In 2025 I bicycled through all the municipalities in the Commonwealth of Massachusetts. Here is the story. It’s long. That’s a lot of bike riding.
Why? At the end of 2024, three things happened.
One, in my role on the board of MassBike we 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 all of those parts of the state I had missed. And do it by bike.
Second, as a dedicated rider for the Pan-Mass Challenge, I pride myself on biking a Day Zero from Massachusetts border to Sturbridge, then ending in Provincetown. I would ride all the way across the state. Putting the “Pan” in Pan-Mass Challenge. A friend point out that it was only “Trans Mass.” Across Massachusetts. “Pan-Mass” means all of Massachusetts.
Third, I was left unsupervised for a week. My wife took the kids to Kansas City to see her mother while I stayed behind with the dog. 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 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 municipality every day. Since I have an office job, that really means seven each weekend. That seemed somewhat possible. Somewhat.
January
I decided I would kick it off on New Year’s Day. Start fresh 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
The following weekend we covered the northern boundary of Massachusetts through Haverill, Dracut, Methuen, Tyngsboro, Dunstable, plus Chelmsford, Lowell, Lawrence, Westford, and Boxford. https://www.strava.com/activities/13837206168
Then down along the southern border with Rhode Island and Connecticut. I skipped over Sturbridge, saving that for the Pan-Mass Challenge. We hit Holland, Wales, Monson, Hampden, East Longmeadow, Springfield, and a big climb in Wilbraham. https://www.strava.com/activities/13901667871
April
April kicked off with the Mix Tape mixed terrain ride. That hit Freetown. I was well ahead of pace so I thought it was okay to have a big group ride instead of focusing on the 351 quest.
The next weekend Christophe joined me for a big ride around the Pioneer Valley. It was chilly but had to stay on target. We started up in Granby on a cloudy day with the temps in the 40s. For that 100 miles we continued through South Hadley, Holyoke, Easthampton, Southampton, Westfield, Granville, Southwick, Agawam, West Springfield, Chicopee, Belchertown.
The next day was trouble. Crashed and broke my shoulder.
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 bad shoulder. During my May indoor rides and from physical therapy I had managed to get some movement in my shoulder. Enough to grab the handlebars and maybe control the bike.
On June 1 I headed off to the bike path to give it a try. It wasn’t great. The shoulder hurt, but I controlled the bike over the 8 miles. I managed to get to Wayland and check it off the list.
The next weekend, after a week of healing, I decided to push it a little harder and jumped up to 20 miles through Medfield, Dover, Needham, Wellesley and Natick.
The next weekend was B2VT. I signed up for this ride months earlier. 140 miles from Bedford, Massachusetts to Windsor, Vermont. That was much, too much for me. Maybe start and see how far I can go. I had a friend willing to come get me. I went to the line with Christophe, taking an easy pace. Went through Bedford, Carlisle, Groton, Pepperell, Townsend, Ashburnham and Ashby. I got close to the New Hampshire line before making the call for a pick up. 40 miles. Great progression.
A few days later it was the annual Plymouth to Provincetown ride. The route is almost 80 miles. A friend was willing to drive the van in support. I could ride as far as I could, then jump in the van. The weather was gorgeous. The friends were beautiful. I made it to the third rest stop at mile 50. I knew that I was not jumping in that van. I made it all the way to Provincetown.
Back to the mission. We headed to central Mass for an 80-mile ride. Christophe and I pedaled through Spencer, North Brookfield, New Braintree, Oakham, Rutland, Hardwick, Barre, Ware, West Brookfield, Warren, and East Brookfield.
July
The heat was on. The riding was. My focus was mostly to get ready for the Pan-Mass Challenge next month.
The next big ride was a Team Kinetic Karma team ride. We headed to Martha’s Vineyard for the six towns on the island. We mapped out a scavenger hunt for locations from Jaws. It was the 50th anniversary of the movie.
With the shoulder feeling better I picked up some of my regular rides and hit a few new towns. There was the hunt for aliens up to the Lincoln Labs radio telescopes in Groton. There was another Team Kinetic Karma team ride to meet our current and prior Pedal Partners.
