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Well since no one with real knowledge has chimed in, I have ridden the Harwich-Brewster-Chatham area and that's pretty nice--I imagine the traffic isn't great but manageable--I would stay away from the main roads like 28 in the summer.

b21
 

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Check out mapmyride, it has some pretty good rides. I live in Sandwich and take a route similar to one on this site that goes down to Falmouth. If you ride the bike trail next to the canal, be aware that they sometimes stop cyclists that are going too fast - depending on how much traffic there is.

You might also consider riding over either the Sagamore or the Bourne bridge or both.....fantastic view of the canal. Watch the glass on the Bourne bridge and on the approach on the mainland side. Also, the rotaries on either side of the Bourne bridge can be intimidating if you're not accustomed to them. The Sagamore bridge is overall a little easier. Each bridge has a sidewalk on one side. the Bourne bridge has a sidewalk on the side that faces Buzzards Bay (West) and the Sagamore Bridge has a sidewalk on the Cape Cod Bay side (East). The approach to the Sagamore Bridge from the Cape side is through the parking lot of The Christmas Tree Shop in Sandwich (largest thatched roof in North America).

The previous suggestion of bike zone is good (capecodcyclist.com). They have a Thursday night (5:30 pm) out of their Hyannis store that has a large crowd and all levels of riders...and it goes through some really scenic areas...including within a block of the Kennedy Compound.

One last thing - highway 6A has lots of interesting shops on it, but it's not the greatest cycling because of the heavy traffic.

If you're into mountain biking be sure to check out trail of tears in Barnstable and Otis.
 
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