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13 events in Worcester County, Massachusetts

From big races to Saturday morning group runs—find running, cycling, triathlon, and swimming events and connect with the local endurance sports community.

  • Harvard Lions Winter Fest 5K [winterfest.harvardlions.com] [Register at runsignup.com]

    Sun, Mar 01, 2026 at 11:00 AM

    Description

    Brrrrrrr.....it’s cold out there, but enough of this cabin fever! Our 5k road race is a great excuse for you to bundle up and go for a run. Bring the family and enjoy our Winter Fest after the race....

    Brrrrrrr.....it’s cold out there, but enough of this cabin fever! Our 5k road race is a great excuse for you to bundle up and go for a run. Bring the family and enjoy our Winter Fest after the race. The faster you run, the warmer you’ll be!

    This well marshaled race is on plowed roads and is chip timed. Racers have free admission to Winter Fest and will be provided with coupons toward the event! Donations to the Harvard Lions Club are always welcomed. More info here: winterfest.harvardlions.com

    5k Run

    14 Massachusetts Avenue, Worcester County, Massachusetts, 01451, United States
    OpenStreetMap Google Maps
  • Patrick Cumming Memorial St. Patrick's Day 5K [runsignup.com]

    Sun, Mar 15, 2026 at 10:00 AM

    Description

    The second annual Patrick Cumming Memorial St. Patrick's Day 5K will be held on Sunday, March 15th at 10am at Krashes Field in Princeton, MA in partnership with the Princeton Firefighter's...

    The second annual Patrick Cumming Memorial St. Patrick's Day 5K will be held on Sunday, March 15th at 10am at Krashes Field in Princeton, MA in partnership with the Princeton Firefighter's Association.

    This race is being held to support the Patrick Cumming Memorial EMS Scholarship Fund and to remember an amazing son, brother, firefighter, soldier and friend. The race will be held rain or shine-and we know that March weather in New England can be tricky! Please join us to honor Patrick's legacy and support our local community.

    Professional race timing, race shirts to the first 250 registrants, food and beverage trucks and music will all be provided. Medals awarded to top three male and female and top male and female youth (under 18) finishers. USATF sanctioned course.

    We look forward to seeing you there and are grateful for your support!

    3.1 Miles 5k Run

    100 East Princeton Rd., Worcester County, Massachusetts, 01541, United States
    OpenStreetMap Google Maps
  • New England OCR Expo 2026 [runsignup.com]

    Sat, Mar 28, 2026 at 8:00 AM

    Description

    Come join the New England OCR Expo for the Largest Celebration of Obstacle Course Racing on March 28th at Ultimate Obstacles! In 2026, we'll be celebrating and honoring America & Our Nation's Heroes....

    Come join the New England OCR Expo for the Largest Celebration of Obstacle Course Racing on March 28th at Ultimate Obstacles! In 2026, we'll be celebrating and honoring America & Our Nation's Heroes.

    Eat, drink, and mingle with fellow racers, with representatives from your favorite race series and many race/health/fitness-related vendors & sponsors from across New England and beyond! Go home with one of many giveaways, discounts, and raffle prizes from the sponsors & vendors! Every guest (14 +) receives a coupon code for 1 FREE Spartan Race at ANY 2026 US or Canada location - Sprint, Super or Beast!

    The New England OCR Expo is passionate about giving back to our heroes! In 2026, our charity partner is Oscar Mike. $5 from every New England OCR Expo ticket will be donated to Oscar Mike's incredible mission. Oscar Mike's mission is to build a vibrant, connected community that keeps America and her Veterans "On-the-Move" by actively supporting and improving mobility, accessibility, mental health, and well-being. Imagine a world without barriers, new adaptive facilities, and expanding adaptive programs. Getting "On-the-Move" has touched countless Veterans' lives.

    Also, support New England OCR Expo's valued partner- Operation Enduring Warrior by registering for the OEW Virtual 5K.

    Operation Enduring Warrior's Mission: HONOR. EMPOWER. MOTIVATE OUR NATION'S WOUNDED MILITARY & LAW ENFORCEMENT OFFICERS. NON-PROFIT 501(c)(3).

    How the Virtual 5K works?

    1.Complete the OEW Virtual 5K at your convenience.

    1. Post the results

    2. Tag #OperationEnduringWarrior, #OEWSupporter and #neocrexpo.

    3. Pick up your medal at the New England OCR Expo on March 28, 2026. If you need the medal shipped, there is another registration option that includes the $10 shipping charge.

