Annual Boston to Provincetown bike rides, 1983-2025
50 years ago, New England was experiencing a heat wave similar to the present. In July 1975, the temperatures in Boston were often over 100. As a college junior of limited means who decided to stay in the (non-air conditioned) dorms over the summer, I was desperate to escape to Cape Cod over the weekend. I had no car, no friends to drive me, the buses were fully booked, and there was no place to stay there anyway.
Perhaps long on academics but short on common sense, I decided to ride my bike. Surely I’d find someplace to camp once I got there. It was way too hot to bike in the daytime, but just three months earlier I’d taken that all night ride following Paul Revere, why couldn’t I do it again? Still on a cheap 10-speed, still with no helmet, but at least I had a light of sorts. Do any of you remember Wonder Lights, those gizmos you strapped to your left knee? The anemic flashlight bulb within would bob up and down as you pedaled, hopefully attracting the attention of drivers.

How to get through the sketchy neighborhoods south of Boston? Simple: just sneak your bike onto the Red Line (illegal back then) and hope nobody caught you before you got to Braintree.
Improbably, it all went off without a hitch. Nobody caught me, and by 11 PM I was cycling down busy Route 3A from Braintree through the South Shore towns of Cohasset, Scituate, Marshfield, and Plymouth. No close calls, the traffic thinned out after 1AM, the sidewalk on the Sagamore Bridge wasn’t too bad, and cruising Route 6A on the Upper Cape in the wee hours was oddly peaceful. I only wished for a place to get a snack and a coffee.
The sun was just rising as I hit Coast Guard Beach in Eastham, and I collapsed gratefully on the sand. I wasn’t dozing for 10 minutes before I was nudged awake by a park ranger.
“You can’t sleep here.”
“ I can’t take a snooze on the beach?”
“You obviously biked a long way with your camping gear, and there’s no camping on the beach. You have to find a campground.”
I called every campground in the Yellow Pages, all were full. The ranger had no suggestions, and kept his eye on me. I saw I had no choice but to return to Boston.
As a college kid, I’d pulled my share of all-nighters, but never like this. I didn’t think you could fall asleep while riding a bicycle, but a couple of times I nodded off on 6A, the wobbling bike snapped me back awake. I tried to lay down in the grass next to the road, but invariably a concerned motorist would stop and ask if I was OK. I was now desperate for coffee, but the only establishments on 6A were real estate offices and antique stores. I somehow made it back to Plymouth at 11 PM, where a Good Samaritan saw me staring dolefully at my map, wondering how to get back through those sketchy neighborhoods after the subways had shut down, and offered to give me a lift to my dorm in his pickup truck. So despite my idiocy, I survived.
Claire Saltonstall wasn’t so lucky. Biking to the Cape by a different route in broad daylight the previous year, the 16-year-old had been killed by a motorist who veered into the breakdown lane. Her grandfather was renowned US Senator Leverett Saltonstall, her father was state senator William, who had advocated for safe bicycle routes for years. The driver was clearly at fault but refused to apologize, on his lawyer’s advice. The high profile trial set the precedent that apologies could no longer be construed as tantamount to an admission of guilt. Anyway, the family funded the creation of a safe route to Cape Cod called the Claire Saltonstall Bikeway. https://en.wikipedia.org/wiki/Claire_Saltonstall_Bikeway
Fast forward to 1983. Older and wiser, with a medical degree to boot, I no longer considered biking without a helmet. I had a fancy new bicycle. And best of all, I had a biking buddy who was game for anything.
A buddy and a mentor. Richard Nelson Bail was the finest doctor I’ve ever known, and I’ve known some great ones (see my On the Shoulders of Giants post a few blogs back.) In an incredible stroke of luck, he was assigned as my principal precptor in my Primary Care Internal Medicine residency, at the Harvard Community Health Plan. Dick had it all: academic rigor, intellectual curiosity, a bedside manner to put Marcus Welby to shame, and a teacher par excellence. He was a role model to aspire to for the rest of my life, even as he set a target I could never hope to reach.

