Upcoming Races Near Middlebury, CT in June, 2026

Name: Fork In The Trail 5k Presented By Peace, Love, Trails
Start: 2026-06-28
End: 2026-06-28
Location: Bedford

Hat City Dash

Danbury, CT

Sunday, June 7th, 2026

Featured

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Belltown Spring Sprint 2M Run & Walk, Kids Run

East Hampton, CT

Tuesday, June 2nd, 2026

View details for race Belltown Spring Sprint 2M Run & Walk, Kids Run

The Big Run 5K/10K - Fleet Feet Poughkeepsie

Poughkeepsie, NY

Wednesday, June 3rd, 2026

10K

Trail

Fast

View details for race The Big Run 5K/10K - Fleet Feet Poughkeepsie

The Big Run Presented by Brooks

West Hartford, CT

Wednesday, June 3rd, 2026

View details for race The Big Run Presented by Brooks

IronHike Endurance Series - Spring 2026 - Mohaw...

Cornwall, CT

Wednesday, June 3rd, 2026

Ultra

Trail

View details for race IronHike Endurance Series - Spring 2026 - Mohawk Mtn, CT, USA

The Big Run Presented by Brooks

Longmeadow, MA

Wednesday, June 3rd, 2026

View details for race The Big Run Presented by Brooks

IronHike Mohawk Mountain Spring 2026

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, June 4th, 2026

Ultra

View details for race IronHike Mohawk Mountain Spring 2026

11th Annual Flanders Field & Forest 5K Trail R...

Woodbury, CT

Friday, June 5th, 2026

Trail

View details for race 11th Annual Flanders Field & Forest 5K Trail Run/Walk

Roxbury Road Race Series #14

Roxbury, CT

Saturday, June 6th, 2026

View details for race Roxbury Road Race Series #14

Muddy Kids - Long Island, NY

Riverhead, NY

Saturday, June 6th, 2026

View details for race Muddy Kids - Long Island, NY

Rockwood Ramble 10K

Sleepy Hollow, NY

Saturday, June 6th, 2026

10K

View details for race Rockwood Ramble 10K

Locust Cider Run

Milton, NY

Saturday, June 6th, 2026

View details for race Locust Cider Run

Iron Hike - Spring Kuwohi Trail Half Marathon P...

Cornwall, CT

Saturday, June 6th, 2026

Trail

View details for race Iron Hike - Spring Kuwohi Trail Half Marathon Plus - 15 Miles | 7,140' Elevation | 12-Hour | Run, Hike or Walk

Iron Hike - Spring Kuwohi Trail Half Marathon P...

Cornwall, CT

Saturday, June 6th, 2026

View details for race Iron Hike - Spring Kuwohi Trail Half Marathon Plus Relay - 15 Miles | 7,140' Elevation | 12-Hour | Run, Hike or Walk

Run the Race 5K

Danbury, CT

Saturday, June 6th, 2026

View details for race Run the Race 5K

Athletic Brewing Company Fairfield Road Races

Fairfield, CT

Saturday, June 6th, 2026

Half

10K

View details for race Athletic Brewing Company Fairfield Road Races

America’s 250th – Greenwich Community 5K & Fun ...

Greenwich, CT

Saturday, June 6th, 2026

1 Mile

View details for race America’s 250th – Greenwich Community 5K & Fun Mile

SongStrong 5K

Guilford, CT

Saturday, June 6th, 2026

View details for race SongStrong 5K

Hamden Fest Half Marathon & 5k

Hamden, CT

Saturday, June 6th, 2026

Half

Trail

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Celebrate! West Hartford FUNd RUNS

West Hartford, CT

Sunday, June 7th, 2026

Trail

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Run for RMC

Westfield, MA

Sunday, June 7th, 2026

1 Mile

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Hat City Dash

Danbury, CT

Sunday, June 7th, 2026

View details for race Hat City Dash

Brookfield Lions Strides to Cure Diabetes 5-Miler

Brookfield, CT

Sunday, June 7th, 2026

Fast

View details for race Brookfield Lions Strides to Cure Diabetes 5-Miler

Run in the Park 5K - to benefit the Milford Rot...

