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  • Annual Dennis Road Race & Walk [runsignup.com]

    Sat, Jul 25, 2026 at 10:00 AM

    Description

    We would like to welcome back the running and walking community to help support our wonderful programs and scholarships for kids in the Dennis area.

    Awards and Post Race Celebration outside at Wixon...

    We would like to welcome back the running and walking community to help support our wonderful programs and scholarships for kids in the Dennis area.

    Awards and Post Race Celebration outside at Wixon School! Benefits Dennis Recreation Department Programs and Scholarships. Free shirt to first 100 online entrants.

    10am start time for both the 5 Mile Run and 3 Mile Walk. Free kids 1 mile fun run prior to main event.

    Day of race registration fee of $35

    There will only be bib pick up day of event.

    6.2 km from East Dennis
    Dennis, Massachusetts, 02660, United States
    OpenStreetMap Google Maps

    3 Miles 5 Miles Fun Run Run Walk

  • GutCheck Cape Cod [gutchecktriathlon.com] [Register at runsignup.com]

    Sat, Sep 19, 2026 at 9:00 AM

    Description

    EVENT INFORMATION

    After five successful years as one of the most difficult sprint triathlons in the world, The GutCheck was reconfigured in 2019 as a point-to-point adventure race within Cape Cod’s...

    EVENT INFORMATION

    After five successful years as one of the most difficult sprint triathlons in the world, The GutCheck was reconfigured in 2019 as a point-to-point adventure race within Cape Cod’s 2000-acre DCR Nickerson State Park. Each year, the course will be different — and no one knows exactly what it will be until shortly before the race. Just know that it will be an endurance workout you won’t soon forget!

    WARNING!

    This is a race for intermediate athletes. Expect cold water, steep hills and difficult cliffside running trails paved with tree roots. While there will be emergency medical support on-site, all participants race at their own risk.

    HOW IT WILL WORK:

    Until shortly before the race, all you’ll know about this year’s GutCheck is that it will combine running, cycling, navigating and water crossing (paddleboard or swimming) in Nickerson State Park. You will present yourself at designated checkpoints along the way. Expect a finishing time of 1 to 2 hours. Whether you compete solo or with a group of your friends (2, 3 or 4 persons), the objective is to use your wits and fitness to scramble your way (including 92 steps built into a cliff) to the finish.

    THE COURSE

    Athletes will receive laminated maps that have checkpoints pre-marked before the race. You will navigate between checkpoints using the map and compass. Teams must check in at all checkpoints and the finish line together. Segments will be categorized as either a run, bike, or swim/paddle discipline. Keep in mind that you may have multiple running, biking, and swim/paddling legs that alternate throughout the race. Also, unlike a relay, 2, 3 or 4-person teams compete together the entire race. This is a point-to-point race, there is no central transition area so plan accordingly.

    HOW SHOULD I PREPARE?

    Prepare yourself for this event by training to be capable of trail running and biking for two-plus hours. There will be no more than four swim segments, and each swim segment will be 1/2 mile or less. Paddle segments will be longer. Biking elevations range from -5% to 8% grades, running elevations up to 18% grade. You can choose between swimming or paddleboarding. Bring your own, or a limited supply will be available to rent. Be prepared for a mile+ of total paddling or 3/4 of total swimming. Be prepared to read and follow the supplied trail map. There will be four race categories: solo, two-person, three-person and four-person. All members of a team race the entire course together, remain in close contact and finish at the same time.

    DISTANCES

    Be prepared to:

    Paddle 1 - 1.5 miles or Swim .5 - 1.0 miles

    Bike (steep hills) 5 - 10 miles

    Run (technical trails) 4 - 6 miles

    USA TRIATHLON

    This is a USAT Sanctioned race! That means that we meet or exceed strict guidelines set by USA Triathlon. This benefits the athlete by providing additional insurance coverage in case of injury.

    You are required to have either an annual or 1-day (Bronze) USA Triathlon membership in order to race in any USAT-sanctioned event. Non-USAT members will be required to purchase a one-day event insurance license from USA Triathlon for $14.99.

    GEAR LIST

    Road Bike

    Bike Helmet

    Paddle board w/ paddle or surf board

    Life vest or safe-swimmer buoy

    If swimming; dry bag for shoes, map etc.

    Running (or trail) shoes that don't mind getting wet

    We'll supply the laminated map

    ADDITIONAL RECOMMENDED GEAR

    Marker to be used on laminated map

    Long pants, tights or leg protection

    Sunglasses or hat

    Bug spray

    Sunscreen

    Compass

    Dry bag or safe swimmer buoy with inner compartment

    RACING AS A TEAM

    Each person registers as an individual, noting the name of your team during the registration process. This avoids the hassle of one person registering the team but then needing to gather info and collect money from everybody. Team members can also decide prior to the event to "race solo," or vice versa. On race day each member of the team must go through check points and finish line together. May the fastest... and smartest... teams win!

