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Favorite Rolling meadows that look like The Shire.
Intermediate/Difficult Intermediate/Difficult

Ice Age Trail: Kettle Moraine State Forest-Southern Unit

32.3 mi 52.0 km 3,479' Up 1060.47 m Up 3,409' Down 1039.1 m Down

Whitewater, WI
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Favorite The Dune Succession Trail.
Intermediate Intermediate

Dune Succession Trail

0.6 mi 1.0 km 79' Up 24.04 m Up 43' Down 13.14 m Down

Ogden D…, IN
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Favorite Tomahawk Slough off of the Orange Trail.
Intermediate Intermediate

Orange Loop

6.2 mi 9.9 km 416' Up 126.77 m Up 420' Down 127.95 m Down

Willow…, IL
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Favorite About to head back on Trail 7 after a long walk on the beach.
Intermediate Intermediate

Trail 10

5.8 mi 9.4 km 63' Up 19.28 m Up 119' Down 36.34 m Down

Chesterton, IN
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Favorite No Photos
Easy Easy

Great Western Trail

17.7 mi 28.5 km 219' Up 66.87 m Up 144' Down 43.78 m Down

Saint C…, IL
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Favorite No Photos
Intermediate Intermediate

Yellow Birch Loop

1.2 mi 2.0 km 24' Up 7.34 m Up 25' Down 7.5 m Down

Bridgman, MI
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Favorite No Photos
Easy Easy

Lyons Woods To Waukegan Savanna Trail

2.0 mi 3.2 km 10' Up 3.08 m Up 90' Down 27.35 m Down

Beach Park, IL
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Favorite No Photos
Easy/Intermediate Easy/Intermediate

Singing Sands Trail

4.5 mi 7.2 km 61' Up 18.68 m Up 72' Down 21.81 m Down

Michiga…, IN
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Favorite No Photos
Easy Easy

Ridge Trail

0.7 mi 1.1 km 51' Up 15.58 m Up 51' Down 15.67 m Down

New Buf…, MI
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Favorite lovely day for a tour
Easy Easy

Prairie Wolf Forest Preserve Trail

0.7 mi 1.1 km 5' Up 1.48 m Up 6' Down 1.8 m Down

Bannock…, IL
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Favorite No Photos
Easy Easy

Rollins Savanna Forest Preserve Trail

3.1 mi 5.0 km 37' Up 11.2 m Up 25' Down 7.55 m Down

Third Lake, IL
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Favorite Kids measuring the size of a tree.
Easy Easy

Warren Woods Trail

0.7 mi 1.2 km 18' Up 5.38 m Up 19' Down 5.88 m Down

Three Oaks, MI
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Favorite No Photos
Easy Easy

North Pond Loop

0.8 mi 1.3 km 13' Up 3.99 m Up 9' Down 2.67 m Down

Chicago, IL
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Favorite South Mountain Park/Preserve.
Easy Easy

Nelson Lake Trail

2.6 mi 4.2 km 33' Up 10.07 m Up 54' Down 16.61 m Down

Batavia, IL
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Favorite Wetland area located near the trail.
Easy Easy

Red Loop

2.9 mi 4.7 km 43' Up 13.13 m Up 42' Down 12.79 m Down

Kildeer, IL
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Favorite No Photos
Easy Easy

Nippersink Forest Preserve Trail

0.8 mi 1.3 km 21' Up 6.52 m Up 21' Down 6.4 m Down

Round Lake, IL
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Favorite No Photos
Easy/Intermediate Easy/Intermediate

Hastings Lake Blue Loop Trail

2.1 mi 3.3 km 63' Up 19.31 m Up 62' Down 19.03 m Down

Lindenh…, IL
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Favorite No Photos
Easy Easy

Fox River Forest Preserve Trail

0.4 mi 0.7 km 3' Up 1.02 m Up 3' Down 0.82 m Down

Port Ba…, IL
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Favorite No Photos
Easy Easy

Half Day Forest Preserve Trail

0.5 mi 0.9 km 3' Up 0.8 m Up 11' Down 3.5 m Down

Lincoln…, IL
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Favorite No Photos
Easy Easy

Independence Grove Forest Preserve Trail

1.7 mi 2.7 km 27' Up 8.34 m Up 26' Down 7.89 m Down

Liberty…, IL
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Favorite No Photos
Easy/Intermediate Easy/Intermediate

Millennium Trail & Greenway

19.5 mi 31.3 km 590' Up 179.75 m Up 569' Down 173.33 m Down

Mundelein, IL
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Favorite No Photos
Easy Easy

Oriole Grove Forest Preserve Trail

0.8 mi 1.2 km 8' Up 2.45 m Up 5' Down 1.48 m Down

Lake Fo…, IL
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Favorite No Photos
Intermediate Intermediate

Grant Woods Forest Preserve Trail

1.0 mi 1.6 km 8' Up 2.39 m Up 17' Down 5.27 m Down

Fox Lak…, IL
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Favorite No Photos
Easy/Intermediate Easy/Intermediate

Waukegan Savanna Forest Preserve Trail

2.3 mi 3.8 km 67' Up 20.34 m Up 68' Down 20.66 m Down

Wadsworth, IL
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Favorite No Photos
Easy/Intermediate Easy/Intermediate

Sunflower Trail

1.2 mi 1.9 km 35' Up 10.64 m Up 5' Down 1.59 m Down

Naperville, IL
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Favorite About two miles in, the Yellow Loop parallels the greenway quite a bit.
Easy Easy

Black Trail

1.2 mi 2.0 km 49' Up 15.03 m Up 21' Down 6.43 m Down

Kildeer, IL
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Favorite No Photos
Easy Easy

Raven Glen Forest Preserve Trail

2.2 mi 3.5 km 41' Up 12.56 m Up 64' Down 19.55 m Down

Antioch, IL
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Favorite No Photos
Intermediate Intermediate

Blue Trail

1.5 mi 2.4 km 29' Up 8.76 m Up 23' Down 6.95 m Down

Wadsworth, IL
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Favorite No Photos
Intermediate Intermediate

Lakewood Forest Preserve Trail

0.6 mi 0.9 km 11' Up 3.4 m Up 13' Down 3.87 m Down

Wauconda, IL
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Favorite No Photos
Easy/Intermediate Easy/Intermediate

Lake Carina Forest Preserve Trail

1.0 mi 1.6 km 7' Up 2.18 m Up 7' Down 2.08 m Down

Gurnee, IL
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