5K Races in Connecticut — 2026

There are 114 5K races in Connecticut scheduled for 2026. The next is the Chasing the Legend; Easton's Lady in White 5K Run/Walk in Easton on October 24. Connecticut 5K races run primarily October.

Diane Burr Memorial 5K Flag Run/Walk

Sun, Nov 8 · Thomaston, CT Thomaston

Diane Burr Memorial 5K Flag Run/Walk

Closed

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Stonington Vineyards Wine Run Turkey Trot 5k

Sun, Nov 8 · Stonington, CT Stonington

5k

From $30 Open Closing Soon

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2026 Colony Grill 'Hot Oil' 5K

Sun, Nov 8 · Fairfield, CT Fairfield

5K - POLICE PERSONNEL5K GENERAL ENTRY5K - Active Military/Veteran +1

From $38 Open 25 spots left

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MPower Youth Running Festival | 5K · 1-Mile · Fun Run

Sun, Nov 8 · Farmington, CT Farmington

Fun Run1-Mile5K Run

From $10 Open

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5th Annual Honor Our Veterans 5k/Health Walk

Wed, Nov 11 · Westport, CT Westport

Honor Our Veterans Health WalkHonor Our Veterans 5K Run

From $35 Open

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A Good Run 5K

Fri, Nov 13 · New Haven, CT New Haven

AGR 5K WalkAGR 5K RunAGR 5K Virtual

From $25 Closed

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Electric Boat Athletic Club (EBAC) Fall Challenge

Sat, Nov 14 · New London, CT New London

4.75 Mile Road Race5k Road Race

From $30 Open

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Jennings Jaguar 5k and Fun Run Supporting Kevin's Afterglow

Sat, Nov 14 · Fairfield, CT Fairfield

5k RunKids Fun Run

From $15 Open

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Hot COCO 5K

Sat, Nov 14 · Cheshire, CT Cheshire

Kids Fun Run1 Mile WalkHot COCO 5K

From $10 Open

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Glastonbury River Runners Race To Fill the Pantry - Presented by Fleet Feet

Sun, Nov 15 · Glastonbury, CT Glastonbury

2 Mile5K

From $30 Open

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Waterford High School 14th Annual 5K Turkey Trot

Sat, Nov 21 · Waterford, CT Waterford

5K Run

From $40 Open

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Run for Max

Sat, Nov 21 · Danbury, CT Danbury

5k Run or Walk

Closed

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Roxbury Road Race Series #35

Sat, Nov 21 · Roxbury, CT Roxbury

4.2 Miles

From $10 Open

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New Canaan Turkey Trot

Sun, Nov 22 · New Canaan, CT New Canaan

5k Run

From $40 Open

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Fischang-Cicchetti Memorial Road Race

Sun, Nov 22 · Waterbury, CT Waterbury

5 Mile5K

From $30 Open

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Annual Kiwanis Turkey Trot Road Race

Sun, Nov 22 · Wallingford, CT Wallingford

Turkey Trot 3.5 Mile Road RaceTurkey Trot 5 Mile Road Race

From $30 Open

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Soul n Body Thanksgiving Trail Run

Thu, Nov 26 · Wolcott, CT Wolcott

Walk (8:30am)Run (7:30am)Run (8:30am) +1

From $25 Open

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2025 Pequot Runners Thanksgiving Day 5-Mile Race with myTEAM TRIUMPH

Thu, Nov 26 · Southport, CT Southport

mTT Captain - 2.6 Mile WalkmTT Angel - 2.6 Mile Walk

From $0 Open

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2026 Southbury Turkey Trot 5K & Kids Fun Run

Thu, Nov 26 · Southbury, CT Southbury

5KKids Fun Run

From $10 Open

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Newtown Turkey Trot

Thu, Nov 26 · Newtown, CT Newtown

2.5K Walk5K Run

From $25 Open Closing Soon

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Rowayton Turkey Trot

Thu, Nov 26 · Norwalk, CT Norwalk

1 Mile Fun Run5K Run

From $20 Open

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Powerhouse Thanksgiving Road Race

Thu, Nov 26 · Berlin, CT Berlin

5K

From $20 Open

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15th Annual O'BRiley 5K Turkey Trot AT 9AM

Thu, Nov 26 · Collinsville, CT Collinsville

15th Annual O'BRiley 5K Turkey Trot

From $25 Open

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Run Turkey Run! Thanksgiving Day 5K

Thu, Nov 26 · Hamden, CT Hamden

5K

From $35 Open

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Pequot Runners Thanksgiving Day Race

