Ultimate Road Trips Every Guy Must Take: 4 Unforgettable Routes Across America

From the rugged peaks of the Rockies to the untamed beauty of the Pacific Coast, America was made for the road trip. The open highway isn’t just about the miles—it’s about the stories, the scenery, and the sheer thrill of the journey. If you crave adventure, these four iconic routes deliver breathtaking vistas, legendary stops, and memories you’ll never forget.

1. Trail Ridge Road, Colorado: Conquer the Roof of the Rockies

Trail Ridge Road, Colorado

For those who thrive on altitude and adrenaline, Trail Ridge Road is a must. As the highest continuous paved road in the U.S., this legendary stretch through Rocky Mountain National Park soars to 12,183 feet, offering jaw-dropping views at every turn. Expect vast alpine tundras, towering peaks, and close encounters with bighorn sheep and elk.

Pro Tip: Time your trip for early fall when the summer crowds fade, and the aspens turn a golden blaze against the backdrop of the Rockies.

2. Going-to-the-Sun Road, Montana: A Journey Into the Wild

Going-to-the-Sun Road, Montana

A masterpiece of engineering and natural beauty, Going-to-the-Sun Road is the crown jewel of Glacier National Park. Spanning 50 miles across the Continental Divide, this road carves through dramatic cliffs, glacier-fed lakes, and subalpine meadows teeming with wildlife.

Don't Miss: Stop at Logan Pass, the highest point on the route, where mountain goats casually stroll beside the scenic overlook. For the full experience, visit in early summer when snow still dusts the peaks.

3. Highway 101, Oregon: The Ultimate Coastal Escape

Highway 101, Oregon

Few drives rival the raw, untamed beauty of Oregon’s Highway 101. Hugging the Pacific Ocean for more than 360 miles, this route unveils windswept beaches, towering sea stacks, and charming coastal towns. Whether you're watching surfers carve waves at Cannon Beach or exploring the eerie remnants of old shipwrecks, this drive is pure West Coast magic.

Unexpected Gem: Stop at Prehistoric Gardens, where 23 life-size dinosaur sculptures lurk in a lush rainforest—a quirky, must-see roadside attraction.

4. Kancamagus Highway, New Hampshire: The Quintessential Autumn Drive

Kancamagus Highway, New Hampshire

For an explosion of fall color, few roads rival the Kancamagus Highway in New Hampshire’s White Mountains. This 34.5-mile stretch, affectionately known as “The Kanc,” winds through fiery-red maples and golden birches, making it one of the best leaf-peeping routes in the country.

Must-See Stop: Pull over at Sabbaday Falls, a three-tiered waterfall accessible via a short, scenic hike. The crisp mountain air and rushing water make it the perfect mid-drive refresher.

 

Road Trip Style: Shirts Built for the Journey

A great road trip isn’t just about where you go—it’s about how you go. Looking sharp and staying comfortable on the road is an art form, and your shirt game matters. Here are the three essential shirts every man should pack:

1. The Tailor-Made Cotton Shirt: The All-Rounder

Pure Cotton - Semi-Spread Collar - Long Sleeve - Olive Diamond Grid

A perfectly fitted cotton shirt never goes out of style. Whether you’re layering it under a jacket for a night out or rolling up the sleeves for a casual drive, a well-tailored shirt ensures you look effortlessly put together.

2. The Wrinkle-Resistant Travel Shirt: Stay Sharp on the Move

Wrinkle-Resistant - Semi-Spread Collar - Short Sleeve - Coffee

When you're clocking in miles, the last thing you need is a crumpled mess. A high-quality wrinkle-resistant shirt made from performance fabrics keeps you looking crisp—no matter how many hours you spend behind the wheel.

3. The Linen Shirt: Lightweight and Road-Tested

Cotton Linen - Camp Collar - Short Sleeve - Light Pink

For warmer climates, linen is king. Lightweight, breathable, and effortlessly stylish, a linen shirt ensures you stay cool while exuding that laid-back, road trip-ready charm.

 

Expert Packing Tips for the Modern Road Warrior

Pack versatile shirts that transition seamlessly from daytime exploring to evening drinks.
Roll, don’t fold—it saves space and minimizes wrinkles.
Carry a portable steamer for quick touch-ups on the go.
Layer smartly—a lightweight jacket over a great shirt goes a long way.

 

Hit the Road in Style

Great road trips are about freedom, discovery, and adventure. Whether you're conquering mountain passes or chasing the Pacific horizon, the right journey—and the right wardrobe—makes all the difference.

So pack your bags, fuel up, and hit the road in style.