En masse or on your own?

My wife, Kerstin, and I got up before 5 a.m. on Sunday, May 29, to drive to Bike The Drive, held annually on Chicago's storied Lake Shore Drive. Once a year, on the Sunday before Memorial Day, Lake Shore Drive (aka LSD) is closed for most of the morning to all vehicles except bicycles.

On this 30-mile ride, attended by thousands of cyclists, you will see all manner of two wheelers, including folks pulling kids and dogs behind them.

After parking near the condo of my son, Jon, and his wife, Becky, we all rode to the staging area, where we encountered some chaos. Even though we'd preregistered, the check-in lines were very long. Eventually a guy came by with wristbands and told us to forget about going through the formal check-in process.

We began by riding the north section of LSD. A light mist prompted me to put away my sunglasses. Kerstin took hers off, too, and put the case, which also contained her clear glasses, into her sweatshirt pocket. Part way up to the turnaround at Hollywood, I saw something fall onto the roadway. I thought at first it was a bike part but then realized it was her glasses case -- which had popped open on impact and spilled both pairs onto the pavement. Kerstin pulled off, as did I. As countless bicycles flew past, she walked into the streaming mass with one hand up as I repeatedly yelled, "Caution!" Miraculously, she returned safely to her parked bike with the case and both pairs of glasses undamaged. We remounted and continued riding.

We'd started off riding with Jon and Becky but soon lost them. This was the first time since 2008 for Kerstin to ride her road bike, and I was having some difficulty getting her to slow down. Jon and Becky were pedaling our loaner fully-suspended, knobby-tired mountain bikes, so it was relatively slow going for them. I was on what I call my "city-trail bike," which is an early '90s hardtail Raleigh mountain bike with the knobbies changed out for smoother tires, and a rack and panniers on the back.

Returning to the starting point near Madison Street, we rejoined Jon and Becky, ate a well deserved Clif Bar, and rested a bit before continuing on the south section of Lake Shore Drive. Jon and Becky said they were going to get a coffee, then do part of the south route. They ended up going to 31st Street before turning around.

The south section of the route ends at 57th Street, and we got there well ahead of the police car that was sweeping stragglers off the Drive. Due mostly to the unexpected delay at the start, we knew we were going to be cutting it close hitting the other checkpoints on time. We were fine until we got to McCormick Place/31st Street, where we were directed onto the bike path. We rode past Soldier Field and the Field Museum of Natural History. We encountered a group of Segway riders and admired the Buckingham Fountain before returning to the staging area.

After picking up our commemorative T-shirts and biking to the parking garage, I racked our bikes just before an absolute deluge of rain. Good timing. Even though we were not favored with the blue skies and sunshine Jon and I enjoyed when the two of us did this same ride in 2008, it was a grand day.

Lakefront Trail ride
Soon after Bike the Drive, my son and his wife bought new bikes. He chose a Specialized cyclocross model, selected after telling his dad the kind of riding he wanted to do and asking what type of machine would best suit his needs. Fast forward to June 19, when Jon and I biked along the same lakefront without a gazillion fellow cyclists surrounding us. He always likes to spend Father's Day with me, and what better way to do so than on bikes?

So once again I drove into the city, and after a quick Dunkin Donuts breakfast, we rode eastward toward the beautiful Lake Michigan shoreline - this time on a clear sunny day. It certainly took me long enough to finally ride Chicago's 18-mile Lakefront Trail.

I've lived pretty much continuously in Chicagoland since graduating from college in 1969. I've always had some kind of bicycle, even if it was just the three-speed Schwinn Corvette I bought used in 1966. I got my first derailleur-equipped bike in '82 and did my first century ride in '86. So why in the world, save that little forced detour at the end of Bike the Drive this spring, had I never before ridden the Windy City's beautiful Lakefront Trail?

Well, in 1987 I began an ultramarathon career (strictly amateur) that lasted a number of years. Then I got hooked on off-road biking, including some racing. I simply wasn't moved to do much of the "easy" stuff. All in all, I guess I just never got around to it. As they say, "My bad," because riding this trail is an unadulterated joy.