Focusing on the 351 Quest, I took off to north-central Mass with Michael for a century. We started at the Wachusett MBTA station, climbed up Mt. Wachusett and ticked Princeton off the list. Downhill through Hubbardston to Petersham. You have to stop at The Country Store in Petersham for a break. It’s a great stop. It was a long ride and hilly ride that hit lots of new towns: Athol, Wichendon, Phillipston, Templeton, and Gardner.
The next big ride was a little further west, but covering the towns just east of the Connecticut River. Unknown to me it was apparently Newt crossing the road day. So many orange newts on the roads in Amherst, Pelham, Shutesbury, New Salem, Orange, Warwick, Northfield, Erving, Wendell, Leverett, Montague, Sunderland, and Hadley.
August
The first weekend in August means the Pan-Mass Challenge and riding across the state. You can see that long lie across the state. I knocked almost two dozen towns off the list. I had arranged my prior rides to mostly avoid these towns knowing that I would come through them on the first weekend in August. The only downside was that I didn’t stop to take pictures in each of the towns.
Later in the month I headed out to the Southern Berkshires. I was up and down the hills of Montgomery, Blandford, Otis, Tyringham, Monterey, New Marlborough, Sandisfield, Tolland, and Granville. I did a great job of mapping in a general store at mile 25. I just assumed I would find some place to stop during the remaining 60 miles. I was wrong. It was a hot day and my water bottles were empty well before I came into the center of Tolland at mile 65. I remembered my friend Rami mentioning that many city building and churches have outdoor spigots as a service. I saw the Tolland library. Stopped. Soaked my head in the glorious water pouring from the spigot. Filled my bottles and continued on. Thank you Tolland tax payers.
September
I knew that I had two towns that would a whole day just for the each town. I bet you could guess Nantucket. Can you guess the second?
Gosnold. Where is that? It’s the chain of island off Woods Hole and west of Martha’s Vineyard. Most of the islands are privately owned and inaccessible. The one I could get to is Cuttyhunk. I got lucky with the weather and it was gorgeous early September day. Kristin, David, Chinny and I grabbed put our fat bikes on the ferry in New Bedford for the ride over. I had been to Cuttyhunk by boat several years ago and saw a sandy beach and a somewhat rocky beach. I assumed we could circumnavigate the island on its sandy beaches. I was wrong. I has see the leeward side of the island. The rest of the coast was inhospitable to bike riding. We did find some great dirt roads to get us around most of the island. By the time we ate lunch and got back to the ferry we had covered most of the island.
The prior week, on Labor Day I tackled the northwest portion of Massachusetts, circling around Mount Greylock. That knocked Pittsfield, Lanesborough, New Ashford, Windsor, Savoy, Washington and Hinsdale off the list of remaining municipalities
The third weekend was Breakthrough T1D Cape Cod ride. I was able to scoop up Harwich, Chatham and Mashpee while I was on Cape Cod. Those were the last three towns on the Cape. Oh, and I raised money for Breakthrough T1D to fight against Type 1 Diabetes.
Next up were nearby towns that I don’t ride through much. Christophe and Michael joined me for a ride up Blue Hills and then through Milton, Canton, Stoughton, Sharon, Foxboro and Dedham.
That was followed by the For Pete’s Sake Memorial ride that raises money for MassBike, in remembrance of Pete Del Sette. Besides raising money for MassBike (one of the reasons I took on the 351 quest) it also allowed be to ride through Georgetown, Rowley, Newbury, Ipswich. Hamilton, and Beverly.
I finished off the month riding through towns on the south shore: Plympton, Pembroke, Marshfield, Kingston, Duxbury, Carver, and Plymouth (again). I managed to miss Norwell, so I stopped on the way home from the earlier ride to cover a few miles in Norwell on my bike.
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 out 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.
On the way back from the Nantucket ferry I stop to take a picture by the Yarmouth town sign. I had already been through town twice: Plymouth to Provincetown and Pan-Mass Challenge. I hadn’t stopped to take a picture either time.
Yarmouth comes last alphabetically so it seemed like good karma to have it be the last picture taken of the Massbike 351 quest.
