Coolest Smallest Towns in America

History, culture, wine, outdoor adventures, and great food in these cool small towns from California to Georgia. Like what you see? Pay these burghs a visit.

A picturesque village, Murphys is known today for its many natural attractions including caverns for public viewing, a charming Main Street with unique shops, spectacular wineries, and art galleries. © Rex Vogel, all rights reserved

A picturesque village, Murphys is known today for its many natural attractions including caverns for public viewing, a charming Main Street with unique shops, spectacular wineries, and art galleries. © Rex Vogel, all rights reserved

Murphys, California

Once a hodgepodge of miners’ tents and lean-tos, Murphys has aged well. The picturesque village is known today for its many natural attractions including caverns for public viewing, a charming Main Street with friendly merchants and unique shops, art galleries, and wineries. A stroll down tree-lined Main Street transports visitors back to the mid-1800s with buildings bearing thick stoned walls, iron shutters, and pastoral gardens. Its leafy streets are lined with white picket fences, oaks and sycamores, eateries, and tasting rooms.

Shipshewana is a bustling village with quaint shop-lined streets, specialty retailers, and home-style dining. © Rex Vogel, all rights reserved

Shipshewana is a bustling village with quaint shop-lined streets, specialty retailers, and home-style dining. © Rex Vogel, all rights reserved

Shipshewana, Indiana

Many of the towns in Amish Country date back 150 years or more. Among these is tiny Shipshewana known for an enormous flea market where 1,000 vendors peddle their wares twice a week from May through October.

Due to the Amish lifestyle you can almost believe you’ve stepped back in time a century or more. To learn about Amish history, tour Menno-Hof. Through multi-image presentations and historical displays, you’ll travel back 500 years to the origins of the Amish-Mennonite story.

Shipshewana is a bustling village with quaint shop-lined streets, specialty retailers, and home-style dining. © Rex Vogel, all rights reserved

Shipshewana is a bustling village with quaint shop-lined streets, specialty retailers, and home-style dining. © Rex Vogel, all rights reserved

Bay St. Louis, Mississippi

Everybody loves a comeback, and Bay St. Louis has come roaring back from Hurricane Katrina (which made final landfall near this Mississippi Gulf hamlet in 2005). Its Historic Old Town has been chugging along for 300 years (French Canadian explorers first sailed into the bay in 1699), drawing visitors to its warm beaches, first-rate fishing, and friendly vibe.

When a town boasts a street called Beach Boulevard, you know you don’t have to look far for fun. If you have trouble finding the beach (you won’t), take Main Street straight to the water. Take your own walking tour of 19th-century homes, Creole cottages, and art galleries.

Embellished with local shops, cozy tea rooms, restaurants, and beautiful local architecture, the streets of Midway offer visitors an exceptional, relaxing experience.© Rex Vogel, all rights reserved

Embellished with local shops, cozy tea rooms, restaurants, and beautiful local architecture, the streets of Midway offer visitors an exceptional, relaxing experience.© Rex Vogel, all rights reserved

Midway, Kentucky

Some of our most pleasant moments always seem to come when we stumble upon one thing while in pursuit of something else. So it was when we unexpectedly came upon the historic town of Midway. Located midway between Frankfort and Lexington, Historic Midway was the first town in Kentucky founded by a railroad.

Today, Midway once again thrives and enjoys its present reputation as one of Kentucky’s favorite spots for antiques, crafts, gifts, restaurants, and clothing. Several freight trains still make use of the active tracks running through Railroad Street, preserving Midway’s unique history and atmosphere.

Located smack-dab in the middle of Hill Country (think: fields of bluebonnets and local wineries), Fredericksburg is a German-influenced town that has maintained its roots. Visit on any given summer afternoon and you’ll find a lively scene of barbecues and beer, singing and dancing. © Rex Vogel, all rights reserved

Located smack-dab in the middle of Hill Country (think: fields of bluebonnets and local wineries), Fredericksburg is a German-influenced town that has maintained its roots. Visit on any given summer afternoon and you’ll find a lively scene of barbecues and beer, singing and dancing. © Rex Vogel, all rights reserved

Fredericksburg, Texas

Hill Country color and craziness, foot-tapping song and dance, wine and wildflowers, LBJ and Lady Bird—it’s all part of the Fredericksburg heritage. Start with the town’s history, as told at downtown’s Pioneer Museum, dedicated to the German settlers who brought Oktoberfest and strudel to the region in the mid-19th century.

The National Museum of the Pacific War dedicates itself to hometown boy Fleet Adm. Chester Nimitz, who signed the Japan’s surrender document in Tokyo Bay on September 2, 1945. With LBJ’s beloved ranch in nearby Stonewall and the Luckenbach Dancehall.

A village with mountain heritage and a touch of Bavaria, Helen has created a unique experience for its visitor. © Rex Vogel, all rights reserved

A village with mountain heritage and a touch of Bavaria, Helen has created a unique experience for its visitor. © Rex Vogel, all rights reserved

Helen, Georgia

Nestled in the Blue Ridge Mountains on the gently flowing Chattahoochee River, Helen is a re-creation of a Bavarian Alpine village, complete with new buildings, old-world trim and detail, and cobblestone alleys. The town packs charm and so much to do: quaint hotels, cobblestone walkways, specialty and import shops, Bavarian food and drink, and festive atmosphere. Surrounded by spectacular mountain beauty, wineries, artisan tours, festivals, and more.

Worth Pondering…

In the words of Willie Nelson, “goin’ places I have never been, seein’ things that I may never see again”, exploring our magnificent country, its natural beauty, historic sites, treasured landmarks, and cool small towns.

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