Skip to Content

14 Winter Road Trip Routes Across America Where Holiday Travelers Never Regret Taking the Long Way

14 Winter Road Trip Routes Across America Where Holiday Travelers Never Regret Taking the Long Way

Sharing is caring!

Winter transforms America’s roads into a scenic wonderland, offering unique experiences for those willing to venture out on lesser-traveled paths.

From snow-dusted mountains to sunlit coastal drives, these routes promise adventure and beauty.

Here are 14 winter road trip routes that holiday travelers never regret exploring, embracing the diverse landscapes and cultures across America.

Pacific Coast Highway (California)

Pacific Coast Highway (California)
Image Credit: Ken Lund from Reno, Nevada, USA, licensed under CC BY-SA 2.0. Via Wikimedia Commons.

The Pacific Coast Highway, with its winding roads, offers a stunning winter escape. Fewer crowds mean you can enjoy the vibrant holiday decorations in seaside towns and the dramatic ocean waves in peace.

Between the breathtaking coastal cliffs and the chance to spot migrating whales, every mile feels like a postcard.

Charming stops like Monterey and Carmel-by-the-Sea glow with festive spirit, making a drive along this route a perfect winter getaway.

Mt. Hood Scenic Byway (Oregon)

Mt. Hood Scenic Byway (Oregon)
Image Credit: U.S. National Archives and Records Administration/ Wikimedia Commons, Public domain.

Mt. Hood Scenic Byway is a winter wonderland, offering a loop through snow-laden forests. Ski resorts on the byway cater to thrill-seekers, while others may prefer the rustic comfort of historic Timberline Lodge.

The lodge, with its cozy firesides, feels like a scene from a winter fairytale.

Alpine lakes, wrapped in a blanket of snow, provide serene stops along the journey, inviting travelers to pause and soak in the beauty.

Cascade Loop (Washington)

Cascade Loop (Washington)
Image Credit: SounderBruce from Seattle, United States, licensed under CC BY-SA 2.0. Via Wikimedia Commons.

In winter, the Cascade Loop offers tranquility away from the summer bustle. Icy waterfalls and snow-covered peaks create an ethereal atmosphere along the route.

Bavarian-themed Leavenworth, with its festive lights, adds a touch of whimsy to the journey.

Mountain passes and quiet trails make this drive feel like stepping into a snow globe, where each stop reveals a new, magical scene.

The Great River Road (Minnesota to Louisiana)

The Great River Road (Minnesota to Louisiana)
Image Credit: Lorie Shaull, licensed under CC BY 2.0. Via Wikimedia Commons.

Embarking on The Great River Road is like experiencing two worlds. Start with the frozen vistas of the Mississippi River in the north, offering stark winter beauty.

As you head south, the chill gives way to the warmth of Southern hospitality.

Jazz-filled river towns come alive with holiday lights, creating an inviting, festive atmosphere that celebrates the season’s spirit.

Alaska’s Seward Highway (Anchorage to Seward)

Alaska’s Seward Highway (Anchorage to Seward)
Image Credit: Wonderlane, licensed under CC BY 2.0. Via Wikimedia Commons.

Winter transforms the Seward Highway into one of the most dramatic cold-season drives in America. The road hugs the edge of Turnagain Arm, where icy tides mirror snow-covered peaks that rise sharply from the shoreline.

Frozen waterfalls cling to the cliffs, moose occasionally wander near the roadside, and belugas sometimes appear in the silvery water below. On clear nights, travelers may even catch the northern lights shimmering above the mountains—an unforgettable bonus for anyone willing to embrace the Alaskan winter.

Despite the rugged setting, the route is surprisingly accessible, making it a rare combination of wild beauty and winter ease.

The High Road to Taos (New Mexico)

The High Road to Taos (New Mexico)
Image Credit: MARELBU, licensed under CC BY 3.0. Via Wikimedia Commons.

In winter, the High Road to Taos offers a quiet, contemplative drive through high-desert landscapes and historic adobe villages dusted with snow.

The route winds past centuries-old churches, artist enclaves, and sweeping views of the Sangre de Cristo Mountains glowing softly in the low winter sun.

