Vermont, Without the Guesswork
Private guided Vermont tours and custom day plans built around what’s actually worth your time.
You don’t need more recommendations.
You need better ones.
Is your time in Vermont worth doing right?
Serving Woodstock, Ludlow, Killington, Weston, and the back roads in between.
5-star TripAdvisor reviews. Limited weekend availability.
What Guests Say
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"There is just no way we could have experienced such beautiful sites on our own."
—Fred G., TripAdvisor review
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"I was also glad to have one day where I was not in charge of the itinerary!"
— Patricia D., TripAdvisor review
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"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."
— Martha J., TripAdvisor Review
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"We had a particular type of tour in mind and Aimee delivered perfectly."
—Val S., Google review
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"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."
— Thomas, Google review
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"We would highly recommend her tour to anyone looking for a relaxing, fun, enlightening, and memory-making day in Vermont."
— Mike, Google review
★★★★★ Consistent 5-star reviews on TripAdvisor and Google ★★★★★
Why Vermont trips disappoint
Planning a day in Vermont should feel exciting. Instead, it often feels overwhelming.
Too many “must-see” lists. Untrustworthy opinions of what to do on social media. Routes that look simple online but waste hours in real life. Crowded stops that feel anything but special.
Vermont looks easy on a map. In real life: parking, crowds, and routes that waste hours and aren’t that fun to drive.
Routes that work on Google fall apart in person
Timing that quietly kills the mood
Popular spots that feel crowded instead of charming
And that’s exactly what Vermont Wayfinders fixes.
Here’s What Changes When It’s Done Right
Instead of rushing from stop to stop, your day flows.
Instead of second-guessing the next turn, the route makes sense.
Instead of fighting crowds, you find quiet stretches that feel like Vermont.
• The drive feels scenic, not strategic
• The timing works with the day, not against it
• Every stop earns its place
• You experience Vermont instead of managing it
A local guide, a private day, zero hassle
We live on these roads. We plan around traffic, crowds, time of year and weather so you get quiet bridges, open views, and easy stops.
You tell us what you love. We design the route. We handle the timing. You relax and enjoy Vermont.
No guessing. No rushed stops. No parking surprises.
Just a thoughtfully planned day that flows.
Simple Three-Step Process
Step 1. Request your date + tell us what you want to see.
Step 2. We design a private route with great timing and excellent back up plans.
Step 3. Relax. Ride shotgun (or in the back seat). We’ll take it from here.
Why It’s Worth Doing Right
Private tours only. No mixed groups, ever.
A custom route built around what you actually want to see.
Smart timing designed to avoid crowds and traffic.
Flexible pacing that adjusts to the day.
Photo stops dialed to light, weather, and season.
Local stories that bring each stop to life.
Built-in backup options when conditions change.
Comfortable, capable Bronco transportation.
Pick up and drop off included.
Clear pricing. No surprises.
What a Day With Vermont Wayfinders Feels Like
More Vermont, less time planning
Authentic stops without the crowds
Private and Personal
Just you and your crew. No crowds, no rush. A relaxed Vermont day at your own pace.
The scenic route, always. Winding back roads, quiet overlooks, and the kind of places you won’t find on a Top 10 list.
Local insight, not a script. Real stories, real context, and the tucked-away details that bring each stop to life.
Your trip, your way. Every Vermont tour is tailored to your interests, because the best adventures aren’t one-size-fits-all.
Who We’re For
This isn’t for everyone. It’s for travelers who want to do Vermont right.
Our guided tours are a perfect fit for:
The planner who wants one day where they’re not managing every decision.
Repeat visitors who want something deeper and quieter this time.
Couples and small groups looking for a truly personal Vermont experience.
Photographers who care about light, timing, and thoughtful routing.
Independent travelers who enjoy exploring but want a local guide to unlock Vermont’s tucked-away corners.
Ready to Spend a Day Doing Vermont Right?
Private. Thoughtfully planned. Designed around you.
No guesswork. No rushed stops. No crowded tour buses.
Just a relaxed Vermont day that actually feels like Vermont.
Still deciding?
Take the Vermont Anchor Day Quiz and see what kind of Vermont experience fits you best.
