Porchfest or the Glow Run? Medway Doesn't Actually Have to Pick This September

If you've lived in Medway long enough, you know the unwritten rule of the town's fall calendar: one big Saturday, one big event, and everybody shows up. This year, that rule broke. On September 26, Medway had two major fall traditions scheduled for the same evening, at opposite ends of town.

The Medway Community Farm had scheduled the third annual Porchfest for 1 to 7 p.m. Roughly a mile and a half away, the Medway Police Association had scheduled the eighth annual Police Chase event to begin at 6 p.m. at the Parks and Recreation facility on Holliston Street, with the 5K Glow Run and Walk at 7 p.m. Two different organizations, two different missions, one date on the calendar. The schedules overlapped, making September 26 a busy evening on Medway's fall calendar.

The Farm's Turn to Host

Porchfest started as a grassroots idea: local musicians performing on porches and lawns across town instead of one stage. It's grown enough in three years that the Medway Community Farm at 50 Winthrop Street now anchors the event alongside dozens of smaller sets happening on actual residential porches. The 2026 listing named acts like 4 Exits Down, Ban Jo Bullywug, and Ben Diagram; it described the event as sponsored by the Medway Cultural Council and free to attend.

Two weeks earlier, on September 12, the farm had hosted FarmFest from noon to 4 p.m., with food trucks including Wootrucks, The Dogfather, Mac Daddy, Easy Street BBQ, and C&C Ice Cream. That's two headline community events at one location inside a single month, which says something about how central the farm has become to Medway's social calendar beyond its original mission of local food access.

Across Town, the Glow Run Changes Its Course

The Police Chase 5K has its own history worth knowing. In its early years, the race launched from Medway High School. By its seventh running in 2025, organizers moved it to a brand-new route at the Parks and Recreation facility on Holliston Street, the first route change in six years. The published schedule for the eighth annual event at that location listed the Kids Fun Run Obstacle Course at 6:30 p.m. and the 5K Glow Run and Walk at 7 p.m., with both scheduled to finish by 8:30.

The race isn't just a fun night out. Proceeds fund Medway High School football and hockey, Medway Youth Baseball, Medway Amateur Basketball, the Medway Lions Club, and Medway Boy Scouts. Bib pickup had been scheduled for two days before the race at Mickey Cassidy's Restaurant on Main Street, so the event logistics ran through a familiar local business rather than an anonymous check-in tent.

What the Overlap Meant

The published schedules overlapped: Porchfest was scheduled for 1 to 7 p.m., while the Police Chase event was scheduled to begin at 6 p.m. The Kids Fun Run was listed for 6:30 p.m. and the 5K for 7 p.m. The schedules allowed time to attend parts of both events, but not all of both.

That overlap reflects how much programming Medway's organizations had scheduled for the fall. A town that used to fit its fall traditions into a single weekend now needs the whole day to hold them.

The 2026 fall calendar included these scheduled events:

• September 12 — FarmFest at Medway Community Farm, noon to 4 p.m., food trucks and family activities
• September 26 — Porchfest at Medway Community Farm, 1 to 7 p.m., free and open to the public
• September 26 — Police Chase 5K Glow Run and Kids Fun Run, 123 Holliston Street, 6 to 8:30 p.m.
• October 30 — Pumpkin Walk at Choate Park, hosted by the Friends of Choate Park, 7 to 9 p.m.

The Night Ends at Choate Park in October

The Pumpkin Walk deserves its own mention because it's the town's quietest tradition and its most particular. It's a flashlight-only event, no exceptions, where residents drop off carved pumpkins under the pavilion earlier in the day and the park goes dark by evening so the display can glow on its own. Parking during the walk shifts to Cassidy Fields off Winthrop Street rather than the park itself, a detail that trips up newcomers every year who show up expecting to park where they always have.

Medway's Main Street offers several dining options. Restaurant 45 has anchored the corner since 2003 with the kind of steady, reliable menu that doesn't need reinventing. Medway Cafe keeps its pub-style crowd happy on the same street. And Kawaii Sushi Asian Fusion is the newer name in town, a fusion spot that's been quietly building a following since it opened.

None of this is a reason to move to Medway. It's a reason to notice the town you already live in: familiar traditions and newer events give its fall calendar a character all its own.

If you're weighing a move within Medway, thinking about a renovation before winter, or just curious what a specific street or listing might be worth in the current market, Francis Curran has spent decades working these South Shore and MetroWest suburbs and knows this town's rhythms as well as its market. Browse more neighborhood guides on the Neighborhoods page, or reach out directly through Contact whenever you're ready to talk. Let's Connect.