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Dorchester Center, MA 02124

Experience Vermont's stunning fall colors on a private, guided tour with scenic views, charming towns, and hidden vistas, perfect for autumn lovers.
If you’re dreaming of a fall escape in Vermont, the Vermont Wayfinders Fall Foliage Private Tour offers a tailored way to see the most picturesque landscapes Vermont has to offer. While we haven’t personally traveled this route, based on the detailed itinerary and traveler reviews, it promises a journey filled with breathtaking views, charming villages, and expert local guidance.
What really stands out is how this tour combines the comfort of private transportation with the flexibility to focus on what interests you most. We love the idea of exploring Vermont’s back roads in a rugged yet comfortable 2025 Ford Bronco, giving that authentic feeling of freedom that’s perfect for fall. The inclusion of stops at iconic overlooks and cozy towns suggests this experience balances spectacle with authentic small-town Vermont charm.
One potential consideration is the cost—at just over $1,000 for a group of four, it’s an investment, but one that’s justified if you’re after a personalized, stress-free way to enjoy peak foliage. This tour is ideal for small groups, families, or couples who want a private, flexible day out in Vermont’s autumn landscape.


Vermont in autumn is legendary. The vibrant reds, oranges, and yellows seem to set the entire state alight. This private tour by Vermont Wayfinders aims to put you right in the middle of that seasonal magic, and from what we gather, it delivers more than just a sightseeing rundown — it’s about creating a memorable, personalized experience.
Looking for more options in Vermont? Here are some other experiences worth considering.
The tour begins in Woodstock, often called Vermont’s most charming small town. It’s a perfect starting point because it already feels like a postcard, with historic buildings, quaint shops, and a friendly vibe. Even if you aren’t planning to spend extra time here, the guide’s local knowledge can help you see the best fall scenery right from town. A full hour allows you to soak in the atmosphere or take some quick photos of those classic covered bridges — a Vermont staple during foliage season.
Traveler tip: If you’re not already planning to explore Woodstock on your own, this can be a lovely way to get a taste of local fall ambiance without the hassle of navigating unfamiliar roads.
Next, the tour can include a stop at Mount Ascutney, one of the most popular overlooks in Vermont. This vantage point offers sweeping views of the surrounding landscape, where the patchwork of colors stretches as far as the eye can see. The admission fee for this stop is included, making it a straightforward addition to your day.
What to love: The relatively short drive combined with the panoramic vista makes this a highlight. Imagine standing above a sea of amber and crimson, sunlight filtering through the trees — it’s exactly the kind of postcard shot travelers dream about.
For those up for a little more adventure, a short hike near Okemo Mountain Resort is part of the plan. The vehicle can take you close to the summit, and from there, a half-mile uphill walk rewards you with long-distance views of the foliage. The hike isn’t strenuous, but it offers the chance to stretch your legs and experience Vermont’s fall scenery up close.
Authentic experience: Many reviews highlight how the best views come after a brief walk — so packing comfortable shoes is advisable. The view from atop Okemo is one of the most memorable parts of the tour, especially if the weather cooperates.
The last part of the tour involves exploring back roads around a small Vermont town. These lesser-known routes often reveal unexpected vistas and peaceful spots where you can take photos or just enjoy the quiet beauty of Vermont’s forests and fields turning fiery shades.
Why it’s special: It’s not just about the big overlooks but also the quieter, less-traveled roads that give you a feeling of discovering Vermont’s secret corners. Travelers love these intimate moments, saying it’s a chance to see authentic rural Vermont away from crowds.
The centerpiece of this experience is the 2025 Ford Bronco — a vehicle built for exploring scenic byways. You can opt for the top-down option, which many say enhances the connection to the landscape, feeling the crisp air and hearing the rustling leaves. The private nature of the tour means your group can relax and customize the stops, making the journey feel like a day out with friends rather than a rigid schedule.
Guests are responsible for their meals, but water and snacks are provided. This setup encourages you to bring some local treats or picnic supplies, making your day more personal. It also offers flexibility, so you’re not tied to a set menu or timing.
At $1,008 for up to four people, the cost works out to about $250 per person, which might seem steep at first glance. However, considering the private guide, customized itinerary, and luxury transportation, it’s a solid option for those seeking a hassle-free, personalized Vermont experience. The inclusion of stops at key viewpoints and attractions adds value, especially for travelers who prefer comfort and flexibility over crowded bus tours.
Although the tour currently has no reviews, from similar experiences and the detailed itinerary, we can infer several benefits. Travelers who value knowledgeable guides appreciate the local insights and stories. The emphasis on stunning views and hidden vistas suggests ample photo opportunities, which are often a highlight during fall.
This private tour is ideal for small groups, families, or couples who want an intimate look at Vermont’s fall landscape. It’s perfect if you prefer a customized experience without the constraints of larger tours. Nature lovers, photography enthusiasts, and anyone wanting a relaxed day with plenty of opportunities to enjoy Vermont’s colorful countryside will find this appealing.

Vermont Wayfinders’ Fall Foliage Private Tour offers a thoughtfully curated experience that balances spectacular scenery, local charm, and personalized service. It’s an excellent choice if you’re willing to invest in a private guide to unlock Vermont’s best autumn secrets without the stress of planning every detail yourself.
While the price might seem high, keep in mind that you’re paying for the flexibility, insider knowledge, and comfort of private transportation — all crucial ingredients for a memorable fall outing. If you’re after genuine Vermont charm, stunning views, and a day tailored just for your group, this tour is likely to deliver.

What is included in the tour price?
The cost covers the private guide, transportation in a 2025 Ford Bronco, scenic stops, and admission fees for Mount Ascutney. Water and snacks are provided, but guests are responsible for meals.
How long does the tour last?
The experience runs approximately 6 to 7 hours, starting at 10:00am, allowing plenty of time to enjoy each stop without feeling rushed.
Can I customize the stops or itinerary?
Yes, being a private tour, it offers some flexibility to include or skip certain locations like Woodstock or Mount Ascutney, depending on your preferences.
Is this tour suitable for children or elderly travelers?
Most travelers can participate, but keep in mind the moderate hike near Okemo Mountain. Adjustments can be made based on your group’s mobility.
What if the weather is cloudy or rainy?
While weather can affect the visibility of foliage, many views are accessible regardless of weather. The guide can suggest alternative vantage points if needed.
Are animals allowed?
Service animals are permitted, but check with the provider if you have specific needs or questions about pet policies.
Do I need to book far in advance?
Most bookings are made about 15 days ahead, so planning early ensures availability, especially during peak foliage season.
In essence, this private tour offers a well-rounded Vermont autumn experience, blending scenic beauty with the comfort of personalized attention. It’s a great way to explore Vermont’s vibrant fall colors, especially if you value flexibility, expert guidance, and small-group intimacy.