2023 Outriders Ride – Boston to Provincetown

Outriders is an organized, supported double metric (200+ km, 128 miles) century ride from Boston to Provincetown. It doesn’t require fundraising, so it’s just for fun.

I signed up for Harbor to the Bay this year, which is also going to be the last H2B ride. I don’t even remember how I came across Outriders, but I was pleased that it doesn’t require any fundraising and it’s supported. So I signed up right away. The registration form says it’d be capped at 150 riders, and I expected it to reach the capacity. It turned out only 57 registered.

I told Mark, a Googler, who did the century with me three weeks ago. And he was worried that he wouldn’t be fit and strong enough to do it. But I think he was confident enough after we finished the century.

The ride was on Saturday, June 17th 2023. However weather wasn’t looking good at all as it approaching. Weather forecast on the night before said it’d be raining all day, with possible thunderstorm in the early afternoon. I was thinking, if Mark texted me saying he didn’t want to do it, I wouldn’t do it either. But he didn’t say anything, so I got prepared the night before, picked my cycling kit and went to sleep early.

I really didn’t know what to wear for a summer rainy day. I have a rain jacket – Gorewear Lupra. But it is not breathable enough. I’ve worn it for commute, which is only 2.5 miles, and I’d be steamed. I have several long sleeve jerseys, but most of them are for winter cycling, except one that was lightweight, which was from a Google group order. So I decided to wear that. Mark also mentioned he’d wear shoe covers, which reminded me a previous ride in Provincetown on a cold wet winter day. And it turned out shoe covers really saved the day for me.

The Route

From Boston to Provincetown, 128 miles. BikeWithGPS says it’s almost 5600 feet ascent, but my Garmin head unit recorded 4400 feet ascent.

I was really worried about the first 20ish miles because it’s mostly in Boston and Quincy. I’m not a morning person, so I’ve always been fighting with traffic when I ride in the city. But it turned out to be the most pleasant segment on this ride…

I’ve biked from Plymouth to Eastham for my metric century; Hyannis to Provincetown three times. The route between Boston to Plymouth would be all new to me. One difference though – I was prepared to walk on Sagamore bridge instead of biking, which was what I did last time. It was terrifying.

There are 5 checkpoints along the way:

  • 30 mile – Halifax
  • 60 mile – Sandwich
  • 81 mile – Yarmouth, on CCRT
  • 108 mile – South Wellfleet, CCRT Trailhead
  • 118 mile – Truro

Each checkpoint provides food, water, simple bike tools, and volunteers who were really helpful and pleasant to chat with.

There’re also green shiny triangle markers along the route at every turn, pointing to left or right or straight.

Before the Ride

On the night before, I started getting prepared. I came up with a packing list with me on the bike:

  • The lightweight long sleeve jersey
  • Ornot cargo bib shorts – Extra pockets will be handy
  • Phone, keys, wallet
  • Two energy gels, two energy bars (CLIF and KIND) – I didn’t pack too much snacks because there’ll be plenty of them at checkpoints
  • Electrolyte pills to put in the water
  • Garmin head unit
  • Garmin Radar / taillight
  • Garmin headlight
  • Heart rate monitor
  • Helmet
  • Cycling shoes
  • Two water bottles
  • KOM Cycling Saddle bag
  • Emergency toolkit: Spare tube, CO2, tire levers

I went to bed around 10:30pm, and set alarm at 5am. I actually woke up before the alarm around 4:50, and I made myself a latte, microwaved a breakfast bowl with sausage, potatoes and eggs, filled up my water bottle, put on the saddle bag, head unit, taillight and I took off to the meeting point.

Boston to Halifax

Check-in point was in South End on Tremont St, which is only 5 mins ride from home. I texted Mark when I left. I started the bike computer right away, but it had some trouble finding satellite signal. I started getting worried, I didn’t want to mess up with it after the ride began to miss part of the ride. Fortunately it started working on Tremont before I reached the check-in point.

I saw Mark right away, there were volunteers wearing Outriders shirts and other riders. I told them my name, and they wrote my rider number on the side of my leg with marker. That’s it. It was that simple. Then Mark and I just took off.

It was 6 am in the morning. Traffic was very sparse. We were feeling great – it was dry, no cars, and we were in high spirit. It felt so nice not having to fight my way in the motor vehicles on the city roads.

