The 25 Most Charming Towns in America

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Slide 1 of 26: There are plenty of places to escape the hustle and bustle this summer, whether it's a rejuvenating weekend jaunt or a month-long road trip. Find your happy place in one of America's many charming small towns. Here are 25 worthy of your 2019 travel plans. 
Slide 2 of 26: As the oldest city in the U.S., St. Augustine's charm is undeniable. The Spanish colonial architecture stands out and there are plenty of sites and attractions worth exploring, from the 17th-century Castillo de San Marcos to walkable St. George Street. Plus, visitors won't be far from the beaches at Vilano and Anastasia State Park.
Slide 3 of 26: A popular stop for hikers navigating the Maryland Heights Trail, historic Harpers Ferry is best experienced through camping. Enjoy dramatic river views from Jefferson Rock or nearby Harpers Ferry Brewing before heading downtown to see John Brown's Fort and Arsenal Square.
Slide 4 of 26: This Bavarian-style mountain village located a little more than two hours outside of Seattle in the Cascade Mountains is a beloved destination for Oktoberfest revelers, but nonetheless maintains its charm year-round. Visitors are sure to fall in love with the Nutcracker Museum and serene Waterfront Park on the Wenatchee River.
Slide 5 of 26: You'll find the Danish village of Solvang about 45 minutes northwest of Santa Barbara. In addition to eye-popping architecture, visitors will discover a wide range of museums showcasing everything from the works of legendary author Hans Christian Andersen to vintage motorcycles. It's also a tremendous destination for wine lovers as it boasts a handful of nearby vineyards and wineries.
Slide 6 of 26: When you imagine an idyllic Rocky Mountain town, it probably looks a lot like Telluride. The former Victorian mining town is beloved by skiers, sure, but you don't have to hit the slopes to appreciate all it has to offer, which includes the walkable Main Street as well as scenic Town Park and Bridal Veil Falls. The latter overlooks Telluride.
Slide 7 of 26: Sitka was actually a part of Russia until the late 1860s and that history is well-preserved at the St. Michael's Orthodox Cathedral, which dates back to the mid-19th century. Outdoor enthusiasts will particularly love Sitka and its 122-acre National Historical Park featuring scenic trails and unique wooden totem poles.
Slide 8 of 26: Located just a few minutes outside of Ocean City, Maryland, Berlin holds the title of "America's Coolest Small Town." It's Main Street is as charming as any as it features a slew of shops, restaurants and art. The Burley Cafe is the place to go for the best local beer, brewery-inspired food and live music.
Slide 9 of 26: Bristol is at it's best on the Fourth of July as it's home to the nation's oldest Independence Day celebration. "America's Most Patriotic Town" is renowned for its July 4 parade, picnics and concerts, but it has so much more to offer visitors year-round, from scenic bike paths and parks, historic buildings like the Bristol County Jail, sensational water views and the Herreshoff Marine Museum dedicated to the region's sailing history.
Slide 10 of 26: This laidback Maui town is the first stop on the Hana Highway and offers visitors access to some of Hawaii's top beaches in addition to a quaint village featuring shops, restaurants and other buildings painted in eye-popping pastel colors that will have you reaching for a surfboard in no time.
 
