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America is a tapestry of cities, each with its unique charms, history, and quirks that make it a haven for travelers. Yet, there are certain cities that, despite their immense cultural and historical significance, often simmer in the shadows of larger, more touristy destinations.

Chattanooga, Tennessee

13 Most Underrated Cities in America
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Once an industrial hub renowned for its role in the railroad and maritime ports, Chattanooga has transformed into an outdoor enthusiast’s haven. The city has received numerous accolades for its livability, outdoor activities, and as a top destination for remote workers.

A standout statistic is Chattanooga’s internet speed, often dubbed the “Gig City” for its pioneering municipal fiber internet service, which has attracted tech startups and innovation labs. With initiatives like the Riverwalk, a 13-mile-long public park that hugs the Tennessee River, and the bustling art scene in the Bluff View Art District, the city offers spaces where history, culture, and nature intersect seamlessly.

Santa Fe, New Mexico

13 Most Underrated Cities in America
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According to the National Endowment for the Arts, Santa Fe is the third-largest art market in the U.S., with over 250 art Galleries and Studios. It is home to the famous Santa Fe Opera and the Georgia O’Keeffe Museum, which pays tribute to the iconic American artist who drew inspiration from the stunning New Mexican landscape. The city’s rich tapestry of history is also evident in its well-preserved Pueblo-style architecture, particularly in the historic district.

Santa Fe’s culinary scene offers an eclectic mix of Native American and Nuevo Latino cuisines that can’t be found anywhere else in the country. The city is also known for its wellness and outdoor activities, including hiking and skiing, which benefit from its location in the Sangre de Cristo foothills.

Madison, Wisconsin

13 Most Underrated Cities in America
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Nestled between the shores of Lake Mendota and Lake Monona, Madison, Wisconsin, exhibits a harmonious blend of natural beauty and urban sophistication. Madison’s uniqueness is characterized by its impressive offering of outdoor activities, bolstered by over 200 miles of biking and hiking trails and pristine lakes that are perfect for paddleboarding and kayaking.

It hosts one of the U.S.’s largest producer-only farmers’ markets, the Dane County Farmers’ Market. Numerous galleries and live music venues, including the iconic Orpheum Theater, showcase the city’s artistic flair.

San Luis Obispo, California

13 Most Underrated Cities in America
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Its commitment to environmental sustainability, boasting a zero-waste goal, and extensive green spaces make it one of the greenest cities in the nation. The iconic Bubblegum Alley, a 70-foot-long alleyway where visitors have been sticking chewed gum on the walls since the 1960s, creates a peculiar yet captivating mural of human interaction.

San Luis Obispo is also home to the Mission San Luis Obispo de Tolosa, a beautifully preserved Spanish mission founded in 1772 and the heart of the city’s cultural and historical narrative. The nearby Morro Bay and Pismo Beach offer stunning coastal landscapes and outdoor activities, from kayaking and whale watching to sand dune adventures.

Charleston, West Virginia

13 Most Underrated Cities in America
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Charleston, situated near the confluence of three rivers, is a city steeped in the history of the Civil War and the Northern migration. It is a cultural powerhouse, with the West Virginia Symphony Orchestra, Charleston Ballet, and live theaters contributing to a vibrant arts scene. Its location on the banks of the Kanawha River, surrounded by mountains, provides stunning landscapes and outdoor activities like hiking, fishing, and whitewater rafting.

The city is home to the Clay Center for the Arts and Sciences, a multifaceted facility with a planetarium, museum, and performing arts center. Additionally, Capitol Market offers a taste of local life with its farmers’ market and specialty shops.

Boise, Idaho

13 Most Underrated Cities in America
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The Boise River Greenbelt, a lush 25-mile pathway following the river through the city’s heart, offers residents and visitors a serene escape to nature. The city is a gateway to outdoor adventures, including skiing at Bogus Basin and exploring the surrounding foothills. Culturally, Boise stands out with its thriving Basque community, one of the largest outside of Spain, which is celebrated through food, festivals, and the Basque Museum and Cultural Center.

The city’s population increased by 2.9% from 2019 to 2020, reflecting its rising status as a desirable place to live. Additionally, its unemployment rate consistently falls below the national average, illustrating the city’s robust job market and economic stability. 

Beaufort, South Carolina

13 Most Underrated Cities in America
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Despite its picturesque waterfront vistas, antebellum architecture, and rich Gullah culture, Beaufort is often overshadowed by its more famous neighbors, Charleston and Savannah. The city’s history spans over 300 years, making it the second-oldest city in South Carolina. Walking through the streets of downtown Beaufort feels like stepping back in time, with its historic homes, quaint boutiques, and oak-lined streets draped in Spanish moss.

