Vermont’s Best Back Roads, Privately Guided
A local guide, a custom route, and a day made for you. Covered bridges, wide-open views, and curated stops without crowds or stress.
Pick your date. We plan the rest.
Explore Woodstock, Ludlow, Killington, Quechee, Weston, Windsor and surrounding areas!
“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.”
Plan your best day in Vermont
Take a one-minute quiz and get a simple, realistic Anchor Day plan built around how you actually like to travel. Just click “Start the quiz” below.
Why Vermont trips disappoint
Trip planning gets messy fast. Too many “must-see” lists, routes that waste hours, and 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 look fine on Google, but don’t work in real life
Timing that kills the mood
Popular spots that feel crowded, not charming
Explore our three most popular tours here!
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 day and drive. You relax and enjoy Vermont.
Sure, you could plan your trip to Vermont using the same Top 10 lists everyone else does… but where’s the adventure in that? Vermont Wayfinders is for travelers who crave something more. The winding back roads, the tucked-away treasures, the stories you won’t find in a guidebook.
We take you beyond the usual stops, into Vermont’s quieter corners, where every turn reveals something unexpected. Our guided Vermont tours mix iconic sights with places that feel like your own little discovery, because that’s what makes a trip truly memorable!
What does a Vermont Wayfinders tour look like? Come on a virtual tour with us now!
If you love scenic detours, charming surprises, and the kind of experiences that make you feel like a local…
Share your date with me, I’ll handle all the details.
A local guide, a private day, zero hassle
The Vermont Wayfinders Experience
More Vermont, less time planning
Authentic stops without the crowds
Private and Personal
Just you and your crew. No crowds, no rush. A relaxed, private Vermont adventure at your own pace.
The scenic route, always. Winding Vermont back roads, hidden nooks, and the kind of places you’d never find on your own.
Local know-how. Your guide isn’t reading from a script, they live in and love Vermont and know the best tucked-away treasures.
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
Our Vermont Guided Tours are perfect for:
The planner who wants one day when they’re not managing decisions
Repeat visitors who want different this time (a deeper, calmer Vermont)
Couples & small groups looking for a truly unique and intimate Vermont experience
Photographers who care about light, timing, and efficient routing
Independent travelers who enjoy exploring solo but want a local guide to unlock Vermont’s quieter corners
Simple Three-Step Process
Step 1. Request your date + tell us what you’re craving.
Step 2. We build a route with great timing and excellent back up plans.
Step 3. Ride shotgun (or in the back seat). We’ll take it from here.
Why Choose Vermont Wayfinders?
Private tours only
Custom route for your interests
Timing to avoid crowds
Comfortable (and fun!) Bronco
Photo stops dialed to light and weather
Local stories and context
Flexible pacing throughout the day
Backup plans if a stop is busy
We pick you up and drop you off
Clear pricing, no surprises
