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  • Distance: 22.5 km from Madison
    Sat, Jul 25, 2026 at 8:00 AM

    Celebrate the Midsummer Festival in historic Old Lyme Village with this family friendly event benefitting the Lymes' Youth Service Bureau (LYSB).The Midsummer 5K Run features a scenic road race, a 5K Run & Walk, and a Kids K. The race will begin at LYSB located at 59 Lyme Street and wind through the beautiful streets of the village. The race is held on the morning of the renowned Old Lyme Midsummer Festival, kicking off a weekend of cultural, artistic and community events at multiple sites throughout Old Lyme’s Historic District.

    Pricing for the 5K (run and walk) is $30 for adults, $15 for youth (18 and under). Registration for the "Kids K" fun run is $10. Chip timing will be provided by Fast Track Timing for 5K runners. Commemorative T-Shirts will be available for the first 200 registered participants. Finisher medals for all.

    The overall top three men and women will be recognized as well as the top age group winner in the men and women divisions. Divisions will be broken down as follows: Youth 14 and under, 15 to 19, 20 to 29, 30 to 39, 40 to 49, 50 to 59, 60-69, and 70 plus.

    Online registration closes at 11:59 p.m. on Friday, July 24th. On site registrations accepted up to race day.

    Tee-Shirts for the first 200 registered runners/walkers.

    Pre-Race Packet pick up on Friday, July 24, 9:00-5:00 p.m. at LYSB (59 Lyme Street, Old Lyme)

    RACE DAY: Saturday, July 25, 2026

    Schedule:

    6:45 am – Registration opens

    8:00 am – 5K Run & Walk

    9:00 am – Kids K

    PACKET PICK UP: Friday, July 24, 2026, 9:00 a.m. to 5:00 p.m. OR on Race Day starting at 6:45 a.m.

    Proceeds from the Midsummer 5K will support LYSB's programs for youth and families including mental wellness, drug & alcohol prevention, juvenile justice, positive youth development, and early childhood.

    For more info about LYSB and the 5K contact LYSB at 860-434-7208 www.lysb.org

    For more info about Old Lyme Midsummer Festival visit Midsummer Festival | exploreoldlyme.com

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    1k5kFun RunRunWalk via RunSignup
  • Distance: 17.5 km from Madison
    Sat, Aug 22, 2026 at 8:30 AM

    The Old Saybrook - Westbrook Exchange Club and the Greater Old Saybrook Chamber partner together annually to raise money for The Exchange Clubs A.C.E. (Accepting the Challenge of Excellence) Award and the Greater Old Saybrook Chamber C. Wilfred Hunter Memorial Scholarship for deserving college bound seniors from Old Saybrook and Westbrook High Schools. Packs can be picked up on Friday, August 21nd at Marathon Sports in Old Saybrook between 4pm-6pm or the morning of the race, starting at 7:30am. Online registration only! Price will increase to $33 for day of registration.

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    5kRun via RunSignup
  • Distance: 17.7 km from Madison
    Sun, Sep 20, 2026 at 9:00 AM

    Choose between a 4 or 9 mile trail race in the Cockaponsett State Forest in Chester, CT.

    The 4 miler is the first part of the 9 mile course. The course consists of roots, rocks, muddy sections and several hills. The first 1/2 mile is on a road which helps spread the runners out prior to the start of the trails. Water stations are at miles 2, 4, 6 and 7.

    NO RACE DAY REGISTRATION. Bib pick up opens at 8 am. Race starts at 9 am. Please note if you have out of state plates, the park requires you to pay a parking fee.

    FREE registration to runners 75 or older.

    Trails to a Cure is part of the Blue Blazed Trail Race series.

    All proceeds benefit PanCAN in memory of Steve Hancock.

    Not a runner but want to support the race? Volunteers are needed to assist with check in process, aid stations and sweeping the course. If interested, please email [email protected].

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    4 Miles9 MilesRunTrail via RunSignup
  • Distance: 14.9 km from Madison
    Sat, Oct 17, 2026 at 9:00 AM

    The Ivoryton Pumpkin Chase is a 5K Road/Trail Race and a Kiddie Pumpkin Fun Run (age 7 and below) to benefit the Ivoryton Library and takes place in peak foliage season of southern New England. The course begins along North Main Street for approximately ½ mile before turning left down Falls River Drive. At the one mile mark, the course enters the Falls River Preserve for a 1.1 mile trail loop that meanders along the Falls River. The trail is double track for about ½ mile before it turns into hilly and rocky single track. Care must be taken on the trail due to the presence some jagged rocks and roots. Please be aware that the trail can be slippery in wet conditions.

    Participants will receive a free t-shirt with registration before September 18. Registrations after September 18 and day of registrations will receive a t-shirt while supplies last.

    Contact Ivoryton Library at [email protected] if you or your organization would like to be a sponsor and have your logo included on our t-shirts.

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    5kFun RunRunTrail via RunSignup
  • Distance: 11.2 km from Madison
    Sun, Oct 18, 2026 at 8:00 AM

    The Bimblers Bluff 50k is an off road foot race that starts at Guilford Lakes School, 40 Maupas Rd, Guilford. Runners will enjoy peak fall New England colors as they traverse through several inter-connected woodland preserves in southern Connecticut. Consisting entirely of rolling forest roads or single track that can be extremely rocky, the course will provide a true test of the runner’s fitness and mental stamina.It's intended to be both an adventure and a challenge and you should only consider entering this race if you are confident you have sufficient running experience such as having completed a recent road or trail marathon. If you have any questions or concerns about your ability to complete this race but would still like to enter, please contact the race director.

    Race Day Schedule

    • Check in from: 06:00

    • Race Start: 8:00

    • Post race refreshments available from 12:30

    Course Cut Off

    Unfortunately cutoffs are necessary to ensure everyone is of off the course before dark, plus the volunteers have homes to go to!

    • Braemore Aid Station 13:00

    • Renee's Way Aid Station: 15:00

    • Route 80 Aid Station: 17:00

    • Finish 18:00

    Entry Fees

    • Before August 1 - $60

    • Before October 1 - $65

    • Thereafter - $75

    • Registration closes at 7:45 am on race day

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    50kRunTrail via RaceRoster
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