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Running Calendar near Middlebury 2026-2027

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Explore the top running races near Middlebury for 2026-2027! We've gathered 157 exciting races in the area. Check out our detailed list below to find your next local race.

Half Marathons Marathons Trail Runs Triathlons
September 2026
Sep
12
Sa

Run 4 Hunger and Health

Road Race 5 km
Sep
12
Sa

Riva Runs the Boardwalk 5K

Road Race 5 km
Sep
13
Su

Macedonia Trail Race

Trail Run 12 km 25 km 50 km
Sep
13
Su

Stride to Provide 5K

5 km
Sep
13
Su

High Watch Recovery Center's Sprint for Sobriety 5K

Road Race 5 km
Monthly updates for Middlebury

Get new running races (and updates) in your inbox every month.
Sep
13
Su

East Haven Community Classic

5 km
Sep
19-20
Sa - Su

Pawling 24 Hour Trail Running Festival

Backyard Ultra
Sep
19
Sa

ARC Run

5 km 10 km
Sep
19
Sa

Roxbury Road Race Series

4 mi
Sep
19
Sa

Laps for Life 5K - Middletown

5 km
Sep
20
Su

Murray Lender Bagel Run 5K

Road Race 2 mi 5 km
Sep
20
Su

Where the Pavement Ends Double Loop

Trail Run 4 mi 8 mi
Sep
20
Su

Farmington River Run 5K Trail Race

Trail Run 5 km
Sep
20
Su

Come Out & Run

5 km
Sep
20
Su

Circle of Care Walk/Run for Kids With Cancer

Road Race 5 km
Sep
20
Su

Half Way to St. Pats Day 5K

5 km
Sep
26
Sa

Pies & Pub Ta-Ta Trot 5K

Road Race 5 km
Sep
26
Sa

New Pond Farm Hayfield Hustle

5 km 5 mi
Sep
26
Sa

Come on Over 5K

Road Race 5 km
Sep
26
Sa

The River Run - Simsbury, CT

Road Race 3 mi 6 mi
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