Slide 11 of 26: Covered bridges, Victorian mansions and sprawling farms help make this part of Vermont among the most charming in all of New England. Beautiful city views await visitors to Mount Tom while the childhood home of U.S. President Calvin Coolidge is located just a few minutes away in Plymouth.
Slide 12 of 26: Another charming town that's a big hit with skiers, Taos is especially unique thanks to its historic adobe buildings. Taos Pueblo is the site of a Native American community that has inhabited the one-of-a-kind homes for more than 1,000 years.
Slide 13 of 26: The namesake lake and national forest will draw visitors to Coeur d’Alene outdoors. Spend a perfect day at Lake Coeur d'Alene, which offers swimming beaches, water sports and even the chance to spot a majestic bald eagle.
Slide 14 of 26: Fans of the Eagles and their hit song "Take It Easy" won't want to miss a chance to stop by Winslow's iconic Standin' on a Corner Park. The La Posada Historic District dating back to 1930 is also a memorable experience for visitors to this small town outside of Flagstaff, Arizona.
Slide 15 of 26: This Ozark Mountain town boasts an exceptional downtown area that's home to relaxing spas, boutique shops, award-winning bars and restaurants and a lively nightlife scene. Meanwhile, travelers will have access to a plethora of outdoor activities such as hiking, biking, kayaking, zip lining and much more. You'll also find the 66-foot-tall Christ of the Ozarks statue here.
Slide 16 of 26: The Manatee Capital of the World, Crystal River is ideal for fishing, watching marine life from the boardwalk at Three Sisters Springs wildlife park and even swimming with friendly manatees. It's one of the few places in Florida where you can legally swim alongside the awesome creatures.
Slide 17 of 26: Located on the Big Island, Hilo is home to several buildings that have been added to the National Register of Historic Places as well as important cultural sites, art galleries, shops and restaurants. Stop by the Hilo Farmers Market for locally grown delights and learn about how the town has changed over the years at the Pacific Tsunami Museum.
Slide 18 of 26: If you're looking to find cottages reminiscent of a fairytale without leaving the U.S., Carmel-by-the-Sea is just the place. This California town also boasts white-sand beaches for bird watching, scuba diving and lounging, stellar shopping on Ocean Avenue and history at the Carmel Mission Basilica Museum dating back to the 18th century.
Slide 19 of 26: Whitefish is a Montana resort town nestled in the northern Rocky Mountains at the edge of Glacier National Park. In addition to some of the country's best mountain biking, Whitefish features a surprisingly eclectic dining scene, energizing live music and an impressive arts community.
Slide 20 of 26: Lambertville is located on the Delaware River between Philadelphia and New York City so it's easy to overlook in favor of the big cities. Still, it's well worth a visit, even if just for a day as the town's historic district dates back more than two centuries. Visitors can shop antiques, admire Victorian homes and stay overnight at the cozy Inn at Lambertville Station.
Slide 21 of 26: Situated on the shore of Alabama's Mobile Bay, charming Fairhope is known for its scenic pier offering out-of-towners beautiful views and fresh seafood. Visitors can also stop by the Fairhope Museum of History to explore the town's past free of charge.
Slide 22 of 26: With a population just over 130 (as of 2017), Medora is undoubtedly a small town—and its charm can't be denied either. Nearby Theodore Roosevelt National Park and the North Dakota Badlands are among the many highlights of this historic town, which offers plenty of sites and attractions to counter the adventure.
Slide 23 of 26: No, not the one in Florida. Jacksonville, Oregon has been recognized by many, including Frommer's, as one of America's coolest small towns. Shop boutiques on Main Street, reward your taste buds on the scenic Applegate Wine Trail and catch a memorable live show at the 2019 Britt Festival this summer.
 
Slide 24 of 26: The birthplace of Fred Rogers, host of the Mister Rogers' Neighborhood, Latrobe is home to a vibrant and inviting downtown featuring shops, restaurants and historic buildings as well as numerous parks and trails. Summertime visitors with a sweet tooth will also want to check out Latrobe's Great American Banana Split Celebration August 23-25.
Slide 25 of 26: Visitors to Decorah are in for a pleasant surprise as this scenic small town and the surrounding region of Iowa is chock-full of charm, whether it's soaring bald eagles, historical artifacts documenting the experience of Norwegian immigrants in America or peaceful parks like Phelps Park on the Upper Iowa River.
Slide 26 of 26: Located just an hour east of Coeur d'Alene, Wallace is a historic mining town founded in the 1880s. It's established quite the legacy as the richest mining town still in existence and the last town entirely listed on the National Register of Historic Places. A quaint downtown, underground mine tours, mountain biking and a whole lot more await visitors to this North Idaho destination.

