🏃 Races in Connecticut

5K race on mostly flat course along the Naugatuck River

Additional race information can be found at Blackhog - O2 Event Productions

This 20th annual open water swimming festival at Quassapaug Sailing Center in Middlebury, CT benefits the sailing center and offers four distance options: a half-mile, 1.5-mile, 3-mile, and 5-mile swim. Entry fees range from $30–$100 depending on distance and registration deadline (with discounts for early postmark dates before May 1st and July 1st), plus an $80–$100 water entry fee applies to all races. Swimmers compete in gender and age-group categories with awards for top finishers, and time limits are enforced for each distance to ensure water safety.

Get ready for a scenic mile that kicks off at the local park and finishes at Booth School in Roxbury, CT! If you're an active military member, veteran, or first responder, reach out to the race organizers about special pricing available just for you.

Head to Oswegatchie Hills Nature Preserve in Niantic, CT for the 5th Annual Run for the Hills, a 5K trail event that loops around Clark Pond with stunning natural scenery, and know that your entry fee goes straight toward preserving this beautiful preserve for years to come. Whether you're a runner or hiker, you're welcome to participate, and you'll stick around afterward for an awards ceremony and refreshments at the preserve starting at 10:30 AM. Registration opens at 8:00 AM with the race kicking off at 9:00 AM, with entry fees of $25 (through August 16th), $30 online, or $35 day-of.

Join the Ledyard Soccer Club on June 20th at Ledyard Center Town Green for their 3rd Annual Soccer Stride, featuring a ¼ mile kids fun run for children 10 and under at 9:30am and an officially timed 5K starting at 10am. The 5K takes you through town on an out-and-back route that goes down to the high school and around the track via the new multi-use pathway, with all young runners receiving medals and the first 100 5K participants earning commemorative t-shirts, plus medals and special gifts for top finishers. Plenty of parking is available in the back lot, accessible from 740 Colonel Ledyard Highway or Town Green Road near Ledyard Congregational Church.

Head to Haddam, CT on Sunday, September 6, 2026 at 9:30 AM for this USATF-sanctioned 5K that starts and finishes at the Fairgrounds, featuring mostly flat country roads with a couple of gentle downhills and one challenging climb. Register early for just $18 ($13 for seniors 65+) and get a t-shirt plus fair admission included, or pay $20 day-of ($15 for seniors)—late registrations between August 16-30 receive the lower price but skip the shirt. Arrive by 7:30 AM at 26 Quarry Hill Road in East Hampton for bib pickup and same-day registration, and enjoy professional chip timing throughout the race.

Get ready to hop on your bike and ride alongside us in Westbrook, CT for a meaningful event honoring those we lost in the tragic boat accident that happened on Labor Day 2024 near the Connecticut River in Old Saybrook. This gathering brings our community together to celebrate their memories and ensure they're never forgotten, with plans to grow this tribute year after year. Come be part of something special that keeps those we've lost close to our hearts.

Celebrate Labor Day by joining us at the start line in New Haven, Connecticut, or participate from wherever you are with our virtual option. If you prefer to go solo, simply run or walk at your own pace and we'll ship your race shirt and bib right to your door!

Get ready to test your triathlon skills on Saturday, September 12, 2026, at Madison Town Beach with multiple options to match your fitness level—choose from the classic Sprint Tri (half-mile swim, 13-mile bike, 3-mile run), bring a young one along for the Youth "Try" event, or go for the new Aquabike format if you want to skip the running portion. You'll kick things off with a refreshing dip in Long Island Sound, cruise through Madison's scenic countryside on your bike, and finish with a lovely seaside run, all while enjoying the perks of competing in a USAT-certified event. The race starts at 7:00 am at Surf Club on Madison Town Beach, so arrive ready to go—there's no rain date, though the director may modify the course if weather doesn't cooperate!

