Exploring small towns with storied pasts can be a delightful adventure if you have a penchant for history and a love for hidden gems. Across the United States, quaint communities once played host to secret speakeasies during the Prohibition era. These towns offer a unique glimpse into a bygone time and charming experiences filled with culture, architecture, and local lore. From underground tunnels to historic saloons, each destination has its tales to tell. Join us as we count down the 18 most unique small towns with historic speakeasies waiting to be discovered.
18. Greendale, Wisconsin: Planned Community with a Hidden Past
Greendale, one of the three “Greenbelt” towns built during the New Deal era, offers a unique blend of small-town charm and historical intrigue. While it may appear as a tranquil village with tree-lined streets and quaint shops, beneath its serene surface lies a past connected to Prohibition-era secrets. The town’s historic buildings and underground spaces were once rumored to host clandestine speakeasies, adding an element of mystery to its heritage.
Visitors can stroll through the Greendale Historic District, exploring the original buildings and enjoying local boutiques and eateries. Festivals and community events keep the town lively, making it a delightful destination that marries history with modern-day enjoyment. Homes in Greendale range from approximately $290,000 to $419,000 for a 3-4 bedroom property.
Where is Greendale, Wisconsin?
Greendale is situated just southwest of Milwaukee and easily accessible via Interstate 43 and U.S. Highway 45. Its proximity to a major city makes it an ideal getaway that feels worlds apart from urban hustle. The town’s planned layout includes plenty of green spaces and walking paths, reflecting its origins as a model community. This picturesque setting provides a peaceful retreat and hints at the area’s storied past, including its lesser-known connections to Prohibition-era activities. Exploring Greendale offers a chance to delve into a chapter of history that’s both intriguing and uniquely American.
17. Sutter Creek, California: Gold Country Town with Historic Bars
Nestled in the heart of California’s Gold Country, Sutter Creek exudes an old-world charm that harkens back to the days of the Gold Rush. The town’s well-preserved 19th-century buildings house various antique shops, art galleries, and, notably, historic bars that once served as speakeasies during Prohibition. Wandering Main Street feels like stepping back in time, where the tales of fortune seekers and secret gatherings still linger.
Wine-tasting rooms and local eateries offer modern delights, while the nearby mines and museums provide a glimpse into the town’s golden past. 3-4 bedroom homes in Sutter Creek are typically priced around $300,000 to $442,000.
Where is Sutter Creek?
Located in Amador County, Sutter Creek is approximately 45 miles southeast of Sacramento, accessible via Highway 49. The town is nestled among rolling hills and vineyards, making the journey as scenic as the destination. Its location in the Sierra Foothills is amid some of California’s most celebrated wine regions and historic sites. The geography made it a hotspot during the Gold Rush and provided the seclusion necessary for speakeasies to flourish during Prohibition. Today, visitors can easily reach Sutter Creek for a day trip or weekend getaway, immersing themselves in its rich history and picturesque setting.
16. Mendocino, California: Coastal Village with Secret Saloons
Mendocino is a charming coastal village known for its dramatic cliffs, Pacific Ocean views, and artistic community. During Prohibition, its rugged coastline and secluded coves provided perfect hideaways for smuggling operations and secret saloons. The town’s Victorian buildings and water towers hint at a past filled with clandestine activities.
Today, Mendocino invites visitors to explore its scenic beauty through hiking trails, boutique shops, and art galleries. The local museums and historical society offer insights into the area’s intriguing past, including tales of the hidden speakeasies that once dotted the coastline. Homes here typically range around $750,000 – $909,000 for a 3-4 bedroom property.
Where is Mendocino?
Mendocino is located along California’s northern coast, about 150 miles north of San Francisco via Highway 1. The drive itself is a breathtaking journey through redwood forests and along the Pacific coastline. Its remote location, perched on a headland above the ocean, adds to its allure and historical significance. The town’s geography made it an ideal spot for clandestine activities during Prohibition, with hidden inlets allowing for discreet deliveries. Despite its seclusion, Mendocino is accessible for those seeking a tranquil escape filled with natural beauty and a touch of historic mystery.