Delightful Destinations

There are plenty of places to escape the hustle and bustle this summer, whether it’s a rejuvenating weekend jaunt or a month-long road trip. Find your happy place in one of America’s many charming small towns. Here are 25 worthy of your 2019 travel plans. 

St. Augustine, Florida

As the oldest city in the U.S., St. Augustine’s charm is undeniable. The Spanish colonial architecture stands out and there are plenty of sites and attractions worth exploring, from the 17th-century Castillo de San Marcos to walkable St. George Street. Plus, visitors won’t be far from the beaches at Vilano and Anastasia State Park.

Harpers Ferry, West Virginia

A popular stop for hikers navigating the Maryland Heights Trail, historic Harpers Ferry is best experienced through camping. Enjoy dramatic river views from Jefferson Rock or nearby Harpers Ferry Brewing before heading downtown to see John Brown’s Fort and Arsenal Square.

Leavenworth, Washington

This Bavarian-style mountain village located a little more than two hours outside of Seattle in the Cascade Mountains is a beloved destination for Oktoberfest revelers, but nonetheless maintains its charm year-round. Visitors are sure to fall in love with the Nutcracker Museum and serene Waterfront Park on the Wenatchee River.

Solvang, California

You’ll find the Danish village of Solvang about 45 minutes northwest of Santa Barbara. In addition to eye-popping architecture, visitors will discover a wide range of museums showcasing everything from the works of legendary author Hans Christian Andersen to vintage motorcycles. It’s also a tremendous destination for wine lovers as it boasts a handful of nearby vineyards and wineries.

Telluride, Colorado

When you imagine an idyllic Rocky Mountain town, it probably looks a lot like Telluride. The former Victorian mining town is beloved by skiers, sure, but you don’t have to hit the slopes to appreciate all it has to offer, which includes the walkable Main Street as well as scenic Town Park and Bridal Veil Falls. The latter overlooks Telluride.

Sitka, Alaska

Sitka was actually a part of Russia until the late 1860s and that history is well-preserved at the St. Michael’s Orthodox Cathedral, which dates back to the mid-19th century. Outdoor enthusiasts will particularly love Sitka and its 122-acre National Historical Park featuring scenic trails and unique wooden totem poles.

Berlin, Maryland

Located just a few minutes outside of Ocean City, Maryland, Berlin holds the title of “America’s Coolest Small Town.” It’s Main Street is as charming as any as it features a slew of shops, restaurants and art. The Burley Cafe is the place to go for the best local beer, brewery-inspired food and live music.

Bristol, Rhode Island

Bristol is at it’s best on the Fourth of July as it’s home to the nation’s oldest Independence Day celebration. “America’s Most Patriotic Town” is renowned for its July 4 parade, picnics and concerts, but it has so much more to offer visitors year-round, from scenic bike paths and parks, historic buildings like the Bristol County Jail, sensational water views and the Herreshoff Marine Museum dedicated to the region’s sailing history.

Paia, Hawaii

This laidback Maui town is the first stop on the Hana Highway and offers visitors access to some of Hawaii’s top beaches in addition to a quaint village featuring shops, restaurants and other buildings painted in eye-popping pastel colors that will have you reaching for a surfboard in no time.
 

Woodstock, Vermont

Covered bridges, Victorian mansions and sprawling farms help make this part of Vermont among the most charming in all of New England. Beautiful city views await visitors to Mount Tom while the childhood home of U.S. President Calvin Coolidge is located just a few minutes away in Plymouth.

Taos, New Mexico

Another charming town that’s a big hit with skiers, Taos is especially unique thanks to its historic adobe buildings. Taos Pueblo is the site of a Native American community that has inhabited the one-of-a-kind homes for more than 1,000 years.

Coeur d’Alene, Idaho

The namesake lake and national forest will draw visitors to Coeur d’Alene outdoors. Spend a perfect day at Lake Coeur d’Alene, which offers swimming beaches, water sports and even the chance to spot a majestic bald eagle.

