Cape Cod Pilgrimage – Van

Trip Dates:
Jun 14, 2014 -- Jun 21, 2014
Plymouth, MA
Booking Status:

Join us this spring on our popular Cape Cod route along the beautiful Atlantic Ocean shoreline. Newly offered in our van-supported format, on this trip we’ll carry your gear, allowing you to enjoy a week of load-free riding and even more time to explore all the area has to offer. We’ll visit historic sites from the days of colonial America, explore quaint shops on Cape Cod and Martha’s Vineyard, and view the seaports, glacially formed kettle ponds, and lighthouses of southeastern Massachusetts. Every day is spent within 15 miles of the Atlantic and each night close to a large body of fresh or saltwater.

This tour is suitable for all riders, and makes a great choice for an early season ride. The riding is gentle, the services are plentiful, and the campgrounds outstanding. What better way to ease your legs into shape for the season ahead? With so much to see and do, this beginner-plus tour has plenty to offer the experienced cyclotourist as well.

Start Date: Jun 14, 2014 End Date: Jun 21, 2014
Start Location: Plymouth, MA End Location: Plymouth, MA
Total Days: 8 Riding Days: 7
Rest Days: 1 Miles: 280
Average Daily Mileage: 40.0 Surface: Paved
Riders: 13 Airport: Logan International, Boston, MA
Tour Leader: Matt Moritz, Chris Mullen Meals: Shared cooking
Accommodations: Camping/Indoors Type: Supported
Physical Difficulty: Beginner+ Level of Support: Van Supported
Cost: $1,449.00

Day 1

We'll meet at our beginning 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 Westport, 48 miles. We’ll enjoy the gently rolling hills, cranberry bogs, and lovely lowlands of southeastern Massachusetts as we depart westward on an inland route toward our destination for the evening, Horseneck Beach State Park. A blend of beach and estuary habitats, this park is regarded as one of the top bird-watching locations in New England, so keep your cameras handy! We’ll make camp along the beach, where we can take a late afternoon dip in the ocean, enjoy our first on-road dinner, and then be lulled to sleep by the crashing of waves.

Day 3

Westport to Sagamore, 45 miles. Riding northeast along the shoreline, we’ll find our way through the city of New Bedford, whaling capital of the world during the mid-19th century. Here we’ll grab lunch and perhaps visit the New Bedford Whaling National Historical Park, where the National Park Service preserves an earlier version of the village replete with cobblestone streets, the world’s largest whaling museum, and a whaling merchant’s home and whaleman’s chapel. Later, we’ll continue our way into the cranberry bogs along quiet farm roads on the approach to “old Cape Cod.” We’ll finish the day with a 15-mile ride along the Cape Cod Canal to our home for the night.

Day 4

Sagamore to Martha’s Vineyard, 42 miles. Turning south again we’ll ride along the Cape Cod Canal after crossing the Sagamore Bridge onto the Cape, proceeding southward to Falmouth and Woods Hole. More bike trails are in store for us today, along with a few “sand rollers,” as the area’s short but very steep hills are known. 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. Later, we’ll hop aboard the ferry to Martha’s Vineyard, looking forward to a two-night stay on the island at a hostel.

Day 5

Layover at Martha’s Vineyard. There is so much to see and do here, we’ll stay for a full day! You may choose to embark on a 40-mile trip around Martha’s Vineyard or ride to one or more of the Vineyard’s four lighthouses, sampling the amazing seafood in the island ports of Vineyard Haven, Oak Bluffs, and Edgartown along the way. Or you may choose to leave your bicycle behind and enjoy hanging out on the white sandy beaches of the Vineyard.

Day 6

Martha’s Vineyard to Brewster, 63 miles. Arriving back at the mainland on an early morning ferry, we’ll launch our longest riding day of the tour as we head inland along the Cape on the Shining Sea Bikeway toward our home for the evening, 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. Today we’ll also ride for a ways on the Cape Cod Rail-Trail, with possible side trips to Hyannis or Yarmouth.

Day 7

Brewster to Provincetown, 35 miles. Continuing along the Cape Cod Rail-Trail, we’ll visit the Cape Cod National Seashore’s information center and trio of lighthouses. Also nearby: the heralded Chatham Marconi Maritime Center, celebrating the history and science of 20th century radio communication. Our last night of camping will be along the outer Cape, a mere stone’s throw from the mighty Atlantic.

Day 8

Provincetown to Plymouth, 15 miles. We’ll wind down our Cape Cod trek with a quick jaunt up the bike path to Race Point Beach and onward into Provincetown, the first landing site of the Pilgrims before they continued on to Plymouth. We can spend the morning exploring the shops, restaurants, museums, eclectic architecture, and picturesque docks of Provincetown, before loading the van for the shuttle back to Plymouth in the afternoon.

"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."

2013 Tour Participant

"Loved seeing seals frolic in the ocean at Race Point, chatting with fishermen, riding the Chappy ferry and seeing "the bridge" and Provincetown action on Saturday afternoon."


"I enjoyed riding north on the west-side trail of the Cape Cod canal with the wind at my back, eating great meals every night, savoring the ride’s every moment, the perfectly sunny summer weather (book ended by the cool rainy days) and generally enjoying the hassle free companionship of the tour group."

2013 Tour Participant

Photo by Selina Kok