Private Vermont Guided Tours
Vermont, one back road at a time.
See more of Vermont. I'll handle the rest.
Private day tours for 1–4 guests, built around scenic back roads, covered bridges, small towns, farms and mountain views. I plan the route and do the driving, with plenty of room to stop, explore and change course when something better comes along.
2027 Fall Foliage Tours Now Booking
A Different Way to See Vermont
The best Vermont days aren't built from a checklist.
The internet can give you plenty of places to visit. What it can't tell you is which road is worth taking, when to go, what's worth stopping for, or when the better choice is to keep driving.
I know the roads, the timing, and the places worth slowing down for. We'll have a plan, but we won't spend the day racing from one stop to the next.
Request a Private TourPickup from Woodstock, Ludlow, Killington, Windsor, Springfield, and surrounding areas.
Meet Your Guide
I'm Aimee. Vermont Wayfinders started with a Jeep and a lot of back roads.
During COVID, my dad and I spent a lot of time exploring Vermont with the top down and no particular destination. We'd pick roads we hadn't traveled before and see where they took us.
A few years later, some of Vermont's best-known photo spots had become so crowded that towns were closing the roads to visitors. People started asking online where else they could go to find those classic Vermont views.
I knew plenty of places. But publishing another list of addresses would eventually create the same problem somewhere else.
So I had a different idea: they'd have to come with me.
Vermont Wayfinders on Good Morning America
A little Vermont on national TV.
Good Morning America included Vermont Wayfinders in its 2026 fall foliage coverage. You can watch the segment here.
Watch the GMA SegmentIn their own words (don't just take my word for it!)
"There is just no way we could have experienced such beautiful sites on our own."
"I was also glad to have one day where I was not in charge of the itinerary!"
"This was hands-down one of the best day tours I've ever taken and I travel a lot. It felt personal, special, and completely unique."
"We had a particular type of tour in mind and Aimee delivered perfectly."
"Aimee took us on backroads, through covered bridges and allowed for multiple photo ops while providing expert knowledge of the area. This was a 5 star experience."
"We would highly recommend her tour to anyone looking for a relaxing, fun, enlightening, and memory-making day in Vermont."
The Experience
So, what does a day with me look like?
No two tours are exactly alike. I'll plan the day around your interests, the season and what's happening in Vermont. Here's a little of what we might get up to.
Take the scenic route
Covered bridges, winding back roads, rolling farmland and mountain views. Sometimes the drive itself is the best part.
Get out and explore
Wander through a village, browse a local shop, visit a farm or stop for photos when something catches your eye.
Make time for the good stuff
There's room for lunch, a little exploring and spending more time somewhere you particularly enjoy.
Change plans when it makes sense
Weather changes. Places get busy. Sometimes we stumble across something better. We adjust and keep going.
The goal isn't to see everything. It's to have a genuinely good day seeing Vermont.
Here's how it works
Request your date
Choose an available date and tell me a little about your group and what you'd like to experience.
We'll plan your day
I'll follow up personally to confirm the details, arrange payment and plan a route around your interests.
Enjoy Vermont
I'll pick you up and take care of the driving, the timing and the details. Your only job is to enjoy the day.
What's included in your private tour
- Just your group. Every tour is private, with room for up to four guests.
- Pickup and drop-off. I'll meet you at an agreed location within my service area.
- A day built around you. Scenic routes and stops selected around your interests, the season and the weather.
- All the driving and logistics. I'll handle navigation, timing and adjustments along the way.
- Plenty of photo opportunities. Covered bridges, mountain views, Vermont villages and whatever else catches our eye.
- A Ford Bronco made for exploring. Comfortable, capable and even better with the top down when the weather cooperates.
Who's riding along?
Some guests are discovering Vermont for the first time. Others have been coming for years. Either way, it's about enjoying a relaxed, personal day exploring Vermont.
- The designated planner Spend a day enjoying the trip instead of organizing everyone else's.
- Repeat Vermont visitors You've seen the familiar sights and are ready to explore different roads and places.
- Couples and small groups Enjoy a private experience with the freedom to spend the day doing what interests you.
- Photography enthusiasts Enjoy scenic drives, beautiful views and time to stop when a good photo opportunity comes along.
- Solo travelers Enjoy exploring with some company, local knowledge and a day without navigating.
Ready to see Vermont for yourself?
Let's make a day of it. Choose your dates, tell me what you're interested in, and I'll take care of the details.
Still deciding?
Take the Vermont Anchor Day Quiz and see what kind of Vermont day is right for you.