Heres a countdown of the 17 best small towns that make this wine trail an unforgettable adventure.

The towns riverside English Landing Park provides a peaceful setting for picnics and strolls.

Rocheport: Charming Retreat on the Missouri River

Rocheport enchants visitors with its historic charm and scenic beauty.

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Located on the Katy Trail, its a haven for cyclists and hikers.

The towns boutique wineries offer intimate tasting experiences with panoramic views of the river bluffs.

The Battle of Lexington State Historic Site tells tales of the past amid well-preserved antebellum homes.

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Bird enthusiasts flock here for eagle-watching in the winter months.

New Haven: Artistic Flair and Wine

New Haven boasts a vibrant arts scene that complements its winemaking traditions.

Its an ideal base for exploring the nearby Current and Jack Fork rivers.

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The towns historic district features quaint shops and eateries that exude small-town charm.

Nearby vineyards take advantage of the fertile soils, offering delightful wines in peaceful rural surroundings.

A visit to Caledonia promises a relaxing experience steeped in history and hospitality.

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Defiance: Outdoor Adventures and Wineries

Defiance perfectly blends outdoor activities with wine tasting experiences.

Situated along the Katy Trail, its a popular stop for cyclists and hikers.

The towns wineries, often featuring live music and events, offer a lively yet laid-back atmosphere.

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Whether youre seeking adventure or relaxation, Defiance delivers with its scenic landscapes and welcoming vineyards.

Genevieve: Oldest European Settlement in Missouri

As the oldest European settlement in the state, Ste.

Genevieve charms visitors with its French colonial architecture and rich history.

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The towns narrow streets and preserved buildings tell stories of the past.

Surrounding wineries embrace this heritage, offering wines that reflect the regions unique terroir.

A visit here feels like stepping into a different era, complete with modern delights.

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For those captivated by its charm, 3-4 bedroom homes in Ste.

Genevieve are available at prices ranging from $223,592 to $350,000, combining history with affordability.

Rollas blend of innovation and tradition makes it a dynamic stop along the wine trail.

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Legend has it that Daniel Boones original burial site is nearby.

The towns proximity to the trail makes it a favorite among cyclists looking to rest and recharge.

Local wineries offer a welcoming respite with delightful wines and hospitality that reflect the towns rich heritage.

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This artistic flair extends to unique shops and eateries that celebrate the towns heritage.

Nearby wineries invite visitors to enjoy Missouri wines, adding a flavorful twist to the nostalgic journey through Cuba.

The towns rolling vineyards and historic wineries offer a picturesque setting for tasting some of Missouris finest wines.

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The town is renowned for its Oktoberfest celebrations and wineries that have been family-run for generations.

Steelville: Gateway to the Ozarks

Surrounded by forests and waterways, Steelville is a haven for outdoor enthusiasts.

Canoeing, fishing, and hiking opportunities abound.

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Amidst this natural playground, rustic wineries provide cozy spots to relax and enjoy locally produced wines.

Steelvilles warm community spirit and scenic landscapes make it a cherished destination along the wine trail.

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