With three kids in tow, the Pickerings of San Diego still make the trek to Fairmont Jasper Park Lodge in Alberta, Canada—a trip they’ve made annually since their honeymoon. “We’ve been going for three weeks for 18 years, and there are still hikes we haven’t done,” says mom Chris.
Being the first to check out the latest high-design hotel may have a certain cachet, but for many families, it’s all about the tried and true. And for many families, returning to a much-loved destination has become an annual vacation tradition.
We talked to 13 clans like the Pickerings—families who travel to the same resort every summer (including one family whose repeat visits have spanned nearly 70 years...and counting). As the setting for milestones like birthdays, weddings, and anniversaries, the resorts have woven themselves into the fabric of each family. And meaningful rites of passage—swimming to the dock in the middle of the lake; becoming old enough to shoot pool in the lodge; bringing along a significant other—have become touchstones as each generation comes of age.
The Rosenbergers, for example, spend vacation days at Skytop Lodge in Pennsylvania’s Poconos, where activities range from Champagne celebrations and performances by the resort’s own orchestra to outdoor pursuits like canoeing and biking. Asilomar Conference Grounds, a cluster of rustic lodges spread over a forested expanse on California’s Monterey peninsula, has hosted the Berliner-Brady family reunion for more than 30 years.
In Michigan, grandmother Carolyn Middleton still returns to the Inn at Watervale, a set of quaint lakeside cottages she first visited as a six-year-old. And so devoted is the Stephens family of Edgewood, Kentucky, to Georgia’s Callaway Gardens that a daughter named her son after the resort’s founder.
So click through and discover what makes these resorts so beloved to their visitors. Whether your gang is activities-inclined or beach-bound, whether you have cousins and grandparents in tow, or even if you’re a family of three—now’s the time to start a vacation tradition of your own.
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