Exploring Chatham by bike can be both relaxing and exhilarating. There is the Chatham Loop, which is a five-mile circuit from Chatham Fish Pier that takes you past Chatham Light, boatyards, and harbors (just follow the signs). The Old Colony Rail Trail goes from Harwich to Chatham. It is nine miles of a paved trail that begins at the Cape Cod Rail Trail in Harwich and ends in Chatham. There is also the Cape Cod Rail Trail, which is 20+ miles of off-road paved bike paths.

The state paved a large swath of abandoned railway tracks and turned them into a beautiful bike path that runs through many charming towns. Locally, the bike trail passes through Chatham, Harwich, and neighboring Brewster.

Chatham Hood Bikes – has a great selection of road and mountain bikes, helmets, lights, bike bags, bicycle parts, and bike repair services.

Wheelhouse Bike Co. – offers a wide range of bike services, located in the heart of Chatham Village.