North Branch Purple Paved Spur
2.0 mi away0.5 mi long · Easy · Forest Preserve District of Cook County
Hiking Biking Cross-country skiing Paved Wheelchair accessible
Walking trails near Winnetka, IL
333 walking trails within 30 miles of Winnetka. Tap a trail for its map, trailhead and directions.
All trails Hiking trails (353) Walking trails (333) Bike trails (322) Mountain bike trails (108) Paved trails (247) Horse trails (54) Dog-friendly trails (14) Snowmobile trails (3) Cross-country ski trails (62) Wheelchair-accessible trails (17) Greenways (3)
North Branch Black Paved Trail
2.1 mi away4.5 mi long · Easy · Dogs on leash · Forest Preserve District of Cook County
Hiking Biking Cross-country skiing Paved Wheelchair accessible Dogs allowed
37 (Illinois)
3.1 mi away58 mi long · Easy · Dogs on leash · Forest Preserve District of Cook County
Hiking Biking Paved Wheelchair accessible Dogs allowed
OBT-8
3.1 mi away37 mi long · Easy · Dogs on leash · Outerbelt Alliance NFP
Hiking Biking Cross-country skiing Paved Wheelchair accessible Dogs allowed
North Branch Blue Paved (Non-FPCC) Trail
3.1 mi away2.0 mi long · Easy · Dogs on leash · Forest Preserve District of Cook County
Hiking Biking Cross-country skiing Paved Wheelchair accessible Dogs allowed
Grand Illinois Trail - McHenry to Chicago
3.1 mi away71 mi long · Easy · Dogs on leash · Forest Preserve District of Cook County
Hiking Biking Paved Wheelchair accessible Dogs allowed
North Branch Blue Unpaved Trail
3.1 mi away1.4 mi long · Easy · Dogs on leash · Forest Preserve District of Cook County
Hiking Biking Horses Cross-country skiing Paved Dogs allowed
Valley Line Trail
3.4 mi away4.8 mi long · Easy · Lincolnwood
Hiking Biking Paved
North Branch Orange Unpaved Trail
3.4 mi away0.9 mi long · Easy · Forest Preserve District of Cook County
Hiking Biking Horses Cross-country skiing Paved
GB - Green Bay Trail - Cook County
3.6 mi away6.5 mi long · Easy · Winnetka
Hiking Biking Paved
GB - Green Bay Trail - Lake County
3.6 mi away2.4 mi long · Easy · Highland Park
Hiking Biking Paved
Old Orchard Road Path
3.6 mi away1.3 mi long · Easy · Forest Preserve District of Cook County
Hiking Biking Paved Wheelchair accessible
East Northbrook Trail
3.6 mi away2.7 mi long · Easy · Northfield
Hiking Biking Mountain biking
Techny Basin
3.8 mi away1.3 mi long · Easy · Northfield
Hiking Biking Paved
North Navy Ditch Trail
3.8 mi away0.8 mi long · Northfield
Hiking
North Branch Blue Paved (North) Trail
3.9 mi away1.0 mi long · Easy · Dogs on leash · Forest Preserve District of Cook County
Hiking Biking Cross-country skiing Paved Wheelchair accessible Dogs allowed
Loyola Trail
3.9 mi away0.7 mi long · Glenview
Hiking
North Branch Brown Unpaved Trail
3.9 mi away1.2 mi long · Forest Preserve District of Cook County
Hiking Biking Mountain biking Horses Cross-country skiing
North Shore Channel Trail
4.0 mi away12 mi long · Easy · Evanston
Hiking Biking Paved
Evanston-Wilmette Community Trail
4.0 mi away2.4 mi long · Evanston
Hiking
North Branch (green) Trail, (north section)
4.4 mi away2.4 mi long · Dogs on leash · Forest Preserve District of Cook County
Hiking Horses Dogs allowed
Trail Through Time,
4.5 mi away0.5 mi long · Northbrook
Hiking Biking Mountain biking
Skokie Valley Trail
4.6 mi away9.6 mi long · Easy · Bannockburn
Hiking Biking Paved
North Branch Tan Unpaved Trail
4.7 mi away0.8 mi long · Forest Preserve District of Cook County
Hiking Biking Mountain biking Horses Cross-country skiing
outer loop trail
5.1 mi away1.6 mi long · No dogs · Northbrook
Hiking
inner loop trail
5.3 mi away0.7 mi long · No dogs · Northbrook
Hiking
Loop Trail
5.7 mi away0.6 mi long · Easy · No dogs · Northbrook
Hiking Paved
Evanston Lakefront Trail
6.0 mi away3.1 mi long · Easy · Evanston
Hiking Biking Paved
Caldwell Avenue
6.3 mi away0.5 mi long · Niles
Hiking Biking Mountain biking
Oakton Street
6.3 mi away0.6 mi long · Morton Grove
Hiking Biking Mountain biking
Nearby cities
Common questions
- How many walking trails are near Winnetka?
- We list 333 walking trails within 30 miles of Winnetka, Illinois. This page shows the 30 closest.
- What is the longest walking trail near Winnetka?
- Grand Illinois Trail - McHenry to Chicago is the longest on this page at about 71 miles, 3.1 miles from Winnetka.
- Are there dog-friendly trails near Winnetka?
- Yes. Map data lists 8 trails on this page as open to dogs, including North Branch Black Paved Trail, 37 (Illinois), OBT-8. Most trails have no dog rule in our data yet, so check signs at the trailhead.