Along the way a young man joined us. I overheard his conversation with Mark – I was leading all the time in the front. He was a recent graduate from BU, and Mark told him we both work at Google.

The first 30 miles was very delightful. The first checkpoint was in the parking lot of West Monponsett Boat Ramp. We had a great conversation with volunteers. We got to know what only 37 out of 57 riders who registered showed up in the morning. Apparently a lot of riders were scared off by the rain. We ate some snacks, orange slices and bananas. We used the porta potty which was still very clean. I stretched a bit, texted Josh (and found out he already woke up) and we took off again.

Halifax to Sandwich

Shortly after we left Halifax, we started feeling raindrops. We wanted to cover as much ground as we could before the rain. It might be late, but it’d come.

We were caught in a real downpour around Plymouth. Raindrops hurt when hitting my face, especially on descending when we were going 25+ mph. I was completely soaked just within a few minutes. At that time the rain wasn’t cold, and we were pedaling hard. It felt so liberating, that we were already soaked, so we couldn’t get wetter. Just let it rain!

We stopped briefly around Plymouth so the young man could put on his raincoat. I don’t think it’d help much. I really didn’t care how much water I got, the only concern I had was not to crash. I knew the road would be slippery and it’d be very dangerous to crash on a descent. Fortunately I was able to control the bike really well, and I started getting used to ride on the wet surface and with wet jerseys.

I basically stopped worrying about being cold and gross, because I was enjoying the ride so much, even in the rain. It already felt a great accomplishment.

Mark’s shorts became soapy in the heavy rain, which I found pretty funny. I think he put too much soap or didn’t rinse it enough when it was washed 🙂

After battling with rolling hills and heavy rain, we reached Sagamore Bridge. I decided to walk my bike like others because it was terrifying last time when I biked on the narrow sidewalk. It was the canal on the left, several hundred feet above the water; and heavy, fast traffic travelling 50+ mph within 2-3 feet away. I am scared of height. So I reminded myself not to look at the water at all, just focusing on walking on the sidewalk. Finally we got over the bridge and I was glad I could ride again.

I almost missed the checkpoint at Sandwich. While I was suspecting why the green arrow on the road didn’t agree with my navigation, I was already 20 feet out since I was always leading the way. But Mark yelled at me so I stopped in time.

The Sandwich checkpoint, as the name, has Peanut Butter Jelly Sandwich. I’ve never had PBJ before because I think it’s kind of stupid – it’s too simple to eat as lunch. But I needed food and energy, and I figured eating some real food would make me feel better than just eating energy bars and fruit. So I had a PBJ for the very first time in my life time. It was OK. Mark seemed to like them a lot! He ate two PBJs!

Checkpoint #2 also had peaches and I loved them. I also had some Oreos and other snacks, and a banana. There’s a bathroom a few miles down the road, but we all decided to use the nature to solve that problem.

One volunteer asked the young man how he found out about this ride. He said he just searched on Google for supported century rides from Boston. The volunteer said they’d need to figure out a way to reach more riders. I really think this is a great ride, so I’d advocate for it to people around me.

We didn’t want to stop for too long. We took off again after roughly 10 minutes or so.

Sandwich to Yarmouth

We were greeted by “Grooved Pavement” in Sandwich just a few minutes after we took off. It was the most awful riding experience. The whole bike and my body were shaking and vibrating and I was just hoping I was not going to get concussion and my bike would be OK. It lasted for about a mile or so, and finally the pavement returned to normal.

My heart rate came down during the stop, so it started feeling very chill when we were leaving Sandwich. I knew I needed to get my heart rate up to keep myself warm. So I pedaled pretty hard for about three to four miles.

And rain stopped when we were approaching Hyannis. Hyannis is the biggest town on the cape cod, so there’re a lot of businesses, shops and a big mall, which means wider, busier roads and much more traffic. Country scenes are always beautiful and relaxing on a bike ride. Not so much for strip malls and cars.

It got quiet again when we turned onto the service road of Route 6. A lot of rolling hills on it, but I’m really good at it. Traffic was really heavy on Iyannough Rd in Hyannis, fortunately we didn’t have to ride too long on it. Then we passed by the airport, some industrial district, and Cape Cod Hospital, Steamship Authority before approaching to the CCRT – Cape Cod Rail Trail. I recognized one rider who was circling back to ride with us, and I took off for a bit because the weather was nice, and my jersey was dried up by then, and there wasn’t much traffic with nice tarmac. He was drafting behind me closely. I didn’t know why he circled back, apparently he was fast and can maintain at least the same speed as me. Then I knew the reason at the trailhead – some construction work blocked the trail head. For someone who hasn’t been there, there’s no way to find it. Fortunately Mark and I were there just three weeks ago, and we knew we could get to the trail from a parking lot next to it. So we directed everyone to the trail.

