The One Saturday That Carries Medway's Whole September

"We have had no significant traffic issues over the years with these events due to everyone taking their time and being patient." That's Medway Police Chief Kingsbury, in a department notice sent out ahead of a Saturday last September when the town ran a yard sale, a music festival, and a food drive all at once. He wasn't complaining. He was managing expectations, because he already knew what was coming.

This year, the cast changes but the pattern holds. On Saturday, September 26, 2026, Medway is once again asking residents to hold two very different events in their head at the same time. The details are different from last year's lineup, but the habit is the same: rather than spreading its fall calendar out, Medway keeps compressing it into single, crowded Saturdays.

The Same Saturday, Two Signups

The afternoon belongs to Porchfest. The third annual Medway Porchfest runs from 1 to 7 p.m., with a rain date the following day if Sunday turns out to be the better call. It's sponsored by the Medway Cultural Council, and the format is the same one that's made porchfests popular across New England towns: local musicians set up on porches and in yards around town, and people wander from site to site with a blanket or a folding chair. There's a hub at Medway Community Farm on Winthrop Street, but the festival itself has no single center. It's built to spread out. A regional guide that tracks these events counted roughly 50 acts across about 29 host sites in a recent edition, and that's the kind of scale that turns ordinary residential blocks into informal concert venues for an afternoon.

The evening belongs to something completely different. The 8th Annual Medway Police Chase 5K Glow Run/Walk and Kids Fun Run Obstacle Course, organized by the Medway Police Association, runs from 6 to 8:30 p.m. at the Parks & Rec facility on Holliston Street. Unlike Porchfest, this one has a single address and a fixed structure: registration, a start time, a course. Bib pickup happens two days early, on Thursday, September 24, from 5 to 7 p.m., at Mickey Cassidy's Restaurant on Main Street, with a second pickup window on race day itself starting at 6 p.m. at the Parks & Rec building. Proceeds go to a list of local groups that will sound familiar to anyone who has a kid in town sports: Medway High School Football and Hockey, Medway Youth Baseball, Medway Amateur Basketball, the Medway Lions Club, and the Medway Boy Scouts, among others.

So on paper, you've got a free, sprawling, all-ages music crawl in the afternoon, and a timed, single-location charity run after dark. Different organizers, different purpose, same calendar square.

Where the Overlap Actually Is

The two events aren't back to back. They actually stack for about an hour, from 6 to 7 p.m., while Porchfest is still going and the Glow Run is getting underway. That means if you're the kind of person who wants to catch a last set on somebody's porch and then head over to watch (or run) the 5K, you have a genuinely tight window, especially once you account for parking near either location.

But the geography works in your favor more than you'd expect. Porchfest's hub sits at 50 Winthrop Street, on the farm. The Glow Run starts at 123 Holliston Street, at the Parks & Rec facility. Those are two different corners of town, connected to two different sets of neighborhood streets. Most Porchfest attendance is dispersed across whichever porches people choose to visit, not concentrated at the farm, so the actual traffic pattern in the late afternoon is a lot of small pockets of people walking short distances, not one crowd converging on one address. The Glow Run, by contrast, is exactly the kind of event where everyone arrives and leaves at roughly the same time from roughly the same parking area.

If you live near Holliston Street, expect the evening crunch. If you live near a Porchfest host site, expect afternoon foot traffic and cars moving slowly as people look for parking spots near a porch they don't know the address of yet. Neither event depends on the other, but both depend on drivers being patient, which is exactly what Chief Kingsbury was getting at.

This Has Happened Before

Last year's version of this same Saturday, September 27, 2025, stacked three things instead of two: a town-wide yard sale with 65 individual home sales plus 13 more consolidated at a central location on Holliston Street, Porchfest running 2 to 7 p.m. with its own significant gathering at the farm from 2 to 6 p.m., and a food donation drive called Box Out Hunger collecting bins at multiple points around town, including the police station on Village Street. That's three separate volunteer-run efforts, three separate organizing bodies, landing on one Saturday.

The town's own police notice about that day didn't ask people to spread the events out. It just asked people to drive carefully and expect minor delays, and noted that this had never actually caused a problem in past years. That's worth sitting with for a second. Medway isn't accidentally overlapping events. It's a town where volunteer organizations, the farm, the cultural council, the police association, all seem to gravitate toward the same late-September weekend, year after year, and the town has simply built its expectations around that instead of trying to untangle it.

Three Addresses, One Month

Zoom out past just the 26th and you can see the same clustering happening across the whole month at three different addresses. Medway Community Farm runs its own FarmFest on September 12, two weeks before it hosts the Porchfest hub, at that same Winthrop Street location. Then, about five weeks after the Porchfest and Glow Run weekend, the town's Pumpkin Walk lights up Choate Park starting at 7 p.m. on October 30.

That's three distinct gathering points doing three distinct kinds of programming within about seven weeks: the farm running its own harvest-season event, then hosting a music festival hub, the Parks & Rec facility running a nighttime charity race, and Choate Park closing out the season with a Halloween-adjacent evening walk. None of these are especially large venues by regional standards, but together they cover most of what a resident might want out of a fall weekend without leaving town.

If You're Only Free for One

Given the overlap, here's the practical version of the day:

• If you want the full Porchfest experience, plan to be moving between sites through the early evening. The festival runs until 7, so you'll be out past the point where the Glow Run has already started elsewhere in town.
• If the Glow Run is the priority, especially for families doing the Kids Fun Run Obstacle Course, get to the Parks & Rec facility with enough buffer before 6 p.m. registration and skip the Thursday bib pickup at Mickey Cassidy's if your schedule allows, since it saves you a stop on race day itself.
• If you're trying to do both, treat the 6 to 7 p.m. window as your pivot point. Anything you want to see at Porchfest needs to happen before then, and anything at the Glow Run needs to happen after.
• Either way, expect slower traffic near Holliston Street in the evening and slower traffic near whichever porches draw the biggest afternoon crowds. Neither is a sign anything's gone wrong. It's just what a Medway Saturday in late September looks like now.

None of this requires advance tickets or reservations. Porchfest is free, and the Glow Run has its own registration process for anyone who wants to run rather than just watch. The only real cost of the day is picking which parts of it you can fit in.

A Note From Eileen

I've lived and worked in this part of Massachusetts long enough to notice when a town has a rhythm, and Medway's September rhythm is a real one. Knowing which weekends the whole town shows up, and where, is the kind of detail that doesn't show up in a listing description but matters once you're actually living somewhere. If you're thinking about what it's like to be a Medway resident day to day, not just what a house costs, I'm always glad to talk through it. You can reach out through Eileen Mason Realty any time. Let's Connect.