15. Dahlonega, Georgia: Gold Rush Town with Prohibition Tales
Dahlonega, the first major U.S. Gold Rush site, is steeped in rich history and Southern charm. The town’s historic square has antebellum architecture, housing shops, restaurants, and wineries. During Prohibition, Dahlonega was no stranger to clandestine activities; the surrounding hills and forests provided cover for moonshiners and secret speakeasies.
Visitors can tour the local gold mine, explore the Gold Museum, and enjoy live music at venues that echo stories from the past. The town’s vibrant arts scene and Appalachian culture make it a captivating destination. 3-4 bedroom homes in Dahlonega are priced around $300,000 – $550,000.
Where is Dahlonega?
Nestled in the foothills of the Blue Ridge Mountains, Dahlonega is about 65 miles north of Atlanta, accessible via GA-400 and Highway 60. The scenic drive through rolling hills and forests sets the tone for a visit rich in natural beauty and history. The town’s mountainous terrain was rich in gold and provided the perfect backdrop for hidden speakeasies during Prohibition. Today, the area’s wineries and outdoor activities, like hiking and fishing, attract visitors seeking adventure and a connection to the past.
14. Port Townsend, Washington: Victorian Seaport with Secret Speakeasies
Port Townsend is a maritime treasure with a remarkable collection of Victorian-era buildings overlooking the Puget Sound. Known for its storied maritime history, the town’s waterfront and historic district once concealed speakeasies within elaborately designed structures. The community embraces its past with festivals, arts, and cultural events throughout the year.
Visitors can enjoy whale watching, explore Fort Worden State Park, or delve into local history at the Jefferson Museum of Art & History. The blend of natural beauty and historic architecture creates a captivating atmosphere. Homes in Port Townsend typically range from approximately $635,000 to $950,000 for 3-4 bedrooms.
Where is Port Townsend?
Located on the northeastern tip of the Olympic Peninsula, Port Townsend is about a two-hour drive from Seattle, including a ferry ride across the Puget Sound. The town’s seaside location offers stunning water views and distant mountains. Its strategic position made it an important port in the past and a discreet location for speakeasies during Prohibition. The journey to Port Townsend involves scenic routes showcasing Washington’s lush landscapes, making the trip as enjoyable as the destination.
13. Natchitoches, Louisiana: Historic Settlement with Hidden Bars
Established in 1714, Natchitoches is the oldest settlement in the Louisiana Purchase territory, rich with French Creole architecture and Southern hospitality. The town’s picturesque downtown, with its brick streets and wrought-iron balconies, evokes a bygone era. During Prohibition, Natchitoches’ hidden bars and speakeasies thrived in the backrooms and basements of its historic buildings.
Visitors can explore the Cane River Creole National Historical Park, tour historic plantations, and enjoy local cuisine that reflects a blend of cultures. The town’s festive atmosphere and deep-rooted traditions make it a unique stop. 3-4 bedroom homes in Natchitoches are typically priced around $177,000 – $350,000.
Where is Natchitoches?
Natchitoches is located in northwestern Louisiana, approximately halfway between Shreveport and Alexandria along Interstate 49. The town is situated on the banks of the Cane River Lake, providing scenic waterfront views. Its location in the heart of Louisiana’s historic plantation country adds to its allure and significance. The area’s rich soil and waterways made it a hub for trade—and, during Prohibition, a discreet location for hidden bars. Traveling to Natchitoches offers a journey through lush landscapes and an immersion into the state’s vibrant history.
12. Paducah, Kentucky: Artistic Hub with Prohibition Stories
Paducah, designated as a UNESCO Creative City, is renowned for its thriving arts scene and historic downtown. The town’s beautifully preserved architecture includes buildings that once housed speakeasies, adding a layer of intrigue to its cultural tapestry. The National Quilt Museum and numerous galleries showcase local and international artistry.
During Prohibition, the town’s strategic location at the Ohio and Tennessee Rivers confluence facilitated clandestine trade and secret gatherings. Today, Paducah offers a vibrant mix of creativity, history, and Southern charm. Homes in Paducah are available for around $180,000 – $450,000 for a 3-4 bedroom property.
