Where will you pick me up? What time do we get started?

Please take a look at the map — if you’re in the highlighted area, you’re good! If you’re close to the highlighted area, send us a note so we can discuss. Generally we can make any area work, but the farther you are from this area, the less time we’ll have for true touring to accommodate travel to pick you up and drop you off.

List of Towns/Villages: Stockbridge, Barnard, Pomfret, Hartford, Hartland, Quechee, Woodstock, Bridgewater, Killington, Plymouth, Reading, West Windsor, Windsor, Weathersfield, Cavendish, Ludlow, Mount Holly, Weston, Andover, Chester, Springfield, Londonderry, Grafton, Windham, Rockingham

Usually we get started between 9-10am and wrap up around 4pm. We’ll confirm a pick up time before your tour.

Where will we go for our tour?

This will be fully customized to you! We have a form for you to fill out once you book your tour that will give you the chance to tell us what you really enjoy doing and seeing… and what you’d rather skip. Sometimes we’ll even hop on a quick call to work out the details to make sure the itinerary is just right!

Check out a sample itinerary here to get a feel for how a tour might go.

What if I don’t know what I want to do? What if I prefer to be surprised?

No problem! We have plenty of great ideas and suggestions and can create a full day’s itinerary for you.

Can I (propose/surprise/celebrate) on the tour?

Oooh! We love fun surprises and can offer some great add-ons to your tour if you’d like! Contact us to coordinate site selection, celebratory food/drinks, photography and more!

What should I wear? What should I bring with me?

If the weather is nice (70ºF or higher and no rain), we’ll be traveling with the top down on the Bronco (unless you request otherwise). Wear sunscreen, sunglasses and a hat and dress in layers. Bring a water bottle, too. We’ll make stops along the way for food and restroom breaks.

What if it rains/is cold?

Our tours operate May through October in all weather during these months. If it’s raining or chilly, we will keep the top on the Bronco to stay dry and warm. We can discuss changing up some stops as we get started if weather is going to dampen the original plan… don’t worry, we have plenty of ideas of alternative things to do to make the most of your day!

Can I bring my dog?

We love dogs - and all animals - at Vermont Wayfinders. But we don’t allow dogs (or any pets) on our Signature Vermont Tours. If you want to explore Vermont with your pup by your side, check out our Vermont Self-Guided Tours. Of course, if you have a service animal, please reach out to us prior to your tour so we can ensure their comfort and safety, as well as yours.

Will we be going off-road?

While off-roading is a lot of fun, we won’t be going THAT far off the beaten path on our tour! We will, however, stick to dirt roads as much as possible, including some Class 4 roads. Class 4 roads are only maintained to the extent the town or state deems necessary so they tend to be a bit narrower and bumpier than other back roads.

If you are looking for an ‘extreme’ off-road adventure, this isn’t that. If you’re concerned about your physical comfort when driving (and probably bouncing) on back roads, please let us know. We’re happy to make the tour as comfortable as possible for our guests.

Will my kids enjoy the tour?

Our Signature Vermont Tours are designed for adults looking to enjoy a relaxed, immersive experience. Kids under 18 likely aren’t going to have much fun. For safety and comfort, the tours are not suitable for children who require car seats. If you want to explore Vermont with your children, we highly recommend checking out our Vermont Self-Guided Tours.