The Rise of Offseason Travel

A century ago, city elites used to decamp to their summer colonies: Bostonians to Cape Cod, Chicagoans to the towns along Lake Michigan, and so forth. Destinations have been shaped by what time of year the leisure class would swoop in.

Consider Cape Cod’s historic Wequassett Resort and Golf Club, which since its opening in 1925 would experience a highly seasonal clientele that visited each summer—and would close each winter. In recent years, the rise of offseason travel suggested that what was once a presumed dead time of year might actually be a frontier for new business. In February 2023, the resort officially transitioned to being open year-round.

Montage Big Sky, Montana / Photo: Courtesy of Wequassett Resort

Summers at the Wequassett revolve around the resort’s tennis courts, waterfront pool and hydrangea-fringed cottages. To attract people in the winter when those things aren’t available, the resort leaned into a strategy of on-site programming and events, including a visiting chefs series in its signature restaurant and a partnership with the British brand Barbour. Kara Lachance, the resort’s director of marketing and sales, credits those partnership efforts, in part, with a 140-percent year-over-year uptick in food and beverage revenue during the month of December—and she expects to see that number rise.

It’s not just domestic markets, either. Destinations such as British Columbia have rebranded their virulent winter as “Storm Watching” season, with hotels like The Wickaninnish Inn, a Relais & Châteaux property, offering galoshes so guests can turn British Columbia’s soggy winters into a thrilling experience. Winter is now one of the most popular times of year to visit. Even the African safari industry has seen shifts in visitorship.

The Supper Club at Wequassett Resort and Golf Club, Harwich, Massachusetts / Photo: Courtesy of Wequassett Resort

Still, you don’t need a passport to find destinations where offseason is becoming fashionable. The cooler months in Yellowstone National Park can actually be more advantageous for wildlife viewing. Without summer crowds clogging up the park’s roadways, it’s much easier to spot more elusive wildlife such as moose or bobcats.

“Most people come in summer, but there is something to see each month of the year,” says Grant Johnson, a guide with Yellowstone Safari Company, which offers driving tours of the park. “There really isn’t a bad time to come.”

While there is no shortage of things to do or see in greater Yellowstone in the spring and fall, there are additional benefits. In May, a room at the tony Montage Big Sky will set you back about half of what it would during a peak weekend in August or ski season. But while shoulder season’s competitive room rates might seem alluring, the freedom to travel wherever, whenever, will remain a pipe dream for most—especially those with school-aged children, according to Brian Tan, founder of Zicasso, a website that matches travelers with agents. That being said, he agrees that there has been an offseason boom of late.

“For 2023, we noted a modest rise in shoulder-season traffic among our travelers,” says Tan. “But for 2024, it’s been an avalanche. We saw double-digit growth in the spring and expect the same for fall.”