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Cape Cod & The Islands

Historic Shores to Island Destinations
Price :
Surface :
Duration :
8 days
Support :
Self Contained
Difficulty :
Level 1

Spend a week cycling along the beautiful Atlantic Ocean shoreline. On this tour, we’ll view the seaports, glacially formed kettle ponds, and lighthouses of southeastern Massachusetts, visit historic sites from the days of colonial America, and explore quaint shops on Cape Cod and Martha’s Vineyard. Attractions of special interest include Cape Cod National Seashore; a full-scale reproduction of the Mayflower; the preserved village of New Bedford, once the whaling capital of the world; and the Chatham Marconi Maritime Center. Every day on this tour is spent within 15 miles of the Atlantic, and each night close to a large body of freshwater or saltwater.

This tour is suitable for all riders and is a great choice for anyone looking to learn the basics of self-contained touring, or for an experienced bicycle traveler looking for a week of relaxed cycling. The riding is relaxed, services are plentiful, and the campgrounds are outstanding. 

Photos by Selina Kok | Lijuan Guo | Selina Kok
Sep 11 - Sep 18, 2021
(Full) Waiting list

"Meeting good people that are all interested in the same thing is great. Sharing experiences and stories about past cycling adventures is part of the charm for this organization."


Day 1. Plymouth, Massachusetts, 0 miles

We'll meet just outside Plymouth, Massachusetts, home to the first sustainable settlement for the Pilgrims after they wintered near Provincetown. Those arriving early can explore the Plymouth Plantation, the Mayflower II (a full-scale reproduction of the original), and the famous Plymouth Rock, traditionally regarded as the spot where William Bradford and the Mayflower Pilgrims disembarked on the mainland.

Day 2. Plymouth to Provincetown, 10 miles (Optional 11-mile loop)

After a short ride from our campground we’ll board a fast ferry to Provincetown. If you didn’t get a chance to visit the Mayflower II we’ll see it as we depart Plymouth harbor. In the afternoon we can explore the Province Lands bike trails to Race Point Beach, the first landing site of the Pilgrims before they continued on to Plymouth. Or you can spend the afternoon exploring the shops, restaurants, museums, eclectic architecture, and picturesque docks of Provincetown. Our campground will be along the inner Cape, a mere stone’s throw from the mighty Atlantic.

Day 3. Provincetown to Brewster, 39 miles

After leaving bustling Provincetown we’ll cycle on bike paths and quiet back roads. Along the way we can visit the Chatham Marconi Maritime Center, celebrating the history and science of 20th century radio communication, a trio of lighthouses, or the Cape Cod National Seashore’s information center. Be sure to stop at the Hot Chocolate Sparrow in Orleans for a late afternoon treat. Our evening destination is Nickerson State Park. The upper campsites at Nickerson are in a setting that feels more like the piney woods of the Carolinas than Cape Cod, where sand dunes and salt marshes are more often the norm. These woods slope down to a series of freshwater kettle ponds, which have no inlet streams — they’re entirely dependent on groundwater and precipitation, so their water levels fluctuate seasonally.

Day 4. Brewster to Nantucket Island, 40 miles

Today’s ride is mostly on paved car-free bike trails. We’ll ride on the Cape Cod Rail Trail and the Old Colony Rail Trail through forests and past kettle ponds. A side trip to the charming town of Chatham, home of the Chatham Lighthouse is well worth the few extra miles. We will meet in the late afternoon at Hyannis Harbor to board our ferry to Nantucket Island. After a short ride we’ll settle into a cozy hostel for the night.

Day 5. Nantucket Island to Martha's Vineyard, 34 miles (shorter option available)

We’ll explore Nantucket Island on a loop ride that will showcase the best of the island. We won’t be here long enough for you to read Moby Dick, but you’ll be able to take in the area’s rich history. Later we’ll hop aboard the ferry to Martha’s Vineyard and take a short ride to our lodging for the next two nights: a wooded island campground.

Day 6. Layover Day in Martha's Vineyard, 0-40 miles

You can ride gear-free today on a 40-mile trip around Martha’s Vineyard, or leave your bicycle behind and just hang out on the white sandy beaches of the Vineyard. Other options include riding to one or more of the Vineyard’s four lighthouses and sampling the amazing seafood in the island ports of Vineyard Haven, Oak Bluffs, and Edgartown.

Day 7. Martha's Vineyard to Sandwich, 28 miles

Our 4th and final ferry ride takes us back to the mainland at Woods Hole. You should have plenty of time to explore the famous Woods Hole Oceanographic Institute, where guided walking tours are a great way to learn about its history and research. More bike trails are in store for us today, along with a few short but very steep hills known as “sand rollers.” We’ll finish the day with a ride along the Cape Cod Canal before reaching our home for the night at Shawme-Crowell State Forest.

Day 8. Sandwich to Plymouth, 26 miles

After crossing the Sagamore Bridge and riding on the opposite side of the Cape Cod Canal we’ll enjoy the gently rolling hills, cranberry bogs, and lovely lowlands of southeastern Massachusetts. Soon we’ll arrive back in Plymouth for one last look at the ocean before we say goodbye to our new friends and head for home.


Additional Details
Start Location:
Plymouth, MA
End Location:
Plymouth, MA
Logan Intl. (BOS)
Total Days:
Riding Days:
Layover Days:
Tour Leader:
Average Daily Mileage:
Shared cooking
Level 1
Rolling Hills
Restricted Bike Type:
eBike, eTrike