Thu, Nov 26 · Southport, CT Southport

2.6 Mile Walk5 Mile Race

From $34 Open Closing Soon

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Stratford Turkey Day Trot

Thu, Nov 26 · Stratford, CT Stratford

Stratford Turkey Day Trot

From $34 Open

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Branford Thanksgiving 5K

Thu, Nov 26 · Branford, CT Branford

Kids Fun Run2 Mile Walk5K

From $10 Open

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Roxbury Thanksgiving Day Charity Race

Thu, Nov 26 · Roxbury, CT Roxbury

Roxbury Thanksgiving Day Charity Race

From $10 Open

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The Joyce Allen Great Turkey Escape

Thu, Nov 26 · Redding, CT Redding

1K Kids Fun Run5k Run5K Walk +1

From $30 Open Closing Soon 35 spots left

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Commodore Hull Thanksgiving Day 5k Road Race

Thu, Nov 26 · Shelton, CT Shelton

Commodore Hull Thanksgiving Day 5K Road Race

From $35 Closed

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Bethel Turkey Trot

Thu, Nov 26 · Bethel, CT Bethel

5K Child ONLY (18 and Under)5K

From $25 Open Closing Soon

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Boys & Girls Club of Ridgefield 45th Annual Turkey Trot

Thu, Nov 26 · Ridgefield, CT Ridgefield

Kids Fun Run5K Turkey Trot

From $20 Open Closing Soon

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Lenny and Joe's Madison Turkey Trot

Thu, Nov 26 · Madison, CT Madison

2 Mile Walk5 Mile Run

From $20 Open

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2026 Web Hill Turkey Trot

Thu, Nov 26 · West Hartford, CT West Hartford

2026 Webster Hill Turkey Trot

From $25 Open

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Falcon 5K Turkey Trot

Thu, Nov 26 · Avon, CT Avon

Falcon 5K Turkey Trot

From $30 Open Closing Soon

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Darien Depot Overstuffed Turkey Trot 5K and 1 Mile Fun Run

Fri, Nov 27 · Darien, CT Darien

1 M Fun Run5K Run

From $45 Open

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Greenwich Alliance Turkey Trot 5K, 1 Mile & Mini-Trot

Sat, Nov 28 · Greenwich, CT Greenwich

1-Mile5KVirtual 5K +1

From $20 Open Closing Soon

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The ODO Gobbler Run & Ruck

Sat, Nov 28 · South Glastonbury, CT South Glastonbury

Lil Gobbler Kids Program (includes Fun Run)5k Run/Walk5-Mile Run +1

From $15 Open

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Run Santa Run

Sat, Nov 28 · New Milford, CT New Milford

Run Santa Run 16 5k

From $25 Open

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Durham Fall 4K Fun Run

Sat, Nov 28 · Durham, CT Durham

Durham Fall 4k 2026

From $20 Open

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Niantic Jingle 5k

Mon, Nov 30 · Niantic, CT Niantic

Niantic Jingle 5kNiantic Jingle Virtual 5k

From $25 Open

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Santa Made Me Do It

Sat, Dec 5 · Bethlehem, CT Bethlehem

5K Road Race2 Mile Walk

From $30 Open

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2026 NIA Jingle Bell Run - 38th Annual

Sat, Dec 5 · Trumbull, CT Trumbull

2026 NIA JBR — 1.25mi Health Walk2026 NIA Jingle Bell Run 5K — 18 yrs and younger only!2026 NIA Jingle Bell Run 5K — 19 yrs & older

From $23 Open

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2026 Jingle Bell Run - Connecticut

Sat, Dec 5 · North Haven, CT North Haven

5K Timed5K UntimedVirtual Jingler +1

From $25 Open Closing Soon

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Joel Barlow 5K Reindeer Run

Sat, Dec 5 · Redding, CT Redding

5K Reindeer Run/Walk

From $25 Open

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Woodburrr (no Y) 1-Miler

Sat, Dec 5 · Woodbury, CT Woodbury

Woodburrr (no Y) 1-Miler

From $25 Open 99 spots left

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Tinsel Fun Run

Sat, Dec 5 · Berlin, CT Berlin

2 Mile Run

From $35 Open Closing Soon

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Christopher Martin's Christmas Run for Children

Sun, Dec 6 · New Haven, CT New Haven

5K

From $36 Open

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6th Annual Roseland Park Christmas Run 5K & Kids Fun Run

Sat, Dec 12 · Woodstock, CT Woodstock

Rudolph Kids Fun Run (1/2 Mile)Jingle Bell 5KHolly Jolly 5 Miler

From $15 Open

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The Holiday Run & Walk For Toys

Sun, Dec 13 · Stratford, CT Stratford

The Holiday 5K Run/Walk For Toys - ages 19 & overThe Holiday 5K Run for Toys - ages 18 & under

From $15 Closed 40 spots left

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