Yarmouth checkpoint was just 2 miles into the trail, at a local park, with real bathroom, running water (especially hot water). We met someone whose rider number was three digits – mine was 2768. He said he did the same ride over 30 years ago in 1991 – when I was born. The young man who was riding with us was born in 2000.

We enjoyed the apples, orange slices, more PBJs and snacks. I used bathroom again, and it felt great to wash my hands with warm running water. When we were about to take off, the early rider fell from his bike, in the parking lot, which was exactly the same situation that happened to me on Wachusett Mountains. I felt bad for him, but I was happy that I wasn’t the only one that had such a dumb incident 🙂 He didn’t mess up his bike, and he wasn’t injured. He joked “at least I have audience”.

CCRT – Yarmouth to South Wellfleet

The next segment was solely on CCRT. I could really take off on the trail, because it was empty. However, Mark was having a hard time keeping up. He “felt much more of a slog” this time, than last time when he had fresh legs. The young man is apparently stronger so he took off.

Then it started raining again, thought not as heavy as around Plymouth, but I got soaked again. I had to wait for Mark all the time, and I was passed by the group of New York riders. I was so not happy about that. They were going at my pace, and I was thinking how nice it’d be if I could ride with them. Then I also kept telling myself I couldn’t just drop my cycling buddy Mark because I wanted to be in a faster pace. It was not a race after all.

Bike trails are good and bad. They are good because they’re separated from traffic, so it’s not dangerous. They are bad because of so many things. On a good weather day it was packed with casual cyclists and pedestrians, runners and families who don’t attend to their children. Some of the bike trails feel like they go on forever. You don’t get the scenery change of riding on the road. Everywhere looks the same on the CCRT. I felt the same – tiring and discouraged – when I rode Minuteman bike path home after riding through those hills from Belmont to Concord.

As we approaching South Wellfleet the rain got harder. I really wanted a PBJ at the rest stop. However, there was no PBJ and not even a shelter. One volunteer was holding a big umbrella moving around, trying to give some protection against the rain, but it didn’t work very well. I just ate some fruits and some snacks. I had one of my energy gels. I didn’t even drink any water from Yarmouth to Wellfleet. The ocean breeze started to feel chill, and I really just wanted to get over the ride.

Mark tried to wipe water off his saddle and handlebar with paper towels, at the same time saying “I don’t know why I do this because it’ll get wet in 5 seconds”, which I totally agree. While he was wasting his energy doing that, I took pics of my filthy new bike.

We met the New York group again here, but this time they arrived earlier than us. While they were leaving, one guy said he was worried about the hills. From the speed they passed by on the CCRT, they had no reason to worry about climbing, if that’s what he meant.

Wellfleet to Truro

The last two segments are only 10 miles – 108 to 118 (Truro), and then 118 to 128 (Provincetown, finish line). There’re a lot of hills in Wellfleet and Truro, the most steep one is Perry’s Hill.

From the end of the trail, we turned right and then left onto Ocean View Road. Yes it’s very scenic and beautiful, but I was wet and cold, nice views were the least on my mind. Before turning onto the Ocean View Road, I thought I was just pedaling normally, but I unexpectedly dropped Mark by 30 seconds to 1 minute.

There is a medium hill once turning onto Ocean View Rd, and I looked back and checked on Mark when I almost finished climbing. However the ocean breeze really chilled me down on that section, so I decided to pedal hard, at probably 70% effort, to get my heart rate up quickly. The consequence? I dropped Mark immediately and he didn’t see me for the rest of the segment, until I stopped at the checkpoint at Truro.

About 5 miles down I was actually slowing down. At my 20-30% effort probably. I was hoping Mark would show up; I was even debating if I should completely stop and wait for him. However that means my heart rate would come down again, and I’d feel cold. So I kept that level of effort until I got to Truro.

