Wayward
Prepared for Hello Burlington
The next decade of Burlington's digital experience.
A working brief on how Wayward would help reimagine helloburlingtonvt.com as an intelligent, flexible, visitor-first platform.
01 / The shift

A destination website used to be a brochure. Today it's the operating system for visitor experience.

The platform era (2010 to 2022)

Static listings. Rigid CMS. A support ticket for every change. One primary channel, the website.

Visitors accepted it because there was little else available. Teams accepted it because most vendors looked remarkably similar.

The intelligence era (2024 onward)

Dynamic experiences. A flexible stack. Live updates across every channel. Intelligence quietly working in the background.

Visitors expect their trip to feel personal, and teams expect their tools to carry more of the load. The destinations investing in this shift now are setting themselves up well for what comes next.

Burlington has a chance to shape what that next era looks like, alongside a partner that builds for the way your team actually works.
02 / Why Wayward

Meet our team, built for a team like yours.

We are not the largest player in the industry, and that is a deliberate choice. Wayward is purpose-built for lean DMOs doing meaningful work with the budget and team you actually have.
Jake Jake
Keegan Keegan
Max Max
Kate Kate
Pete Pete
Allison Allison

Small and attentive

A focused team that moves quickly. Good ideas find their way into the product without waiting on a release calendar.

Human support, no tickets

Reach out by text, call, or Slack whenever you need us. You are working directly with the people who build and run the platform.

Budget friendly

Pay for what you use. Pricing is scaled to the size of your team, not to a feature list designed for an enterprise of a hundred.

Purpose-built for DMOs

Every feature exists because a destination team asked for it. Built cleanly from the ground up, with nothing inherited from a larger platform.

Real-time everything

Publish a change in seconds. Fix a pin, add an event, swap a hero. Nothing waits in a queue.

A roadmap shaped by partners

You are a close partner, not an account number. What you need next quarter shapes what we ship next quarter.

03 / The map is the interface

The map is the interface, present from the first moment a visitor arrives.

Accurate, editable, and built for how visitors actually plan a trip. A few ways we would think about using it in Burlington, with a look at what the platform supports underneath.
Wayward interactive map example
Example map from Downeast Acadia Regional Tourism
Sample experiences
  • A perfect weekend in Burlington
  • Lake Champlain adventure trail
  • Burlington brewery challenge
  • Seasonal itineraries (summer, fall, winter)
  • Neighborhoods beyond downtown

Illustrative examples only. The shape of the experience library is something we would build collaboratively with your team.

Map capabilities
  • Sponsored POI placements
  • Comprehensive, verified destination data
  • Backend access for quick and easy edits
  • Custom filters and layers
  • Build-your-own-itinerary tools for visitors
  • Third-party integrations (AllTrails, Untappd, and more)
04 / The integrated platform

One partner for the whole solution. Platform, advertising, content, and print — fully integrated.

Most DMOs manage four or five vendors to do what Wayward handles in one place. We cover everything — so your team spends less time coordinating and more time on Burlington.
01

Platform & Presence

Website, maps, itineraries, CRM, listings, and events — all in one console. This is what replaces Simpleview.

  • Website & CMS
  • Interactive maps
  • Itineraries & experiences
  • CRM & contacts
  • Listings & events
02

Advertising & Media

Paid media managed in-house, tied directly to your destination content, with real visitation attribution.

  • Wayward DSP
  • Meta, Reddit & Google
  • Creative production
  • Visitation attribution
03

Content, Print & Brand

Annual visitor guide, print ads, partner co-op, and in-destination touchpoints — all treated as first-class deliverables.

  • Annual visitor guide
  • Print advertising
  • Partner co-op
  • In-destination touchpoints
Services overview
Creative Agency
Brand, editorial, design, and print production — from annual guides to in-market campaigns.
Ad Management
Paid media across Wayward DSP, Meta, Google, and Reddit — with real visitation attribution.
Social
Content strategy, creator campaigns, and social execution tied directly to your destination brand.
PR
Media outreach, press content, and earned coverage — coordinated with your broader marketing calendar.
Burlington, VT
Your brand stays yours. Your stack gets simpler. Everything that matters stays in place.
05 / The Intelligence Layer

Where Wayward stands apart.

Every piece of content, every listing, and every experience on your site flows into and through the Wayward Intelligence Layer. That connected foundation is what powers every output — from visitor-facing answers to on-brand copy to market insights. No separate AI bolt-on, no hallucinations from missing context.
Core asset
Maps & Experiences
Dynamic trip planning, curated discovery.
Core asset
Website & Content
Destination pages, guides, traveler-facing content.
Core asset
Digital Footprint
All owned and syndicated channels and listings.
Output
Visitor Chat & Email
Real-time assistant answering visitor questions.
Output
Press & Brand Content
On-brand press, editorial, and campaign copy.
Output
Market Intelligence
Trend surfacing and strategy recommendations.
Coming
More outputs
New capabilities as the platform grows.
Foundation

Wayward Intelligence Layer

The connected core that links every piece of destination content, powering every visitor-facing output across the platform.

