Cycling Shore to Shore

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Whether you live west of the Chesapeake Bay Bridge or east, there are excellent cycling options and groups to engage with this popular sport

Annapolis, Anne Arundel County, the Eastern Shore, and the surrounding region have no shortage of ways to explore the outdoors and enjoy the scenery. Because of our prime location, locals and visitors often direct their focus to the water. That’s always an excellent choice. But it turns out an equally viable source for adventure and beauty can be found on our roads and trails. 

Imagine the wind brushing your skin as you cruise past hills, ponds, historic barns, horses, flowers. You don’t have a care in the world as you feel the road underneath you and hear the bleats of the goats you just passed. You inhale the fresh air and can’t help but feel relaxed even though you are getting a fabulous workout. Then you’ll reach a charming destination and gather with the rest of the group who have been riding by your side the entire way. Together you will lightheartedly chat over a coffee and snack. The rest of the day, you will feel invigorated and revitalized. This is the world of cycling, and you all are invited.

Most of us learned to ride a bike when we were young children. You may not have ridden one in a while, or you might enjoy periodic short rides around the neighborhood with loved ones, or you might consider cycling as a primary source of exercise. No matter your skill level, cycling can be an amazing source for overall physical and mental health. Area cyclists couldn’t agree more.

“Cycling benefits my mental health, overall health, and general fitness, even in that order,” said local cyclist, Mark Kavanaugh. “Cycling gives me focus, mental clarity, purpose, and organization while being a dependable healthy outdoor outlet for exercise and enjoyment. It takes some, but very little, discipline to enjoy. It’s really for everyone.” 

As cycling enthusiast Lisa Lauer puts it, “I enjoy cycling because it’s easier on my joints than running. I enjoy feeling the speed and the wind against my face. I’m always surprised by the calories I burn during each ride, because it feels so effortless sometimes!” For less advanced cyclists, riding in the back of a group of riders can also allow them to draft off the group, making the ride feel even easier.

Many riders come from other activities and sports and discover their love for cycling later in life. “I was a marathon runner who always trained solo,” said local enthusiast, Chris Boyd. “When my knees and joints gave out, I decided to take up cycling. Recently, I decided to meet up with a group and just kind of follow behind. But the group ended up being so welcoming and supportive. In a total surprise to me, I found myself wanting to stick around after the rides for the group coffee at a local shop. Now, I’ve been riding with this group regularly for over a year. They are my social group.”

“It’s so easy to find a group to ride with,” Kavanaugh says. “I simply googled riding groups in the area and information will pop up about local rides with times and locations. The first time you ride up to the group is the hardest part. But it’s never a problem. Groups are always excited and happy to welcome you on a ride. And now everyone is on the App, Strava. Once you’ve ridden with people, they will show up on your Strava, and then you can always be in contact with them for future rides. It is completely acceptable to reach out to cyclists you’ve only ridden with once to join them again. There are endless opportunities. People will post that they want to ride a certain distance and tell people to just show up!”

This may all sound like it’s for people who ride all the time and already know the ropes, but area cyclists insist that even beginning riders can feel welcomed into group rides to enjoy the activity. Riding alone on the road can be daunting for safety purposes, and some might find it boring to go long distances by themselves. Riding with a group provides a sense of camaraderie, support, and safety. “There is no judgment,” Boyd says. “There is a huge range of riders with all levels of gear. And some groups will specifically say that the whole group will only go as fast as the slowest person. It’s all about enjoying the activity.” These are referred to as “No Drop” rides. The Severna Park Peloton has an organized ride on Saturday mornings that operates like this. “When riding with others, I feel safer because there is more visibility with a larger group,” Lauer says. “I also really enjoy the camaraderie and the competitiveness. We are all there to support, push, and learn from each other.”

The routes to enjoy cycling are plentiful. “I was living in Mitchellville, when a ride I was on brought me to this area,” said Severna Park cyclist, Jim Littlejohn. “I thought this was such a nice neighborhood and then I discovered the trails. I am so thankful at how much I can ride on the nice trails and roads around here.” The main trail he is referring to is the B&A Trail. Cyclists love that they can hop on that trail and go into downtown Annapolis or ride all the way up to the airport without having to deal with much, or any, traffic.  “The trails and roads around here are beautiful, and people are very accommodating. Nobody is upset about cyclists,” said local cyclist, Chip Adams. “In fact, it’s fun to ride the trail, then stop at the Big Bean in Severna Park as a group, where they have tables right off the trail.”

