5K Races in Connecticut

2026 Athletic Brewing Co. Fairfield 5K with myTEAM TRIUMPH

Sun, May 24 · Fairfield, CT Fairfield

Open

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Oh Boy 5K

Mon, May 25 · Waterbury, CT Waterbury

Road 5K

From $0 Open

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Jim Fixx Memorial Day Run

Mon, May 25 · Greenwich, CT Greenwich

Road Kids Half Mile Run (8+)Kids Half Mile Run (7&U)5K Run

From $10 Open

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Woodland Ramble Trail Run

Sat, May 30 · Mystic, CT Mystic

Trail 5K Trail Run

From $31 Open 100 spots left

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The River Run 5K and Kids Fun Run

Sat, May 30 · Old Saybrook, CT Old Saybrook

Road The River Run Kids Fun RunThe River Run 5K

From $15 Open Closing Soon

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Spring Street Mile & 5K Presented by PTSMC

Sat, May 30 · Manchester, CT Manchester

Road Men's MileWomen's MileSpring Street 5K

From $20 Open

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17th Annual Barkhamsted River Run 5K

Sun, May 31 · Barkhamsted, CT Barkhamsted

Road 1M Kids Fun Run5K

From $10 Open

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Run the Vineyards - Jonathan Edwards 5K

Sun, May 31 · North Stonington, CT North Stonington

Road 5K

From $44 Open

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Glastonbury Education Foundation 5K Run/Walk (GEF5K)

Sun, May 31 · Glastonbury, CT Glastonbury

Road GEF5K Run/Walk

From $40 Open

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Athletic Brewing Company Fairfield Road Races

Sat, Jun 6 · Fairfield, CT Fairfield

Road Lil' Stags Kids Fun Run (1/2 Mile)Athletic Brewing Beer Mile!5K +2

From $10 Open 70 spots left

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America’s 250th – Greenwich Community 5K & 1 Mile Fun Run

Sat, Jun 6 · Greenwich, CT Greenwich

Road America 250 Greenwich 1 Mile RunAmerica 250 Greenwich 5K Run

From $10 Open

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SongStrong 5K

Sat, Jun 6 · Guilford, CT Guilford

Virtual 5KKids Fun RunVirtual 5K

From $10 Open

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Heart of Eastford 5K

Sat, Jun 6 · Eastford, CT Eastford

Road 2026 Heart of Eastford 5k

From $30 Open

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Run the Race 5K

Sat, Jun 6 · Danbury, CT Danbury

Road Run the Race 5K

From $35 Open

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The 25th Annual Laura's Garden Community Run

Sun, Jun 7 · Wethersfield, CT Wethersfield

Road 3K5K

From $25 Open

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Brookfield Lions Strides to Cure Diabetes 5-Miler

Sun, Jun 7 · Brookfield, CT Brookfield

Road Brookfield Lions Strides to Cure Diabetes 5-Miler

From $30 Open

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O'Neill's 5K

Sun, Jun 7 · Norwalk, CT Norwalk

Virtual O'Neill's Virtual 1 Mile Health WalkO'Neill's 5KO'Neill's Virtual 5K

From $35 Open

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Celebrate! West Hartford FUNd RUNS

Sun, Jun 7 · West Hartford, CT West Hartford

Road Kids' K5K5K - YOUTH CLUBS: Zoomerangs, Girls In Stride, MPower, CHS Soccer, Grace Webb Running Club

From $5 Open

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6th Annual A. W. Stanley Park 5K

Sat, Jun 13 · New Britain, CT New Britain

Virtual 1 Mile Walk UntimedVirtual 1 MileVirtual 5K +2

From $30 Open

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Red, White and Blue in Bethany 5K

Sat, Jun 13 · Bethany, CT Bethany

Road 5K run

From $35 Open

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Gaylord Gauntlet

Sat, Jun 13 · Wallingford, CT Wallingford

OCR Gaylord Gauntlet 2026

From $60 Open

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52nd Annual Rooster Run

Sat, Jun 13 · Newtown, CT Newtown

Road 5K (In Person) RACE START 8:20 AM10K (In Person) RACE START 8:20 AMLittle Dash (Ages 3 to 8) RACE START 8 AM

From $10 Open

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Run For The Rock

Sun, Jun 14 · Bridgeport, CT Bridgeport

Road Run for the Rock 5K Run or Walk ages 18 & under ONLYRun for the Rock 5K Run or Walk ages 19 & over

From $25 Open

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Darien 5K-Run / 1-Mile Walk ( in Support of Ukraine )

