Vermont Wayfinders
Custom Trip Planning
A custom plan for your Vermont trip built by a local who knows the roads, the best stops, and the timing that makes a day feel right.
You’re planning your Vermont trip. You just want to get it right.
You've been looking forward to this trip for weeks. Maybe months. But somewhere between the tenth "Top 10 Things to Do in Vermont" list and the conflicting restaurant reviews, the excitement starts to feel like homework.
Where do you actually go? Which route makes sense? Are those places worth it, or are they just the ones that show up first on Google? Is that covered bridge going to be packed when you get there? What if it rains?
You don't need another list of things other tourists do. You need someone who lives here to tell you how to spend the day.
That's what this is.
A Vermont Wayfinders Custom Trip Plan is a personally built itinerary for your trip to Vermont. Not generated by an algorithm. Not pulled from a template. Built by me. A local who drives these back roads year-round and knows which spots are worth your time, which ones to skip, and how to string together a day that actually flows.
You tell me when you're coming, who you're with, and what kind of trip you're after. I build the plan for a day (or more!) of your visit. You show up and enjoy it.
What’s in your plan
A few things worth knowing
I’ll build your plan and hand it to you ready to go, so you can spend your time traveling, not researching.
You’ll handle any bookings, but I’ll make it simple with direct links, phone numbers, and a few helpful notes. Then you’ll have an itinerary you can follow confidently, including backup options in case the day shifts.
I plan trips primarily in central Vermont, focused on Woodstock, Killington, and Ludlow and surrounding areas. I know this area really well. I grew up riding horses on these back roads and I take privately guided tours around these areas in my Bronco all Summer and Fall.
Plans cover up to three days. Staying longer? We can add a guided tour day, where I get behind the wheel and you just enjoy Vermont unfolding out the window.
"I could probably figure this out myself."
Yup. You absolutely could. And for some people, that's part of the fun.
But if you've ever spent the first morning of a vacation still Googling where to eat lunch, or driven 40 minutes to a "must-see" spot only to find it underwhelming and overrun… that's what this solves.
The free itineraries you'll find online or that AI creates send everyone to the same five places. They don't know which back road has the best views, or that the restaurant everyone recommends is actually better for lunch than dinner, or that the covered bridge on Route 4 is gorgeous but there's one 20 minutes south you'll have completely to yourself.
That's the difference between a list and a plan built by someone who lives here.
Every season here is worth planning around
Fall I'll route you through peak foliage on roads most visitors never find, time your stops to dodge the crowds, and point you toward photo-worthy scenes that other people won’t know about.
Winter Whether you ski or not, I'll build you a day that balances cozy Vermont towns, great food, and the kind of quiet winter scenery that reminds you why you came.
Spring Mud season is real, but so is maple season. I'll plan around the messy parts and get you to sugarhouses, early green-up drives, and the first farmers markets of the year.
Summer Long daylight, swimming holes, farm stands, and outdoor dining. I'll build a day that takes advantage of everything summer here has to offer without the stress of figuring it out yourself.
Your trip. Your pace. My roads.
Tell me what kind of Vermont day you're after, and I'll build the plan.
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At least two weeks before your trip for standard delivery, or 10 days for rush. During peak foliage season (late September through mid-October), I'd recommend reaching out even earlier as availability fills up.
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Central Vermont. The Woodstock, Killington, and Ludlow corridor and the scenic back roads around them. If your trip is based elsewhere in the state, this isn't the right fit yet, but I'm expanding coverage over time.
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I don't, but I make it easy. Your plan includes direct links, phone numbers, and tips on the best times to go. Some of the best spots here don't take reservations anyway.
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Let me know as soon as possible. If I haven't started building your plan, I can adjust the dates. Once work has begun, payment is non-refundable, but I'll do my best to accommodate.
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Plans generally cover up to 3 days. If you're looking for something more hands-on, my private guided tours might be a great fit for one or two of those days.
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Your plan includes backup options for exactly this. Indoor stops, rainy-day scenic drives, cozy spots that are honestly better when the weather's moody. Vermont's like that.
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Not even close. Free itineraries send everyone to the same places. Your plan is built around your interests, your pace, and your travel dates, using routes and stops I know from driving these roads year-round. I'll tell you what to order, where to park, and which covered bridge you'll have to yourself.
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You'll receive your plan as [format], accessible on your phone, plus a printable overview.
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If I haven't started building your plan yet, I can issue a full refund. Once work has begun, payment is non-refundable. If your dates shift but you're still coming to Vermont, I can usually adjust the plan to fit your new schedule.
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I'll review your trip details and get back to you within 1 to 2 business days. If it's a good fit, I'll confirm your turnaround time and send a payment link. If I'm at capacity, I'll let you know where you stand on the waitlist and when to expect an opening.
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Your plan is designed to stand on its own, with backups and alternatives built in so you're covered no matter what. If something in the plan isn't clear or you need a quick clarification before your trip, just reply to your email and I'll sort it out.
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It works for any group size. Whether it's just you, a couple, a family with kids, or a group of friends, I'll build the plan around your group's mix of interests and energy levels. The intake questionnaire gives me what I need to get it right.
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Absolutely. Fill out the questionnaire with as much as you know about the person's trip and preferences, and note that it's a gift. I'll work with what you know but always strongly prefer to have the actual traveler complete a preferences form themselves.
Still have questions?
Send an email to tours@vermontwayfinders.com and I’ll get back to you quickly. ~Aimee