserved

20. Breaux Bridge, Louisiana

Enjoy the quaint yet lively Breaux Bridge. Known as the Crawfish Capital of the World, the small town of Breaux Bridge offers rich history, world-class restaurants, and a very lively Cajun and Zydeco music and art industry.

Breaux Bridge is also home to the world-famous Breaux Bridge Crawfish Festival which is celebrated every May (May 5-7, 2023). This is to pay homage to the sea creature that brought fame and wealth to the town.

Aside from being a popular stopover, you might also want to stay in the quaint town for a couple of days.

Woods Hole © Rex Vogel, all rights reserved

21. Woods Hole, Massachusetts

The quaint New England village of Woods Hole lies at the far southwestern tip of Cape Cod with Buzzards Bay to its west and Vineyard Sound to its east. Because of its excellent harbor, Woods Hole became a center for whaling, shipping, and fishing before its dominance today through tourism and marine research.

Woods Hole is a small village and is easily strolled. The village is a world center for marine, biomedical, and environmental science. It houses two large, private organizations: the Marine Biological Laboratory and the Woods Hole Oceanographic Institution. A total of 49 Nobel Laureates have taught, taken courses, or done research at the Marine Biological Laboratory.

Woodstock © Rex Vogel, all rights reserved

22. Woodstock, New York

To assume that Woodstock is only notable for its namesake 1969 music festival would be a major blunder—the festivities weren’t even held within city limits. In reality, Woodstock is a quaint little Catskills oasis where residents prop up an art, religion, music, and theater scene worthy of national attention. The Woodstock Byrdcliffe Guild continues to attract artists hoping to retreat from city life and hone their craft and visitors can tour the grounds and see where magic was made.

Medora © Rex Vogel, all rights reserved

23. Medora, North Dakota

One would think getting Broadway-quality performers to spend their summers in the middle of nowhere, North Dakota would be tough. But it’s barely a chore when you’re drawing them to quaint Medora, home of the Medora Musical and gateway to Theodore Roosevelt National Park.

The once-depressed cattle town was brought back to life when businessman Harold Shafer sunk millions into it turning it into an Old West Revival that avoids being too campy. Saloons and steakhouses offer stellar food; day hikes along the Pancratz Trail, just outside the Badlands Motel offer sweeping views; and a trip to the Burning Hills Amphitheater—a sort of Hollywood Bowl in the Badlands—is a must for musicals and steak-on-a-pitchfork dinner. The entire town obliterates expectations of what one would expect to find in North Dakota.

Jacksonville © Rex Vogel, all rights reserved

24. Jacksonville, Oregon

Life slows a pace or two in quaint, historic Jacksonville. Steeped in history, the entire town of Jacksonville is designated a National Historic Landmark. Explore the roots of the area from the days of the 1850’s gold rush to now through a variety of historical tour options including a self-guided walking tour as well as trolley and haunted history tours. A quintessential western town, you’ll find yourself enthralled in how things used to be.

La Conner © Rex Vogel, all rights reserved

25. La Conner, Washington

La Conner is one of those places in Washington State that people love to visit—time and time again. The reasons are many, but one that stands out is that La Conner is a quaint, historic waterfront village.

This riverfront town has a lovely setting located on the Swinomish Channel overlooking Fidalgo Island with plenty of waterfront restaurants.

Downtown La Conner has a wonderfully preserved Historic District with 27 vintage buildings from the 1860s to the early 1900s. Many of these were constructed during La Conner’s heyday in the 1890s when it was a major steamboat hub between Seattle and Bellingham.  

Get more tips for visiting La Conner: La Conner: Charming, Picturesque & Quaint.

Worth Pondering…

I say half your life is spent trying to get out of a small town and the other half trying to get back to one.

—Anon