Legacy Migration: Heritage Trails Foundation Goes JAMstack

Project Background

Heritage Trails Foundation is a non-profit organization dedicated to preserving and documenting historical sites. Their WordPress site, launched in 2009, had grown to over 50,000 pages of invaluable historical content.

The Breaking Point

By 2024, the site was struggling:

• Security vulnerabilities - Outdated plugins created constant attack vectors
• Performance issues - 12+ second load times on content-heavy pages
• Hosting costs - $800/month for managed WordPress hosting
• Editorial friction - Writers avoided the slow, complex admin interface
• Maintenance burden - IT spent 20+ hours monthly on updates and fixes

Migration Requirements

The foundation had strict requirements:

1. Zero content loss - Every article, image, and metadata must be preserved
2. URL preservation - Existing URLs must continue to work (SEO critical)
3. Editorial experience - Non-technical staff must be able to edit easily
4. Budget constraints - Non-profit budget of under $100/month for hosting

Technical Strategy

Content Extraction

We built a custom migration pipeline to extract WordPress content:

// Simplified migration flow
WordPress DB → JSON Export → Markdown Transform → Eleventy Build

Phase 1: Database Export

• Custom SQL queries to extract posts, pages, and metadata
• Media library mapping with original URLs
• Taxonomy and category preservation

Phase 2: Content Transformation

• HTML to Markdown conversion with custom handlers
• Shortcode parsing and replacement
• Image path rewriting for new structure

Phase 3: Validation

• Automated comparison of rendered output
• Link checking for internal references
• SEO metadata verification

Architecture Design

┌─────────────────────────────────────────────────────────┐
│                    CloudCannon CMS                      │
│              (Visual editing for staff)                 │
└────────────────────────┬────────────────────────────────┘
                         │
                         ▼
┌─────────────────────────────────────────────────────────┐
│                   Git Repository                        │
│              (Markdown + front matter)                  │
└────────────────────────┬────────────────────────────────┘
                         │
                         ▼
┌─────────────────────────────────────────────────────────┐
│                      Eleventy                           │
│               (Static site generation)                  │
└────────────────────────┬────────────────────────────────┘
                         │
                         ▼
┌─────────────────────────────────────────────────────────┐
│                       Netlify                           │
│              (Hosting + CDN + Functions)                │
└─────────────────────────────────────────────────────────┘

Search Implementation

With 50,000+ pages, search was critical. We implemented Algolia:

• Indexed during build process
• Faceted search by era, location, and content type
• Instant results with highlighting
• Zero-config frontend integration

URL Preservation

We created a comprehensive redirect strategy:

• 1:1 mapping for all existing URLs
• Pattern-based redirects for category pages
• Custom 404 page with search integration
• Redirect validation in CI pipeline

Content Structure

We organized content into logical collections:

src/
├── articles/           # Historical articles (45,000+)
├── sites/              # Heritage site profiles (3,000+)
├── people/             # Historical figures (2,000+)
├── timelines/          # Interactive timelines (500+)
├── pages/              # Static pages (100+)
└── _data/              # Shared data and metadata

Front Matter Schema

Each article includes structured metadata:

---
title: "The Roman Aqueducts of Segovia"
date: 2015-03-12
era: "Ancient Rome"
location:
  country: "Spain"
  region: "Castile and León"
  coordinates: [40.9429, -4.1088]
categories:
  - Architecture
  - Engineering
  - Water Systems
author: heritage-team
image: /assets/images/segovia-aqueduct.jpg
---

Editorial Experience

We configured CloudCannon for non-technical editors:

Visual Editor

• WYSIWYG editing for content
• Drag-and-drop image uploads
• Real-time preview

Structured Data

• Form-based front matter editing
• Dropdown selections for categories
• Date pickers for historical dates

Workflow

• Draft/Published states
• Preview deployments for review
• Git-based version history

Results

Performance Comparison

Metric	WordPress	JAMstack	Improvement
Time to First Byte	2.4s	0.05s	48x faster
Full Page Load	12.3s	1.2s	10x faster
Lighthouse Score	34	100	Perfect score

Cost Comparison

Item	WordPress (Monthly)	JAMstack (Monthly)
Hosting	$800	$0 (Netlify free tier)
CDN	$150	Included
Security	$100	Not needed
Maintenance	20 hours	2 hours
Total	$1,050+	~$50

Security Improvement

• Zero vulnerabilities - No dynamic attack surface
• No database - Nothing to breach
• Git history - Complete audit trail
• Atomic deploys - Instant rollback capability

Lessons Learned

1. Automate validation - With 50K pages, manual checking was impossible. Our automated comparison tools caught 200+ edge cases.

2. Preserve URLs religiously - We created a redirect for every single old URL. This preserved SEO value and prevented broken links.

3. CloudCannon bridges the gap - Non-technical editors actually prefer the CloudCannon interface to WordPress. Training took 30 minutes.

4. Static doesn't mean limited - With Algolia search and Netlify Functions, we replicated all WordPress functionality with better performance.