For anyone who enjoys biking, the Cape Cod Rail Trail is a gold mine—a never-ending mix of history and beauty that stretches from South Dennis to just east of Wellfleet. 
The Cape Cod Rail Trail, which follows the former route of the Old Colony Railroad for 21.9 miles, is paved and relatively flat. Biking along it, you’ll pass through five charming and historic villages—Dennis, Harwich, Brewster, Orleans, Eastham, and Wellfleet—providing lots of opportunity to hop off your bike to eat, shop, or explore.
Starting at the trailhead in South Dennis, you’ll also find wonderful spots for picnics on a beach or town green, and places to commune with nature. Nickerson State Park, around mile 11, is a shady section of the route, with walking trails and swimming (and restrooms!). Orleans is a great little lunch stop.
For a good portion of the trail, the path is along the Cape Cod National Seashore. Just past the Inn here in Eastham, you will see the Salt Pond Visitors Center, a great place to learn about our local history. Continuing on, enjoy the pretty views from the overlooks as you head into the south Wellfleet trailhead (bathroom break!). If you’d like, you can continue on from here, biking Le Count Hollow Road, to Maguire Landing Beach and be rewarded with stunning ocean views.
Cape Cod Rail Trail
21.9 miles
East Dennis Road/SR 134, South Dennis to LeCount Hollow Road, South Wellfleet
Whalewalk Inn is smack-dab in the middle of the Cape Cod Rail Trail. A good way to enjoy the ride is to do it in two parts, biking one day from the Inn to Dennis and back; the next day going from the Inn to Wellfleet and back. Plan to stay with us, and we’ll be happy to offer places to dine along the way, or good spots to pick up a picnic.