Less Planning, More Vermont: Start With One Great Day

Planning a Vermont trip sounds simple. Until it isn’t.

There are dozens of towns worth visiting, scenic roads in every direction, and no shortage of opinions about what you “have to see.” The result for most travelers is either overplanning or giving up and hoping for the best.

Here’s the truth: you don’t need a perfect itinerary. You just need a solid starting point.

That’s why I created the Vermont Anchor Day concept.

What is a Vermont Anchor Day?

Your Anchor Day is one great day that sets the tone for your trip. It’s built around how you actually like to travel. Not how a guidebook thinks you should.

Some people want slow scenic drives and room to wander. Others want walkable towns, food stops, and local culture. Some want to hike, explore, and cover ground. None of those approaches are wrong, but trying to mix all of them into one day usually leads to frustration.

An Anchor Day gives you clarity. One day that fits your pace, interests, and energy. From there, everything else gets easier.

How the quiz helps

The Vermont Anchor Day quiz takes about a minute. It asks a few practical questions about how you like to spend your time and what matters most to you when you travel.

At the end, you’ll get:

• Your Anchor Day style

• Guidance on pacing and types of stops that fit you

• A downloadable worksheet to help you plan one great day without overthinking

It’s not a rigid itinerary. It’s a framework that helps you make better decisions and avoid trying to do too much.

Why start with one day?

Because one well-planned day is better than three chaotic ones.

Once you have an Anchor Day, you can build around it. Add another town. Extend a drive. Or decide you’re perfectly happy keeping things simple. Either way, you’re no longer guessing.

If Vermont planning has started to feel overwhelming, this is an easy place to reset.

Take the Vermont Anchor Day quiz and find your starting point.