In 2025 I bicycled through all the municipalities in the Commonwealth of Massachusetts. At the end of 2024, three things happened.
One, in my role on the board of MassBike we had were working on the organization’s mission statement. We made it explicit that it was state-wide and for all people throughout Massachusetts. I realized that even though I had lived in Massachusetts for almost my entire life, I had not been to large parts of the state. I felt the need to explore of the state by bike.
Second, as a dedicated rider for the Pan-Mass Challenge, I pride myself on biking a Day Zero from the New York border to Sturbridge, then ending in Provincetown. I would ride all the way across the state. A friend point out that it was only “Trans Mass.” Across Massachusetts. “Pan-Mass” means all of Massachusetts.
Third, my wife took the kids to Kansas City to see her mother while I stayed behind with the dog. I was left unsupervised for a week. My office was closed. Lots of time to think and let crazy ideas run through my head.
Would it be feasible to ride a true PAN-Mass and bike through all the towns in Massachusetts?
First, the list. There are 351 municipalities. See my live list: https://docs.google.com/spreadsheets/d/1RBLkph2d5Buh-d1l5jpkWieLxIQJ6U35rHFPG-lqk8Q/edit?usp=sharing
Quick lawyer math lead me to the conclusion that I would have to ride through one a day. Since I have an office job, that really means seven each weekend. That seemed somewhat possible.
January
I decided I would kick it off on New Year’s Day and see how it might go. How to begin? I was faced with a long list of blank spots. Easiest choice was to start at the beginning.
Abington comes first alphabetically. I plotted a route that would take me through eleven municipalities. Damp and 48 degrees is not pleasant, but great for a Boston January. I was already ahead of the needed pace getting through Abington, Holbrook, Pembroke, Hanson, Whitman, Randolph, Weymouth, Avon, Brockton, Whitman, Rockland, and Holbrook. https://www.strava.com/activities/13240153346.
Eleven done on the first day. That put me way ahead of the need pace to complete the quest. Of course it’s stupid to extrapolate from a single event. But who said this quest was about being smart.
Next up on the alphabet was Acton. That’s a regular cycling destination. I’ll put that town off for later.
That meant Acushnet was next. I had no idea where that was. Of course, finding out where that town is located was one of the reasons for doing this quest. I learned that Acushnet is next to New Bedford. I was off to the South Coast to ride through Achushnet, Fairhaven, New Bedford, Westport, Dartmouth, and Mattapoiset. The Mattapoiset rail trail is wonderful. https://www.strava.com/activities/13265871471
I decided to balance off those southern rides with a more northern ride. I put Lynn, Winthrop, Revere, Chelsea and Everett on the list. That included my first ride on the Northern Strand Rail Trail. That was a delightful discovery. https://www.strava.com/activities/13274631844
Next weekend, it was back in my old neighborhoods, riding through Bridgewater, East Bridgewater, West Bridgewater, and Halifax. https://www.strava.com/activities/13327946495 Again to balance, back to the north with a ride through Peabody Swampscott, Marblehead, Salem, Danvers, Wenham, and Topsfield. https://www.strava.com/activities/13336805936
Up next was squeezing in three very different rides. The first was along familiar roads I frequent around Medfield. https://www.strava.com/activities/13391011725. The second was a more urban ride on unfamiliar roads north of Boston in Melrose, Wakefield, Stoneham, Woburn, Winchester, and Medford. The third was on Southern New England Trunkline Trail and through towns on the Southern border. https://www.strava.com/activities/13400201222
I finished up the month with a short ride around Worcester before the MassBike Annual Meeting. https://www.strava.com/activities/13450384531 Later in the weekend, we continued along the southern border of Massachusetts through Dudley, Webster, and Southbridge. https://www.strava.com/activities/13459810423 I was saving Sturbridge for the Pan-Mass Challenge.
It still doesn’t look like much on the map. I was way ahead of schedule on the number of towns.
February
Good thing I got that running start because February had some snow that kept me off the roads for a few weekends.