    Gaylord Specialty Healthcare has been named the beneficiary of the New England OCR Expo Teddy Bear Crawl. Gaylord Specialty Healthcare is located in Wallingford, Connecticut, on a beautiful 400-acre campus. As a leading health system exclusively dedicated to medical rehabilitation, they offer a comprehensive continuum of care. Whether you're seeking inpatient or outpatient services, we stand by you at every step of your journey, from illness or injury to attaining the highest level of recovery imaginable.

    Again this year, besides the Olympic-style 100M course and DEKA STRONG hosted by Ultimate Obstacles, the New England OCR Expo is excited to offer a FREE kids course presented by Obstacle Wonderland at Wallkill, NY. While the next generation of racers grow their love for the sport, donations will be accepted for WONDERKIDS. And to make the day even more special, medals and incredible kid swag will be awarded while the giveaways last. Bring the whole family to the New England OCR Expo. FAMILY FUN FOR EVERYONE!

    Trophies will be awarded to top female and male athletes, and the NEOCR Expo will crown the Ultimate Champion, measured by results from 100M and DEKA events combined. Watch for the 100M exclusive medal!

    Register today! Come create priceless memories with the New England OCR Expo family!

    DEKA STRONG REGISTRATION LINK

    If you are registering for the DEKA STRONG you do not need to register for the EXPO- The EXPO and the FREE Spartan Race is included in your registration on the DEKA STRONG site. If you are planning to register for DEKA STRONG click the link above.

    5k Spartan Virtual

    121 Shrine Ave, Worcester County, Massachusetts, 01583, United States
    OpenStreetMap Google Maps
  • Bulfinch Bee Run [runsignup.com]

    Sat, May 02, 2026 at 11:00 AM

    Description

    We are very excited to host our fourth annual "Bulfinch Bee Run" on May 2, 2026! The name is inspired by the huge colony of bees that was discovered and rescued from our bell tower in 2011 during...

    We are very excited to host our fourth annual "Bulfinch Bee Run" on May 2, 2026! The name is inspired by the huge colony of bees that was discovered and rescued from our bell tower in 2011 during renovation. This will be a 5k community fun run/walk/roll (costumes highly encouraged!) in the neighborhood of Lancaster's historic Bulfinch Meetinghouse. It will conclude on the lawn with food, beer, prizes, live music and more! The proceeds this year will offset our costs for our Community programming and building maintenance.

    Age 0-5 Free

    Age 6-18 $20

    Don't Wait! First 100 registrants will receive this years T Shirt!

    5k Fun Run Run Walk

    725 Main Street, Worcester County, Massachusetts, 01523, United States
    OpenStreetMap Google Maps
  • LONGEST MILE FOR BRAVEST MINDS [runsignup.com]

    Sun, May 03, 2026 at 11:00 AM

    Description

    Join us on Sunday, May 3, 2026, at 11:00 AM as we kick off Mental Health Awareness Month with the inaugural Longest Mile for Bravest Minds. This professionally timed, one-mile uphill fundraiser takes...

    Join us on Sunday, May 3, 2026, at 11:00 AM as we kick off Mental Health Awareness Month with the inaugural Longest Mile for Bravest Minds. This professionally timed, one-mile uphill fundraiser takes place on scenic Oak Hill Road in Harvard, Massachusetts, climbing 180 feet along a course that may be short in distance but carries powerful meaning. Runners, walkers, families, and first responders will come together for a shared purpose: supporting mental health.

    Hosted by the Harvard Fire-EMS Association, this event will benefit On-Site Academy, a nonprofit in Westminster, Massachusetts, dedicated to serving first responders and military veterans. A portion of the race proceeds will be donated to support their mission. The goal of this event is simple but important: to bring first responder mental health to the forefront and encourage open, honest conversations throughout the entire community.

    First responders and veterans face situations that test even the strongest individuals. Behind every uniform, whether firefighter, EMT, police officer, dispatcher, corrections officer, military member, or hospital staff, is a human being. Some calls leave lasting emotional impacts and recognizing that it is okay to ask for help is a critical step toward healing. Through this event, we stand together to support one another and reinforce that no one must carry those burdens alone.

    The experience continues beyond the finish line at Carlson Orchards, where participants and spectators are invited to stay and enjoy a community celebration. There will be live music, a food truck, and hard cider on tap. Families can also enjoy the Touch-A-Truck, where kids and adults alike can explore emergency vehicles, climb inside, and meet the first responders who operate them.

    First responders are encouraged to participate in whatever way feels meaningful to them. Some may choose to run or walk in turnout gear, a uniform, or a weighted vest. Others may simply show up and stand alongside their peers. Every step taken is a visible reminder of solidarity and support for mental health.

    Whether you run, walk, jog, or cheer from the sidelines, this event is open to everyone. You can make it competitive, casual, or simply a chance to be part of something bigger than yourself. One mile. One hill. One community, united for mental health.