The city is surrounded by water, offering ample kayaking, fishing, and boating opportunities. Its proximity to the Atlantic Ocean also means that beautiful beaches are just a short drive away. For those interested in arts and culture, Beaufort hosts an annual international film festival that attracts filmmakers and enthusiasts from around the globe.

Bend, Oregon

13 Most Underrated Cities in America
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Bend is a paradise for outdoor enthusiasts, offering year-round activities from skiing and snowboarding at Mount Bachelor in the winter to kayaking and paddle boarding on the Deschutes River during the warmer months. Its high-desert location promises 300 days of sunshine a year.

The city is also a burgeoning hub for craft beer enthusiasts, home to over 22 breweries that underscore Oregon’s reputation as a craft beer mecca. The Bend Ale Trail, the most extensive beer trail in the West, allows visitors to sample these local brews in a structured yet leisurely fashion. The city’s First Friday Art Walks in the Downtown area offers a glimpse into the local talent and hospitality that make Bend unique. Its high-desert location promises 300 days of sunshine a year.

Burlington, Vermont

13 Most Underrated Cities in America
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Burlington is best known for being the birthplace of Ben & Jerry’s ice cream and a picturesque college town that overlooks the pristine waters of Lake Champlain. Burlington’s relatively small size and population mean you’re likely to experience its community’s genuine warmth and friendliness. 

The Church Street Marketplace, a pedestrian-only, open-air mall brimming with boutiques, cafes, and street performers, offers a glimpse into Burlington’s vibrant local scene. The Lake Champlain Waterfront is home to the Echo Lake Aquarium and Science Center, a family-friendly attraction with hands-on exhibits on the region’s ecology. The art scene transforms the city into a musical haven, from the Flynn Center for the Performing Arts to numerous galleries and the annual Burlington Discover Jazz Festival. 

Helena, Montana

13 Most Underrated Cities in America
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Helena was founded during the Montana gold rush in the late 19th century, and it quickly flourished into a wealthy city, a story preserved in its stunning Victorian architecture. The Montana Historical Society Museum houses one of the best collections of Native American artifacts and historical exhibits in the Northwest. The city is surrounded by over 75 miles of accessible trails right from downtown, making it a paradise for hikers, bikers, and nature lovers. 

Cultural pursuits can be satisfied by visiting Reeder’s Alley, Helena’s oldest street, or exploring the impressive Montana State Capitol building. The Last Chance Tour Train takes visitors around Helena’s historic districts. The city is home to the iconic Cathedral of Saint Helena, with its Gothic Revival architecture and stunning stained-glass windows. The summer and early fall are ideal for enjoying the full range of outdoor activities and events.

St. Augustine, Florida

13 Most Underrated Cities in America
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St. Augustine is the oldest in the United States (founded in 1565 by Spanish explorers). The city’s streets are a living museum, with the 17th-century Spanish fort (Castillo de San Marcos) standing guard over the coastline. The narrow cobblestone streets in the historic district, lined with quaint cafes, art galleries, and boutiques, evoke the feeling of stepping into a Spanish village.

The Lightner Museum, housed in the former Alcazar Hotel, showcases a diverse collection ranging from fine art to natural history. Its unique attractions, such as the hauntingly beautiful St. Augustine Lighthouse & Maritime Museum and the magical Nights of Lights during the holiday season, make it a must-visit location for those searching for culture, history, and natural beauty.

Bloomington, Indiana

13 Most Underrated Cities in America
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With a population of just over 85,000, this city combines the charm of small-town living with the amenities and diversity of a larger city, primarily due to the influence of Indiana University, which calls Bloomington home. The city is a hub for the arts, demonstrated through landmarks such as the Eskenazi Museum of Art. Jacobs School of Music: Indiana University Bloomington is recognized worldwide, hosting over 1,100 performances a year, including operas and concerts.

The city is a gateway to the Hoosier National Forest, offering miles of trails, camping sites, and the beautiful Monroe Lake – Indiana’s largest landlocked body of water – ideal for kayaking, fishing, and swimming. Despite its plethora of amenities and attractions, the cost of living in Bloomington is about 10% lower than the national average, according to the U.S. Bureau of Labor Statistics. 

Portsmouth, New Hampshire

13 Most Underrated Cities in America
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The Strawbery Banke Museum, an outdoor history museum, offers a glimpse into over 300 years of American history, with restored houses and exhibits showcasing the city’s rich past. Prescott Park, located right on the banks of the Piscataqua River, hosts various outdoor concerts, theater performances, and flower gardens, making it a perfect spot for cultural and recreational activities.

The Portsmouth Harbor Lighthouse, a historic beacon dating back to the 18th century, offers panoramic views of the harbor. Additionally, the city’s craft brewery scene is flourishing, with several spots like Portsmouth Brewery and Smuttynose Brewing Company offering tours and tastings. Visit during summer for the best weather and a full roster of coastal activities and events.

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