A real Renaissance man, his bio is so long it would make this post unwieldy, I encourage you to read this tribute. https://www.communitieswithoutborders.org/the-passing-of-richard-nelson-bail/ Suffice it to say his altruism and community involvement matched his medical skills. To top it off, he was a great athlete, one of those 2% body fat guys. He biked to work year round, and ran during his lunch hour. No fancy bike for him, he had a beat up 1960s Raleigh Grand Prix, a milk crate bolted to an old child seat rack in back plastered with a bumper sticker for Moosehead Beer: The Moose is Loose! It didn’t matter—12 years younger, I couldn’t keep up with him.
That summer we hit upon the idea of trying to bike from Boston to the tip of Cape Cod in a single day. We would do it in June when the days are the longest, leave at the crack of dawn and hopefully get in before it got dark. The Saltonstall Bikeway was over 130 miles and Dick, who had grown up in southeastern Massachusetts, suggested enhancements (many involving beaches, scenic bike paths and detours to places like Plymouth Rock and Wellfleet Harbor, favorite swimming holes, and ice cream stands) which made the total closer to 150.
Once again, it went off without a hitch. Well OK, I was a little numb in the crotch for a couple of hours but overall, we were delighted. After spending the night in Provincetown, we took the ferry back to Boston, passing right over Stellwagen Bank, where all the whale watch ships go. Entering the city by sea is a moving experience.
We thought it would just be a one-off, a stunt, but the following year we realized we’d liked it so much we tried it again, and brought some other friends along. It turned into an annual tradition in spite of ourselves, and with further embellishments and refinements we dubbed it Beantown to Ptown with Claire. Sometimes, as many as 15 people would join us.
Other groups had similar ideas, organizing supported group rides, fundraisers for multiple sclerosis and AIDS research, and most notably the Pan Mass Challenge to support the Dana Farber Cancer Institute. An LGBTQ group, the Outriders, marks their route with distinctive green arrows on the pavement http://www.outriders.org/index.html.
I’ve followed some of these routes, but still like ours the best. It makes maximal use of bikepaths such as the Cape Cod Rail Trail, the National Seashore and Cape Cod Canal bikepaths, the Emerald Necklace paths in Boston, and the D.W. Field Parkway in Brockton. Almost all of the rest is on quiet back roads, with very few stretches on busy arterials, most of these are encountered in the early morning when there is minimal traffic. The only dicey section is a 3 mile stretch along Route 6A in Barnstable and Yarmouth, the shoulder is marginal but this is part of the official Bikeway, and the motorists are generally quite tolerant. Every year we’ve tweaked the route, keeping up with bike infrastructure enhancements and updating maps, cue sheets, and most recently navigation software. There are hundreds of turns, I’ve curated the directions to eliminate any ambiguity or confusion, and even thrown in some fun facts. Here is the latest route, field tested just last May: https://ridewithgps.com/routes/50798046
Irresistible. Sort of a greatest hits of the South Shore and Cape Cod. Mostly flat, with a few short hills. I can’t stop doing it. This year marks my 40th time (I skipped a few years when my children were born). Lately it’s just been me; older and fatter, I’ve slowed down and have had to take two days these last few years. 40 is a nice round number, I think from now on, I’ll do it on an E bike.
Alas, Dick is no longer with us. I mentioned his altruism and dedication to public service, in the early 90s he did a two year stint with the World Health Organization in Brazzaville, Congo, and contracted hepatitis C, which was endemic there. Nowadays the infection can be cured with a single sofosbuvir/velpatasvir tablet daily for 12 weeks, but back then all we had were injections of interferon and ribavirin. Dick gave these to himself weekly for years, they always made him feel punky so he skipped a dose when we took our annual bike rides. These delayed but did not halt the progression to cirrhosis, and he ultimately required a liver transplant. At that time, he was found to have a hepatocellular carcinoma (a known complication of cirrhosis) which responded to chemotherapy, but ultimately recurred, and he passed away on May 29, 2019.
So emblematic of his selfless dedication to help others, his noble efforts led directly to his untimely demise. A hero for the ages. I will continue these annual bike rides in his honor for as long as I’m able, with my thoughts full of how he enriched my life, and countless others. With due respect to Claire, I’d like to rename it the Dick Bail Memorial Bike Route. I encourage you to try it sometime. But watch out, it can be habit forming.