    Sign up, lace up, and join us!

    NOTE: IF YOU ARE CREATING A TEAM AND SIGNING UP 5+ RUNNERS, PLEASE USE THE CONTACT LINK BELOW TO REQUEST A DISCOUNT CODE.

    1 Miles Run Walk

    115 Oak Hill Rd, Worcester County, Massachusetts, 01451, United States
    OpenStreetMap Google Maps
  • Longest Mile for Bravest Minds [runsignup.com]

    Sun, May 03, 2026 at 11:00 AM

    Description

    Join us on Sunday, May 3rd at 11:00 AM for the Longest Mile for Bravest Minds, a one mile fun run and walk with a powerful purpose. This scenic course climbs Oak Hill Road in beautiful Harvard,...

    Join us on Sunday, May 3rd at 11:00 AM for the Longest Mile for Bravest Minds, a one mile fun run and walk with a powerful purpose. This scenic course climbs Oak Hill Road in beautiful Harvard, Massachusetts and offers a challenge that is short in distance but big in meaning.

    This event is a fundraiser benefiting the Harvard Fire-EMS Association, with a strong focus on mental health awareness for first responders and the community as a whole. A portion of the proceeds will also be donated to OnSite Academy, supporting their mission to promote emotional wellness, resilience, and connection.

    The fun does not stop at the finish line. After the race, participants and spectators are invited to an after event gathering at Carlson's Orchard, where ciders will be on tap and a food truck will be on site to serve hungry runners and walkers. It is the perfect chance to relax, connect, and enjoy one of Harvard’s favorite local spots.

    At the finish line, families can enjoy a touch a truck experience, giving kids and adults a hands on look at fire and emergency vehicles and a chance to meet the people behind them.

    Firefighters, police officers, EMTs, military members, and all fellow first responders are encouraged to participate in their gear if they choose. Whether you wear turnout gear, a weighted vest, or a uniform shirt, it is a powerful way to show solidarity, raise awareness, and stand together in support of mental health.

    Whether you run, jog, walk, or cheer from the sidelines, this event is for everyone. Make it competitive, make it casual, or make it a team effort. One mile. One hill. One community coming together for mental health.

    Sign up, lace up, and join us for a great cause and a great time.

    1 Miles Fun Run Run Walk

    115 Oak Hill Rd, Worcester County, Massachusetts, 01451, United States
    OpenStreetMap Google Maps
  • Wachusett Mountain Race [wachusettmountainrace.com] [Register at runsignup.com]

    Sat, May 23, 2026 at 9:30 AM

    Description

    Race Fees: Register Early for Best Price!

    $25 for the 3-Mile or 10K race until March 17th

    $35 for the 3-Mile or 10K race until April 20th

    $40 for the 3-Mile or 10K race until May 22nd

    $50 for the...

    Race Fees: Register Early for Best Price!

    $25 for the 3-Mile or 10K race until March 17th

    $35 for the 3-Mile or 10K race until April 20th

    $40 for the 3-Mile or 10K race until May 22nd

    $50 for the 3-Mile or 10K race on race day

    Members of the Central Mass Striders in good standing that are 70 years of age or older on race day are FREE. Please select the correct option when registering. If your CMS membership and age cannot be verified by the close of online registration, your registration may be removed. Please contact Kim at [email protected] with questions.

    We have an official race policy of NO REFUNDS.

    If there is a natural disaster or other type of similar emergency that causes a cancellation, every effort will be made to schedule a postponed race later in the year. However, refunds will not be available. If you need to defer due to medical issue or pregnancy, please contact the Race Director.

    3 Mile and 10K Race Information

    The Wachusett Mountain Race is a proud part of the USATF-NE Mountain Circuit 2026.

    For circuit scoring, you will run the 3 mile course uphill to the top of Mount Wachusett.

    Optionally, you can continue on with us to the Finish Line located at the bottom of the mountain to complete a full 10K. All 10K runners will receive their race split at the top of the mountain (which is the number used for mountain circuit scoring) as well as their 10K time. Either option is the same price.

    Cash prizes for the male, female, and non-binary winners of the 3 Mile Race and the 10K Race.

    Merchandise prizes for the age group winners (0-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-79, 80+) of the 10K race. There are no age group prizes for the 3 Mile Race.

    Mugs for the first 400 runners!

    Packet Pick-Up

    Bib and mug pick-up will be on race day beginning at 8:00 am in the parking lot for the Ski Lodge.

    3 Miles 10k Run

    499 Mountain Road, Worcester County, Massachusetts, 01541, United States
    OpenStreetMap Google Maps
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