We ranked these by a combination of scenery, trail quality, and the feeling you get at the end. Every entry includes what it actually takes: time, fitness, cost, and the stuff other lists leave out. The list spans all five regions and all difficulty levels, from a 78 km backcountry traverse to a 30-minute boardwalk.
Challenging 6 km | 4-6 hours | Scrambling on all fours | $18 vehicle permit | No cell coverage | North Shore
Killarney's most popular and most difficult trail. The gentle start is deceptive: it quickly demands scrambling on all four limbs. The view from the top — clear lakes in every direction, white La Cloche ridges — is genuinely extraordinary. Follow red markers (red on trees in forest, red posts on rock). If you see only blue, turn back immediately — that is the 78 km La Cloche Silhouette. Bring 2L water minimum per person. Parking fills by 9 am summer weekends. Not suitable for children under 7 or inexperienced hikers. Do not attempt in wet conditions — the polished quartzite becomes treacherous.
Moderate 5.2 km | 2-3 hours | Cave scrambling + cliff lookouts | Free | South Georgian Bay
The trail that gives you everything: escarpment cliff-edge lookouts, cave scrambling unlike anything else on the Bruce Trail, and old-growth cedar forest. The Keyhole Side Trail is the highlight — you physically remove your backpack, push it through the rock opening, and squeeze through after it. Bring a headlamp for the cave sections. Free parking at the trailhead on the Nottawasaga Sideroad (small lot, fills early on fall weekends). Fall colour from the cliff edge is spectacular late September to early October.
Moderate 3.5 km | 1.5-2 hours | 90 m gain | Ontario Parks permit | Parry Sound
The quintessential Georgian Bay day hike. Wind-sculpted white pines on pink granite, turquoise water stretching to distant islands. The landscape the Group of Seven painted. Blue blazes mark the route across open rock. Pick up the numbered trail guide from the box at the parking lot. Arrive before 10 am in summer for parking. This is rattlesnake habitat — stay on trail.
Moderate 2 km | 1-2 hours | 100 m gain | $18 vehicle permit | North Shore
Maximum scenery per metre of trail. Only 2 km but involves genuine scrambling over polished pink granite with 360-degree views across Killarney's interior. On clear days: Manitoulin Island on the horizon. The rock is glacier-polished and becomes extremely dangerous when wet. Do not attempt in rain. Hiking boots with aggressive grip essential. The best short lookout in the region for view-to-effort ratio.
Moderate 8 km | 3-4 hours | Rolling terrain | Free | South Georgian Bay
South Georgian Bay's best-kept secret. The hemlock creek section through the ravine is the jewel: a spring-fed creek under dense hemlock canopy that feels genuinely wild. In autumn, the surrounding hardwood forest produces colour rivalling Blue Mountain with essentially zero visitors. Some sections poorly marked — bring an offline map. Access from County Road 2 between Ravenna and Feversham. Mud in spring.
Moderate 8 km loop | 3-4 hours | 150 m elevation | Free, no facilities | South Georgian Bay
Ridge walk above a glacial valley with a steep descent to old-growth hemlock on the valley floor. The contrast between the exposed ridge and the cool, quiet valley bottom is remarkable. Spring wildflowers in the valley; fall colour cascading down the walls. Non-operating park: no washrooms, no staff, no camping. Access from Pretty River Road. Underrated.
Moderate 2.5 km | 1-2 hours | 90 m gain | Free | Parry Sound
Billion-year-old pink granite dome east of Parry Sound on Highway 141. Classic Shield panorama from the summit: forest, rock, and lakes to every horizon. In late July, blueberries ripen in the rock crevices. Free access with informal roadside parking. One of the most rewarding short climbs in the region.
Challenging 78 km | 7-10 days | 300+ m cumulative | Backcountry permit required | North Shore
Ontario's toughest backpacking route. Every experienced source says 7-10 days; under 5 days is high-risk. Go clockwise (easier waterfall ascent, The Crack descent at end instead of start). Book campsites months ahead through Ontario Parks. Buy a map from Friends of Killarney beforehand. No cell coverage. This is a serious undertaking requiring backcountry experience and thorough preparation, but it is the finest multi-day hike in the region.
Easy 800 m | 30-45 min | Flat | Ontario Parks permit | Parry Sound
The best sunset walk in the Georgian Bay region. Only 800 metres but every step counts. Smooth pink granite meeting open bay water, western exposure catching full evening light. On calm evenings the water turns gold. Wear grippy shoes despite the short distance — polished granite is slippery.
Moderate Various 1-4 km | 2-4 hrs on island | $25 DayTripper boat | Honey Harbour
The boat ride to Beausoleil Island (15 min from Honey Harbour, $25/person, reservations required, Friday-Tuesday Victoria Day to Thanksgiving) is part of the experience. Chimney Bay trails on the north end are the best hiking. Fairy Trail climbs to ridge lookouts over the 30,000 Islands. Cedar Spring area has beaches, rentals, and Parks Canada programs. Book the DayTripper ahead for weekends — it fills up.
Moderate 2 km | 45 min | 70 m gain | Free | Parry Sound
Quick-hit lookout right in town. Lookout tower with 360-degree views over the bay and Shield. Short enough for a pre-dinner or sunset outing. Combined with a meal in Parry Sound, makes a perfect half-day trip without a park commitment.
Easy 1.5 km | 30-45 min | Flat, wheelchair-accessible | Free | Wasaga-Collingwood
Proof that easy can be excellent. Fully accessible boardwalk into one of southern Ontario's best wetland birding spots. Turtles, herons, marsh wrens, migrating waterfowl in spring. The best family trail in the region. Bring binoculars.
Moderate 4 km | 1.5-2 hours | 80 m gain | Inland
Trail through old-growth white pine to a restored fire tower. The 360-degree view shows unbroken lakes and forest to the horizon. Communicates the scale of Ontario's wilderness like nothing else in the region. Worth the drive to Dorset.
Easy 1-3 km | 30 min-1.5 hrs | Flat | Ontario Parks permit | Wasaga-Collingwood
A completely different landscape from the rest of Georgian Bay: parabolic sand dunes with rare plant species. Boardwalks through open grassland and juniper thickets. Most beach visitors never discover this behind the beach. Monument Hill for panoramic views. Combine with beach time.
Easy 10+ km section | 3 hours | Flat | Free | Inland
The best long flat walk in the region. Former rail trail along Severn Sound with views to the outer islands. Crushed limestone, level, suitable for all abilities. The Midland end connects to the town waterfront and Discovery Harbour. For distance without elevation.
For permits, parking, cell coverage, and gear lists, see our Trail Planning Guide. New to hiking? Start with our Beginner's Guide. For seasonal conditions, fall colour timing, and mud season info, see Shoulder Season Trails.