Begin your ride in the Town of Essex on the 22-kilometre Cypher Systems Greenway Trail, a safe, car-free route stretching across Essex County to the historic Town of Amherstburg. Once an abandoned rail line, this scenic corridor now features smooth multi-use paths and gently rolling terrain, making it ideal for cyclists of all skill levels. Along the way, the trail intersects the Chrysler Canada Greenway Trail and Trans Canada Trail in McGregor, allowing riders to extend their journey or link to other scenic routes. Native trees, open fields, and wetlands provide changing scenery and opportunities for wildlife and bird spotting.

Arriving in Amherstburg, take time to explore one of Southwestern Ontario’s most charming and historic communities. Stroll the quaint streets lined with 200-year-old buildings, enjoy the award-winning gardens at King’s Navy Yard Park, and discover the town’s rich history at the Amherstburg Freedom Museum, which explores the Underground Railroad, or at Fort Malden National Historic Site, highlighting Amherstburg’s War of 1812 heritage. History enthusiasts can also visit the Park House Museum, a well-preserved historic home offering a glimpse into local life in the 19th century.

Cyclists can refuel at Ure’s Country Kitchen, a popular stop serving hearty meals, fresh baked goods, and a taste of local flavour. Families and friends can also enjoy a round of Mini Golf on site, making it a fun stop for all ages before continuing along the trail.

For a nature-focused stop, pack a picnic and ride to Holiday Beach Conservation Area, a sandy Lake Erie shoreline featuring a boardwalk, observation tower, nature trails, and world-class birding. This is also the gateway to EPIC (Essex Pelee Island Coast) Wine Country, with scenic vineyards and tasting rooms just a short pedal away. Continue along to Colchester Beach, a family-friendly lakeshore with playgrounds, splash pads, washrooms, and a concession stand — perfect for a well-earned rest and lakeside views.

The Cypher Systems Greenway Trail offers cyclists a unique combination of car-free riding, natural beauty, historic exploration, and connections to wine country, making it one of Windsor Essex’s most rewarding routes. Whether you’re looking for a half-day ride or a full-day adventure, this trail blends outdoor activity with scenic, cultural, and culinary experiences.

Beginning in the town of Essex, the 22-kilometre Cypher Systems Greenway Trail allows you to cross the County to the historic town of Amherstburg, avoiding nearly all the traffic of the roadways. Formerly an abandoned rail line, this stretch of land is now a beautiful trail, intersecting the Chrysler Canada Greenway and Canada’s Great Trail in McGregor.

Once in the Town of Amherstburg, take your time and explore one of the prettiest and oldest communities in Southwestern Ontario. Stroll the award-winning public gardens, including King’s Navy Yard Park. Get a glimpse into our region’s history and discover the quaint streets lined with 200 year old buildings. Visit the sights of the Underground Railroad at the Amherstburg Freedom Museum, or discover our links to the War of 1812 at the National Historic Site of Fort Malden.

Pack a picnic and head to Holiday Beach. This sandy stretch along the Lake Erie shoreline boasts a boardwalk, nature trails, a three-story observation tower, and incredible birding. This is also the start of EPIC  (Essex Pelee Island Coast) Wine Country. Be sure to stop for a tasting along your way to Colchester Beach, one of Essex County’s most attractive beaches. As part of Colchester Harbour, the beach is adjacent to a playground, splash pad, washroom facilities and a concession stand.