Milford, CT

Sunday, June 7th, 2026

Trail

View details for race Run in the Park 5K - to benefit the Milford Rotary and the Beth-El Center

Fire Tower Trail Races

Cross River, NY

Sunday, June 7th, 2026

Half

10K

Trail

View details for race Fire Tower Trail Races

The 25th Annual Laura's Garden/Keane Foundation...

Wethersfield, CT

Sunday, June 7th, 2026

View details for race The 25th Annual Laura's Garden/Keane Foundation Wethersfield Community Run

Muddy Princess - Long Island, NY

Riverhead, NY

Sunday, June 7th, 2026

View details for race Muddy Princess - Long Island, NY

O'Neill's 5K

Norwalk, CT

Sunday, June 7th, 2026

1 Mile

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2026 New England Series - Day 1 (CT)

Simsbury, CT

Monday, June 8th, 2026

10K

Half

View details for race 2026 New England Series - Day 1 (CT)

Northport Downhill Mile

Northport, NY

Saturday, June 13th, 2026

1 Mile

Fast

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Roxbury Road Race Series #15

Roxbury, CT

Saturday, June 13th, 2026

10K

View details for race Roxbury Road Race Series #15

52nd Annual Rooster Run

Newtown, CT

Saturday, June 13th, 2026

10K

View details for race 52nd Annual Rooster Run

6th Annual A. W. Stanley Park 5K

New Britain, CT

Saturday, June 13th, 2026

1 Mile

10K

View details for race 6th Annual A. W. Stanley Park 5K

Litchfield Hills Road Race

Litchfield, CT

Sunday, June 14th, 2026

View details for race Litchfield Hills Road Race

Run For The Rock

Bridgeport, CT

Sunday, June 14th, 2026

View details for race Run For The Rock

Devil Dash 5k

Stratford, CT

Sunday, June 14th, 2026

View details for race Devil Dash 5k

4th Annual Bloomfield Juneteenth 5K

Bloomfield, CT

Saturday, June 20th, 2026

View details for race 4th Annual Bloomfield Juneteenth 5K

Rhulen Rock Hill Run and Ramble 5K

Holiday Mountain Ski Area, NY

Saturday, June 20th, 2026

Fast

View details for race Rhulen Rock Hill Run and Ramble 5K

Summer Sizzler 2-Miler

Sherman, CT

Saturday, June 20th, 2026

View details for race Summer Sizzler 2-Miler

Roxbury Road Race Series #16

Roxbury, CT

Saturday, June 20th, 2026

View details for race Roxbury Road Race Series #16

Acrisure Branford Road Race

Branford, CT

Sunday, June 21st, 2026

1 Mile

View details for race Acrisure Branford Road Race

MRC Track & Field Series presented by Marathon ...

Manchester, CT

Saturday, June 27th, 2026

View details for race MRC Track & Field Series presented by Marathon Sports

Rocky Hill America 250 Fun Run & 2 Miles

Rocky Hill, CT

Saturday, June 27th, 2026

View details for race Rocky Hill America 250 Fun Run & 2 Miles

Westport Road Runners Summer Series

Westport, CT

Saturday, June 27th, 2026

1 Mile

15K

View details for race Westport Road Runners Summer Series

EDRRC - Pawling Moonlight Trail Run 5K

Pawling, NY

Saturday, June 27th, 2026

Trail

View details for race EDRRC - Pawling Moonlight Trail Run 5K

Centurion Trail 33 Hour Ultra

Stratford, CT

Saturday, June 27th, 2026

Trail

View details for race Centurion Trail 33 Hour Ultra

Roxbury Road Race Series #17

Roxbury, CT

Saturday, June 27th, 2026

View details for race Roxbury Road Race Series #17

Tunnel to Towers 5K Run & Walk - Bethel, CT

Bethel, CT

Sunday, June 28th, 2026

Fast

View details for race Tunnel to Towers 5K Run & Walk - Bethel, CT

11th Annual Milford Moves for Veterans 5K

Milford, CT

Sunday, June 28th, 2026

View details for race 11th Annual Milford Moves for Veterans 5K

Fork In The Trail 5k Presented By Peace, Love, ...

Bedford, NY

Sunday, June 28th, 2026

Trail

View details for race Fork In The Trail 5k Presented By Peace, Love, Trails

Explore more in Middlebury, CT

Distances:

5K 10K Half Marathon Marathon

Months:

April May June

Tags:

Trail Boston Qualifiers Fast Courses

State:

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