Maui, Hawaii
The lesson: Seek out positive energy.
Waking up in Maui goes something like this: check the weather as though it’s anything but a perfect 80-degree day. Down a glass of fresh-squeezed orange or papaya juice. Then gear up for a day of cycling that rivals riding the island’s famous waves. Like the surf, the cycling in Maui is smooth, rolling, and so dreamy. Sure it’s hilly—after all, the island is a massive volcano—but I love to climb (and even suffer) under the tropical sun. Prefer not to suffer? There’s no shame in opting for an e-bike so you can fully enjoy Maui’s world-class riding while going a little easier on your legs. The Road to Hana ended up being one of my favorite off-the-grid routes of 2020, and Maui’s energy is electric: positive vibes, happiness, and health (all within easy reach for my California friends).
Big Sur, California
The lesson: Don’t let your bucket list get long.
You could be on the Amalfi Coast. Or the Amalfi Coast could be in Big Sur. Either way, there are few cycling destinations as spectacular as the Pacific Coast Highway passing through Big Sur. It’s a popular road to be sure, but riding it early in the morning is still a mist-shrouded, lesser-traveled treat. It awakened all my senses: the crash of the surf gives rhythm to your ride, the silhouettes of migrating whales are like playing a game of I Spy from the saddle. As far as cycling is concerned, it might be the most European place in America. I swear, the road could be in Corsica or Croatia—but instead, you’re slicing through the wild beauty of the American West. Without a doubt, Big Sur should top everyone’s bucket list (and in 2020, we’ve come to understand why we ought to turn our bucket lists from long-term aspirations into near-term goals).
Ride here on DuVine’s California Coast Bike Tour.
Aspen, Colorado
The lesson: Growth comes from pushing outside your comfort zone.
In Aspen, it’s always a competition. Someone you know will always be a stronger cyclist, have a better bike, or be sporting a cooler kit. But you don’t have to be the best to appreciate the magic of Aspen Valley—you just have to be open to the beauty. Manicured roads passing mountain streams. Pale clusters of aspen trees. Elk, birds, and even black bears undisturbed by your presence and you gulp the crisp mountain air—after all, most of the riding in Aspen is at an elevation over 7,000 feet, so you can expect your legs and lungs to be challenged in ways they aren’t normally at sea level. From the 21-mile climb up Independence Pass to a gentle ride through the valley ending at Woody Creek Tavern, an invigorating long weekend in this mining town feels like striking gold.
North Haven Island, Maine
The lesson: Traditions can still be meaningful when they change.
Like most New Englanders, I’ve been going to Maine all my life and have a favorite lobster shack, coastal inn, and local diner—all the nostalgic places I return to. But in 2020, I visited Maine grateful for its proximity to my home base in Boston, in full scouting mode, searching somewhat feverishly for new cycling spots. I found the Penobscot Bay islands, close to the mainland but blissfully traffic-free thanks to the limited car ferries. I found Isleboro with its clapboard mansions and rocky coves; Vinalhaven with its quarries and lobstermen; Isle au Haut’s rocky ride at the very edge of the map. I love them all, but North Haven takes the cake. From the tiny main town, you ride into New England idylls, out to Crabtree Point for killer coastal views, then circle around the island’s northern edge. It’s the kind of place where you buy bags of fresh oysters from an unmanned shack on the honor system, and my only complaint is that it’s all over much too soon: 20 miles of heaven out in the middle of the water, and a departure from my go-to haunts that could easily become my new favorite.
Ride the islands on our Maine Family Bike + Adventure Tour.
Malibu and Santa Monica Mountains, California
The lesson: Nature deserves our respect and awe.
Southern California already has the beach, the gorgeous year-round weather, and the celebs. Is it really fair for it to have the best cycling, too? Luckily, it seems this area hasn’t been found out yet and some part of me wants to keep it that way. When I ride up Latigo Canyon or Piuma, I find myself saying: “where is everyone? Why no cyclists?” Malibu and the Santa Monica Mountains are a secret cycling playground: winding roads, nice grades on the climbs, spectacular views of the Pacific. Fires have ravaged the area in recent years, but Malibu’s regrowth is steady and it’s well on its way to being lush and green again. It’s a reminder that bike travel is a way to explore our planet while being kind to it: leave nothing behind and take nothing with you (except maybe the memories of the insane sushi at Nobu Malibu, following a full day of heavenly riding…)
Hudson Valley, New York
The lesson: Love the one you’re with.
I’ve ridden my bike in Europe every year of my adult life. In 2020, I had to pivot and find my silver linings stateside, and the Hudson Valley came to compete with some of my top destinations across the Atlantic. It may not have Ventoux’s climbs or Mallorca’s coastal scenery (for that, you’d need to head to Colorado or California). But what it lacked in challenges, the Hudson Valley made up for with its European panache. Call it the American Tuscany or Burgundy of the States: the European-style road density in Dutchess County means you never need to ride on main thoroughfares, and the potential for loops lined with country homes, sprawling lawns, and white picket fences are quite literally endless. The food is also Euro-inspired while incorporating distinctly American details: think salads piled high with farm fresh grilled veggies or a sophisticated plate presented by chefs who escaped New York City in search of better work-life balance.
Experience la vie en rose on our Hudson Valley Bike Tour.
Woodstock, Vermont
The lesson: Don’t give credence to your fears.
I’d heard so much talk about gravel riding recently, but when I think of gravel all I picture is breaking my elbow in some torn-up hotel parking lot. In September, my friend Tim Johnson finally convinced me to give gravel a shot, and we spent three days riding (I swear) every “gravel” road in and out of Woodstock, Vermont. My conclusion: gravel gets a bad rap. The roads in Vermont are unpaved, yes, but in the same way you’d call a baby unshaven—they’re butter-smooth at baseline. Forget the mental image of loose rocks rolling around under your tires. This “gravel” is actually dirt tamped down to the consistency of pavement and the holes, washboards, and other small hazards keep you alert (and honestly, aren’t exclusive to unpaved roads, as any cyclist well knows). What there aren’t on these roads is cars, allowing you to pick your line and really lose yourself in the scenery: old red barns, stone walls, pastures full of Ben and Jerry’s dairy cows. I got so into it that I felt a tiny pang of disappointment whenever we had to get back on the pavement. The trip may have burnt my legs, but I was on my way back to Vermont the very next weekend.
