The year 2026 is going to be a momentous one for the United States as it celebrates its 250th anniversary. Across the country, national parks, historic sites, and cities will gear up to show up—and show off—in ways big and small. Against this backdrop, how does one pick where to visit? Inevitably, we were led by some nostalgia: Route 66, for instance, was an easy one. Next year, visitors can commemorate 100 years of cruising the Mother Road, and whether you’re driving on stretches in Missouri or New Mexico, you’ll not only get to appreciate a neon-lit glow-up but you’ll also be reminded of the role this byway has played in America’s history and how its story has been told. Celebrations will also be underway on Catalina Island, the tiny but beguiling island off the Southern California coast that will celebrate its own centennial as a resort destination with some thoughtful nods to its glamorous past. We were inspired even more so by stories of reinvention: Former industrial cities Portland, Oregon, and Buffalo are both looking to script new futures anchored in cultural openings and urban revitalization efforts. And over in Deer Valley, Utah, the end of one dazzling chapter (the Sundance Film Festival) just means there’s room for a new one: in this case, the largest ski resort expansion in North American history.
But this list, which covers countries in North America and the Caribbean as well as Mexico, is about so much more than just the US—or 250 years of history. The earliest human settlers arrived on these noncontiguous lands tens of thousands of years ago, and the entity itself is, quite literally, a layer cake of ancient geological evolutions accrued over billions of years. It is upon one such ancient limestone seabed that Prince Edward County in Southern Ontario, Canada, sits, which gives the region’s new cool-climate wines their distinctive old-world character. PEC has long been a weekend destination for East Coast Canadians, but a spate of boutique hotels, family-run wineries, and excellent restaurants is sure to draw crowds from farther afield. And over in Jalisco, Mexico, another historically rich region, the one that birthed the thriving city of Guadalajara, there’s another kind of rebirth—one that’s helmed by creative entrepreneurs and artists eager to pave a path for Mexico’s second city that’s distinct from ever-popular Ciudad de Mexico.