The Truro checkpoint was also very simple – again no PBJ. And the New York group was long gone. Just a few minutes I stopped, Mark showed up. The first thing he said was “What the Hell Jerome?!” I can understand if he’s frustrated. It’s never easy to play catch-up all the time, but I’ve never needed to catch up with my friends because I am the fastest (also lightest). I explained to him why I took off, and he said he understood, and he’d still allow me to have dinner with him 🙂

The two girls we passed in Boston caught up and they didn’t want to stop at all. They checked in and left. That was what I was thinking, but I decided it’d be better if I waited until Mark showed up. We just had some snacks and took off to our final destination – Provincetown.

Truro to Provincetown

This section doesn’t have as much hills as in Wellfleet, but it involves 1.5 miles on highway US Route 6, which is the major highway running through all the towns on Cape Cod. Definitely not fun.

We didn’t have to wait too long to cross the highway from Castle Rd, so that was good. Shoulder is wide enough not to be splashed by cars driving by at 50+mph. The long descending into Truro Center with strong cross winds got me a bit scared. My wheels are 40mm deep carbon wheel, and it was very wobbly in the cross wind. I focused on controlling and holding steady, while applying brake gently because the road was so wet.

When the descending was finally over, I was so relieved and started another little climb. We took the exit to Highland Rd and climbed the last steep hill before Provincetown.

We can see the ocean and the Provincetown Monument from the last hill, and from there it was very very flat, along the coast line. I tried to sprint a bit, keeping at around 20+mph in headwind. After sprinting a bit I’d look back and check on Mark. I was debating if I should just sprint ahead and cross the finish line myself, or wait for him and finish together. Eventually I decided to do it together. We started together and should finish together.

There was no finish line or anything, but I saw Josh and Shabu waiting for me, so I knew that must be where the ride concluded. Mark’s wife was also waiting for him, and we took some pictures before heading over to the hosting hotel to check in and got our T-shirt.

I believe it was only about 4:15pm, and we had a dinner reservation at 7:15pm at Tin Pan Alley. I hopped in the truck and Josh put the bike on the bike rack. I had a really long shower in the hot water, which felt fantastic.


What an EPIC ride! Now I can brag that I rode 128 miles from Boston to Provincetown in the heavy rain, being soaked twice. It definitely has a great sense of accomplishment at the finish line, and the bad weather only added more to it.

I started watching the Netflix documentary show Tour de France: Unchained. If there’s one thing I get from the show, it’s that: Cycling is suffering, especially endurance cycling. At 100+ miles, everyone’s body will hurt. You’ll feel pain everywhere: your shoulders, your hands, knees, your legs start feeling sore, plus the external uncontrollable elements like cold windy weather. But crossing the finish line is also so rewarding, that you’ll learn to ignore the pain, and just keep grinding towards completion. Eventually you’ll learn to love suffering and love the pain because it gives you such a great sense of accomplishment.

Outriders need to be advocated much more! Every volunteer we encountered was so helpful and friendly. All support points were very well organized. Please Boston cyclists – if you’re looking for an epic ride, a well organized and supported long century ride (double metric century!) which doesn’t require fundraising, look no further! Register for Outriders! They took a hit during the pandemic, and now they’re slowly recovering. Another group ride on the same route is Harbor to the Bay, but 2023 will be their last ride. I hope Outriders can keep doing what they love, and keep this tradition and legacy going for future cyclists.

The route was well planned too. Outriders changed the route of 6A to some smaller, less busier roads in Hyannis, from the feedback of riders in the past years.

The biggest saver on this ride is my shoe covers. They worked so well to keep my feet dry(ish). Only my toes were wet a little after the long ride in the heavy heavy rain. Mark was also wearing shoe covers, apparently his didn’t work so well. His feet were still very wet and cold. But it was still much better than not wearing anything at all. The young man told us his feet were already soaked like in the puddle of water after the first downpour.

One thing I really wish I had was a highly breathable waterproof lightweight shell, that I can put on in the rain, and take off and stuff in the pocket of my jersey when I don’t need it, if such thing exists. Like I mentioned, I do have a rain jacket (Gorewear Lupra), but it isn’t breathable so I’d be steamed. But I’m happy that I had that Google group ordered lightweight long sleeve jersey. It is certainly better at keeping me a bit warmer than short sleeve jerseys, and also lightweight enough so I didn’t overheat when weather was dry.

I’m sure I’ll sign up again for next year! Hope it’ll be a more enjoyable ride!

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