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Top Rated Trails
near Winding Cypress, Florida
Winding Cypress, Florida 
Recommended Routes, Photos, & More
4.7
mi
7.5
km
#1West Delray Trail
Intermediate/Difficult
Villages of Oriole, FL
|
Intermediate/Difficult
|
Villages of Oriole, FL |
42
|
|
2.0
mi
3.2
km
#2Prosper
Intermediate
North Port, FL
|
Intermediate
|
North Port, FL |
1
|
|
|
0.4
mi
0.7
km
#3Chupacabra
Intermediate/Difficult
Miami Lakes, FL
|
Intermediate/Difficult
|
Miami Lakes, FL |
1
|
|
1.8
mi
2.9
km
#4Orange Trail
Easy
Bonita Springs, FL
|
Easy
|
Bonita Springs, FL |
1
|
|
|
1.4
mi
2.2
km
#5Red Trail (Billy G. Cobb Memorial Trail)
Easy
Bonita Springs, FL
|
Easy
|
Bonita Springs, FL |
1
|
|
|
1.4
mi
2.2
km
#6Little Razor Back
Intermediate/Difficult
Miami Lakes, FL
|
Intermediate/Difficult
|
Miami Lakes, FL |
1
|
|
|
1.8
mi
3.0
km
#7Yellow Trail South
Easy
Bonita Springs, FL
|
Easy
|
Bonita Springs, FL |
1
|
|
|
0.2
mi
0.3
km
#8Deep Dark Forest - a winding section of trail with lots of roots.
Intermediate/Difficult
Weston, FL
|
Intermediate/Difficult
|
Weston, FL |
1
|
|
0.3
mi
0.5
km
#9Rock Garden - Lots of rocks to navigate through and a couple o…
Difficult
Weston, FL
|
Difficult
|
Weston, FL |
1
|
|
|
0.2
mi
0.4
km
#10Fishing Hole Loop - A great trail for beginners and is also ac…
Easy
Weston, FL
|
Easy
|
Weston, FL |
1
|
|
|
0.1
mi
0.1
km
#11Iguana Ridge - A short advanced ridgeline with an optional tec…
Difficult
Weston, FL
|
Difficult
|
Weston, FL |
1
|
|
|
1.1
mi
1.8
km
#12Coffee Trail
Easy
Miami Lakes, FL
|
Easy
|
Miami Lakes, FL |
1
|
|
|
0.8
mi
1.2
km
#13Potato Vine
Easy
Opa-locka, FL
|
Easy
|
Opa-locka, FL |
1
|
|
|
0.5
mi
0.8
km
#14Gobble Gobble
Easy
Hialeah, FL
|
Easy
|
Hialeah, FL |
1
|
|
|
0.4
mi
0.6
km
#15Gobble Gobble
Easy
Miami Lakes, FL
|
Easy
|
Miami Lakes, FL |
1
|
|
|
0.7
mi
1.1
km
#16Little Tortoise
Easy
North River Shores, FL
|
Easy
|
North River Shores, FL |
1
|
|
|
2.0
mi
3.2
km
#17Old Grove Trail
Easy
Stuart, FL
|
Easy
|
Stuart, FL |
1
|
|
|
1.6
mi
2.7
km
#18Tortoise Trail
Easy
North River Shores, FL
|
Easy
|
North River Shores, FL |
1
|
|
|
0.5
mi
0.7
km
#19Armadillo
Intermediate/Difficult
Weston, FL
|
Intermediate/Difficult
|
Weston, FL |
5
|
|
|
0.4
mi
0.7
km
#20Warm Up Loop
Intermediate/Difficult
Weston, FL
|
Intermediate/Difficult
|
Weston, FL |
3
|
|
|
1.3
mi
2.1
km
#21Gunrange Trail
Difficult
Weston, FL
|
Difficult
|
Weston, FL |
7
|
|
|
15.8
mi
25.4
km
#22Everglades Shark Valley Trail
Easy
Tamiami, FL
|
Easy
|
Tamiami, FL |
2
|
|
|
27.5
mi
44.2
km
#23Everglades Conservation Levee Greenway
Intermediate
Weston, FL
|
Intermediate
|
Weston, FL |
4
|
|
|
15.3
mi
24.6
km
#24Tram Road
Easy
Tamiami, FL
|
Easy
|
Tamiami, FL |
8
|
|
|
1.9
mi
3.0
km
#25Far East
Intermediate/Difficult
Alva, FL
|
Intermediate/Difficult
|
Alva, FL |
8
|
|
7.9
mi
12.7
km
#26BoldlyGo Trail
Easy/Intermediate
Plantation, FL
|
Easy/Intermediate
|
Plantation, FL |
7
|
|
0.6
mi
0.9
km
#27Alligator Alley and Blacksnake
Very Difficult
Weston, FL
|
Very Difficult
|
Weston, FL |
3
|
|
|
4.8
mi
7.7
km
#28South of the Border
Easy/Intermediate
Plantation, FL
|
Easy/Intermediate
|
Plantation, FL |
3
|
|
|
0.2
mi
0.4
km
#29Area 51
Difficult
Weston, FL
|
Difficult
|
Weston, FL |
3
|
|
|
0.2
mi
0.3
km
#30Turtle Slide
Intermediate
Weston, FL
|
Intermediate
|
Weston, FL |
3
|