“The trails continue to develop and improve, which makes me feel so lucky,” Boyd says. “There are also wonderful roads to take to Davidsonville, or through the countryside to South [Anne Arundel] County, down to Chesapeake Beach, or up to Ellicott City. I have discovered so many quaint and scenic places that I might not have seen before if it wasn’t for cycling.” 

Cyclists can also transport their bikes across the Bay Bridge and enjoy fantastic routes starting on the Eastern Shore. The Harriet Tubman Underground Railroad Scenic Byway offers 125 miles of scenic country roads from Cambridge to Goldsboro. “You feel like you are in the middle of nowhere and it’s so peaceful,” Kavanaugh says. “But then you come across an interesting museum, cute town, and other interesting historical sites. It’s really a lot of fun.” 

There are many gorgeous, quiet country roads that also lead out to Rehoboth Beach. “I’ve even worked with other cyclists to put together Capital-to-Capital-to-Capital rides (Annapolis to D.C. and back), which takes us right to the middle of the National Mall,” Kavanaugh explains. It seems if the will is there—which it seems to be among cyclists—there is a way to enjoy cycling in several stunning environments. 

“I have lived here for 30 years,” Adams says. I started cycling after meeting a fellow enthusiast and I have now been part of the “5:45 Ride” for 20 years. I have no plans for stopping anytime soon.” That’s 5:45 a.m. for those who are interested. But rest assured that other groups go at different times with safety always the primary consideration.

I will admit that my husband is also an avid cyclist. I am what you might call a “Bike Widow.” He rides early in the mornings and then takes long rides on the weekends over 100 miles. I wondered if he was alone in his feverish love of cycling. What I discovered when interviewing local cyclists is that they could rhapsodize for hours about their experiences. “Talking about biking is like a break to me,” Kavanaugh says with a laugh. 

“I just never thought I would be excited to wake up early in the morning to go for a ride and then socialize with my friends. But now I’m like a toddler at the holidays. I wake up early and wish that it was already time to go,” Boyd says in agreement. 

“I don’t want to ever let go of it,” Adams says. “It’s such a big part of my life and I love it so much. To me, this is the one thing I do that is the centerpiece of everything else.”  

Local Cycling Groups

Here is a sampling of organizations that promote cycling and organize rides throughout our region. For even more club listings, visit bikemaryland.org. 

Annapolis Bicycle Club – annapolisbicycleclub.org; Founded in 1993, the nonprofit, service marked, growth oriented cycling organization is dedicated to advancing cycling skills in endurance, speed, performance, route variety, group dynamics, and the interests of recreational cycling enthusiasts. Schedules hundreds of group rides annually.

BikeAAA – bikeaaa.org; Short for Bike Annapolis & Anne Arundel, BikeAAA is a cycling advocacy and ride organization based in Arnold, but covering the regional scene. The nonprofit is behind events, such as the Lifeline 100 ride, and many community programs, including Wheels of Hope, Cycling Without Age, and more. 

Black People Ride Bikes – blackpeopleridebikes.com; Black People Ride Bikes (BPRB) is a Baltimore-based cycling and advocacy organization of black cyclists in every age bracket, from children to adults. The organization is made up of both casual riders and avid cyclists, who regularly participate in cycling events throughout the country.

Chesapeake Cycling Club – ridec3.org/road-cycling-club-maryland-eastern-shore-easton; Adult bike club located on Maryland’s Eastern Shore, offering multiple cadence and distance options for people who love road cycling.

Chesapeake Wheelmen – chesapeakewheelmen.org; Founded in 1946 is one of the oldest clubs in the United States and the oldest in the state of Maryland. 

Club Crabtowne – clubcrabtowne.org; Club Crabtowne is an Annapolis-based ski, cycling, and events club that has been organizing exciting events for more than forty years.

Shore Velocity – facebook.com/ShoreVelocityCycling; Eastern Shore group based in Salisbury that organizes distance rides throughout the region.