Exploring Stillwater, MN, with a Private Guided Tour

Imagine winding along the steep river bluffs of Stillwater in a private vehicle, passing through a town famed for its Victorian architecture and storied lumber industry. For about two hours, a knowledgeable guide takes you through the highlights of this scenic Minnesota town—starting on the outskirts, then down quaint Main Street, ending with some sweet treats at a local candy shop. The cost is $480 for up to two people, which makes it a more personal, flexible experience than group tours.
What we love about this experience is how personalized it feels—you’re not just another face in a crowd, but a private group with dedicated attention from your guide. Second, the chance to enjoy stunning views of the St. Croix River and detailed stories about the homes and historic landmarks enriches the visit.
A small consideration is that the tour does not include interior visits to homes or buildings, so if you’re eager to go inside, you’ll need to plan extra time on your own. This tour best suits those who appreciate history, architecture, and scenic views, and who want a relaxed, insider perspective on Stillwater’s charm.
Key Points
- Private, personalized experience with dedicated guide and transportation
- Stunning views of Victorian homes and the St. Croix River valley
- Concise two-hour format with a mix of riding and walking
- History and architecture insights, especially about Stillwater’s role as the “Birthplace of Minnesota”
- Walk down Main Street and visit a favorite candy store for treats
- Flexible options for transportation and further exploration
Planning more time in Minnesota? We've covered other experiences worth considering.
A Closer Look at What This Tour Offers

This private tour begins conveniently in the parking lot of Culver’s, where your personal vehicle remains parked during the tour. The experience is deeply personalized, with a professional driver and guide, which means you won’t be lumped into a large group and can enjoy the journey at a relaxed pace. For $480, the price might seem steep at first glance, but when you consider the private aspect, personalized stories, and the flexibility, it’s a good value for couples or small groups seeking an authentic Stillwater experience.
The Riding Portion: Victorian Architecture & River Views
Your journey kicks off with a scenic ride through the outskirts of Stillwater, where you’ll get sweeping vistas of Victorian mansions from the 1800s—built by lumber barons and luminaries. Expect to see Queen Anne-style homes that have been beautifully restored, along with other architectural styles that highlight the town’s prosperous past. Your guide shares colorful stories about the owners, adding layers of context to what you’re viewing.
We loved the detailed commentary about how these homes symbolize the town’s bygone days of lumber wealth. The views of the St. Croix River valley from the bluffs are especially stunning—perfect for picture-taking. This part of the tour is ideal for architecture buffs and scenery lovers alike.
The Walking Portion: Downtown Charm & Sweet Treats
After the riding segment, you’ll walk through downtown Stillwater, which exudes small-town charm. The tour includes a quick overview of Main Street, famous for its antique shops, boutique stores, and inviting restaurants. You’ll get a brief look at the city hall, library, and the Rivertown Inn—a beautifully restored Victorian mansion that continues to serve as a popular B&B.
A highlight is a visit to Candyland, the local’s favorite candy shop. Here, you can pick up popcorn or sweets (at your own expense), providing a fun break and a taste of small-town sweetness. Many reviewers mention the friendly, knowledgeable guide Douglas, who goes out of his way to make the experience memorable—one reviewer called him “exceptional.”
Historic Landmarks & Local Stories
The tour also features stops at the Washington County Historic Courthouse and the Stillwater Veterans Memorial. These landmarks offer insight into why Stillwater earned its nickname as the “Birthplace of Minnesota” and its contribution to early American history, especially around the Civil War.
The Sauntry Mansion, an imposing Victorian home, is another highlight—its dramatic story of early entrepreneurship mixed with tragedy adds depth to the visual beauty. The drive-by of city hall and the civic center emphasizes how the town balances its historic roots with modern life.
- Canoe National Forest Lakes (Lutsen/Grand Marais)
- Kayak Trips on Lake Superior, Two Harbors, MN (Grand Superior)
- Group Rock Climbing in Interstate Park
- Boundary Waters Day Trips, Lutsen/Grand Marais
- Self-Guided Minnesota Scavenger Hunt: A Minnesota Miracle
- Minnesota River Valley 14-Line Thrilling Zipline Canopy Tour
Iconic Stillwater Sights
A memorable part of the tour is crossing the Stillwater Lift Bridge, a vintage 1930s mechanical lift bridge that still operates today. It’s a symbol of Stillwater’s heritage and an excellent photo opportunity—especially as it’s transformed from a vehicle bridge to a pedestrian-friendly crossing.
The tour concludes with a quick stop for restrooms and a walk along Main Street, where you can browse shops, enjoy more historic architecture, or grab a snack at LoLo or other popular eateries. The flexibility of this tour allows you to extend your stay independently—whether that means more shopping, dining, or exploring the iconic St. Croix River.
Is This Tour Right for You?
If you’re someone who appreciates history, architecture, and scenic views, and you prefer a private, intimate experience, this tour hits the mark. The stories and personal attention make it more engaging than a typical group outing. It’s perfect for couples, small families, or friends wanting a gentle, informative overview of Stillwater’s highlights.
Those eager to peek inside historic homes or indulge in extensive shopping might find the tour somewhat limited, but the overall experience offers a wonderful sense of the town’s spirit and stories. The flexibility to extend your visit afterward makes it suitable for travelers who want to craft their own exploration beyond the tour.
Why We Recommend This Tour