Celebrate 25 years of community spirit at this beloved southeastern Connecticut race along the scenic Ocean Beach shoreline, where you'll enjoy a flat, professionally certified course with stunning Long Island Sound views—perfect whether you're gunning for a personal record or taking a relaxed morning stroll with loved ones. Every participant helps fund the James A. Greenleaf, Jr. Memorial Scholarship Fund, supporting full scholarships and financial assistance for deserving students. Lace up on Saturday, September 12, 2026 at 9am for a meaningful morning that combines great running with a great cause!

Come join us for a fantastic 5K run and walk adventure along Eastern Point Beach in Groton, CT, brought to you by the Greater Mystic Chamber of Commerce and Groton Utilities! After you cross the finish line, stick around to enjoy live music, delicious food, and a brewfest celebration. Whether you're a serious runner or prefer a leisurely walk, everyone's welcome to participate—plus there's a free kids run (just register ahead of time), and registered participants receive tech shirts while they last!

Join us on September 12th at 10:00 am in Harwinton, CT for the 5th annual 5K run honoring Kailey Jaie Prenoveau, a local student-athlete who was fully committed to everything she did—whether it was competing on her crew and swim teams, singing in concert choir, or caring for those around her. This meaningful event celebrates Kailey's legacy of kindness, dedication, and making sure no one felt left out, with proceeds supporting a scholarship in her memory. Lace up and run with us at 421 Hill Rd to remember a remarkable daughter, sister, granddaughter, cousin, and friend who touched so many lives.

Get ready to kick off the end of summer at Bayley Beach with this fun-filled day featuring several swimming events for all ages! You'll have the chance to tackle the iconic one-mile Lighthouse Race starting from Green's Ledge Lighthouse (with check-in at 8:30 AM and a 10:30 AM start), take on the Buoy Race running simultaneously, or join the kids' non-timed races organized by age groups along the beach. Top it all off with an awards ceremony and family fun activities to celebrate your accomplishment!

Get ready for West Haven's hottest new fall event at the scenic Riva waterfront spot, where you'll enjoy a flat and beautiful 3.11-mile boardwalk route perfect for all fitness levels. Stick around after your run for live entertainment, snacks, refreshments, and the after-party—plus everyone 21+ gets a complimentary beverage to celebrate! RIVAGIVESBACK is proud to host this community run and walk where the vibes are as great as the views.

Get ready to tackle a scenic 6.4-mile lollipop loop through Roxbury, CT, featuring South Street and Falls Road with a charming bridge crossing! If you're active duty military, a veteran, or serve as a first responder, reach out to the race organizers—they've got a special discount waiting for you.

Get ready to make a difference in Newtown on September 12, 2026, when the 7th annual Run 4 Hunger and Health brings the community together to support FAITH Food Pantry and Newtown Youth and Family Services—an organization that's been strengthening local families and minds for over 30 years. We believe that nourishing both body and spirit creates a healthier community, and your participation helps us do exactly that! Join us for just $30 plus 3 canned goods for the main race (register early for $5 off!) or bring the kids along for only $5 plus 3 canned goods.

Get ready to experience classic small-town charm while running through Suffield's beautiful historic Main Street and picturesque countryside—this scenic 5K and 10K road race (plus a 2.5K walk option) has something for everyone! The first 200 registered runners snag a free race tee, with the chance to upgrade to a performance shirt for just $10, plus there's over $1,000 in prize money up for grabs. Bring the whole family for a fantastic community event featuring a kids' fun run, bounce house, music, and free activities for the little ones!

Get ready to explore some amazing marked trails—up to nine miles of them—while soaking in stunning views of the Connecticut River! This 2026 event in Lyme, CT is the perfect chance to enjoy a beautiful run through gorgeous scenery.

Head to Babe Blanchette Memorial Fields in Baltic, CT for a laid-back 1-mile run where everyone's welcome—just grab your spot quickly since waves are capped at 30 runners each! You'll be hand-timed on a walking/running track rain or shine, so come prepared for any weather and bring what you might need since facilities aren't guaranteed. This is a straightforward, no-fuss event, so please be respectful of the town's generosity in letting us use their space!