Where is Paducah?
Paducah lies along Interstate 24 in western Kentucky, making it accessible from Nashville, St. Louis, and beyond. The town’s riverfront location offers picturesque views and opportunities for riverboat excursions. Its geography not only contributed to its historical significance but also its role during Prohibition as a nexus for hidden activities. The accessible yet tranquil setting makes Paducah a convenient destination for those seeking an enriching experience steeped in art and history.
11. Marietta, Ohio: Riverfront Town with Underground Secrets
Marietta, the first permanent settlement in the Northwest Territory, is a town steeped in American history. Its location at the Muskingum and Ohio Rivers confluence made it a bustling trade hub. Underneath its brick streets lies a network of underground passages and basements that were once used as speakeasies and safe havens during Prohibition.
Visitors can explore historic sites like the Blennerhassett Museum, take riverboat cruises, and enjoy the charm of the Harmar Village. Festivals and ghost tours add to the town’s allure, offering a glimpse into its storied past. Homes in Marietta can range from $169,000 to $859,000 for a 3-4 bedroom property.
Where is Marietta, Ohio?
Marietta is located in southeastern Ohio, near the West Virginia border, accessible via Interstate 77. Its riverfront setting provides scenic views and a tranquil atmosphere. The town’s geography played a significant role in its development and its clandestine activities during Prohibition, with waterways facilitating discreet transportation. Today, Marietta’s rich historical landscape and accessibility make it an inviting destination for history enthusiasts and casual travelers alike.
10. Savannah, Georgia: Historic Squares and Hidden Speakeasies
Savannah captivates with its cobblestone streets, moss-draped oaks, and historic squares. As one of the largest National Historic Landmark Districts in the U.S., the city’s architectural beauty is matched by its intriguing past. During Prohibition, Savannah’s underground tunnels and secret rooms became speakeasy hotspots.
Today, visitors can explore these hidden aspects through guided tours, enjoy the vibrant nightlife, and dine-in establishments that preserve the ambiance of yesteryears. The city’s artistic energy, rich history, and Southern hospitality ensure a memorable experience. Homes in Savannah typically range from approximately $449,000 to $525,000 for 3-4 bedrooms.
Where is Savannah, Georgia?
Located on the eastern coast of Georgia, Savannah is accessible via Interstate 95 and U.S. Highway 17. The city sits along the Savannah River, near the Atlantic Ocean, providing picturesque waterfront views. Its coastal position contributed to its historical prominence and facilitated discreet importation during Prohibition. The city’s layout of interconnected squares and parks makes it ideal for exploration on foot or by trolley, weaving through stories of the past and present.
9. St. Augustine, Florida: Oldest City with Secret Speakeasies
St. Augustine is historically significant as the oldest continuously inhabited European-established settlement in the continental U.S.. Its Spanish colonial architecture, historic forts, and narrow streets create an enchanting atmosphere. During Prohibition, St. Augustine’s coastal location and maze-like streets made it a prime spot for hidden speakeasies and rum-running.
Visitors can explore Castillo de San Marcos, stroll along St. George Street, and relax on pristine beaches. The blend of history, culture, and coastal beauty makes St. Augustine a unique destination. Homes in St. Augustine are typically priced around $509,000 to $525,000 for a 3-4 bedroom property.
Where is St. Augustine, Florida?
St. Augustine is situated on Florida’s northeast coast, approximately 40 miles south of Jacksonville, accessible via Interstate 95. The city’s coastal location along the Atlantic Ocean offers stunning views and maritime activities. Its geography was ideal for clandestine activities during Prohibition, with easy access by sea. Today, the city’s accessibility and rich historical tapestry make it a favorite among travelers seeking relaxation and exploration.
8. Astoria, Oregon: Coastal Town with Prohibition-Era Hideouts
Astoria, the oldest American settlement west of the Rockies, sits at the mouth of the Columbia River, where it meets the Pacific Ocean. The town’s maritime heritage and historic downtown are steeped in stories of exploration and clandestine activities. During Prohibition, Astoria’s waterfront warehouses and underground tunnels served as speakeasies and smuggling routes.
