The weather was looking good, so I decided to make this bike ride a “go.” I have always wanted to pedal from Boston to Montreal, but I decided to add another day. It just sounded better, got me close to 500 miles total, and covered some totally different and unique geography and history. I am glad I did it. 

Kara and I took the ferry from Boston to Provincetown, Massachusetts, on Thursday evening. It was sweltering in Boston, so the boat ride was perfect. We took the Fast Ferry, which blasts across Boston Harbor to Provincetown at the tip of Cape Cod. If you don’t know where it is, it’s worth a Google. It’s a unique place in the world and this time of year is beautiful. There was a summer storm in view—fortunately in the distance—so we caught a sweet lightning storm and rainbow but didn’t get wet. We pulled into a bright marina in P-Town, with its sand dunes, boats, marinas, and lighthouses, all of which make it such a great and unique spot. 

We ate at Sal’s in Provincetown, which I highly recommend. The owner Siobhan is so special and awesome, and they prepare an amazing dinner in the restaurant or served at tables in the sand. We stayed at the AWOL, which I also recommend. This hotel has a great location off the Main Street, overlooking some salt marshes. I didn’t spend much time there, but did get a good night’s sleep before I rolled out at 6 a.m. the next morning. 

After one hour of pedaling, I was fortunate to have my first stop at THE BEST bakery, maybe in Massachusetts? New England? It’s possible! I certainly don’t know a better one than PB Boulangerie in Wellfleet. The place is indescribably perfect. I overate with a friend of mine from work and packed my pockets before I hammered to Boston. The ride through the Cape is a great one. There are historic homes; 20 miles of rail trail; old trees (including huge beech trees); stone walls; Plymouth, where the Pilgrims landed; Quincy, where John Adams was from; and so much more. It’s definitely recommended! 

On Day 1, my overall ride from Provincetown to Boston was 126 miles.  

Day 2: Boston to Brattleboro, Vermont: 102 miles 

Day 3: Brattleboro to Waitsfield, Vermont: 125 miles 

Day 4: Waitsfield, up and over the Green Mountains of Vermont at Mad River Glen and into Montreal, Canada: 137 miles  

Total: 490 miles 

I made it a point to pedal as much of Route 100 in Vermont as possible. Route 100 is known as the spine of Vermont and runs the length of the state from Canada to Massachusetts, passing by many of Vermont’s famous ski resorts, such as Mt. Snow, Okemo, Killington, Mad River Glen (ski it if you can!), and Stowe. The route goes through many historic towns like Warren. The foliage is almost tropical and lush this time of year, and the farms, views, old silos, rivers, flowers, and views are epic Americana! Plus, the hills are real in Vermont. They call them “rolling” hills or rollers but they are more than that! Some are 5-7 mile climbs. Some are long up-hills and/or 7- to almost 15-mile mostly downhills. Some are 7-9-12% grades. Rollers are deceiving. The overall elevation gain may not be as big as a day in the Western U.S., but the overall effort can be harder. You push harder to crest these summits and the MANY efforts all add up from a strain perspective. 

I did the ride in four days but could have done it in three. I had more in the tank each day and wanted to pedal more, but wasn’t able to find hotels. They DO exist; I just didn’t look too hard. There are tons of small, unique properties along these roads that just take a little more effort to find. For example, I stopped in Brattleboro because I didn’t think there were any hotels for 50 miles, but when I branched onto Route 30 north, there WERE places to stay. The same was true after Waitsfield, toward Mad River Glen on Route 17 north—there were places I could have kept going to. 

Some highlights of the ride include:  

One funny story worth noting was when I crossed the border. The Canadian border patrol agent was such a nice guy, and crossing the border on a bike, in a small town like that, was really cool—a first for me and something I hope to do a lot more of, ideally across Europe. The border patrol agent said to me, “Do you always ride your bike in the rain?” To which I replied, “Only when it is raining!” We both thought about it for a second and he said, “Yeah, I guess that makes sense!” 

Overall, the weather was perfect for the ride. Even the last 60 miles from Vermont into Montreal, when it was raining, were actually great. It was warm enough, so it wasn’t a problem. The last 25 miles were through a total downpour, but again, it wasn’t a problem at all and it didn’t take away from the ride. I hoped to hit 500 miles, but the rain, plus the fact it was getting cold, I didn’t know the city well, and it was congested made me decide against riding the final 10 miles through the city.  

So, I ended up doing 490 miles total over four days, including 12.950’ of climbing. It was a GREAT ride—I highly recommend it. And I am psyched to get my THIRD event of the Big Belt Buckle Challenge completed. I will try for my second attempt of the Grand Teton in a week and a half! 

In addition, Tommy Café and Joe Beef are worth a shout-out in Montreal! Unfortunately, Kouing Amann was closed for the month for a well-deserved vacation. Kouing Amann rivals PB Boulangerie. I suspect it’s the best bakery in Quebec!