Sun, Jun 14 · Darien, CT Darien

Virtual 1-Mile Walk5K RunVirtual 5K Run / walk

From $30 Open

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Milford Rotary Run in the Park 5K

Sun, Jun 14 · Milford, CT Milford

Road Milford Rotary Run in the Park 5K - at Eisenhower Park, Milford, CT

From $25 Open

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Acrisure Branford Road Race

Sun, Jun 21 · Branford, CT Branford

Road 1 Mile Mark Gilhuly Family Fun Run2 Mile Health Walk5 mile

From $11 Open

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8th Annual 5k Walk/Run for Overdose Awareness

Thu, Jun 25 · Shelton, CT Shelton

Road 8th Annual 5k Walk/Run for Overdose Awareness

From $40 Open

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

Sun, Jun 28 · Bethel, CT Bethel

Road First Responders & Military RegistrationAdult RegistrationTeen Registration 13 to 17 yrs +1

From $5 Open

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11th Annual Milford Moves for Veterans 5K

Sun, Jun 28 · Milford, CT Milford

Road 5K Runner or Walker 18 & under5K Runner or Walker 19 & over

From $22 Open

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Milford Road Runners Independence Day 5K

Sat, Jul 4 · Milford, CT Milford

Road 5K

From $30 Open

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East Shore 5k

Sun, Jul 5 · New Haven, CT New Haven

Road 5k Walk5k Run

From $10 Open

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Point O' Woods Beach 5K Run/Walk

Sat, Jul 11 · Old Lyme, CT Old Lyme

Road 5k

From $25 Open

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Enfield 4th of July 5k

Sat, Jul 11 · Enfield, CT Enfield

Road 5k

From $35 Open Closing Soon

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Petit Family Foundation 5K

Sun, Jul 12 · Plainville, CT Plainville

Road 5KFitness Walk

From $30 Open

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THE FAIRFIELD POLICE SUNSET 5K - Presented by Moneco Advisors

Wed, Jul 15 · Fairfield, CT Fairfield

Road Fairfield Police Sunset 5K Run - Presented by Moneco AdvisorsFairfield Police Sunset .8 MILE untimed WALK - Presented by Moneco AdvisorsFOOD TRUCK TICKET- NON REGISTERED ONLY - Presented by Moneco Advisors

From $20 Open

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Ambulance Driver 5K at BADSONS Brewery

Wed, Jul 15 · Derby, CT Derby

Road Ambulance Driver 5K

From $40 Open

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Move! with the Urban League

Sat, Jul 18 · Hartford, CT Hartford

Road 5K

From $20 Open

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Woodmont 5K

Sat, Jul 25 · Milford, CT Milford

Road 5K Run

From $30 Open

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Valley of Hartford 5K Road Race

Sat, Jul 25 · Newington, CT Newington

Road 22nd Valley of Hartford 5K Road Race

From $30 Open

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LYSB Midsummer Run

Sat, Jul 25 · Old Lyme, CT Old Lyme

Road Kids K5K Run5K Walk

From $10 Open

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Roxbury Road Race Series #20

Sat, Aug 1 · Roxbury, CT Roxbury

Road 4.7 Miles

From $10 Open

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Stonington Cross Country 5K

Wed, Aug 5 · Pawcatuck, CT Pawcatuck

Open

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The Perogie Dash

Sat, Aug 8 · Danbury, CT Danbury

Road 1K Kids Fun Run5K Run and Health Walk

From $25 Open

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Run the Vineyards - Priam Vineyards 5K

Sun, Aug 9 · Colchester, CT Colchester

Road 5K

From $42 Open

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Battle of Stonington 5K

Tue, Aug 18 · Stonington, CT Stonington

Road 5K: Walk or Run

From $32 Open

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Amber Room Run from the Sun 5K

Thu, Aug 20 · Danbury, CT Danbury

Virtual 5KVirtual 5K

From $45 Open

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17th Annual Saybrook Point 5k Road Race 2026

Sat, Aug 22 · Old Saybrook, CT Old Saybrook

Road Saybrook Point 5K

From $30 Open

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Quassapaug Sailing Center Open Water Swim

Sat, Sep 5 · Middlebury, CT Middlebury

1/2 Mile1.5 Mile1.5 Mile and 1/2 Mile +4

From $30 Open

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Run for The Hills

Sat, Sep 5 · Niantic, CT Niantic

Trail Run for the Hills

From $25 Open

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Faxon Law New Haven Road Race

Mon, Sep 7 · New Haven, CT New Haven

Virtual 1/2 Mile Kids Fun Run5KHalf Marathon Relay +4

From $8 Open

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