Visitors can delve into history at the Columbia River Maritime Museum, climb the Astoria Column for panoramic views, and enjoy the charming riverwalk with shops and eateries. Homes in Astoria typically range from $505,000 to $536,000 for 3-4 bedrooms.
Where is Astoria, Oregon?
Located in northwestern Oregon, Astoria is accessible via U.S. Highway 101 and is about a two-hour drive from Portland. Its position on the Columbia River and proximity to the Pacific Ocean made it strategically significant historically and during Prohibition. The town’s dramatic landscapes, with nearby beaches and forests, provide a stunning backdrop for exploration. The blend of natural beauty and rich history makes Astoria a captivating destination for visitors.
7. Galena, Illinois: 19th-Century Town with Basement Speakeasies
Galena’s well-preserved 19th-century architecture transports visitors back to a time when it was a bustling lead mining and steamboat hub. The entire downtown area is listed on the National Register of Historic Places, with brick buildings housing antique shops, bed-and-breakfasts, and eateries. During Prohibition, many of these buildings concealed speakeasies in their basements and backrooms.
Today, the Ulysses S. Grant Home and local museums offer insights into the town’s significant past. The rolling hills and scenic vistas add to Galena’s charm, making it a picturesque getaway. 3-4 bedroom homes in Galena typically range from $299,000 to $375,000.
Where is Galena, Illinois?
Situated in the northwestern corner of Illinois, Galena is accessible via U.S. Highway 20, about a three-hour drive from Chicago. The town is nestled among the hills near the Mississippi River, providing scenic landscapes and outdoor activities like hiking and golfing. Its remote location during the Prohibition era made it an ideal spot for hidden speakeasies. Today, Galena’s accessibility and enchanting setting draw visitors seeking both relaxation and a touch of history.
6. Leadville, Colorado: Historic High-Altitude Speakeasies
At over 10,000 feet above sea level, Leadville is the highest incorporated city in the United States. Once a booming silver mining town, it boasts a rich history with colorful characters and legendary tales. During Prohibition, Leadville’s remoteness and rugged terrain covered secret speakeasies tucked away in the mountains.
Visitors can explore the National Mining Hall of Fame and Museum, take scenic train rides, and walk the historic downtown lined with Victorian-era buildings. The surrounding peaks offer outdoor adventures year-round, from skiing to hiking. 3-4 bedroom homes in Leadville are priced from $500,000 to $600,000.
Where is Leadville, Colorado?
Leadville is located in central Colorado, accessible via Highway 24, about 100 miles west of Denver. Nestled in the Rocky Mountains, its high-altitude setting offers breathtaking views and a cool climate even in summer. The town’s remote location contributed to its secretive activities during Prohibition, adding to its appeal today. Travelers can enjoy a scenic drive through mountain passes, with opportunities to explore nearby national forests and parks.
5. Jerome, Arizona: Ghost Town with a Speakeasy Past
Perched on Cleopatra Hill overlooking the Verde Valley, Jerome was once known as the “Wickedest Town in the West.” This former mining boomtown transformed into a near ghost town before becoming a haven for artists and history enthusiasts. The hillside is dotted with historic buildings that housed brothels and speakeasies during its heyday.
Visitors can explore the Jerome State Historic Park, art galleries, and dine-in establishments that retain vintage charm. Its narrow, winding streets and panoramic views add to its unique character. Homes in Jerome typically range from approximately $180,000 – $330,000.
Where is Jerome, Arizona?
Jerome is located in central Arizona, accessible via Highway 89A, about 100 miles north of Phoenix. The town’s clifftop location offers stunning vistas of the surrounding valley and mountains. Its elevation and rugged terrain provided seclusion ideal for Prohibition-era activities. The journey to Jerome involves scenic drives through red rock country and forests, making it a destination rich in both history and natural beauty.
4. Wallace, Idaho: Silver Mining Town with Hidden Bars
Wallace, nestled in a narrow valley in the Bitterroot Mountains, is a town where every downtown building is on the National Register of Historic Places. Once a thriving silver mining center, Wallace has a storied past that includes tales of Prohibition-era speakeasies hidden within its underground networks.