It’s a serene mix of culture and scenery, where crisp air and calm roads make the journey feel timeless and deeply New Mexican.

Route 100 Through Vermont

Route 100 Through Vermont
Image Credit: Doug Kerr, licensed under CC BY-SA 2.0. Via Wikimedia Commons.

Route 100 in Vermont is New England charm personified in winter. Snow blankets covered bridges, turning them into picturesque landmarks straight out of a storybook.

Craft shops and sugaring cabins offer unique local treasures, enhancing the cozy feel of quaint ski towns.

After a day of exploring, warm up with fireside cocoa, embracing the region’s inviting hospitality and rustic beauty.

Kancamagus Highway (New Hampshire)

Kancamagus Highway (New Hampshire)
Image Credit: Theletterm1973/ Wikimedia Commons, Public domain.

The “Kanc” in winter provides a tranquil escape with its quiet forest landscapes and frozen streams.

This peaceful drive offers a true sense of wilderness, yet warm mountain lodges are never far away.

The untouched snow and serene beauty make it a perfect retreat for those seeking solitude and nature’s pristine elegance.

Skyline Drive (Virginia)

Skyline Drive (Virginia)
Image Credit: MPSharwood, licensed under CC BY-SA 4.0. Via Wikimedia Commons.

Skyline Drive offers mesmerizing winter views of the Shenandoah Valley. With leafless trees, the panoramas stretch endlessly, revealing the valley’s quiet beauty.

Winter also makes wildlife spotting easier, adding adventure to the serene drive.

Nearby, cozy Appalachian inns provide the perfect retreat after a day of exploration, combining rustic charm with modern amenities.

Blue Ridge Parkway (North Carolina)

Blue Ridge Parkway (North Carolina)
©Doug Kerr/ Flickr

A dusting of snow transforms the Blue Ridge Parkway into a peaceful winter haven. Reduced traffic ensures an uninterrupted, serene experience, highlighting frosty overlooks and misty ridgelines.

The region’s natural beauty shines through, providing a stunning backdrop for a memorable drive.

Every turn reveals a new vista, inviting travelers to pause and reflect on the wonders of winter.

Natchez Trace Parkway (Tennessee to Mississippi)

Natchez Trace Parkway (Tennessee to Mississippi)
Image Credit: Lasermanmcgee, licensed under CC BY-SA 4.0. Via Wikimedia Commons.

Natchez Trace Parkway offers a relaxed winter journey through history and nature. Mild weather makes for an enjoyable drive through historic sites and scenic landscapes.

The quiet cypress swamps create a mysterious allure, offering glimpses of Southern beauty.

This peaceful route allows travelers to enjoy the simplicity and charm of the South at a leisurely pace.

San Juan Skyway (Colorado)

San Juan Skyway (Colorado)
©Ken Lund/ Flickr

San Juan Skyway in winter is a journey through snow-tipped peaks and charming Victorian mining villages.

Each town glows with holiday lights, creating a festive atmosphere against the rugged mountain backdrop.

Hot springs offer a warm respite from the cold, inviting travelers to relax and enjoy the striking contrasts of winter in the Rockies.

Route 66 (Chicago to Santa Monica)

Route 66 (Chicago to Santa Monica)
Image Credit: Prayitno from Los Angeles, USA, licensed under CC BY 2.0. Via Wikimedia Commons.

Route 66 offers a nostalgic journey through America’s heartland, starting with snow-covered stretches in the Midwest.

As the road heads west, the landscape transitions to desert sunshine, vintage motels, and neon diners.

This iconic route blends past and present, offering quirky roadside stops and a timeless sense of adventure.

Florida Keys Overseas Highway

Florida Keys Overseas Highway
Image Credit: David Broad, licensed under CC BY 3.0. Via Wikimedia Commons.

The Florida Keys Overseas Highway is the ideal winter escape for those seeking warmth. Turquoise waters and breezy bridges create a tropical paradise perfect for shaking off winter fatigue.

The highway’s relaxed vibe is complemented by unique tropical holiday lights, adding a festive twist.

This sunlit drive offers a refreshing change from winter’s chill, inviting travelers to embrace a different kind of holiday spirit.