Get ready for a fun five-week spring running adventure in East Windsor where kids from Pre-K through 8th grade tackle weekly age-appropriate races featuring distances from 50-yard sprints to one-mile runs! Your registration covers all five weeks of races, a runner shirt, race bibs, a finisher medal, and sponsor giveaways, plus there's a special Challenger Division with a 75-yard adaptive race designed for children with disabilities and special needs who can run with family support and any assistive devices they need. If the full series doesn't work for you, no problem—single-day registration is available one hour before each race, and top finishers in each age group earn trophies to celebrate their achievement!

Come celebrate in Farmington and support The Cove's vital programs that help grieving children and families throughout Connecticut—including their Family Program, Camp Compassion, Virtual Program, Summer Program, and Professional Development offerings. You'll enjoy a 2-mile Memorial Walk along Memory Lane, a fun Kids' Fun Run with medals, and family-friendly activities, plus the option to create a personalized memorial sign featuring your loved one's photo for just $30 (raised by September 3). Register before noon on September 11 to lock in the best price, and don't forget to select your event t-shirt size!

Join hundreds of friends and neighbors for a scenic 2-mile stroll down West Haven's gorgeous boardwalk—it's a fantastic way to celebrate the Community House's 85 years of service while having a blast! As you walk, you'll hit fun activity stations to collect raffle tickets and show off your skills, plus early registrants (by August 28th) snag a commemorative shirt and have the chance to win prizes for best costume, top fundraiser, and team spirit. Grab some snacks, check out raffle baskets, and help support the programs that make our community thrive!

Join the Eastern Dutchess Road Runners Club on Sunday, September 13th, 2026 at 9:00 AM for a 5K run/walk in Kent, CT that supports a great cause—all proceeds benefit the High Watch Recovery Center's Wilson Bed Scholarship. Whether you're a club member ($20) or non-member ($25), you'll get packet pickup starting at 8:00 AM at Kent Town Hall, plus a chance to compete for awards across multiple age groups and overall categories. Come rain or shine and help make a difference while enjoying a fun morning of running with fellow enthusiasts!

Get ready for a fun-filled September Sunday in Oakdale, CT, where the Montville Rotary Club and local departments are hosting an exciting Race Day featuring a timed 5K, a USATF-certified 10K, and a untimed Color Run for all ages! All events kick off at Camp Oakdale Pavilion, and you'll have the chance to earn custom medals while competing for top honors in your age group (including an Over 40 category). Stick around after crossing the finish line to enjoy bounce houses, snow cones, hot dogs, chair massages, raffles, and plenty of family-friendly festivities!

Get ready to make a real difference while enjoying a fun 5K run or walk in Wallingford, CT! Every dollar of profit from this PTSMC-presented event goes straight to Master's Manna, Inc., a local nonprofit that's been fighting hunger and homelessness in the Wallingford/Meriden community since 2006. Lace up, hit the pavement, and help support families and individuals facing food insecurity in your own backyard!

Get ready to lace up for a great cause at this beloved community event supporting INTEMPO! You can join in person at St. Francis Episcopal Church in Stamford on Sunday, September 20th at 9:00 AM (bring your furry friend too—there's even a Dogapalooza celebration with fun contests!), or complete your 5K virtually anytime between September 14-20 from wherever you choose. Whether you want an official time recorded on our USATF-certified course or prefer to go at your own pace, this friendly run/walk welcomes all fitness levels and abilities.

Get ready to lope through the scenic grounds of historic Ives Farm in Cheshire, where the Cheshire Community YMCA and Cheshire Land Trust have teamed up to bring you a fantastic fall running experience! You'll enjoy a beautiful loop through fields and trails, starting and finishing at a gorgeous restored barn, all while supporting important community initiatives at the YMCA and the land trust's exciting plans for the property. Stick around before or after your run for a kids' Pumpkin Dash, plus tons of family fun like pumpkin decorating, face painting, games, live music, and a festive photo booth—it's a celebration for all ages!

Get ready for a day of racing in Cromwell, CT where you'll check in between 7:15 and 8:20am before the action kicks off. The schedule flows smoothly with Boys JV starting at 8:55am, followed by Girls JV at 9:30am, Boys Varsity at 10:00am, and Girls Varsity at 10:40am. Stick around after your race to celebrate everyone's efforts at the awards ceremony!

