Martha’s Vineyard is an island of as many fancies as the flavors of ice cream at Mad Martha’s. Tourists flock to its lighthouses, the Flying Horses Carousel, the Gingerbread Houses of Oak Bluffs and natural wonders like the Aquinnah Cliffs. A short ferry ride from Cape Cod, the island feels like a true escape, complete with luxury accommodations such as the historic Harbor View Hotel in Edgartown. And while the average vacationer seeks relaxation or quaint retail therapy, the Vineyard also offers amazing outdoor adventures.
Whether you want an easygoing bike tour or a more intense 50-mile off-road ride, the Vineyard’s systems of dedicated paths, less-traveled roads and rustic trails will scratch your itch. For those seeking aquatic thrills, the winds and protected waters off Chappaquiddick and other spots have made the island a kiteboarding mecca. Additionally, a more mellow entry into kiting has also emerged in the form of wing foiling over the past few years.
So, if you think beaches are wonderful, but you’d rather have more active pursuits, here are a few options on Martha’s Vineyard that will certainly get your heart rate up.
Kiteboarding and Wing Foiling
“I’ve been chasing wind and waves since I was a little kid boogie boarding and windsurfing,” says Mark Begle, Martha’s Vineyard native and owner of Skyhigh Kiteboarding & Wing Foiling. After college and a postgraduate boatbuilding program, Begle moved to Oregon’s Hood River Gorge, an epicenter of hardcore windsurfing. Here, he worked in the Northwave sail loft, building sails.
On the side, he helped construct some of the prototypes for kiteboarding pioneer Cory Roeseler and was quickly swept away by the fledgling sport. “It was like snowboarding to skiing, new and radical,” he recalls. But Begle found the Gorge too windy for kiting. The prevailing south-westerlies of his home Massachusetts waters, however, proved ideal, so he decided to move back to the Vineyard.
As anyone who has kited or witnessed kiteboarding knows, this sport is not for the faint of heart. Boarders can regularly catch 20-plus feet of air. When the boarders kite off Edgartown’s State Beach, spectators think they’re jumping over the road. “It’s like a carnival show, great to watch, but it’s never been a sport for the masses,” Begle says. With a steep learning curve, it also takes a lot of stubbornness and dedication. “The kite will just drag you around. You get pulled downwind like a human fishing lure,” he says. “Finally, on day four or day six, most people are able to start riding. But everyone learning to kite has a mental breakdown, a freakout before they transform.”
Just as hydrofoils have taken over in the America’s Cup, the concept of foiling (which allows a watercraft to rise from the water and minimize drag) has taken off in the kiteboarding world. Recent innovations and the realization that a full kite is no longer necessary to achieve liftoff have led to the emergence of wing foiling. Because the new sport is safer and more accessible, it has also moved to the forefront of Skyhigh’s instructional programs. “The wing only has 1/10th the power of a kite, and it’s much more intuitive,” Begle says. “There are no lines. You don’t need a harness. You can kneel on the board when you’re learning.” After just one or two lessons in wing foiling, students can grow confident enough to practice independently. “It’s going to be tame at first, not as adrenaline-packed,” he says. “But no one in their right mind would go teach themselves to kite.”
Most of the kite instruction that Begle provides these days is for experienced boarders seeking coaching to develop and refine their skills. But if you have the desire and time to learn, he’s happy to teach beginners, too. “I still teach kiting, but everyone I know is going over to wing foiling,” he says. “Anyone can try it — I’ve taught students from eight to 78 years old.”
Cycling
Back on land, bike adventures around Martha’s Vineyard may feel more familiar than kiting, but there’s plenty of range within the sport. “It’s a pretty awesome place to get around by bike, for sure, with a lot of paths and some quiet roads for beginners, like Atlantic Drive, along South Beach,” says Steve Kasacek, former project manager for the International Mountain Bike Association. “It’s really pretty, with the open ocean right there. Just need to be mindful on windy days.”
Kasacek’s wife is a native islander, and the couple has lived here for seven years. He has ridden every inch of Martha’s Vineyard but spends most of his time on dirt. “People love the road-riding scene here, but I mostly stick to gravel and trails, mostly up-island,” he says. “It’s perfect for my hardtail, with a lot of singletracks open to bikes. And fun fact: the highest point on Martha’s Vineyard — Peaked Hill at 311 feet — is higher than the highest spot on the Cape.” One of his favorite rides, at Cedar Tree Neck, is a real “rugged” one where riders can enter off the top, drop down through singletrack and come out right at the ocean.
In terms of bona fides, the local cycling scene boasts world-class athletes, including former Olympic mountain bikers and national champions in criterium and cyclocross. Frank Jennings, the founding owner of Edgartown Bicycles, holds the vaunted stars-and-stripes jersey after taking the 2023 Cyclocross National Championship in Louisville, Kentucky, where he won the Men Masters category for participants 70-plus. Jon Malone, shop manager at Edgartown Bicycles, recently returned from Leadville, Colorado, with the goal of establishing a better corral position for the prestigious Leadville 100 race in the near future. “I’m gonna be 50 in November, so I have my work cut out for me to compare with this local crew,” he says.
Malone is like a kid in Ben & Bill’s Chocolate Emporium when he describes all the happenings on Martha’s Vineyard these days. “There are a lot of nice, easy bike path rides from the shop,” he says. “You can head south to Katama and South Beach or go north to State Beach, which is more family-friendly. Both are super accessible.” Another path runs west, beyond the airport and around the state forest.
“We’re about to launch a series of guided tours,” Malone adds. These will cater to all levels and types of riders, from the casual to competitive, on paths, tarmac, dirt roads and trails. “We’ll be offering some high-end guided mountain bike tours,” he says. “And with our backdoor access to local farms, we will incorporate food tastings and educational components.” A new skills area will open soon, with skinnies and a pump track. “We’re also working with a private landowner to develop short-track mountain biking as well as a cyclocross course,” Malone says.
Along with the cycling community, Malone has kept the biking torch burning. Edgartown Bicycles puts on the Kraken Series: the 50K Fire Kraken held on July 4 and the 100K Full Kraken. “These races are on about 94% dirt, and the 100K has about 4,600 to 4,700 feet of vertical,” Malone says. “There’s been an active mountain biking scene here since the infancy of the sport, back in the ’70s and ’80s. We’re constantly seeking new routes off the tarmac, building new trails, creating better connectivity.”
If organized races feel intimidating, group rides on the Vineyard are inclusive, welcoming and easy to join. “The road scene is still happening here, too,” Malone says. “There’s a huge island ride on Sunday mornings, usually about 50 to 70 miles.” Edgartown Bicycles and other island shops such as Wheel Happy, Corner Cycles and Brickyard Bicycles rent everything from cruisers to performance machines, and they’ll happily share routes and advice with visitors.
