Give me a vacation in September over any other month of the year. Crowds wane, temperatures mellow and popular destinations relax from the tourist crush and ease back into the local routine. I love how the food changes with the season too: peach pies are amazing, chestnuts and cranberries begin to appear in markets, apples are absolutely perfect and wine and produce festivals are scheduled every weekend.
I have great expectations for most any kind of travel this month. But a few places in particular stand out.
Vermont
It’s virtually impossible to think of Vermont in fall and not imagine leaf peeping. Peak foliage up north starts in late September. Go earlier in the month to see touches of red, orange and yellow mixed with green on the trees and, with the weather still on the fairer side, you can spend more time outside comfortably biking through quaint towns and hiking the hills with fewer layers. Strolling the shores of Lake Champlain the first week of September is positively delightful.
September is also prime apple-picking month. Stock up on apples and sip locally pressed cider at countless orchards. It’s never too cold for maple-flavored creemees (the state’s version of soft serve). Vermont Cheese Week happens in early September; the event sold out in 2025, so plan to snag tickets ahead of time. Should you miss out, there’s always the Vermont Cheese Trail, a string of 45 dairy farms where you can sample everything from crème fraîche to aged cheddar.
The fall term at Middlebury College starts mid-month. Tour the campus—ranked one of the most beautiful in the country—when students are around for a nostalgic vibe. The town itself (population of about 7,500) is a gem, backed by the Green Mountains.
In Woodstock, stop and see the beautiful Sunflower House at the Billings Farm & Museum; the half-acre living attraction only blooms from about mid-August through the first week of September. And if the mountains are your mecca, explore the resort towns of Stowe, Killington and Mad River Valley.
Learn more about Backroads’ Vermont trips.
Basque Country
The high fervor of tourism in Spain’s Basque Country softens slightly in September. The Bay of Biscay still holds the warmth of summer with water temperatures comfortable enough for swimming, but swells in San Sebastián become more consistent and stronger, pushing beginner surfers out of the lineup in favor of more experienced wave riders.
Cooling winds begin to blow in from the coast, a balm to hikers on the trail all day. The famed Camino de Santiago sees fewer pilgrims en route, which some say invites a more authentic experience of introspection and meaningful connections, but accommodations and eateries that cater to trekkers have not yet closed for the season.
The Basque Coast Geopark, San Juan de Gaztelugatxe and Picos de Europa are all prime lands for adventuring. The Geopark is a wonder of rock formations—shard-like flysch cliffs, karst strata and unique caves. Sixty miles northwest, travelers visit San Juan de Gaztelugatxe to climb the 241 steps across a medieval stone bridge leading to a hermitage built atop a small, rocky promontory. And the Picos (“peaks” in Spanish) are a hiker’s dream—a national park full of 8,000-foot mountains, beech forests, high mountain pastures and grazing cattle.
Getting a true sense of daily life in Basque Country is a great reason to visit in September. You’ll see fishermen unloading their catch in the early mornings, residents choosing from pintxos (plates of small snacks) at bars around midday and vineyard crews busy picking grapes for wine production.
Harvest season also shifts how Spaniards eat. Restaurants transition to heartier fall dishes like soups and stews, and ingredients like wild mushrooms, sweet roasted peppers and quince paste appear on menus. In this region of northern Spain, it goes without saying that sampling the cuisine is a priority for many visitors. The Basques are rightly proud of this heritage.
Learn more about Backroads’ Basque Country trips.
Nova Scotia
Another quieter destination, closer to home, is the eastern Canadian province of Nova Scotia. One of its biggest draws is the Bay of Fundy, home to the world’s highest tides. Plan on spending a full day here to marvel at the remarkable difference in landscape between high and low tides and to raft a tidal bore, a unique white water excursion. Toward the end of the month, when the leaves begin to change color, the scenery becomes even more spectacular.