Join the Deep River Parks & Recreation Department for a fun-filled 5K that winds through town and takes you down to the beautiful river as part of Deep River Family Day celebrations! This USATF-certified course starts at Devitt Field and loops you through Main Street, along the scenic riverside, and back again for a finishing kick at the bottom of the hill. Register early and save—entry is just $20 for early birds ($25 after September 2nd, $30 race day), with group discounts available for teams of six or more at $15 per person.

Get ready to hit the trails in beautiful Pomfret Center while helping support your local school community! This fun-filled event features a 5K trail run for adults and a shorter 1/2 mile option for kids, with all proceeds going directly to the Pomfret Community School PTO to fund teacher support, classroom activities, and enrichment programs. Sign up before July 15th for the best rates ($35 for the 5K, $10 for kids), enjoy age-group awards, and earn a well-deserved finisher medal!

Get ready for a fantastic running experience in Somers, CT, where you'll earn a custom Bumpa Built finisher medal and score free entry to the amazing 4-Town Fair—perfect for celebrating after you cross the finish line! This beloved 25th annual event is more than just a 5k; stick around for the fair festivities and parade to make it a full day of fun. Best of all, every dollar raised goes directly to support the Somers Recreation Department!

Get ready to lace up and make a difference at this exciting fundraiser happening September 19, 2026, in Meriden, CT—featuring both in-person 5K and 10K races plus a virtual option running through mid-September! Our USATF-certified course winds through Meriden and Wallingford, celebrating our long history serving these communities while giving you the chance to earn a marathon-qualifying time. Can't run but still want to help? We'd love to have you as a sponsor or cheerleader—there are tons of ways to jump in and support our mission!

Head to scenic Sound View Beach in Old Lyme, CT for this dual-distance road race offering both a speedy 5K (nice and flat!) and a 10K with gentle rolling terrain. Both races finish with views of the beach along historic Hartford Avenue, and you'll enjoy post-race refreshments included with your entry. The 10K is USATF certified and doubles as the state championship for 2025-2026, wrapping up the USATF-CT Road Grand Prix series!

Get ready to pound the pavement while supporting a great cause—this event in Bozrah, CT brings together runners of all ages to help the local fire department! Little ones can kick things off with their fun run at 9:00 am, followed by the main 5k at 9:30 am for everyone else. Snag your registration early if you want a guaranteed t-shirt in your size, since only the first 75 sign-ups are promised one!

Get ready to pound the pavement in Middletown, CT, where your running efforts will fuel a meaningful cause while bringing the community together for an awesome day of fitness and fun. Kids (under 13) can join for just $25, early birds score deals at $35, and regular runners are $45—plus, fundraise $100 and snag two free entries for friends! Head over at 9:00 am for check-in, race kicks off at 10:00 am, with top male and female finishers earning $50 gift cards to celebrate their wins.

Get ready to make a difference at this exciting community event happening Saturday, September 19th, 2026 in Enfield, CT! Whether you prefer hitting the pavement for the 5K run/walk, taking a more leisurely 2-mile walk, or joining virtually from anywhere, there's a perfect option for everyone. Come celebrate with us starting at 9:00 AM, enjoy fantastic awards for top finishers across multiple age groups and team categories, and support an important cause!

Get ready for a 4.3-mile adventure through Roxbury, CT that loops clockwise around High Bridge! If you're serving or have served in the military, or work as an active first responder, reach out to the organizers—they've got special pricing waiting for you.

Lace up and help young soccer players achieve their goals at this welcoming one-mile community event in Enfield, CT! Whether you're a runner, walker, or cheerleader, your participation supports the Enfield Soccer Association's youth programs by funding travel, registration fees, and competitive opportunities. All ages and fitness levels are invited to be part of this family-friendly celebration that makes a real difference in helping ESA players experience teamwork, growth, and unforgettable memories on the field.

