5 Top Route 66 Side-Trips

Updated April 11, 2023

As you set off on your Route 66 road trip you'll soon discover that the highway is also a gateway to a slew of other enticing destinations. Yes, the great road is dotted with several detours that have attained their own fan-following over the years. These side-trips are golden opportunities to experience some extra thrills on your Route 66 adventure.

As you ponder which of these excursions to undertake, ask yourself this – if not now, then when? When will you next have the luxury of time and resources to see the Grand Canyon, revel in the neon-lit wonderland of Las Vegas, and so on? These diversions aren't mandatory, of course, but they are certainly worth considering, especially for international travelers who may not have the chance to explore these nearby gems otherwise. And let's not forget that the pioneers of the original Route 66 also embraced these same side-trips in their heyday.

So, without further ado, I offer you my top five Route 66 side-trips, presented in no particular order...

1. Santa Fe

Okay, so technically this one may not be classed as a side-trip, seeing as how for the first dozen years of its existence, Route 66 actually passed through Santa Fe. But as many folks these days opt to forego this pre-1938 alignment, I reckoned it might be worth our while to take a little gander. Nowadays, you'll find that a fair number of guidebooks (particularly the EZ66 Guide) refer to it as the pre-1938 alignment, or more colorfully, the "Santa Fe Loop".

Santa Fe is a bustling and vibrant destination, with beautiful architecture and colourful market areas. There's all manner of tourist spots to check out in Santa Fe, from the oldest house in the United States and the “miraculous” staircase at the Loretto Chapel.

If you're of a mind to take things at a more leisurely pace, you can always meander over to the Georgia O'Keefe Museum, or take in some live music at the Santa Fe Plaza. And why not treat yourself to a little Native American jewelry while you're at it? There's no shortage of things to see and do in Santa Fe, that much is certain.

2. Grand Canyon National Park

Since it’s birth Route 66 has guided many families on vacation towards the Grand Canyon. And why not? With the likes of Williams and Kingman just an hour away, it’s a breeze to hop off the mother road and see one of the great natural wonders of the world.

if you're looking for a quick and easy day trip, the Grand Canyon won't disappoint. But, if you're feeling a bit more adventurous, why not stay overnight within the park and witness the magic of a sunrise over the canyon or even take a short hike down into its depths?

On my visit I stayed at one of the many lodges within the national park and set my alarm for an hour before sunrise. My wife and I packed a few snacks and drinks and took a short walk into the canyon to watch the sunrise. There was something about the view that seemed unreal, like a painting, as if we could reach out and touch it. We walked as far as we could in an hour before stopping to admire the views and then starting our ascent.

3. Monument Valley

If you're cruising down Route 66 and thinking about taking a side-trip to Monument Valley, you'd better be prepared for a serious detour. I'm talking about a whopping 400-mile journey!

If you're pressed for time and trying to cram in as much Route 66 as possible, you might want to think twice about making this particular trek. If you're on a tight schedule, trying to hit all the major Route 66 attractions in a week or two, you might find yourself stretching your itinerary a little thin if you try to squeeze in a visit to Monument Valley.

However, if you've got the luxury of time on your side then this is an opportunity you may not want to pass up. If you're feeling adventurous a detour from Flagstaff is possible that allows you to return to the exact same spot to pick up Route 66 right where you left off.

Perhaps the most famous example of the classic American West landscape, Monument Valley's stunning vistas and rugged terrain has been the backdrop for numerous Hollywood films. Part of the Navajo reservation, the views at Monument Valley are nothing short of breathtaking.

If you're lucky enough to snag a room or cabin at The View Hotel then you're in for a real treat. This place lives up to its name, offering some of the most spectacular views you'll find anywhere in the American West. But beware, folks - this place fills up fast, especially during peak season. So, if you want to soak up all the breathtaking scenery that Monument Valley has to offer, you better plan ahead and book your accommodation well in advance.

4. Las Vegas

If you're contemplating a side trip to Las Vegas, it's worth considering that you may have to sacrifice a portion of California's iconic Route 66. But fear not, intrepid traveler, if you have the luxury of time, you can always backtrack from Sin City and resume your journey where you left off. Just be prepared for a long and solitary drive through the barren desert. Personally, I found the experience of driving through the desert to be a real joy - there's something captivating about the arid landscape that has always appealed to me.

Las Vegas isn’t to everyone’s tastes but I have to admit, I relished every moment of the Las Vegas experience. The dizzying array of cocktails, slot machines, themed hotels and spectacular shows is enough to keep anyone occupied for days on end. It's tacky, gaudy, and shamelessly indulgent, but if you can embrace it for what it is and take it at face value it's also incredibly fun.

Nowadays, gambling is no longer the sole attraction in Las Vegas. While I did spend a brief period of time testing my luck on the slots (it would have been rude not to!), the true highlights of the city lie beyond the casino floor. The fountains outside the Bellagio are a sight to behold with a cocktail in hand, and the many bars and restaurants also feature live entertainment of some sort. 

During the daytime, you can simply stroll along the famous Las Vegas Strip, immersing yourself in the buzzing atmosphere. The many exhibitions, street performers, and even zoos provide ample entertainment for visitors of all ages. All in all, a visit to Las Vegas is an unforgettable experience that's not to be missed.

5. Highway 1

Again, this isn’t a true side-trip but more like a little addendum to your Route 66 adventure. If you're headed westward, then your jaunt along Route 66 culminates in Los Angeles. But should you have the luxury of a few more days to gallivant about, why not take the breathtaking Highway 1 up the Pacific coastline to San Francisco?

This beautiful journey can be comfortably accomplished in a mere three days, allowing you to savor some truly great stops en route, including Santa Cruz, Monterey, and San Luis Obispo, before finally arriving at your destination of San Francisco.

The breathtaking coastal views will truly take your breath away - that is, if you're lucky enough to catch them on a clear day. The fickle west-coast fog can shroud even the most stunning views in a thick veil, but if you time it just right, you'll be treated to a sight that will stay with you for a lifetime.

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