Likely you’ll fly into the provincial capital of Halifax, where the average high in September is 68 degrees Fahrenheit. Wander its waterfront boardwalk lined with historic ships, seafood restaurants and art galleries, then head up to the hilltop Citadel for a grand view of the city and harbor. Mid-month, Halifax hosts the Atlantic International Film Festival.
An hour’s drive north, Grand-Pré National Historic Site commemorates the history of the Acadians—French settlers who lived in this region for 70 years in the 17th century before being expelled when they refused to declare fealty to the British Crown. For a deep dive into Native heritage, the wilderness of Kejimkujik National Park is part of the Mi’kmaq tribe’s homelands. In September, you can hike through protected old-growth forests of hemlock and sugar maple, bike along rivers and past waterfalls, paddle through bogs, swim in clear bays and birdwatch for loons in the park.
Finally, a journey to Nova Scotia wouldn’t be complete without a visit to Lunenburg, a UNESCO World Heritage Site west of Halifax known for its brightly painted colonial buildings and picturesque harbor. Join a sailboat cruise, feast on fresh seafood, visit the local bladesmith and wooden-boat maker and buy a piece of fused glass to remember your time here.
Learn more about Backroads’ Nova Scotia trips.
Italy
Where to begin a description of Italy in September? The focus for Italians turns from coastal vacations and hours spent at the sea to inland delights and recreation like hiking and biking. Truffles are being hunted and grapes harvested. The arts season begins, with performances filling theaters around the country. And festivals big and small draw locals and visitors alike to celebrate in piazzas everywhere.
In Tuscany, there are festivals for pecorino cheese, antiques and paper lanterns. In Venice, if you time your visit right, you can watch a regatta with boaters wearing 16th-century costumes on the Grand Canal, catch Hollywood glitterati showing up for the renowned Venice International Film Festival or wander the various pavilions of the Biennale art exhibition. In Naples, thousands of faithful flock to the Festival of San Gennaro, the city’s patron saint. And up north, some of the world’s best classical musicians play concerts at sold-out venues in Milan and Turin at an event called MITO SettembreMusica.
The Dolomites are stunning in September, as the needles of the area’s larches turn bright yellow before dropping from the trees completely by winter. You’ll also notice trails littered with spiky chestnuts that have been blown from branches. Temperatures are brisk, days tend to be clear (though the first snows can happen at high elevations late in the month) and both the mountain rifugi (huts) and gondolas remain open but aren’t filled to capacity. You might also catch shepherds herding livestock down through towns to pasture in low-lying valleys, a lovely experience to witness, as herders often dress up in traditional Tyrolean clothing and adorn their animals with wreaths.
Learn more about Backroads’ Italy trips.
New York’s Catskills
A two-hour drive north of New York City, Woodstock is the artistic hub of the southern Catskills and an ideal home base for outdoor exploration. Hike to the fire tower atop 3,140-foot Overlook Mountain for amazing panoramas across the Hudson River Valley, down to the Ashokan Reservoir and, starting in mid-September, an ocean of hardwood trees beginning to turn rich colors. A quick drive north of town will take you to 260-foot-high Kaaterskill Falls, the second-tallest waterfall in the state. Detour 20 miles west to the iconic Phoenicia Diner, serving comfort food like fluffy pancakes and other hearty plates made with locally sourced ingredients.
The Hudson River is best crossed via the 1.5-mile-long Kingston-Rhinecliff Bridge, by car, bike or foot. Carry on eastward to the town of Rhinecliff, which celebrates fall with the Hudson Valley Wine and Food Festival each September. Festival season is in full swing in the Catskills this month; seek and you’ll find events dedicated to garlic, sunflowers, arts and crafts, music, cider and more.
Other outdoor attractions worth exploring this month are the 200-acre Mountain Top Arboretum near Tannersville, and all manner of farms and orchards, where you can get lost in corn field mazes, take a hayride and treat yourself to cider doughnuts and apple pies.
Learn more about Backroads’ Catskills trips.
