Be at one with nature. Hike, cycle or ride on horseback on our gorgeous, scenic trails.

Downtown Bolton to Bender and Graves Tract to Duffins Creek

274 KM/170 MILES

DAY 1: HEADWATERS

Headwaters has hundreds of kilometres of scenic trails for cyclists, hikers and horseback riders of every level. Surrounded by rolling hills and panoramic rural landscapes, the trails of Headwaters are even more breathtaking than the drive into the region.

The Hampton Inn & Suites will be the ideal home base for your stay. Located in Bolton, this hotel features 95 guest rooms and suites, an indoor pool and fitness centre, and easy access to the region’s most impressive trails.

A 15-minute drive north will take you to Albion Hills Conservation Area. Here, you will experience some of the most spectacular mountain biking in southern Ontario, with more than 50 kilometres of trails waiting to be explored.

Group of Hikers in Forest at Albion Hills

After an active day on the trails, gear down and refuel at Cheeks Homemade Burgers & Good Eats, a local favourite with great food and friendly service. Order a homemade burger and fries with a pint of local craft beer. After dinner, take an evening stroll through Bolton’s quaint downtown before retreating to your hotel to recharge for another day in Headwaters.

Day 2: HEADWATERS

Rise with the sun on day two and fuel up with a complimentary breakfast at the hotel. Or head west for fresh-baked breakfast goods and an Americano from Gabe’s Country Bake Shoppe. Buy some snacks and a hearty sandwich from the deli counter and you’re set to hit the Caledon Trailway.

This 35-kilometre, multi-use trail crosses some of the most ecologically significant landscapes in Ontario such as the Humber and Credit Rivers, the Oak Ridges Moraine and the Niagara Escarpment. This scenic trail will appeal to hikers, horseback riders and cyclists, and is an essential part of every visit to Headwaters.

Before returning to Bolton, check out Albion Orchards Apple Farm & Country Market. Open daily all summer, this country store has a wide array of fresh Ontario produce, cider, cheese, handmade preserves and gift baskets to take home and share with friends.

Day 3: York

Amble down Newmarket’s Historic Main Street and enjoy a hearty breakfast on the patio at The Maids’ Cottage. Be sure to get one of their famous butter tarts for the road. Spend the day taking in Newmarket’s one-of-a-kind shops, restaurants and pubs, or go on a geocaching adventure in one of York Region’s forests. The Bendor and Graves Tract is an excellent place to start your geocaching hunt. Part of The Oak Ridges Moraine, this 201-acre trail has a variety of pine, white spruce, European larch, eastern cedar and hemlock trees to admire on your hike.

Treat yourself to dinner at Sheraton Parkway Toronto North’s Crave Restaurant. This upscale-casual restaurant combines modern decor and an international menu sure to satisfy any craving. Check-in to your elegant room and take advantage of luxury amenities such as two indoor pools, an outdoor saltwater pool, squash, badminton and basketball courts, whirlpools, steam rooms and a fitness centre and spa.

Day 4: York

Front Entrance and Fountain at  Gallucci Winery

Take a short drive to Gallucci Winery, a family-run vine-to-bottle winery. Sit on the picturesque bistro patio overlooking the vineyard and order a deli and cheese board, fresh panini, pizza or salad as you relax in the summer sun. Enjoy another tasting at nearby Applewood Farm and Winery, and take home a bottle or two of Applewood’s award-winning fruit wine, ale or cider.

Head back down to southern York Region and wander around Historic Unionville. Stroll along Main Street and discover the many charming shops in the heritage village. Cap off the evening like a local with an ice cream or handmade treat from The Old Firehall Confectionery.

Macarons at Old Fire Hall Confectionary in York Durham Headwaters

Day 5: Durham

Load up the bikes and head to Darlington Provincial Park, where you can connect to the 1,600-kilometre-long Great Lakes Waterfront Trail. Set up camp and explore the trails or borrow a fishing rod from the camp store and try landing the big catch. Go for a swim at the beach, then pedal west along the Waterfront Trail through McLaughlin Bay Wildlife Reserve, the largest urban wetland in the Greater Toronto Area. Oshawa’s beautiful Lakeview Park is just around the corner. Take a look inside the Community Museum, or stay outside and gorge on lakeside summer treats from the food trucks.

