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Dorchester Center, MA 02124

Discover Vermont's hidden gems with a personalized guided tour in a convertible, exploring scenic dirt roads, charming towns, and breathtaking views.
Planning a trip to Vermont and craving a tailored experience that reveals the state’s lesser-known treasures? The Signature Vermont Wayfinders Private Guided Tour offers just that—a fully customizable day exploring Vermont’s scenic back roads, charming towns, and stunning vistas, all in a fun, open-air vehicle. While it’s a pricier option at $850 for up to four people, the personalized attention and unique route make it a worthwhile investment for those seeking an authentic, off-the-beaten-path adventure.
What sets this tour apart? First, the fully tailored itinerary means you tell your guide what interests you most—whether it’s farm scenery, photography, artisans, or simply soaking up Vermont’s natural beauty. Second, the small-group, private format ensures a relaxed, flexible experience that’s all about your preferences.
However, a potential consideration is the cost, which may seem steep for some travelers, especially if you’re on a budget. The tour’s value really shines if you appreciate personalized service, unique vistas, and customized exploration rather than a cookie-cutter sightseeing bus. This tour is ideal for couples, small groups, or families wanting a special day with a local guide who knows Vermont intimately.


The Signature Vermont Wayfinders Private Guided Tour offers an appealing blend of flexibility and adventure, perfect for travelers eager to see Vermont beyond the typical tourist spots. As a small, private experience, the tour provides the kind of personal touch that larger group excursions often lack. You’ll travel in a built-for-backroads Bronco, with the top down (weather permitting), giving you an open-air perspective on Vermont’s landscape—something that truly enhances the scenic element of the journey.
If you prefer having a local expert, these guided Vermont experiences could work well
The route begins in Brownsville, where your guide will take you along less-traveled back roads. Here, you’ll get sweeping views of Mount Ascutney—a Vermont icon that dominates the landscape. The stops are brief—about 30 minutes each—but enough to soak in the scenery and snap some memorable photos. One traveler noted, “The backroads and beautiful views were a highlight,” emphasizing how the quiet, traffic-free roads elevate the experience.
Next, in the quaint town of Reading, you’ll enjoy more dirt roads and panoramic vistas—a true glimpse of Vermont’s rural charm. Here, the emphasis is on natural beauty, with the opportunity to breathe in fresh air and appreciate the peaceful countryside. The reviews highlight how well the guide’s local knowledge makes these lesser-known spots shine.
In Plymouth, the landscape continues to impress with lakes and lush greenery. Optional stops at Plymouth Cheese or the Calvin Coolidge Homestead can add a cultural or culinary twist, if you wish. While these add-ons are not included, they reflect the flexibility of the tour.
Moving on, the tour pauses in Woodstock, often called Vermont’s quintessential town. With its art galleries, shops, and picturesque streets, Woodstock is perfect for a longer break—about an hour—to stroll, browse, and take photos. One reviewer mentioned, “Woodstock’s charm was perfect for a relaxed exploration,” highlighting how this stop balances sightseeing with leisure.
The final scenic stop is in Barnard, a town dotted with farms, fields, and woods. There’s a pretty lake here that can become your lunch spot or a place for stretching and taking in the scenery. The opportunity to include a picnic or simply enjoy the quiet makes Barnard a fitting end to a day of exploration.
With a maximum of four travelers, this tour maintains a personalized atmosphere. The guide, Aimee, is praised for her local expertise and knowledge, making the experience more than just a drive—it’s a curated journey. One happy guest said, “Aimee’s knowledge and experience made the day special,” underscoring how crucial a good guide is in creating a memorable trip.
Traveling in a convertible Bronco adds an element of fun and adventure, especially with the top down, offering unobstructed views of Vermont’s rolling hills, forests, and farms. Air-conditioning and bottled water are provided, making the journey comfortable despite Vermont’s unpredictable weather.
At $850 per group, the price is on the higher side, but the value lies in the customized experience. Compared to organized group tours, this private day offers flexibility, insider access, and a personal touch that can be hard to find elsewhere. It’s especially appealing for those who want a day designed around their interests—whether that’s photography, foodie experiences, or simply relaxing in nature.
The reviews reflect high satisfaction, with a perfect 5-star rating. One guest noted, “Being a local, Aimee knew how to take the backroads and show off Vermont’s beauty,” capturing the essence of what makes this tour special: insider knowledge and authentic sights. The flexibility to customize the stops and the personalized service are often cited as highlights.
This Signature Vermont Wayfinders Private Guided Tour is a splendid choice for travelers who value tailored experiences, want to explore Vermont’s lesser-known scenic routes, and enjoy the comfort of a private guide. It’s perfect for small groups or couples who want to avoid the cookie-cutter tour buses and prefer a more intimate, authentic encounter with Vermont’s natural beauty and charming towns.
Those seeking a photography-focused day, a foodie adventure, or just a relaxing, scenic drive will find this experience wonderfully suited to their interests. And if you’re someone who loves local insights and off-the-beaten-path roads, this tour could easily become the highlight of your Vermont visit.
However, if you’re on a tight budget or looking for a quick, mass-market tour, this might not fit. But for those craving a personalized, scenic escape with a local guide, this tour offers memorable vistas, genuine Vermont charm, and the flexibility to make your day truly your own.
“The Signature Vermont Wayfinders Private Guided Tour was a very good guided tour by Aimee. Being a local, Aimee knows how to take the backroads an…”

What is included in the tour?
The tour includes private transportation in a convertible Bronco, bottled water, snacks, and a customized itinerary based on your preferences.
Can I choose where to stop?
Yes. The tour is built around your interests, so your guide will adjust stops and routes to suit what you want to see and do.
Is the tour suitable for all ages?
Most travelers can participate. Service animals are allowed, and the tour’s natural, scenic focus makes it suitable for families and solo travelers alike.
How long does the tour last?
Expect approximately 6 to 7 hours, starting at 10:00 am, with multiple stops along the way.
Can I add optional activities?
Yes. You can include extras like heading to Killington’s top or a horse-drawn carriage ride, depending on availability and your interests.
What is the maximum group size?
Up to four people, which ensures a small, personalized experience.
What if I need to cancel?
You can cancel free of charge up to 24 hours before the start, and receive a full refund.
Is the vehicle climate-controlled?
The Bronco is an open-air vehicle with a top that can be lowered (weather permitting), offering a breezy, scenic ride rather than traditional climate control.
How far in advance should I book?
On average, travelers book about 29 days ahead, so planning early is recommended to secure your preferred date.
In essence, the Signature Vermont Wayfinders Private Guided Tour offers a personalized, scenic journey into Vermont’s hidden corners, perfect for those seeking a flexible, authentic experience in a beautiful setting.