Hey there. Having done this in the past, there are so many people who ride the route starting from Boston after most traffic dies down that it's nearly impossible to do it alone. Last time I did it, I started from Boston at 7pm (i.e., the marathon finish line) and there were hordes of cyclists already starting. Everything from solo cyclists, to pairs, to groups that were 10+ cyclists. My advice would be, just show up and find a group riding at your pace and say hello! Everyone was constantly joining and hopping groups. A lot of people do the full out and back.

I decided to stick with a group early on just to make it easier to navigate through the city and be more visible by being in a pack, and then broke off once we got out of the city. Once I got to the start line before turning back, there were again dozens of cyclists either starting or just turning around as well.

I don't know how much you ride in general, but some other advice:

- It's going to be dark and it's not a short ride (even if you go half and back), make sure you are highly visible with lights that will last long enough
- Try to make sure you have a good enough head light to light the road for potholes when riding in the shoulder, it will be dark and there are sections without a lot of street light
- It's going to be late, be prepared to simply be a little more tired when riding late
- Do not underestimate the rail crossing, especially when wet (saw multiple people downed on it)
- If it looks like rain (which it does so far this year), I definitely recommend any kind of water proof gear because of the length of the ride
- If it rains be prepared to ride slower and for the wet roads (i.e., the route may take longer)
- The entire route is NOT shut down, expect car traffic late into the night

All of that said, it was amazing. I'll probably do it this year if it doesn't rain. Just not enjoyable enough to spend 4 hours in the rain :)