On your mark, get set, register! Spring is road race season, and Wellesley and area towns welcome runners of all talent levels for a host of runs. There’s still plenty of opportunity to train, so hop off that couch and put in the miles.
Don’t see your local road race listed here? Email theswellesleyreport@gmail.com for inclusion.
Wonder Run—Wellesley
DATE: Sunday, May 17, 2026
START LOCATION: Wellesley High School track, 50 Rice St.
DESCRIPTION: The Wonder Run is a celebrated part of Wellesley Wonderful Weekend. Sponsored by the Wellesley Hills Junior Women’s Club, hundreds of participants and great community support are anticipated again this year. Proceeds generated from the Wonder Run directly support community groups, scholarships for deserving local students, and grants to organizations and programs that provide education, enrichment, and essential services to the local population.
REGISTER HERE
Walk to End Homelessness—Natick
DATE: Sunday, May 3, 2026
LOCATION: Natick High School, 15 West St.
DESCRIPTION: Join Family Promise Metrowest at Natick High School for a 2.3 mile walk to help raise funds and awareness about the impact of lack of affordable housing on families in our community. All funds raised support programs that help families stabilize their housing and build brighter futures.
PERKS: Food, music, and fun are free!
REGISTER HERE
NCLS Dragon’s Path & CAAN Newton AAPI 5K/1K Race
DATE: Sunday, May 10, 2026
LOCATION: 154 Wells Ave., Newton
DESCRIPTION: A joyful celebration of Mother’s Day, Asian American and Pacific Islander (AAPI) Heritage Month, healthy living, and the vibrant spirit of our community! Whether you’re running, walking, or cheering from the sidelines, all ages and abilities are welcome! Enjoy a flat, fast, tree-lined course along the scenic Wells Ave loop in Newton.
REGISTER HERE
Schofield 5k—Wellesley
DATE: Sunday, June 7, 2026
LOCATION: Schofield Elementary School, 27 Cedar St., Wellesley
REGISTER HERE
DESCRIPTION: 9:30m 5K (USATF Certified Course); 10:30am Kids Fun Run & Award Ceremony; 10:45am-12:45pm Fun Fair
Please help The Swellesley Report run with a tax-deductible donation.
These events have passed:
JR’s Paws for a Cause Dog-Friendly 5k walk/run—Natick
DATE: Sunday, April 26, 2026
LOCATION: Natick High School Football Field parking lot (corner of Windsor Ave. and West St.)
DESCRIPTION: Proceeds go to various non-profits that benefit canines.
REGISTER HERE
Dana Chang Foundation 5k Run/1k Walk—Natick
DATE: Sunday, April 26, 2026
LOCATION: Walnut Hill School for the Arts, 12 Highland St., Natick
DESCRIPTION: The Dana Chang Foundation 5K Run/1K Walk is an annual event dedicated to raising awareness about congenital heart conditions and the importance of early detection. This event honors the memory of Dana Chang, a young artist who passed away suddenly in 2024 from an undiagnosed heart condition, and supports programs that promote education, early screening, and community awareness.
REGISTER HERE
Boston Marathon—comes right through Wellesley
DATE: Monday, Apr. 20, 2026
LOCATION: Starts in Hopkinton, ends on Boylston St., Boston
WATCH IN WELLESLEY: The runners will speed through Wellesley via Washington St. Great places to watch—we like the Wellesley College Scream Tunnel; Wellesley Square; in the Town Hall area; near the Hunnewell tennis courts; Sprague Clock Tower area; at the Rec Center.
DESCRIPTION: Although registration has closed for the storied 26.2-mile race, you can cheer on the runners and get inspired for next year.
DONATE to Wellesley runners supporting a variety of non profits.
New Life 5k/10k—Medfield
DATE: Saturday, April 11, 2026
LOCATION: McCarthy Park & Fields, Medfield
DESCRIPTION: Course winds through tree-lined streets, past rolling fields, and along serene nature trails, offering a mix of paved roads and well-maintained paths. Runners will experience gentle hills and open stretches that showcase the town’s beauty, making for a dynamic and enjoyable race experience. Participants of all abilities—from seasoned runners to casual walkers—can enjoy a fun day out.
REGISTER HERE
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