Winslow, Arizona

Fans of the Eagles and their hit song “Take It Easy” won’t want to miss a chance to stop by Winslow’s iconic Standin’ on a Corner Park. The La Posada Historic District dating back to 1930 is also a memorable experience for visitors to this small town outside of Flagstaff, Arizona.

Eureka Springs, Arkansas

This Ozark Mountain town boasts an exceptional downtown area that’s home to relaxing spas, boutique shops, award-winning bars and restaurants and a lively nightlife scene. Meanwhile, travelers will have access to a plethora of outdoor activities such as hiking, biking, kayaking, zip lining and much more. You’ll also find the 66-foot-tall Christ of the Ozarks statue here.

Crystal River, Florida

The Manatee Capital of the World, Crystal River is ideal for fishing, watching marine life from the boardwalk at Three Sisters Springs wildlife park and even swimming with friendly manatees. It’s one of the few places in Florida where you can legally swim alongside the awesome creatures.

Hilo, Hawaii

Located on the Big Island, Hilo is home to several buildings that have been added to the National Register of Historic Places as well as important cultural sites, art galleries, shops and restaurants. Stop by the Hilo Farmers Market for locally grown delights and learn about how the town has changed over the years at the Pacific Tsunami Museum.

Carmel-by-the-Sea, California

If you’re looking to find cottages reminiscent of a fairytale without leaving the U.S., Carmel-by-the-Sea is just the place. This California town also boasts white-sand beaches for bird watching, scuba diving and lounging, stellar shopping on Ocean Avenue and history at the Carmel Mission Basilica Museum dating back to the 18th century.

Whitefish, Montana

Whitefish is a Montana resort town nestled in the northern Rocky Mountains at the edge of Glacier National Park. In addition to some of the country’s best mountain biking, Whitefish features a surprisingly eclectic dining scene, energizing live music and an impressive arts community.

Lambertville, New Jersey

Lambertville is located on the Delaware River between Philadelphia and New York City so it’s easy to overlook in favor of the big cities. Still, it’s well worth a visit, even if just for a day as the town’s historic district dates back more than two centuries. Visitors can shop antiques, admire Victorian homes and stay overnight at the cozy Inn at Lambertville Station.

Fairhope, Alabama

Situated on the shore of Alabama’s Mobile Bay, charming Fairhope is known for its scenic pier offering out-of-towners beautiful views and fresh seafood. Visitors can also stop by the Fairhope Museum of History to explore the town’s past free of charge.

Medora, North Dakota

With a population just over 130 (as of 2017), Medora is undoubtedly a small town—and its charm can’t be denied either. Nearby Theodore Roosevelt National Park and the North Dakota Badlands are among the many highlights of this historic town, which offers plenty of sites and attractions to counter the adventure.

Jacksonville, Oregon

No, not the one in Florida. Jacksonville, Oregon has been recognized by many, including Frommer’s, as one of America’s coolest small towns. Shop boutiques on Main Street, reward your taste buds on the scenic Applegate Wine Trail and catch a memorable live show at the 2019 Britt Festival this summer.
 

Latrobe, Pennsylvania

The birthplace of Fred Rogers, host of the Mister Rogers’ Neighborhood, Latrobe is home to a vibrant and inviting downtown featuring shops, restaurants and historic buildings as well as numerous parks and trails. Summertime visitors with a sweet tooth will also want to check out Latrobe’s Great American Banana Split Celebration August 23-25.

Decorah, Iowa

Visitors to Decorah are in for a pleasant surprise as this scenic small town and the surrounding region of Iowa is chock-full of charm, whether it’s soaring bald eagles, historical artifacts documenting the experience of Norwegian immigrants in America or peaceful parks like Phelps Park on the Upper Iowa River.

Wallace, Idaho

Located just an hour east of Coeur d’Alene, Wallace is a historic mining town founded in the 1880s. It’s established quite the legacy as the richest mining town still in existence and the last town entirely listed on the National Register of Historic Places. A quaint downtown, underground mine tours, mountain biking and a whole lot more await visitors to this North Idaho destination.

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