10 Bicycle Adventures to Take This October

October is the first full month of fall, and one of the best times to travel. Leaves change from vibrant green to crisp yellows and deep reds. Grapes are plump on the vine, ready for late harvest. Mornings are cool and fresh, inviting an invigorating bike ride. Squeeze the most out of these beautiful days on a bike before winter sets in, and travel during shoulder season in these destinations that are in their prime in autumn.

Culinary treasures are ripe for the picking in October, from fully-formed white truffles to plump olives pressed into extra virgin olive oil. Daytime temperatures stay in the 70s (20 °C) thanks to late-autumn sunshine, but those lesser few degrees make logging the miles a little easier. Spend the days riding through ancient Etruscan villages, and eat with the seasons to discover Tuscany’s distinctive fall flavors—chestnuts, porcini mushrooms, and cinghiale (wild boar).

See October departure dates in Tuscany.

At the tail end of high season, Puglia still has inviting weather in October—plus a relatively low average rainfall. Southern Italy is still plenty sun-drenched but the beaches are blissfully devoid of summer tourists, so the cycling stays quite car-free. Just bring a jacket for the brisk A.M. coastal rides, and the warm espresso you stop for in towns like Locorotondo will taste even better than usual.

See October departure dates in Puglia.

October is a magical time for wine lovers. After September’s grape harvest, Bordeaux goes underground, so it’s all about the cellar as oenologists keep a watchful eye on their new wines. On our tours, producers provide tremendous insight into this crucial moment of vinification, making decisions about blending and barreling. And don’t forget the vineyard rides—this is the brief time of year when the vines turn those fiery fall colors.

See October departure dates in Bordeaux.

With wide-open spaces and unmatched farm-to-table appeal, the Hudson Valley isn’t just a beautiful place to bike—it’s a little slice of pastoral paradise. With departures through October, you can witness the peak of autumn’s golden hues, pedal tranquil country roads, and cozy up by the fireplace at the historic Troutbeck, our charming on-tour retreat.

See October departure dates in Hudson Valley.

In October, the island of Mallorca is peaking. It’s warm enough (average daytime temperatures in the mid-70s or mid-20s °C) that the sea might still be inviting for a post-ride dip! Though it feels like summer, the Tramuntana mountains are starting to turn crimson, and the holiday tourists have headed home. This month, Mallorca also celebrates its seasonal bounty with festivals dedicated to pimentón peppers and sobrasada sausage.

See October departure dates in Mallorca.

Pleasant, warm, and abundant with blue-sky days, Portugal’s cork capital hits its stride when the seasons are changing in other parts of the world. The region’s famous cork trees are stripped in the summer, leaving a gorgeous landscape of ochre trunks behind. During the day, golden hills with grazing sheep look beautifully autumnal, and by night, you can head into wine cellars and homes of our local friends if it’s slightly too cool to dine outdoors.

See October departure dates in Alentejo.

October reveals California wine country at the exact moment when grapes are ripe and ready in the country’s best vineyards. California weather is famous for being seasonal year-round, and rides along the coast and through redwood forests don’t disappoint. The tasting rooms in Healdsburg are open for business, and the excellent oysters from Tomales Bay are always in season.

See October departure dates in Sonoma.

Basque Country is truly special in September and October—harvest time in Northern Spain. On sun-warmed fall days, this interior region is best explored by bike, following the famous Camino de Santiago and staying at Frank Gehry’s famous Hotel Marqués de Riscal. The vineyards of Rioja’s bodegas are shifting from brilliant green to those kaleidoscopic fall hues, and Gran Riserva wines pair perfectly with warming wood oven-roasted lamb and hearty Riojana stews.

See October departure dates in Rioja.

The extreme temperatures of Sicily’s summers can be intense, so an October visit presents just the right weather for riding. It’s also the end of Sicily’s high season, meaning charming cities like Ragusa are still bustling with local life but the crowds have thinned dramatically. With coastal rides, winery visits, and plenty of seafood in local trattorias, our Sicily bike tour is a lovely way to prolong the sweetness of summer.

See October departure dates in Sicily.

Each autumn, Burgundy abounds with gourmet pleasures. Already-harvested vines are turning a sunny shade of yellow as you pedal on vineyard roads through Gevrey-Chambertin, Châteauneuf, Pommard, and other famous appellations. The dishes in Michelin restaurants are infused with the treasures of France’s fall truffle season. And for those looking to embrace the change of seasons, the temperature in Burgundy actually feels like fall—the better for a lightly bundled stroll through Beaune’s Saturday market.

See October departure dates in Burgundy.