Ultimate Cross-Country Road Trip Itineraries

The Timeless Allure of Route 66

Embarking on Route 66 is like stepping back in time, with each stop revealing a chapter of America’s past. Beginning amidst the skyscrapers of Chicago, the journey traverses expansive Midwest prairies, passes through vintage diners and neon-lit motels, and immerses travelers in local legends. Highlights include Springfield’s Abraham Lincoln heritage, quirky Cadillac Ranch in Texas, and the magnificent deserts and canyons of Arizona. Finally, the route culminates at the sun-soaked Santa Monica Pier, where the Pacific Ocean signals both an end and a new beginning. This highway is a living museum of bygone eras, offering a drive rich in character and unforgettable roadside charm.

Route 66 is famous for its roadside kitsch and distinctly American oddities. Along the way, travelers encounter the Blue Whale of Catoosa, the dazzling lights of Tucumcari’s motels, and Seligman’s nostalgic diners in Arizona. These attractions bring the journey to life, serving as landmarks for adventure and snapshots for memory books. Each small town beckons with unique stories, local eats, and a warm welcome from communities who keep the Route’s heritage alive. Whether it’s marveling at the Wigwam Motel or snapping photos at the world’s largest ketchup bottle, these attractions capture the whimsical essence of the great American road trip and offer countless opportunities for discovery.

Perhaps the most enduring element of Route 66 is the journey itself—the sense of freedom on the open road. Here, travelers bond over shared meals, swap stories at roadside stops, and find solace in the landscapes unfolding beyond the windshield. Sunrises on the plains, fiery mesas at dusk, and countless small-town encounters contribute to a mosaic of experiences. Every mile offers new possibilities, and the randomness of discovery is all part of the magic. Route 66 is more than a line on the map; it’s an invitation to lose oneself in history and find meaning in wanderlust.

Pacific Coast Splendor: The Great Western Drive

Your great western drive kicks off in Washington, where evergreen forests meet rugged Pacific beaches. Olympic National Park sets the stage with its towering trees and winding coastal roads. As you head south, countless viewpoints offer glimpses of jagged cliffs and roaring surf. The drive through Oregon features charming seaside villages like Cannon Beach, with its iconic Haystack Rock, and a tapestry of tidepools, lighthouses, and windswept dunes. This stretch seamlessly blends wild landscapes with quaint hospitality, offering plenty of opportunities to hike, surf, and savor freshly caught seafood before continuing into the Golden State.

Across the Heartland: The Northern Tier Adventure

Your journey begins in the historic, leafy enclaves of New England. Coastal roads wind past lighthouses, clapboard houses, and old fishing wharves in Maine before heading inland. Vermont and New Hampshire dazzle with mountain views, maple forests, and idyllic hamlets. Each town offers a taste of local heritage, from lobster shacks to covered bridges. As you push westward, the rugged beauty of New York’s Adirondacks and the Great Lakes come into view, promising new adventures and a rich sense of Americana at every turn.