Destination Knowledge
Traveler Personalization
Content Intelligence
Engagement Signals
Market Awareness
Brand Voice
This is not a chatbot bolted on top. It is intelligence built into the foundation — so it makes your team more effective from the first week.
06 / Bandwidth

More time for the work only your team can do.

Wayward quietly handles the repetitive platform work in the background. Your team spends more of the week on Burlington, and less of it inside the tools.
What Wayward quietly handles
Less of this on your plate
  • Filing tickets to fix a map pin or a small content update
  • Re-entering the same event or listing in several tools
  • Waiting on a vendor release cycle
  • Sorting visitor emails and inbound chat by hand
  • Reconciling reports across siloed systems
  • Bridging integrations that were never designed to talk
Your week, reframed
More of this, with the hours back.
  • Strategy, narrative, and the Burlington story
  • Partner relationships and stakeholder work
  • Local business visibility and co-op programs
  • Creative projects that move the destination forward
  • The parts of the job only a human on your team can do
Built for the DMO of one to five, not the agency of fifty.
07 / Our work
Case 01 Regional DMO

Visit Unforgettable Forgottonia.

Western Illinois • Client since 2023

A little-known region of western Illinois needed a full-service partner to put it on the map, both literally and figuratively. They came to Wayward looking for help building digital discovery and driving awareness of the area's hidden character.

A white-labelled tourism map with 260+ points of interest, 17 custom itineraries and experiences, content creator campaigns, social media management, print and digital ad management, and a full-service PR push for a flagship event launch. SEO, AEO, and analytics infrastructure rounds out the stack.

Forgottonia went from obscure to discoverable. A rich library of itineraries and creator content now gives visitors a genuine reason to explore the region, and the team has a platform built to grow with them.

"Wayward's tourism management software helps us easily showcase Visit Unforgettable Forgottonia's hidden gems. They're an extension of our team committed to making a trip to Forgottonia a more unforgettable experience."
Jock Hedblade, Executive Director, Visit Unforgettable Forgottonia
Map POIs
260+
Itineraries built
17
Forgottonia interactive map
Visit Unforgettable Forgottonia View live map
08 / Our work
Case 02 Regional tourism

The Downeast Acadia Map.

Coastal Maine • Client since 2023

Downeast Acadia's coastal corridor spans a vast and complex geography that visitors find hard to navigate. The region needed a map-first experience that could turn that complexity into genuine discovery, and a content layer to support it.

A custom white-labelled map with 228+ points of interest and 700+ trails, 11 documented itineraries including scenic byways developed in support of a State grant, four content creator campaigns, Reddit digital ad campaigns, and a full SEO and AEO setup.

The region now has one of the most comprehensive coastal tourism maps in New England, backed by itinerary content and creator campaigns that tell a richer destination story across every channel.

Downeast Acadia interactive map
Downeast Acadia itineraries
Downeast Acadia Regional Tourism View live map
Map POIs
228+
Trails mapped
700+
Itineraries built
11
Creator campaigns
4
09 / Our work
Case 03 Regional tourism

Sugar River Valley & Visit Verona.

Wisconsin • Client since 2023

A small Wisconsin tourism organization needed a full creative partner who could handle everything from print to social to live events, without the overhead of a large agency. They needed their brand voice, their visitor guide, and their community events all to feel cohesive.

A comprehensive annual print visitor guide with seasonal updates, social media management, four content creator campaigns including images and written stories, a videography campaign, and full event design and coordination for a flagship "Poker Run." Branding design covering both graphic identity and brand voice rounds out the partnership.

A cohesive creative partnership that built a lasting brand voice, produced a polished print guide, and brought visitors to Verona through engaging, authentic content. A small team now punches well above its weight.

"Working with the Wayward team has been awesome. They've helped us create fun, engaging content that really shows off the best of Verona. It's been a great partnership and we love what we've built together."
Allison Plumer, Tourism Coordinator, Visit Verona WI
Creator campaigns
4
Services
Print, social, events
Sugar River Valley Poker Run
Verona Visitor Guide p3 Verona Visitor Guide p2 Verona Visitor Guide cover
Sugar River Valley View on Wayward
10 / Let's keep going

Let's keep the conversation going.

We would love to come back for a Burlington-focused working session. Bring whoever on your team should be in the room, and we will bring the Wayward team. Offered with no cost and no commitment attached.
A 45-minute working session
Focused on what Burlington's next digital experience could look like, grounded in the work Wayward is already delivering for destinations around the country.
01

A live platform walkthrough

A look at Wayward in action with current destinations, including real maps, real experiences, and real content layers.

02

Concepts for Burlington

A few concrete directions for what we would build, shaped by what we heard in our conversation with Tom.

03

Open questions, thoughtful answers

Anything you are weighing for the next site. There is a good chance we have worked through something similar.