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2 cycling, running, and walking events in Watertown, Massachusetts

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

2 events
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Watertown

2 events in Watertown
  • Sat, May 02, 2026 at 8:30 AM

    [StStephensLogo.jpg]

    Welcome to the fourth annual SSAES 5k to support St. Stephen’s Armenian Elementary School (“SSAES”), a private, bilingual school serving students from preschool through grade 5 in Watertown MA. Founded in 1986, SSAES currently serves 160 students from more than 15 zip codes in the Boston area, providing a curriculum that is a unique blend of the arts, humanities, STEM, Armenian studies, and experiential learning. Please visit www.ssaes.org to learn more about our school!

    The money raised from this year’s race will go directly to support funding of school programs. We look forward to seeing the community again for this annual tradition!

    Race Day Details

    Our 5k course will begin and end on Artsakh St. in front of St. Stephen’s Armenian Apostolic Church and will be officially timed by Second Wind Race Timing.

    • Runners and walkers are welcome!

    • Bring the kids! Family friendly entertainment will be provided following the race

    • Prizes will be awarded to the overall 1st place male and female finishers and the top male and female runner by age group, and also to the fastest team!

    Schedule

    • Check-in and day-of registration starts at 7:30am

    • There will be no registration after 8:00am

    • Race starts at 8:30am

    • Awards will be presented after the race

    Donations

    • Whether you choose to register for the race or not, we welcome you to consider making a donation to the school in honor of our 5th annual 5k. Click here to donate
    See full details
    5kRunWalk via RunSignup
  • Mount Auburn Cemetery Maintenance Garage #20 Cottage Street, Watertown, Massachusetts, 02472, United States
    OpenStreetMap Google Maps
    Fri, Jun 19, 2026 at 8:00 AM

    Join MassBike and coalition partners on Friday June 19, 2026, for the fourth annual Kittie Knox Ride! This community bike ride around Boston, Cambridge, Watertown, and Waltham features the history of Katherine “Kittie” Knox, a bi-racial woman cyclist and barrier-breaker in the 1890s.

    Riders will learn about Kittie as a bicycling pioneer and we’ll ride and reflect on issues we’re facing today in terms of racial and gender representation in bicycling and advocacy. A historical site summary will be provided for this ride by local historian Larry Finison, author of “Boston's Cycling Craze, 1880-1900".

    The rain date for this event will be June 21, 2026. Details on times will be announced soon.

    Check-In and Start Times

    • 35-mile riders: 2:30pm

    • 20-mile riders: 2:30pm

    Start Time: 3:00 pm

    End Time: The event will end around 7pm.

    Stick around after the ride for food and conversation with your fellow riders and take a tour of Mount Auburn to visit Kittie's gravesite.

    Riders will leave in groups of 10 with a ride leader based on check-in time. If you would like to ride with a friend, plan to arrive at the same time to be put together in a group.

    Routes

    There are two routes for the Kittie Knox Ride, both will start at the Mount Auburn Cemetery Maintenance gate entrance off Cottage Street (24 Cottage St, Watertown, MA 02472). Bikes are not allowed in the cemetery but the start point is accessible from the Watertown-Cambridge Greenway bike path.

    While this ride will be guided, we ask participants to download the GPS file or print cue cards in advance.

    • 20-mile Route

    • 35-mile Route

    Volunteer

    We’re seeking ride leaders to guide our rides and check-in support! If you have friends/family/bike enthusiasts in your life who may want to volunteer to support rider check-in or rest stops, sign up for the volunteers categories above!

    Please only sign up to be a ride leader if you have experience.

    If you have any questions, please reach out to MassBike at [email protected].

    See full details
    Cycling via BikeReg
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