Great Lakes to Greenbelt–Lake Ontario Watershed Cycling Network

195 km

The Highland Hustle delivers 3 great cycling experiences!

Do the full 194 km over two days or break it up over two weekends by riding the Highland Hustle West (114 km) and then the Highland Hustle East (95 km).  Whatever you choose you’ll get a great mix of bakeries, breweries, the hills of Northumberland, and the beautiful shores of Lake Ontario.

Highland Hustle (Full Loop)

This 2-day tour takes you through the pastoral green hills and drumlins of Durham and Northumberland and along the bright water of the north shore of Lake Ontario. You’ll visit 4 locally famous (read: “don’t-miss”) farmer’s markets and bakeries, scenic overlooks, beaches and historic locales, including a still-operating historic mill and blacksmith.

The route could never be described as flat, and that’s part of its appeal!  There are hills aplenty but obviously what goes up must come down!” 

Jo Sharland

Check Jo’s blog post “Doing the Highland Hustle”

Day 1- Whitby Waterfront to Cobourg along the Greenbelt Route contains some challenging hill riding, justifying any baked goods and ice cream you may just happen to eat along the way.

Day 2 -Cobourg to Whitby is more of a cruise along roads and off-road trails.

Make sure you are stocked up on necessities.

Tip: To shorten each day’s ride, consider a stay in Port Hope.

Start/Finish: Port Whitby Rotary Park. 48 hour overnight parking available at the Whitby GO Station,1350 Brock St S, Whitby, ON L1N 6G3. There  is a signed connection from the GO Station to the Waterfront Trail.

Terrain: Rolling hills throughout the Greenbelt. Flat day’s ride on Day 2 along the Waterfront Trail.

Surface: Combination of paths and roads. Paved and some gravel roads. Suitable for hybrid bikes and road bikes fitted with wider tires.

Level: Recommended for more experienced cyclists who are comfortable riding longer distances with periodic amenities.

Accommodations: Hotel Carlyle & Restaurant, 86 John St, Port Hope, ON L1A 2Z2  OR  Best Western Plus Cobourg Inn & Convention Centre, 930 Burnham St, Cobourg, ON K9A 2X9

Maps: Download RidewithGPS Map and Cue Sheet.  The interactive map and detailed cue sheets include a picture of signs you’ll follow.

Highland Hustle West: 

The 114km western arm of the Highland Hustle can be ridden as a single-day blast or over two-days.  You’ll roll out from the waterfront in Whitby, through the trails in Heber Down Conservation area to get your hustle on in some of the Greenbelt’s most scenic highlands, with the lovely rural vistas. By the time you hit the 60km mark for lunch in Orono, you’ll pass 3 unique bakeries, one of which operates a mill and blacksmith shop. From there you’ll enjoy a downhill ride into Newcastle, where you can enjoy the beach at Bond Head, and rejoin the Great Lakes Waterfront Trail.

If you’d like to extend your stay, you’ll find plenty of accommodations in Bowmanville. With just 40km left in the loop, you can spend the next day really taking your time enjoying the coast with stops at Bowmanville Harbour, Darlington Provincial Park, and the many waterfront parks and venues of Whitby.

Download the Easy print pdf route map.

Download the Ride with GPS maps.

Highland Hustle East:

The 80km eastern arm of the Highland hustle is day-long jaunt from the beachfront in Bond Head to Orono and Port Hope where you can enjoy a waterfront lunch along the Ganaraska River and a crazy cookie (or 3) from the Dreamer’s Cafe. With most of the hustle behind you, you’ll cruse near the Lake Ontario Coast back for a final dip in Bond Head.

Download the Easy-print pdf route map.

Download the Ride with GPS Maps

Share your trips with the #greenbeltroute and #waterfronttrail hashtags.

Read Jo Sharland’s blog on the Highland Hustle

…a great couple of days of fall cycling with some challenging hills and amazing views… featuring the best of the Greenbelt Route and the Great Lakes Waterfront Trail.

About the Greenbelt

At 2 million acres, it’s the world’s largest permanently protected greenbelt. The Greenbelt preserves diverse and scenic landscapes such as the Oak Ridges Moraine and the Niagara Escarpment, keeping our farmlands, forests and wetlands safe and secure. The Greenbelt Foundation, who spearheaded the creation of the Greenbelt Route, works to help keep farmers successful, strengthen local economies, protect natural features, and promote sustainable growth.

Learn more at

Great Lakes to Greenbelt Lake Ontario Watershed Network

Stretching over 3600 km, the Great Lakes Waterfront Trail connects 155 communities and First Nations along the Canadian shores of the Great Lakes region. The signed, 475 km Greenbelt Route spans seven regions, nearly two million acres of protected Greenbelt lands,  from Northumberland to Niagara.

With support from the Greenbelt Foundation, the Waterfront Regeneration Trust is leading work to develop a Lake Ontario Watershed network of signed routes that link the two extraordinary trails to protect, connect and celebrate Lake Ontario’s watershed. 

Ontario by Bike

Find certified bicycle-friendly accommodations, restaurants, cafes, attractions, visitor information centres, and bike store locations across the Greenbelt with Ontario By Bike, a premier trip planning resource

for cycling experiences. For Ontario By Bike Bike-friendly certified businesses visit Ontario by Bike.