    CAN TEAMS SHARE A PADDLEBOARD?

    Yes! Up to 2 team members can be on 1 paddleboard at a time.

    TRANSFER/REFUND POLICY

    There will be no refunds , transfers or wait list.

    TIMING

    Results are expected to be posted to the GutCheck website and the NEEE website with in one day.

    TRAVEL

    For those traveling from afar, Cape Cod is awash with hotels, motor lodges, inns, bed and breakfasts, vacation cottages and AirBnB offerings.

    6.6 km from East Dennis
    Brewster, Massachusetts, 02631, United States
    OpenStreetMap Google Maps

    Cycling Run Swim Trail Triathlon

  • Paul Funk's Dolphin Dash [dolphindash.org] [Register at runsignup.com]

    Sat, Oct 03, 2026 at 10:00 AM

    Description

    The mission of the Dolphin Dash is to reduce or eliminate athletic, marching band and color guard user fees for Dennis-Yarmouth High School Students.

    A committee of dedicated volunteers is working...

    The mission of the Dolphin Dash is to reduce or eliminate athletic, marching band and color guard user fees for Dennis-Yarmouth High School Students.

    A committee of dedicated volunteers is working diligently to organize the DOLPHIN DASH 5K ROAD RACE to raise money for the purpose of eliminating high school student user fees.

    We would also like to use this unique opportunity to showcase and celebrate the Dennis-Yarmouth school community and the great things happening in all of our schools.

    We want this to become an annual D-Y DAY & Showcase Celebration.

    The Dolphin Dash is part of the Cape Cod Foundation which is a licensed 501c3.

    8.8 km from East Dennis
    210 Station Avenue, Yarmouth, Massachusetts, 02664, United States
    OpenStreetMap Google Maps

    5k Run

  • ANDREA HOLDEN THANKSGIVING 5K ROAD RACE [andreaholden.org] [Register at raceroster.com]

    Sat, Nov 28, 2026 at 10:00 AM

    Description

    CELEBRATING 25 YEARS!

    The Annual Andrea Holden Thanksgiving 5k walk/run is a non-profit 501(c)(3) organization, dedicated to the health and wellness of children in our local community.

    The race is a...

    CELEBRATING 25 YEARS!

    The Annual Andrea Holden Thanksgiving 5k walk/run is a non-profit 501(c)(3) organization, dedicated to the health and wellness of children in our local community.

    The race is a celebration of the memory of Andrea Holden, a Beautiful and loving Ezra Baker School second grader who suddenly passed away on November, 27, 1990.

    This popular community benefit 5k Run/Walk welcomes all and is held each year on the Saturday after Thanksgiving, starting at the Dennis Inn, on Scarsdale Rd, @ 10:00 sharp. Parking is at the Dennis Playhouse.

    About buying Andrea Holden Shirts

    This year we are going to stay with the long sleeve cotton shirts.

    We offer sizes:

    Youth large, Woman's small,medium, large, Men's medium, large, X-large, XX-large.

    SPONSORS

    This race has become an amazing community event, with so many of our family, friends, and neighbors coming together to celebrate a beautiful little girl lost way too early.

    This is our 25th year, and we would love you to consider becoming one of our local sponsors.

    Road signs Business name, two sided, along the race route $100 donation

    One line Business name on the line of shirt, plus road sign $150 donation

    Small logo Smaller business logo on shirt, plus road sign $250 donation

    Large logo Larger business logo on shirt, plus road sign $500 donation

    Gold level Large Logo on shirt, road sign, 5 free registrations $1000+ donation

    For donations of $150 or over you receive a shirt. Men's shirt: size_____ Woman's shirt size______

    Andrea Holden Thanksgiving Race - P.O.Box 542, South Dennis, Ma 02660

    3.9 km from East Dennis
    25 Scarsdale Road, Dennis, Massachusetts, 02638, United States
    OpenStreetMap Google Maps

    5k Road Run

  • Old Town House Park parkrun [parkrun.us]

    Every Saturday at 9:00 AM

    Description

    parkrun is such a simple concept: turn up every Saturday and volunteer, walk, jog or run 5k.

    9.1 km from East Dennis
    Old Town House Park, 144 Old Town House Road South, Yarmouth, Massachusetts, 02664, United States
    OpenStreetMap Google Maps

    5k parkrun Run Walk

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