44 Upcoming Races Near Portland, CT - Matching: Trail Races

Smile Like Jack 5k/10k/Fun Run

East Otis, MA

Saturday, July 11th, 2026

10K

Trail

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Roxbury Road Race Series #18

Roxbury, CT

Saturday, July 11th, 2026

Trail

View details for race Roxbury Road Race Series #18

Pirate's Beer Run! - A 0.5k Run For Cancer

Colchester, CT

Saturday, July 11th, 2026

Trail

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Run the Vineyards - Pindar Vineyards 5K

Peconic, NY

Sunday, July 26th, 2026

Trail

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Pete Hawley People's 7

Barkhamsted, CT

Saturday, August 1st, 2026

Trail

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It's All Downhill From Here 5K

Wilton, CT

Saturday, August 1st, 2026

Trail

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The Hamden Combo

Hamden, CT

Saturday, August 1st, 2026

Trail

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The Perfect Ten & Five Mile Road Race

Hamden, CT

Saturday, August 1st, 2026

Trail

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2nd Annual Rocky Hill 2M Run & Kids Run

Rocky Hill, CT

Saturday, August 15th, 2026

Trail

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PATH TO THE PARADE 5K

Hamden, CT

Friday, August 21st, 2026

Trail

Fast

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Shore 2 The Pour Beach Run 2026

Stratford, CT

Saturday, August 22nd, 2026

Trail

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Run for The Hills

Niantic, CT

Saturday, September 5th, 2026

Trail

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2026 Gulf Beach Half Marathon

Milford, CT

Saturday, September 12th, 2026

Half

Trail

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2nd Annual PCS Harvest Hustle 5K & Kids Run

Pomfret Center, CT

Saturday, September 19th, 2026

Trail

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17th Annual Farmington River Run 5K Trail Race

Farmington, CT

Sunday, September 20th, 2026

Trail

View details for race 17th Annual Farmington River Run 5K Trail Race

Where the Pavement Ends Single & Double Loop

Ridgefield, CT

Sunday, September 20th, 2026

Trail

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Cockaponsett Trails to a Cure

Chester, CT

Sunday, September 20th, 2026

Trail

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No Sto Defeats MSA 5K and Fitness Walk

North Stonington, CT

Saturday, September 26th, 2026

1 Mile

Trail

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IronHike Mohawk Mountain Fall 2026

Mohawk Mtn Ski Area, Cornwall, CT

Thursday, October 1st, 2026

Ultra

Trail

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Forbidden Forest 30 Hour Ultra

Stratford, CT

Saturday, October 3rd, 2026

Trail

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2026 Rail Trail 10K Race

Hamden, CT

Saturday, October 3rd, 2026

10K

Trail

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Run for the Pumpkins Trail Run

Westerly, RI

Saturday, October 3rd, 2026

10K

Trail

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Norfolk Land Trust Trail Race Series/Haystack M...

Norfolk, CT

Sunday, October 4th, 2026

10K

Half

Trail

View details for race Norfolk Land Trust Trail Race Series/Haystack Mountain Challenge

Run Stanley

Westfield, MA

Sunday, October 4th, 2026

1 Mile

Trail

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Apple Harvest Road Races

Southington, CT

Sunday, October 4th, 2026

1 Mile

Trail

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Gemstone Sparkle Sprint 5k

Wilton, CT

Saturday, October 10th, 2026

1 Mile

Trail

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Ivoryton Pumpkin Chase

Ivoryton, CT

Saturday, October 17th, 2026

Trail

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Hope Children's Fund 22nd Annual Larry Hohler B...

Shoreham, NY

Saturday, October 17th, 2026

Trail

View details for race Hope Children's Fund 22nd Annual Larry Hohler Bi-Continental 5k Fun Run/Walk

Tom Centinaro Memorial "Dam" Race

Wolcott, CT

Saturday, October 17th, 2026

Trail

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Mt. Tom Trail Race

Holyoke, MA

Saturday, October 24th, 2026

10K

Trail

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Grills Trail Run

Westerly, RI

Saturday, October 24th, 2026

10 Miles

10K

Trail

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Cheshire Community YMCA Harvest Trail Race and ...

Cheshire, CT

Saturday, October 24th, 2026

Trail

View details for race Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

RACE FOR THE GREENWAY 5K RUN / WALK

Riverhead, NY

Sunday, October 25th, 2026

Trail

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Hamden Hall Middle School Invitational

Hamden, CT

Wednesday, October 28th, 2026

Trail

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Hamden Hall CISAC League Race

Hamden, CT

Saturday, October 31st, 2026

Trail

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Collinsville Trick or Trot

Collinsville, CT

Saturday, October 31st, 2026

Trail

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Centerville Bank Thompson Turkey Trot

Thompson, CT

Sunday, November 8th, 2026

Trail

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Stonington Vineyards Wine Run Turkey Trot 5k

Stonington, CT

Sunday, November 8th, 2026

Trail

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Roxbury Road Race Series #35

Roxbury, CT

Saturday, November 21st, 2026

Trail

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Storybook Half Marathon

Stratford, CT

Saturday, November 21st, 2026

Half

Trail

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Frosty Forest 5k

Stratford, CT

Saturday, December 19th, 2026

Trail

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The Scrooge Scramble 5K - Rails to Trails - Ve...

Vernon Rockville, CT

Friday, December 25th, 2026

Trail

View details for race The Scrooge Scramble 5K - Rails to Trails - Vernon

2nd Annual Camp Mountain Laurel - Color Run & T...

Hamden, CT

Saturday, May 8th, 2027

Trail

View details for race 2nd Annual Camp Mountain Laurel - Color Run & Trail Run

Woodland Ramble Trail Run

Mystic, CT

Saturday, June 5th, 2027

Trail

View details for race Woodland Ramble Trail Run

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