What Are The Best Historical Tours In Branson? Our Top 2 Picks

Discover Branson’s top historical tours, from a Jeep-drawn farm trip exploring "The Shepherd of the Hills" to a wine and brewery experience with local stories.

Branson isn’t just about lively shows and Silver Dollar City rides. This Ozark city has a surprising depth of historical attractions that reveal its authentic roots and literary heritage. Whether you’re interested in riding through scenic farms that inspired classic novels or learning about regional culture over a glass of local wine, Branson’s historical tours offer meaningful experiences.

Many visitors appreciate how these tours focus on local stories and landmarks that shaped the area. Unlike generic sightseeing, these experiences dive into Harold Bell Wright’s iconic novel and the history behind the Ozarks’ development. If you’re a history lover, or just someone looking for a meaningful way to connect with Branson’s past, these options are well worth considering.

1. Shepherd of the Hills Historic Tour

Shepherd of the Hills Historic Tour

Explore a 160-acre farm that inspired Harold Bell Wright’s beloved novel with this Shepherd of the Hills Historic Tour. This tour removes the need to walk or arrange transport — instead, you’ll hop onto a Jeep-drawn tram guided by a true Ozark native. The guide shares insights about the farm, the book, and the characters, making the story come alive.

What sets this tour apart is its focus on key sites like Inspiration Point, Old Matt’s Cabin, and Morgan Church — all tied to the novel’s setting and Wright’s life. The cabin itself is on the National Register of Historic Places, and the view from Inspiration Point is breathtaking, justifying the name. The 1-hour ride covers significant landmarks without demanding much of your day, making it ideal if you’re short on time.

Reviewers rave about the knowledgeable, friendly guides — one called Cowboy John “connected the dots” between the story and real history, making it a memorable experience. It’s especially great for families wanting a quick, engaging history lesson with beautiful scenery.

Bottom line: This tour offers a compact, informative look at the farm that inspired a legendary American novel. It’s perfect for those wanting a taste of Ozark literature and history without a big time investment.

2. Bear Creek Winery and Brewery history, tasting, with lunch tour

Bear Creek Winery History and Property Tour of the Ozarks

For around $99.95 per person, the Bear Creek Winery and Brewery tour takes you off the beaten path for a relaxed, story-filled experience. It lasts about 1 hour 30 minutes and combines a walking tour of the scenic property with local history and a taste of the Ozarks’ wines, brews, and homemade food.

The tour begins at the family-owned Bear Creek property, which grew from a small inn into a complex with water gardens, two chapels, an event center, and a beloved bed and breakfast. The owner, a local born and raised in the Ozarks, shares stories about the property’s development and her family’s history in the region. You’ll also visit the water garden, two chapels, and the inn, getting a genuine sense of local Ozarks culture.

What makes this tour compelling is its personal touch — chatting directly with someone who has deep roots here and understanding how local traditions influence the lifestyle. Plus, sampling the wines and seeing the gardens adds sensory richness.

Reviewers note that the tour is a peaceful, engaging way to connect with Ozark life from a local’s perspective. It’s also a great choice for anyone interested in regional food and drink history.

Bottom line: This tour offers a slower, more personal connection to local Ozark culture, with beautiful scenery and tasty samples—ideal for wine lovers or history enthusiasts seeking an authentic experience.

How to Choose

Choosing between these two tours depends on your interests and schedule. If you want a quick, literary-focused experience that highlights Harold Bell Wright’s classic novel, the Shepherd of the Hills Historic Tour provides a concise peek into Ozark farm life and storytelling. It’s especially suited for families or anyone short on time.

On the other hand, if you’re looking for a relaxed, immersive experience that combines local history, regional culture, and wine tasting, then the Bear Creek Winery and Brewery tour is a better fit. It’s great for those wanting a leisurely walk with meaningful conversations and tasty samples.

Consider your budget, time, and interests: the farm tour is more affordable and concise, while the winery tour offers a broader cultural experience, albeit at a higher price.

Booking early is recommended for both, especially during peak seasons, to secure preferred times and ensure availability.

Branson’s historical tours provide a well-rounded look into Ozark stories, whether through the lens of literature or local traditions. For a quick historical fix, the Shepherd of the Hills farm tour offers a captivating glance at the setting that launched an American classic. If you prefer a more in-depth cultural experience, the Bear Creek tour combines local history with regional hospitality. Both tours will deepen your understanding of Branson’s authentic past—so pick one that fits your schedule and interests, and enjoy a richer visit to the Ozarks.