Oswego County Trail Maps, NY | Trailmonger

Explore by activity

Mountain biking

135Total miles

46Campsites

22Boat launches

4Waterfalls

7Trailheads

Oswego Recreational TrailMTB24.5 mi Kevin Orwell Trail5.2 mi Winona - Winona Way Trail5.0 mi Winona WayHikeMTB5.0 mi Pine Grove TrailHike3.6 mi Winona State Forest Trails3.5 mi Barclay Kasog Trail3.4 mi Winona - Bargy Road3.1 mi Alice's AlleyHikeMTB2.4 mi Old Hobbit & Elf TrailHike2.4 mi Great Bear - Rivers Landing Loop2.3 mi Winona - Alices Alley2.3 mi Thunder_Barclay_Kasog Park Trail2.2 mi Orange TrailHike2.1 mi Great Bear - Wheel Wash2.1 mi Winona - Bills Belly Trail2.1 mi Raspberry TrailHikeMTB2.0 mi Winona - Raspberry Trail2.0 mi Shady ShuttleHike1.9 mi Winona - Shady Shuttle1.9 mi Trail 1HikeMTB1.8 mi Backus Bend TrailHike1.8 mi Winona - Backus Bend Trail1.8 mi Hiscock TrailHike1.7 mi Winona - Hiscock Trail1.7 mi Great Bear - Deer Run1.7 mi Frog Pond TrailHike1.6 mi Hawley PFARMTB1.5 mi Winona - Hawley Tucker Roads1.5 mi Great Bear - Whiskey Island1.4 mi Bill's BellyHikeMTB1.2 mi 440 RidgeHikeMTB1.2 mi Green TrailHike1.2 mi Wheel Wash ExtensionHike1.1 mi Red Fox TrailHike1.1 mi Little Sandy Creek TrailHike1.0 mi Winona - Little Sandy Creek1.0 mi Great Bear - Pumphouse Loop1.0 mi Blue Forest TrailHike1.0 mi Blue TrailHike0.9 mi Dog LegHikeMTB0.9 mi Winona - Dog Leg Trail0.9 mi Lakeshore TrailHike0.9 mi Red TrailHike0.9 mi Bills Belly TrailHike0.9 mi Deer Creek BoardwalkHike0.8 mi 52CHike0.8 mi Stinson Creek TrailHike0.8 mi Winona - Stinson Creek Trail0.8 mi O&W Pedestrian Promenade and BikewayHikeMTB0.8 mi Trail 2HikeMTB0.8 mi Long TrailHikeMTB0.7 mi Lower Turtle TrailHikeMTB0.7 mi Alec's TrailHike0.7 mi Look Out TrailHikeMTB0.6 mi Jimmys Jaunt TrailHike0.6 mi Winona - Jimmys Jaunt Trail0.6 mi Ted's TurnHikeMTB0.6 mi Winona - Teds Turn Trail0.6 mi Great Bear - Mishamokwa Springs0.6 mi Mishamokwa SpringsHikeMTB0.6 mi Smokey Road TrailHike0.5 mi Drumlin TrailsHike0.5 mi Winona - Blood Road0.5 mi Root HillHike0.5 mi Cross Leg TrailHikeMTB0.5 mi Winona - Cross Leg Trail0.5 mi Bernard's BypassHikeMTB0.5 mi Trail 5HikeMTB0.5 mi Trail 6HikeMTB0.5 mi Whiskey IslandHikeMTB0.4 mi Great Bear - Root Hill Bench0.4 mi Deer RunHike0.4 mi Brownell RoadHike0.4 mi Great Bear - Scotch Pines0.4 mi Scotch Pines TrailHike0.4 mi Dog Leg ExtensionHikeMTB0.4 mi Winona - Winona Way Extension0.4 mi Trail 3HikeMTB0.4 mi Otso's RidgeHikeMTB0.4 mi Salmon River Falls TrailHike0.3 mi Great Bear - Six Loop0.3 mi Winona - Tie Trail0.3 mi Flintstone Wheel Wash (Turtle Trail)HikeMTB0.3 mi Pumphouse TrailHike0.3 mi Highline TrailHike0.3 mi bicycleMTB0.3 mi Stone Wall SouthHikeMTB0.3 mi Spring HollowHike0.2 mi Trail 7HikeMTB0.2 mi Trail 4HikeMTB0.2 mi Apple TrailHike0.2 mi TowpathHikeMTB0.2 mi Stone Bridge TrailHikeMTB0.2 mi Tractor RoadHike0.2 mi Homestead TrailHikeMTB0.2 mi Six SouthHike0.2 mi Six NorthHikeMTB0.2 mi Buck Alley TrailHike0.2 mi River WalkHike0.1 mi Blue Trail;Orange TrailHike0.1 mi BackHikeMTB0.1 mi Couch Hill Stone StairsHikeMTB0.1 mi Double WideHike0.1 mi

More New York counties

144 trails · 314 mi

370 trails · 675 mi

7 trails · 62.3 mi

40 trails · 28.7 mi

131 trails · 334 mi

329 trails · 361 mi

580 trails · 1,458 mi

Westchester County

549 trails · 826 mi

433 trails · 1,165 mi

← All of New York

Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt August 9, 2026.