Upcoming Races Near Oregon, WI - Matching: Trail Races

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Tutty Baker Fest 5K

Freeport, IL

Saturday, July 11th, 2026

Featured

5K

Trail

View details for race Tutty Baker Fest 5K

Casual Hikers 10k Walk/Run

Whitewater, WI

Saturday, August 1st, 2026

10K

Trail

View details for race Casual Hikers 10k Walk/Run

2026 New Glarus Woods Trail Run

New Glarus, WI

Saturday, August 15th, 2026

5K

Trail

View details for race 2026 New Glarus Woods Trail Run

Prairie Dog Trail Run

Verona, WI

Saturday, September 5th, 2026

5K

10K

Trail

View details for race Prairie Dog Trail Run

Hobo Trail Runs 10k-25k-50k

Rockford, IL

Friday, September 11th, 2026

Ultra

10K

Trail

View details for race Hobo Trail Runs 10k-25k-50k

DoLittle Marathon

Oconomowoc, WI

Saturday, September 12th, 2026

Marathon

Half

10K

Trail

Fast

View details for race DoLittle Marathon

Stone Bridge Half Marathon and 5k

Roscoe, IL

Saturday, September 26th, 2026

Half

5K

Trail

Fast

View details for race Stone Bridge Half Marathon and 5k

Fall Color Festival

Whitewater, WI

Saturday, September 26th, 2026

Ultra

Half

1 Mile

Trail

View details for race Fall Color Festival

Autumn Leaf Run

Freeport, IL

Saturday, October 3rd, 2026

5K

Trail

View details for race Autumn Leaf Run

S'more Fun Trail Run

Baraboo, WI

Saturday, October 3rd, 2026

1 Mile

5K

10K

Trail

View details for race S'more Fun Trail Run

Trail Run At Indian Lake

Cross Plains, WI

Saturday, October 3rd, 2026

Trail

View details for race Trail Run At Indian Lake

Fall into Fall Trail 5k Run/Walk

Janesville, WI

Saturday, October 3rd, 2026

5K

Trail

View details for race Fall into Fall Trail 5k Run/Walk

JAIMIE COX MEMORIAL RUN

Roscoe, IL

Saturday, October 17th, 2026

Trail

View details for race JAIMIE COX MEMORIAL RUN

Among the Trees

Dousman, WI

Saturday, October 31st, 2026

Ultra

Trail

View details for race Among the Trees

ARKTOS

Dousman, WI

Saturday, February 27th, 2027

Trail

View details for race ARKTOS

Donald Dash Trail Run

Mount Horeb, WI

Saturday, May 1st, 2027

5K

15K

1 Mile

Trail

View details for race Donald Dash Trail Run

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