Visitors can tour the Sierra Silver Mine, explore the Oasis Bordello Museum, and enjoy the town’s charming atmosphere. The nearby Route of the Hiawatha offers a unique biking experience through historic train tunnels and over towering trestles. 3-4 bedroom homes in Wallace are priced around $256,000 – $362,000.
Where is Wallace, Idaho?
Located in northern Idaho along Interstate 90, Wallace is about 50 miles east of Coeur d’Alene. The town is surrounded by national forests and provides easy access to outdoor activities like hiking, skiing, and mountain biking. Its remote mountain location made it a perfect spot for secret speakeasies during Prohibition. The scenic drives through the rugged landscapes add to the adventure of visiting this historic gem.
3. Deadwood, South Dakota: Wild West Town with Speakeasy Lore
Deadwood is a legendary town that rose to fame during the Black Hills Gold Rush. Known for its Wild West history and notorious figures like Wild Bill Hickok and Calamity Jane, Deadwood’s historic streets are lined with saloons and casinos that echo its lawless past. During Prohibition, the town’s reputation for vice continued with speakeasies operating behind the façade of legitimate businesses.
Visitors can catch reenactments of old Western shootouts, visit the Mount Moriah Cemetery, and try their luck at gaming establishments. The town’s mix of history and entertainment makes it a lively destination. 3-4 bedroom homes in Deadwood are typically priced around $310,000 – $605,000.
Where is Deadwood, South Dakota?
Deadwood is located in the Black Hills region of western South Dakota, accessible via U.S. Highway 85. It’s about an hour’s drive northwest of Rapid City. The town is nestled in a narrow canyon, with lush forests and rugged terrain surrounding it. This geography not only made it rich in gold but also provided seclusion for Prohibition-era activities. Visitors can enjoy the scenic beauty of the Black Hills while immersing themselves in Deadwood’s vibrant history.
2. Bisbee, Arizona: Mining Town with Prohibition-Era Secrets
Bisbee is a picturesque town set in the Mule Mountains of southern Arizona. Once a thriving copper mining community, it became known for its cultural vibrancy and architectural beauty. The town’s steep streets and historic buildings conceal a labyrinth of tunnels and underground passages. During Prohibition, these tunnels were used to operate speakeasies and smuggle liquor.
Today, Bisbee is a haven for artists, offering galleries, eclectic shops, and unique accommodations like the Shady Dell Vintage Trailer Court. Tours of the Queen Mine provide a glimpse into its mining heritage. 3-4 bedroom homes in Bisbee are priced from approximately $245,000 to $319,000.
Where is Bisbee, Arizona?
Bisbee is located about 90 miles southeast of Tucson, accessible via Highway 80. The town’s elevation of over 5,500 feet provides a cooler climate and stunning mountain views. Its proximity to the Mexican border increased its strategic importance during Prohibition, facilitating smuggling operations. The drive to Bisbee offers scenic desert landscapes, and the town itself is a rewarding destination for those seeking history and a creative atmosphere.
1. Eureka Springs, Arkansas: Hidden Speakeasies in the Ozarks
Eureka Springs is a Victorian-era resort town in the Ozark Mountains, known for its natural springs and winding streets lined with historic buildings. The entire city is listed on the National Register of Historic Places. During Prohibition, the town’s maze-like layout and underground passages became ideal for hiding speakeasies. Today, visitors can explore the historic district on foot, discovering unique shops, art galleries, and eateries.
The Crescent Hotel, often called America’s most haunted hotel, adds a touch of mystery. Outdoor activities like hiking, boating on nearby lakes, and exploring caves enrich the experience. 3-4 bedroom homes in Eureka Springs range from approximately $335,000 to $499,000.
Where is Eureka Springs, Arkansas?
Eureka Springs is located in northwest Arkansas, accessible via Highway 62, about an hour’s drive from Fayetteville. The town’s mountainous setting provides a serene backdrop and a wealth of natural beauty. The Ozarks offered seclusion during Prohibition and contributed to the town’s appeal today. Winding roads through forests and hills make the journey to Eureka Springs as enchanting as the destination, offering a perfect blend of history, nature, and charm.