I did sneak in a ride from Easton, Raynham and the Norton-Mansfield Rail Trail. I’m going to have to get back to that trail when it’s not covered in snow and ice. https://www.strava.com/activities/13576163917 Then down to Marion and Rochester. https://www.strava.com/activities/13576163885
Back to some familiar roads in Medway and Norfolk. https://www.strava.com/activities/13698963880
I finished it off by riding along the Rhode Island border from Attleboro down to Fall River, through Seekonk, Swansea and Somerset. https://www.strava.com/activities/13707811140
The winter weather impacted the ability to get miles in and limited the number of towns.
March
I kicked off the month with a circumnavigation of Worcester and the Wachusett Reservoir. Worcester circumnavigation for MassBike351. Mistakes were made. I wanted to bike the Blackstone River Greenway. It was mostly covered in ice. I still managed to tick off 13 towns. I also made my first route planning mistake. In that big loop, I failed to bike through Boylston. I went right around it, leaving a hole in my accomplishments.
We battled the cold the next day with a loop out of Burlington, through Middleton, up to Andover and back. https://www.strava.com/activities/13771562632
April
May
Nothing. I did a few indoor rides with my arm in a sling.
June
The doctor said he wasn’t going to tell me not to ride my bike. But I definitely could not fall on the shoulder.
July
August
The first weekend in August means the Pan-Mass Challenge and riding across the state. I had saved most of those cities and towns on Day Zero and Day One from my earlier routes.
September
October
October brought the PMC Unpaved. It would only be two untraveled towns for me: Lenox and Richmond. But Christophe and I decided to make along weekend of it. On Friday, we headed west and rode through eleven new towns (for me) out of the Pioneer Valley and into the Berkshires. Saturday was the celebration of the PMC Unpaved. Sunday was the southwest corner of the state: Great Barrington, Sheffield, Mount Washington, Egremont, and Alford.
I missed the crew’s ride on Cape Ann. That was a hole I had to fill on Columbus Day. Unfortunately, there was also nor-easter hitting the region, so it was a miserable solo ride in the cold, rain and blowing wind.
Cathy and John hosted a ride starting in their town of West Newbury and covering the northernmost part of the state. Chasing John and Cathy around Northern Mass.
I had to fix two mistakes. In my circumnavigation around Worcester and the Wachusett Reservoir, I had missed Boylston. A routing mistake. I had also failed to plan a ride to through Boxborough. Those mistakes were easily fixed with a great ride back and forth from both town’s town halls. Box Boy for MassBike351
The penultimate ride was planned to be a beast. I had laid 13 towns in the Northern Berkshires, most of Franklin County. It was going to be 90+ miles with 9000+ feet of climbing. Getting this done is one push would leave just one town left. Martin, Christophe and Jessica were willing to take on this beast with me.
We should have noticed the omen as we passed by the Turner Falls Dam. A dozen vultures were sitting on the edge of dam, wings spread
November
I knew Nantucket would be a challenge. It’s a lot of effort to get there. Although I’m willing to ride my bike in storms, the ferry will cancel service in storms. I had hoped to get to Nantucket on November 1. The day before the PMC check presentation on November 2. High winds had cancelled the ferry service on October 31 and carried over the next day.
Nantucket would have to wait. I had two months. Waiting also meant that the days would keep getting shorter and the temperatures getting colder.
Finally, on November 15th, I had an opening in my schedule and the weather was as good as could be expected. It was forecast to be cool, sunny and light wind.
I got a crew of Kristie, Jessica, Celia, and Christophe to join me on this last town. My wife came along to stroll downtown and get some lunch while re biked. It was a beautiful day. How far to ride? You’ve seen the maps. I needed to just ride enough to light up the heat map. We rode out to the Sankaty Head Lighthouse on the eastern side of the island, down to Sconset Beach and were headed back to the center of the island to explore the western half.
I got a message from my wife that she was sitting down to lunch and wondered if she should get a table for six and order food for us. Enough biking. Let’s stop and celebrate. That was 351. Quest complete.