Mother and Father and their Three Kids standing Next to Tent

Cycle north along the 7-kilometre Joseph Kolodzie Oshawa Creek Bike Path. As you meander along the picturesque Oshawa Creek Valley, you will connect to vibrant downtown Oshawa, home of The Canadian Automotive Museum, Parkwood Estate, Botanical Gardens and the Robert McLaughlin Gallery.

Exterior View of The Robert McLaughlin Gallery

Take advantage of Oshawa’s burgeoning foodie scene, with everything from barbeque and poutine to vegetarian and gluten-free cuisine. And whatever you do, please save room for dessert at the famous Hollywood Cone ice create store!

Day 6: Durham

Start your morning with a campfire breakfast beneath the trees. Then head west to Ajax, Ontario’s first designated Bicycle Friendly Community. Drive toward Lake Ontario and check in with your hosts at Before The Mast B & B. Bike west along the waterfront and you’ll encounter the winding bridge stretching over Duffins Creek and lakefront bluffs. Refresh with a swim at Beachfront Park or enjoy the shops of the Nautical Village. Take a break at PORT Restaurant, a local favourite that features the best of Ontario on its menu.

Exterior View of PORT Dining Bar and Restaurant

After a day in the saddle, it’s time to pony up at Ajax Downs racetrack. Or channel your inner cattle rancher at Picov’s Tack Shop, where you’ll find cowboy boots of every size, shape and colour.

For more information about cycling in Ontario, visit:

Ontario by Bike Logo Green Belt Logo

Do you like the Boots & Bikes theme, but might want to do something a little different?

Boots & Bikes Alternate Route

Ajax Downs

Ajax Downs

50 Alexander's Crossing
Ajax, ON

Albion Hills Conservation Area and Campground

Albion Hills Conservation Area and Campground

16500 Hwy. 50
Palgrave, ON

Albion Orchards

Albion Orchards

14800 Innis Lake Road
Caledon East, ON

Applewood Farm And Winery

Applewood Farm And Winery

12416 McCowan Road
Stouffville, ON

Before The Mast Bed & Breakfast

Before The Mast Bed & Breakfast

1144 Shoalpoint Rd,
Ajax, ON

Canadian Automotive Museum

Canadian Automotive Museum

99 Simcoe Street South
Oshawa, ON

Cheeks Homemade Burgers and Good Eats

Cheeks Homemade Burgers and Good Eats

18 King St E
Bolton, ON

Darlington Provincial Park

Darlington Provincial Park

1600 Darlington Park Road
Bowmanville, ON

Gabe's Country Bake Shoppe

Gabe's Country Bake Shoppe

15977 Airport Road
Caledon, ON

Gallucci Winery Inc.

Gallucci Winery Inc.

13204 Ninth Line
Stouffville, ON

Hampton Inn & Suites by Hilton Bolton

Hampton Inn & Suites by Hilton Bolton

12700 Highway 50
Bolton, ON

Hollywood Cone

Hollywood Cone

1 Simcoe Street
Oshawa , ON

Joseph Kolodzie Oshawa Creek Bike Path

Joseph Kolodzie Oshawa Creek Bike Path

Lakeview Park
Oshawa, ON

McLaughlin Bay Wildlife Reserve

McLaughlin Bay Wildlife Reserve

Colonel Sam Drive
Oshawa, ON

Old Firehall Confectionery

Old Firehall Confectionery

170 Main Street
Unionville, ON

Parkwood National Historic Site

Parkwood National Historic Site

270 Simcoe Street N
Oshawa, ON

PORT bar-dining room-patio

PORT bar-dining room-patio

1289 Wharf Street
Pickering, ON

Sheraton Parkway Toronto North Hotel Suites & Conference Centre

Sheraton Parkway Toronto North Hotel Suites & Conference Centre

600 Hwy 7 E
Richmond Hill, ON

The Maids' Cottage

The Maids' Cottage

223 Main Street S.
Newmarket, ON

The Robert McLaughlin Gallery

The Robert McLaughlin Gallery

72 Queen Street, Civic Centre
Oshawa, ON

Town of Caledon

Town of Caledon

6311 Old Church Road
Caledon, ON