2manybikes

I have not gone out to chappy for a couple of years either. If my memory is right the road turns to sand a long way from the bridge. In places it is loose sand. It's a lot of work on mountain bike. On a road bike one needs to constantly correct as the front wheel wants to wash out in the sand. Unless you're an experienced dirt rider I would not take a road bike all the way to the bridge. There is a nice public oriental garden on the way. If you don't mind the work or don't mind almost sliding out the front wheel almost all the time, try chappy.

I did it on 27x1 1/4 105 psi road tires, I have decades of dirt motorcycle and mtb racing experience, I fell over once at slow speed. It's a lot of work keeping upright on a road bike. On a hybrid if you lower the tire pressure and you're careful it's do able. But still a lot of work correcting the front wheel all the time. Did you ever try to ride a road bike on beach sand?

I would suggest going back another time with an MTB and try 25 psi in the tires. If you have the time, you can walk a road bike in the soft places.

Edit I'll see if I can find photos of Chappy. Do you want a couple of biking photos posted from M.V.? The path/ road along the water between Edgartown and Oak Bluffs is probably the most scenic place I have ever ridden a bike.