Weekend Walking Routes for Fall

The best stretch of a long-distance route can be walked in two days, and fall is the finest season to do it.

• Three sections of Italian long-distance routes that close between Saturday morning and Sunday afternoon, with distances and times taken from the official route websites.
• The Sentiero del Viandante on Lake Como is the easiest to organize, because every stage end has a train station.
• The Umbrian stretch of the Via di Francesco climbs on foot toward Assisi from the hills, then drops through olive groves toward Spello.
• In fall the variable that decides your day is light rather than mileage: count the usable hours before you leave.

A full route takes ten days, and the vacation days ran out in August. The way around it is to take the stretch that holds the best of that route and walk it over two days, sleeping one night halfway. Fall is when the idea works best: the heat is gone, the hills of central Italy are walkable again at midday, and the woods turn color in the same weeks the trails empty out.

Two Days Are Enough for a Stretch That Counts

Three conditions decide which section to take, and mileage is the last of them. You want an arrival worth the trip, because walking toward something changes your pace. You want a town at the halfway point where you can sleep and eat. And you want a way back to the start on public transit, otherwise the only option left is a second car parked at the finish, which doubles the logistics and halves the appetite.

Walking for two days covers the part that the other eight days exist to reach, rather than a scaled-down version of the whole. The difference is practical as much as it is a matter of principle, because a multi-day route asks for a different kind of planning, built on load management across the week, laundry in the evening, progressive recovery. Over two days all of that disappears. What’s left is a light pack, one change of clothes, and a train timetable.

As a working measure, a comfortable day runs between seven and twelve miles on mixed ground. Past fourteen you’re in another category: it can be done, but the afternoon turns into a march and you end up seeing the arrival town from a chair.

The Three Routes

The Sentiero del Viandante, the Wayfarer’s Path, runs at mid-slope along the eastern shore of Lake Como, above the railway and the main road, on old mule tracks. The natural weekend starts at Abbadia Lariana, sleeps in Lierna, and closes at Varenna: about twelve and a half miles in total, with the lake below you the whole way and a chestnut wood that drops burrs on the trail in October, so you walk on a carpet that crunches. Of the three, this is the one I’d suggest for a first walking weekend, and that has less to do with the distance than with the rail line following the shore, a station in every town, which turns the trip home into a ten-minute matter.

The Umbrian stretch of the Via di Francesco between Gubbio and Spello runs to nearly forty miles and splits into four days. The portion worth a weekend is the final one: Saturday from Valfabbrica to Assisi, 8.3 miles with three quarters of it on dirt, the last section opening onto the valley and showing the Basilica from a distance; Sunday you leave Assisi for Spello along the stage that continues to Foligno, through terraced olive groves on the flanks of Monte Subasio. The climb through the woods that opens the Valfabbrica day is the best part of the whole stretch, and it deserves Saturday-morning legs rather than Sunday-afternoon ones.

In Tuscany the classic weekend is the pair of Via Francigena stages linking San Miniato to Gambassi Terme and then Gambassi to San Gimignano. Twenty-three miles all told, almost all of it on the ridges of the Val d’Elsa, with medieval pievi marking the way and a short second day that leaves the afternoon free for the town of towers. It’s the most demanding of the three, thanks to the nearly six full hours of the first day.

Distances, Times, and Getting Back to the Start

Two notes on the return trips. The Assisi station sits at Santa Maria degli Angeli, two and a half miles below the town and connected by city buses; Valfabbrica has no railway and is reached by intercity buses from Perugia or Assisi, which in fall run on the school calendar and need checking before you leave. San Gimignano is in the same position: no train, and buses toward the Valdelsa towns that do have a station.

What Changes When You Walk in Fall?

In fall, light is the constraint rather than mileage, and it has to be counted backward. A five-hour stage takes seven once you add the stops and the long midday break, so a nine o’clock start leaves you margin for as long as the sun goes down at seven. Once the clocks go back at the end of October, the light is finished by five in the afternoon: the same stage has to start two hours earlier, or get shorter.

The second change is underfoot. Wet leaves over stone, and the stepped sections of the mule tracks, make the most treacherous surface of the year, because they hide what’s underneath and give no warning when they give way. On long descents, trekking poles stop being an accessory and become two more points of contact.

Then there’s the temperature swing, which in the hills in fall can pass 18°F between dawn and early afternoon. You start cold, you’re sweating within twenty minutes, and by four the slope falls into shadow and the temperature drops all at once, the way it does when you step into a cellar. You handle it by dressing in thin layers and taking the first one off before you start sweating, rather than after. The trade-off runs enormously in your favor: you walk all day without chasing shade, and the hill towns in October are beautiful.