I would double check this route, as I recently re uploaded it from memory. This route starts in Woods Hole. However, you can start in Falmouth by riding then end of the ride, to Woods Hole, at the beginning. You can also shave about 10 miles from the ride by not riding all of the canal trail.
The outbound portion of the ride is on lots of relatively quiet streets, though even the numbered routes have shoulders and are not busy. There is a rest room break at Old Silver Beach around mile 10. The next break will be Bourne Bridge.
At about mile 14 the route cuts inland to bring to the canal path at the Bourne Bridge around mile 20. For the full 51 miles, turn right for the 10 mile out and back to the end of the path. For the 41 mile version, turn left and continue the ride.
A popular lunch stop is The Lobster Trap a mile 32 or so.
The return ride to Falmouth and Woods Hole is routed along the road. You could take the parallel Shining Sea Bikeway, if you prefer. Outside of Falmouth you ride along the shore and past the Nobska Lighthouse back to the start — where there is coffee, pastries, ice cream and beer at the various shops.
I haven’t ridden this trail for years, but, if you only want to do part of it, go to the middle of the trail somewhere, and ride North East (toward Eastham and Orleans). It is stunning. There are lots of food and rest stops on the trail or immediately off the trail.
From the northern end of the Cape Cod Rail Trail, the ride starts through the park and along the shore.
The whole ride outbound is on quiet scenic roads.
Plan to lock your bike and spend some time in Provincetown. It is a fun city.
Come back another time in your car and go whale watching. The feeding grounds are in this area and it is not unusual to see multiple whales at a time.
This is one of my absolute favorite rides in the area. GPS Route 54 miles You can save 8 miles by turning right at mile 29.6, Menemsha Crossroad. You will skip the the ride to the point, however.
The ride starts on this map from Vineyard Haven (the ferry from Woods Hole). However, you can also pick up the ride in Oak Bluffs (the ferry from Falmouth).
As you exit this section to the left look for Edgartown Bicycles(you will pass it on Main Street). In the summer it is a natural rest stop. They have a bathroom and water as well as some really great bicycle shirts.
This loop actually by passes downtown Edgartown. Tourist time would be at the beginning or end of your ride in Vineyard Haven or Oak Bluffs.
Instead, you will continue toward another beach, with a ride along the beach road. You will then head inland, with some winding roads and wind up on Edgartown – West Tisbury Road. Please read the note on the photo about riding on the road vs the bike trail.
If you ride on the bike trail you will eventually see a sign for the Martha’s Vineyard Hostel. It is a pleasant rest stop. In the past they had water and access to their outhouse. If you wish to skip that stop, a few miles up the road is a large general store, with anything you may need.
After the general store, you turn right to get to Middle Road, down towards the end of the island. This is a more scenic way, with less traffic than South Road.
At Menemsha Crossroad, the route continues south to the end of the island for a great overlook and a 4 minute ferry ride to Menemsha for lunch. If you want to cut off 8 miles, turn right at Menemsha Crossroad and bicycle directly into town.
After touring the southern part of the ride, and taking a break for the overlook, you will ride on Lobsterville Road toward the bike ferry.
Menemsha is a great place to stop for lunch. If it is really hot outside, the food cabin right by the ferry landing has a covered porch. For a treat, however, go around the block to one of the fisheries for a lobster roll and chowder. Eat in the back on the wood crates, right on the habor.
There is plenty of food and shopping here.
After lunch it is a about 12 miles back to Vineyard Haven and 15 to Oak Bluffs. It is a steady uphill most of the way, but few steep areas. If you have time before your ferry, look for Martha’s Ice Cream, in either town.