2026 is shaping up to be a banner year for travel across North America, Mexico, Canada, and the Caribbean. The United States marks its 250th anniversary with programs and celebrations at national parks, historic sites, and cities. At the same time, cities and regions from coast to coast are reinventing themselves—new cultural institutions, major sport and festival dates, expanded outdoor infrastructure, and hotel and dining openings make next year an exciting moment to plan trips both nostalgic and forward-looking.
Arkansas
Go for: world-class mountain biking and new riverfront trails.
Known as the Natural State, Arkansas is doubling down on outdoor adventure in 2026. Two new chairlift-served mountain-bike parks—one at the Trails at Mena in the Ouachitas and OZ Trails Bike Park near Bella Vista—will open with hundreds of miles of trails for riders of all abilities, plus hiking and running routes and a lively base area with food and gathering spaces. New segments of the Delta Heritage Trail will complete an 84.5-mile corridor alongside the Mississippi River. When you need an indoor detour, Bentonville’s Crystal Bridges Museum continues to expand its galleries, and new boutique hotels such as The Compton provide stylish bases close to trails and museums.
Boston, Massachusetts
Go for: America’s 250th, Sail Boston, and the 2026 FIFA World Cup.
Boston will be a focal point for national celebrations in 2026 and also hosts FIFA World Cup matches, bringing fresh energy to the city. Sail Boston returns with tall ships filling the harbor, and the urban fabric is shifting as new hotels and neighborhood projects spread activity beyond downtown. Boston’s food scene—restaurants that highlight diverse American cuisines and outstanding seafood—continues to thrive, and evolving arts and retail corridors in neighborhoods like Dorchester and Allston make the city feel newly dynamic.
Buffalo, New York
Go for: waterfront revival, architecture, and cultural reopenings.
Buffalo’s long-term revitalization accelerates in 2026 with expanded waterfront parks, reopened green spaces, and new pedestrian connections. The first phase of Ralph C. Wilson Jr. Park and Wilkeson Pointe add trails, kayak and bike access, and future public beach amenities. A new stadium and cultural investments—such as a Hispanic Heritage Cultural Institute and refreshed visitor access to Frank Lloyd Wright’s Graycliff—complement architectural-focused projects like the Lipsey Architecture Center on the Richardson Olmsted Campus. The result is a city with renewed public spaces and cultural programming.
Catalina Island, California
Go for: a century of island resort glamour and outdoor escapes.
Just an hour by ferry from Los Angeles, Catalina Island celebrates 100 years as a resort destination in 2026. Avalon’s Art Deco Casino (a theater and event space) and the island’s conservation legacy set it apart: 88 percent of the island is protected, home to endemic species including the Catalina fox. Hike the 38.5-mile Trans‑Catalina Trail, snorkel at Lover’s Cove Marine Reserve, spot bison in the interior, or paddle to hidden coves. Historic spaces—including the Casino’s former ballroom—have been repurposed for creative uses such as roller skating, and refreshed stays like Mt Ada offer updated historic rooms and amenities.
Deer Valley, Utah
Go for: Sundance’s final Utah run and massive ski expansion.
Deer Valley has long been synonymous with impeccably groomed skiing and the Sundance Film Festival. In January 2026 Sundance will mark its final Park City season before relocating, and Deer Valley will be opening the biggest ski-resort expansion in North American history under the Expanded Excellence initiative. Skiable terrain more than doubles, adding nearly 100 runs, dozens of lifts and new village development with hotels, shops, and restaurants—expanding mountain access while retaining the resort’s upscale service and abundant snowfall.
East Coast, Barbados
Go for: rugged Atlantic scenery, surf, and more access.
Barbados is easier to reach in 2026 thanks to new nonstop routes and port upgrades, and the island’s wild east coast offers dramatic surf, cliffside scenery, and quieter village life away from the west coast resorts. Bathsheba’s Soup Bowl is world-renowned for waves, and coastal trails and protected reserves preserve much of the eastern shoreline. New smaller-port facilities and moorings support luxury yacht calls, and recent upscale villa and resort openings bring higher-end lodging to the area while local fish fries and village gatherings keep the island’s community character alive.
Guadalajara, Mexico
Go for: festivals, FIFA matches, and a flourishing creative scene led by women.
Guadalajara is stepping into the spotlight in 2026 as a host city for the FIFA World Cup and as the site of long-running cultural gatherings like the Guadalajara International Film Festival and the International Book Fair. The city’s artisanal traditions—mariachi, ceramics, and regional food—are being reinterpreted by a new generation of creatives. Women are prominent in politics, the arts, and culinary leadership; community-driven studios and ateliers like Cerámica Suro offer hands-on experiences, and a lively food scene showcases ancestral ingredients and matriarchal influences.
Portland, Oregon
Go for: bold cultural and culinary projects that reshape the city story.
Portland’s next chapter in 2026 includes major openings that highlight local wood architecture, art, and food systems. The final phase of Portland International Airport’s new terminal, noted for mass-timber design, and a large expansion at the Portland Art Museum add public-facing architecture and galleries. After years in planning, the James Beard Public Market is slated to open as an indoor-outdoor food and producer marketplace. Portland’s quirky soul persists—independent bookstores, vast urban green space, and longstanding performance venues remain core to the city’s identity.
Prince Edward County, Canada
Go for: a cool-climate wine region with boutique hotels and restaurants.
Prince Edward County (PEC) has become a favorite weekend escape for food and wine lovers. A wave of renovated and new hotels has turned towns like Picton into community hubs, and the county’s wineries now produce elegant cool-climate wines with a distinctive character. Dining is increasingly sophisticated with small, local-driven restaurants and tasting rooms. Outdoor activities such as sailing, lakeside spas, and farm-to-table experiences round out visits to this compact and charming region.
Riviera Nayarit, Mexico
Go for: elevated barefoot-luxury resorts and destination dining.
The Riviera Nayarit coastline north of Puerto Vallarta is gaining infrastructure and international flights that make it more accessible in 2026. New or recently opened luxury properties and residences are creating a high-end hospitality scene, while acclaimed chefs are launching restaurants that spotlight regional ingredients and inventive cuisine. Improved airport capacity and faster road connections make reaching Nayarit easier from both U.S. and Canadian gateways.
Route 66, USA
Go for: the Mother Road’s 100th anniversary and revived neon Americana.
Route 66 turns 100 in 2026, and celebrations along preserved stretches of the historic corridor highlight restored midcentury neon, classic diners, and car-culture events. Communities along the route are staging centennial kickoffs, classic-car parades, and festivals that celebrate the road’s cultural role. The anniversary is also prompting deeper conversations about the many tribal nations whose lands the highway traversed; Indigenous-led museums and cultural centers provide fuller, more accurate stories of the peoples and places affected by this iconic route.
Whether you’re drawn to new mountain-bike parks and ski expansions, seaside islands and surf breaks, revitalized cities, or decades-old highways freshly restored for a centennial, 2026 offers an unusually rich calendar of reasons to travel across North America and the Caribbean. Use these destinations as starting points to plan trips that combine history, reinvention, and unforgettable outdoor and cultural experiences.