Cambridge Montessori School Webster O'Brien 5K

Cambridge, Massachusetts. Danehy Park. The Cambridge Montessori School Webster O'Brien 5K returns on Saturday, June 6, 2026, starting at 10:00 AM EDT. A three‑loop course circling Danehy Park — each loop uses the park's paved paths, finishing with a sprint to the finish. Honoring Webster O'Brien, a beloved CMS community member, board chairman, and instrumental figure in developing the school's athletics program. A travel stipend will be given to a CMS alum who has graduated from the middle school program. High‑quality synthetic running t‑shirts for all participants (children's and adult sizes).

Location — Danehy Park, Cambridge, Massachusetts:

• Danehy Park is a 50‑acre park in North Cambridge, between Porter Square, Harvard Square, and Fresh Pond
• Address: 99 Sherman Street, Cambridge, MA (start/finish area)
• The park features paved paths, open fields, playgrounds, and a sledding hill — a central part of the Cambridge Montessori School experience
• The course is a loop that circles the park three times before the final sprint to the finish

Honoring Webster O'Brien — Legacy of Leadership and Athletics:

• Webster O'Brien was a beloved member of the Cambridge Montessori community
• Father of two CMS alums, husband of a former CMS teacher
• Served as chairman of the board for four years
• Instrumental in developing the school's athletics program
• The 5k was started to honor Webster and build on his legacy

Travel Stipend for CMS Alum:

• A travel stipend will be given to a CMS alum who has graduated from the middle school program
• To inquire about how to apply for the travel stipend, email cms5k@cambridgemontessori.org

What's Included:

• High‑quality synthetic running t‑shirt (children's and adult sizes — while supplies last; registrations on race day not guaranteed a shirt)
• Finisher medal? Not specified — check event website
• Chip timing? Not specified — likely manual or app‑based timing
• Aid station on course? Not specified — likely water at start/finish
• Medical support? Not specified — likely minimal

Number Pick‑Up — Race Day Only:

• Bibs can be picked up on race day from 9:00‑9:45 AM at the table in Danehy Park
• No pre‑race day pickup mentioned

Parking — Several Lots Available:

• Sherman St. lot across from 96 Sherman St.
• Sherman St. lot by the St. Peter's baseball field
• Garden St. lot next to the CMS Toddler Primary building (161 Garden St.) — 5‑minute walk to the start
• Arrive early — parking in Cambridge can be tight

Logistics — Family‑Friendly, Community Event:

• No refunds? Check with event organizer Nikki Jacobs
• No dogs allowed? Not specified — check event rules (Danehy Park allows leashed dogs, but race course may restrict them)
• Strollers allowed (start at the back)
• Walkers welcome
• This is a community fundraiser, not a competitive elite race — focus on fun and honoring Webster's legacy

Cambridge Montessori School — Montessori Education:

• Cambridge Montessori School (CMS) is a private Montessori school serving toddlers through middle school
• Webster O'Brien's leadership shaped the school's direction and athletic programs
• The 5k is a fundraiser and community‑building event

Nearby Attractions (post‑race — make a day of it in Cambridge):

• Danehy Park — stay to enjoy the playgrounds, walking paths, and open fields
• Fresh Pond Reservation (0.5 mile north) — 2.25‑mile walking/jogging loop around the reservoir
• Harvard Square (1 mile south) — shops, restaurants, bookstores, and Harvard University campus
• Porter Square (0.5 mile east) — dining, shopping, and the Porter Square T station (Red Line)
• Alewife Station — parking and access to the Minuteman Bikeway (paved rail‑trail)
• Downtown Boston (15 minutes east) — Freedom Trail, Faneuil Hall, Boston Common, and the Museum of Science

Contact: Nikki Jacobs via Race Roster.