Private Vermont Tours from the Okemo Valley
Scenic, private guided day trips for travelers staying near Ludlow, Okemo, Plymouth, Weston, and the surrounding area.
Staying near Okemo gives you a strong starting point for a Vermont day trip. From here, a private tour can head toward covered bridges, mountain roads, small villages, local food stops, scenic overlooks, and the kinds of places that are easy to miss when you are just following map pins.
100% private - only you and your guests (up to 4 people) will be on your tour
Fully customizable itinerary based on your preferences - this isn’t a scripted bus tour!
Transportation provided in a back-road-ready Bronco
See more of Vermont, with a local showing you the way
What is a Vermont Wayfinders tour like?
Small, private, and built around your pace instead of a schedule.
It's just you and your group in the Bronco. No big bus, no rushed checklist, no script I'm reading off a clipboard. I plan a route that flows well, then we follow the day as it comes. If a farm stand looks worth stopping for or the light over a field is too good to drive past, we stop. If you'd rather sit at an overlook for twenty minutes than rush to the next thing, that's what we do.
Where do the Okemo Valley tours go?
Around the Okemo Valley and the back roads, villages, and scenery beyond.
A typical day moves between small towns like Reading, Weston, Chester, Grafton, Plymouth, and Cavendish, with stretches beyond Route 100: the quieter roads most visitors never find their way onto.
Every tour is a little different.
Who are these tours for?
Couples, families, and small groups who'd rather enjoy Vermont than plan it. And I love to host solo travelers too!
If the idea of mapping out a route, sorting good stops from tourist traps, and timing the whole day sounds like work, that's exactly what I take off your plate. These tours suit people who value a great day over a packed itinerary, and who want the version of Vermont a local would actually show a friend.
How do I book a tour?
Pick a date, tell me a little about your group, and I'll take it from there.
Check available dates on the booking page.
Send a quick note about who's coming and anything you're hoping to see.
I'll plan the route and confirm the details before your day.
Full day tours start at $800 for a Signature Tour.
We also offer Fall Foliage tours, Experience tours, Covered Bridges tours and a half-day Sampler tour.