We loved how the guide’s storytelling brought Stillwater’s architecture and history to life—each home and landmark feels more meaningful when you know the stories behind it. The view of Victorian mansions perched along the river, combined with the small-town charm of Main Street, encapsulate what makes Stillwater special.
The private setup means your experience is tailored and relaxed, without the rush of larger tours. Plus, the inclusion of scenic spots like the Lift Bridge ensures you’ll leave with memorable photos. This tour offers a well-balanced mix of scenic beauty, history, and local flavor, all wrapped into an efficient two-hour package.
Overall, it’s a fantastic way to get a taste of Stillwater’s character, especially if you’re short on time but want a meaningful, insider perspective. For history buffs, architecture enthusiasts, or anyone looking for a charming escape, this private tour makes for a memorable visit.
FAQ

Is the tour suitable for all ages?
Yes, most travelers can participate, and the tour is designed to be accessible and comfortable for a wide age range.
Does the tour include interior visits to homes or buildings?
No, it does not include interior tours. You’ll see the exteriors and hear stories but won’t go inside the historic homes or buildings.
Is transportation provided all the way from the Twin Cities?
Private transportation to and from the Twin Cities metro area is available—just inquire when booking.
How long is the walking part of the tour?
The walking portion lasts about 30 minutes, with a quick overview of Main Street and a visit to Candyland.
What should I expect at the Candyland stop?
Candyland is a favorite local shop where you can purchase popcorn or sweets on your own—it’s a fun, sweet break during the tour.
Can I extend my visit after the tour?
Absolutely, the tour concludes at Culver’s, and you’re free to explore more shops, dine, or walk across the Lift Bridge at your leisure.
What is the price for this tour?
The cost is $480 for a private group of up to two people, which covers guided narration, private transportation, and bottled water.
In the end, this tour is a valuable snapshot of Stillwater’s historic charm and scenic beauty. Its private, flexible nature makes it ideal for those who want a detailed, authentic experience without the rush. Whether you’re a history lover, architecture fan, or simply seeking a peaceful escape, this experience offers a memorable way to enjoy one of Minnesota’s most picturesque towns.
More Tours in Minnesota
More Tour Reviews in Minnesota
- Kayak Trips on Lake Superior, Lutsen, MN (Lutsen Sea Villas)
- Minnesota River Valley 14-Line Thrilling Zipline Canopy Tour
- Self-Guided Minnesota Scavenger Hunt: A Minnesota Miracle
- Boundary Waters Day Trips, Lutsen/Grand Marais
- Group Rock Climbing in Interstate Park
- Kayak Trips on Lake Superior, Two Harbors, MN (Grand Superior)