Join us on Sunday, September 20, 2026, for a beautiful 5K adventure around Alexander's Lake in Dayville, CT—the perfect opportunity to get moving while supporting youth health and wellness programs in our community! This family-friendly celebration features a scenic route on private roads, a kids' fun run, professional photos, live radio coverage, and a festive post-race celebration at The Lake Tavern. Your participation directly helps NOW continue offering free wellness programming for young people in the area.

Lace up for this year's edition on Sunday, September 20th, 2025, at Winding Trails in Farmington, CT, where you'll tackle a scenic 5K trail route winding through 300 beautiful acres around Walton Pond. Registration kicks off at 9am with the race start at 10am at 50 Winding Trails Drive. You'll have a shot at awards for overall winners and age groups (18 & Under, 19-49, and 50+), plus the special Lee Chisholm Award for the top local finishers!

Get ready for a cherished autumn tradition that's been bringing folks together for nearly half a century! You'll have your pick of two exciting timed races—sprint the 1.5-mile Fun Run/Walk or challenge yourself with the full 5-mile course—followed by community fun under the tent, all while supporting The Community Fund of Darien's 75-year mission to help neighbors access food, housing, healthcare, jobs, and youth programs. Every registration dollar goes directly to over 30 local nonprofits serving the greater Stamford, Norwalk, and Darien area, so you'll be running for a reason!

Join Circle of Care's Annual Walk/Run for Kids With Cancer in beautiful Westport, CT, and make a meaningful difference in the lives of children battling cancer! Whether you walk or run, you'll be part of a supportive community coming together for an amazing cause.

Head to Chester, CT and tackle either 4 or 9 miles of beautiful (and challenging!) trails through Cockaponsett State Forest—featuring roots, rocks, mud, and hills that'll keep you on your toes. You'll start with a half-mile road section to get warmed up, then hit the trails with water stops conveniently placed along the way (just remember, no day-of registration, so sign up ahead of time and grab your bib at 8 am for the 9 am start). This race is part of the Blue Blazed Trail Race series, and all the funds raised support PanCAN in honor of Steve Hancock, so you'll be doing good while getting a great workout!

Celebrate pride, diversity, and unity at this beloved community gathering in Wilton, brought to you by Wilton Pride and Wilton Library! Whether you're running, walking, or bringing the whole family (furry friends included), you'll enjoy live music, food, festivities, and prizes while supporting the LGBTQIA+ community and allies. Kids under 10 run free, and every participant gets a commemorative giveaway, digital photos, and access to the post-race celebration.

Get a head start on St. Patrick's Day spirit with this fun, brand-new 5K tradition happening in Stratford—think of it as the ultimate six-month warm-up to the big day in March! You'll enjoy a flat, scenic route through quiet neighborhoods starting from the iconic Little Pub in Lordship, complete with a commemorative green shirt, post-race snacks, refreshing beverages, and awards for top finishers in eight age groups. Lace up your shoes and join the celebration—everything else (the fun, the Irish vibes, the green) is already taken care of!

Join us for the 15th running of this beloved community race on Sunday, September 20, 2026, right here in Woodbridge at the beautiful JCC campus—and don't worry about childcare because we've got babysitting covered! Whether you're ready to tackle the USA Track & Field certified 5K course through scenic neighborhoods, prefer a more relaxed two-mile family walk, or want to cheer on the kids in their costume race, there's something for everyone. Lock in your spot before September 1st to snag a free race tee and enjoy 20% savings!

Get ready for a scenic 13.1-miler through Connecticut's picturesque countryside on September 26, 2026 at 8:30 a.m., where you'll cruise along quiet country roads near the Farmington River with a gentle 100-foot downhill advantage on this USATF-certified course. You'll enjoy six well-stocked aid stations (complete with gels at two of them), a killer race shirt, custom finisher medal, and fantastic post-race food, plus chances to win fun raffle prizes. Whether you're competing for overall honors or aiming to place in your age group, this race rewards the top 3 finishers across multiple divisions, making it a great day to challenge yourself in the beautiful towns of Riverton, Pleasant Valley, Hartland, and Colebrook!