Jon and I began by heading south. We stopped at a few of the historic beach houses, one of which had been in a sad state of disrepair until recently restored. Now there are fountains shooting plumes of water toward the heavens, and there's space available for events. After pedaling through a tunnel under Lake Shore Drive, we traveled through historic Jackson Park. For a lot of south siders, summer here means one thing: family barbecues. My ham-and-egg breakfast sandwich were a distant memory the moment the delicious aroma of grilled baby back ribs wafted under my twitching nostrils.

On a beautiful tree-lined, newly laid section of the bike path, it occurred to me that if I'd been brought there blindfolded and asked where I was, I would have offered many answers, and I never would have guessed "Chicago."

We stopped at a baseball diamond and took in a few minutes of amateur action. Outside the Museum of Science and Industry, a tour group received a history lesson. We stopped at a park with a lagoon, waterfall and arched stone bridge - an unexpected combination of Zen and Paris in the Windy City.

A sledding hill seemed to beckon Jon. "Hey, Dad," he said. "You want to climb up to the top with me?" I declined, opting to take a breather instead. I enjoyed watching him attack the hill. (I did not enjoy hearing he had stayed in the big chain ring all the way up. Life is not fair.)

With boats on Lake Michigan, Soldier Field (home to "Da Bears") and a gorgeous city skyline in the background, we stopped for a short break on Northerly Island at what used to be Chicago's Meigs Field, the airport which Mayor Richard M. Daley famously ordered destroyed during the middle of the night in 2003.

Near downtown we found a great little sidewalk cafè where we enjoyed a tasty lunch and entertainment courtesy of a guitar-bass-drums jazz trio. And guess what? I ordered baby back ribs. They tasted almost as good as the ones in Jackson Park smelled.

From there we pedaled across the massive iron bridge carrying Lake Shore Drive over the Chicago River. On this part of the trail and its adjacent Lake Michigan beaches, you will see just about everything: bikers, runners, inline skaters, suntanners, swimmers, young lovers and beach volleyball players. On another day we'd likely have ridden further north, but Jon had a soccer game to get to. (Later my strapping 30-year-old son would confide that perhaps a 33-mile bike ride right before a soccer game was not the greatest idea.)

LSD vs. the trail
So which is better, biking downtown Chicago en masse or on your own? I'd actually recommend both, with some qualifications:

I've done Bike The Drive twice now, and I've enjoyed the experience. Yes, there is a pretty stiff entry fee ($32 for early registration), but there are costs involved in putting on such a huge event, and the remaining proceeds go toward a good cause. For me, it's cool to ride with so many other people, especially on a route available to cyclists just once a year.

But I know such things are not everybody's cup of Gatorade. Organized rides like this one fall generally in the rain-or-shine category. Some folks love Bike the Drive and do it every single year, without fail. I am not in that category.

As for riding the Lakefront Trail, this is something I need to do more of. Aside from spending the gas money to get there, riding it is free. In fact, the Metra lines have certain trains that allow bikes onboard, so I could reduce my carbon footprint by riding the rails to the city. Even better, if I wanted a real workout, I could bike from my house in the northwest exurbs, tour the lakefront, and then ride back home. Hmm. I'd better think that one over first.

Other benefits of riding in the self-guided mode include bowing out if the weather looks too iffy and being able to stop whenever the mood strikes without the worry of being swept off the course (as long as you quit by 11 p.m. You're really able to see more when you're on your own.

So my advice is to do Bike the Drive at least once and then come to your own conclusion. If you live in or near Chicago or can travel there on occasion, by all means hit the Lakefront Trail. There's always something new to see.

"Pirate Bob" Friend, of Wauconda, Illinois, has completed 20 American Birkebeiners ski marathons and seven Chequamegon 40 mountain bike races. He is a veteran of Paris-Brest-Paris and many other ultramarathon cycling events. His goal is to come out of athletic retirement to do wilderness canoeing and backpacking and more biking.