October in Guilford and Madison: The Walks Both Towns Actually Put on the Calendar
What's happening in Guilford and Madison, CT this October? Both towns run free guided walks straight through the fall — Guilford's sunset walk on the Paul Trail October 10 and a Full Moon Hike October 24, and the Madison Land Conservation Trust's Mica Ledges hike October 3.
The Fair packed up Sunday night and our town exhaled. That's usually the week people start asking me the same question: what's actually left on the calendar between now and the holidays?
More than you'd think. And almost none of it shows up on the lists that get shared around.
Here's the thing I've learned in twenty years of working Guilford and Madison — the two towns have some of the best-maintained trail networks in this part of Connecticut, both run by volunteers, both free, and both quietly posting a full autumn schedule that hardly anyone outside the regulars ever sees. So I went and pulled the real dates off the towns' own calendars. Times, trailheads, where to park, all of it.
Guilford's October: three dates with real trailheads
Guilford's calendar is the more detailed of the two right now. These are pulled from visitguilfordct.com/events, checked this morning.
Paul Trail sunset walk — Saturday, October 10, 5:00–6:30 PM
This is the one I'd put on the calendar first. It's an easy walk of about a mile and a half, led by Westwood's Trails Committee chair Paul Proulx, out over rocky outcrops that look down on the 150-acre Great Harbor Marsh with Long Island Sound in the distance. In mid-October, at five in the afternoon, that light is something else.
Meet at the entrance on Sachem's Head Road, across from Community Nursery School. Park on the curb alongside the road and bring a flashlight — you'll be coming back in the dark. Rain date is Sunday the 11th at 5:00.
Full Moon Hike — Saturday, October 24, 5:30 PM
Peddlers Road trailhead. That's what's posted, and that's all that's posted — no distance, no difficulty rating. Bring a light and dress warmer than you think you need to.
Porchfest — Saturday, October 3
Music on porches all over Guilford. I'll be straight with you: the date is the only thing every source agrees on, so check the route before you head out rather than showing up at one spot and hoping.
One more for the walkers — there's an East River Preserve Trail Run on Sunday, September 27 at 8:00 AM, meeting at the large Sullivan Drive lot by the Stump Dump entrance. That one's this weekend, so if you're reading this Monday you've got six days.
Madison's October: the land trust is the answer
For months I couldn't find a decent events source for Madison 06443. Turns out it's been sitting on the town's own site the whole time — the Madison town calendar runs months ahead and carries far more than board meetings.
And what it surfaced is the piece I'd been missing: the Madison Land Conservation Trust. Founded in 1964, one of the oldest land trusts in the country, all-volunteer, protecting close to 2,000 acres across Madison with more than 35 miles of trails on it. That is an enormous amount of protected open space for a town this size, and it is almost never part of the conversation when people talk about what Madison is.
Mica Ledges hike — Saturday, October 3, 10:00 AM
The Trust is marking Mica Ledges' 30th anniversary with a guided hike. The town's listing has the date and the time but not yet the meeting spot, so check madisonlandtrust.org before you go. Worth noting that this lands the same Saturday as Porchfest in Guilford — a hike in Madison in the morning, porches in Guilford in the afternoon, and you've had a very good day without leaving 06443 and 06437.
Murder Mystery Hike — Saturday, October 31
A Halloween history hike, also run by the Land Conservation Trust, built around two 19th-century Madison cases. No time is posted on the town calendar yet. If that's your kind of thing, the Madison Historical Society is running a preview talk at the Allis-Bushnell House on Boston Post Road on Friday, September 25 at 6:00 PM.
What this has to do with selling your house
Here's the connection, and it's more practical than sentimental.
October is when buyers who spent the summer looking actually decide. They've toured, they've compared, they've gotten serious. And in Guilford and Madison, a lot of what closes that decision isn't the house — it's the Saturday. It's whether the town feels like somewhere you'd want to spend a fall.
The numbers say those buyers are still moving. Over the three months ending August 2026, the median sale price in Guilford 06437 was $766,968, up 9.6% year over year, with 66.7% of homes selling above list price. In Madison 06443, the median was $797,155, up 13.1%, with 55.6% above list. Two towns four miles apart, both strong, running at genuinely different speeds.
But here's the piece of October nobody plans for. Homes in Guilford are taking a median of 39 days to sell right now; in Madison it's 43. Which means a house that goes on the market in the first week of October is, on average, still on the market when the clocks go back the first Sunday in November — and suddenly it's dark at 4:30 and every weeknight showing is a showing in the dark.
That changes things. It means exterior photos need to be shot now, while the leaves are still doing the work for you. It means the walk from the car to the front door needs light on it. It means the timer on the lamps matters more in November than it did in June. None of that is expensive. All of it is the difference between a house that shows well at 5:30 PM and one that doesn't.
Frequently asked questions
Are the guided walks in Guilford and Madison free? The Guilford walks listed on the town tourism calendar don't post an admission cost, and the Madison Land Conservation Trust's hikes are run by an all-volunteer nonprofit. Confirm on the event listing before you go, and consider joining or donating to the land trust if you use the trails often.
When is the best time to list a home in Guilford or Madison in the fall? Earlier in October gives you more daylight for showings and better exterior photography than November does. With homes in Guilford 06437 taking a median of 39 days and Madison 06443 a median of 43, a listing that launches in early October is usually still active when the clocks change — so plan the lighting and the photos for that, not for the day you list.
Is Madison or Guilford more competitive for sellers right now? Through August 2026, Guilford had the higher share of homes selling above list price at 66.7% versus Madison's 55.6%, while Madison carried the higher median sale price. Neither is "better" — they're different markets, and the right pricing strategy depends on which one your home sits in.
If you've been quietly thinking about your next chapter, this is a beautiful season to explore your options — and October is a genuinely good month to be on the market in our town.
Call or text me at 203.687.6997 — I'd love to talk through what your home could do in this market.
I'll see you around town.
Jules G. Etes | Guilford | Madison Real Estate Strategist Top 1% Nationally | $283M+ Sold | MBA William Pitt Sotheby's International Realty 203.687.6997 | [email protected] "Opening the doors to your real estate dreams…"
