This tour available for custom groups of 15 or more
From $1,600 depending on group size
8 days

Fall Foliage in New England cycling the nooks and crannies of Cape Cod, Massachusetts — renowned for miles of glorious coastline, quaint villages, scenic byways and a rejuvenating ambiance. This exciting bicycle vacation from the Cape Cod Canal to Provincetown will also enjoy a weekend on Martha's Vineyard and day-trip to Nantucket.

Day 1: Hyannis - Check-in and Welcome

Our bicycle trip begins on Friday in Hyannis — the Cape's busiest town. You'll check-in throughout the day at Heritage House Hotel located across the street from the transportation center and a five minute walk from the harbor.

If you arrive early, you can take a tour of the area or a spin on your bikes to visit the Kennedy Memorial and nearby Hyannisport-home of the Kennedy Compound. That evening, you'll meet your fellow cycling friends at a wonderful Welcome Dinner in our hotel's dining room.

Day 2: Visit to Nantucket

It's just a short walk to the Hyannis harbor where we catch the fast ferry to the historic island of Nantucket. We'll enjoy a full day exploring the cobblestone streets of the preserved town center and learn the over 200 year history of a once great whaling center known worldwide.

Roger and Suzie will lead a 2 hour tour to show you the wonderful bike paths and beautiful beaches we feel are the true personality of Nantucket!

Day 3 & 4: Martha's Vineyard (43 miles or optional direct ferry from Hyannis Harbor)

Sunday morning, we enjoy a hearty breakfast and embark on a quiet ride to the Cape Cod Canal. On our way we'll visit the historic town of Sandwich for sightseeing and snack at the popular Marshland Restaurant.

Following the scenic Shore Road we stop at Aptuxcet Trading Post, site of the first commercial trade between the Wampanoag Indians and first settlers. Then we'll hop onto the new 10 mile Shining Sea Bike Path and on into Woods Hole to catch the afternoon ferry to Martha's Vineyard.

You are the best! We enjoyed our Cape adventure from beginning to end; met some wonderfully interesting and fun people, laughed out loud every night and I looked forward to capturing every detail along the way with my eyes and ears.

~ Jim and Jean Marie Fitzgerald, New Jersey

Suzie and Roger lead daily group rides, but we encourage exploring "at your leisure". M.V is a large island with lots to do and see. You can choose your daily mileage from 10 to 70 miles-or leave the bicycle behind and enjoy sightseeing by trolley, a hike along the many beautiful beaches and trails, or a kayak tour. Our weekend enjoys inviting accommodations at the Madison Inn, a gourmet dinner at the Ocean View Restaurant and "the best breakfasts on M.V." at Linda Jean's Restaurant-all in beautiful Oak Bluffs.

Day 5: Orleans with option to visit Chatham (28 or 40 miles)

On Day Five, Tuesday, we'll enjoy a scrumptious breakfast and meet the fast ferry heading back to the Cape mainland. From the Hyannis harbor we head east along the quiet beaches skirting the Bass River into Yarmouth for a unique visit to the Judah Baker Windmill.

Then on into historic Dennis where we'll meet the Cape Cod Rail Trail; our cyclists can choose to pedal directly to Brewster or take a diversion to the lovely town of Chatham to see the great Chatham Lighthouse. Our lodging is right off the Rail Trail in Brewster at the Old Sea Pines Inn. Built in 1907 on a 300 acre estate, this sprawling Vistorian was once a renowned finishing school for young women. We'll enjoy a wine and cheese party followed by a fabulous dinner this evening in the windowed dining room overlooking the lovely property grounds.

Day 6: Provincetown (35 miles)

Wednesday, a wonderful breakfast at our Inn- then rejoin the Cape Cod Rail Trail and head to the tip of the National Seashore and one of the Cape's favorite destinations — Provincetown. Today we take the most direct and scenic roads so we can make the most of our time- sightseeing the historic center of this unique tourist mecca oozing history of the first settlers experience on New World soil.

We reach Provincetown via the incredible dunes of the Province Lands and check in at our beachfront lodging — Surfside Inn — with rooms overlooking the water. You'll want to put away the bike and take to the streets walking to find out why Provincetown is such a popular and unique place. Visitors relish not only the artsy atmosphere of "Commercial Street", but the town's natural beauty, preserved architechture, remote beaches and famous Whale Watch Tours.

Day 7: Dennisport (43 miles)

Thursday after breakfast we head back towards the "elbow" of the Cape along gorgeous Ocean Drive and into the town of Orleans for lunch at the "Chocolate Sparrow"- one of our favorite spots. On our way we stop for plenty of sightseeing- first the community of Welfleet well known as an artists enclave, then Marconi Station where the first transatlantic wireless communication between the U.S. and England in 1903 was sent. Skirting the Atlantic we find the beautiful Nauset and Two Sisters Lighthouses and through the old fishing community of Rock Harbor into Orleans.

Our final miles pass historic homes and beautiful sandy beaches of the Harwiches and Bells Neck Nature Preserve. We finish our day just a block from the pristine beaches of Dennisport. We'll celebrate tonight's farewell dinner at the Wee Packet Restaurant- an area favorite.

Karen and I wanted to thank you for the VIP treatment we received in Cape Cod. What a pleasure it has been traveling with you.

~ Gina Garcia and Karen VanDerhoof, New Jersey

Day 8: Back to Hyannis (15 quick & easy miles)

A favorite end to our trip, we'll enjoy breakfast at the popular Breakfast Room on Friday morning. Then it's just a short 15 miles through historic Yarmouth and back to Hyannis to say our good-byes to a great trip!

  • Seven nights motel and inn lodging
  • All breakfasts and five dinners- including LOBSTER!
  • Wine and cheese party
  • Ferry tickets to Martha's Vineyard and Nantucket
  • Day trip on Nantucket Island
  • Support van, luggage transport and en route ride leaders
  • Ride packet with cue sheets, maps & entrance to selected excursions

Trip Difficulty

The terrain in Cape Cod is gently rolling with hilly terrain on Martha's Vineyard and also along the National Seashore towards Provincetown. We bike or give option to cycle as many miles as possible along Cape Cod's bicycle paths. However, many of the trip miles are cycled on public roadways shared by cars. We try and select quiet, picturesque routes with as little car traffic as possible and that provide at least a 2 foot shoulder for cycling.

For full enjoyment of the trip, you will want to come prepared to cycle the total tour mileage. However, we do offer shorter routes on some days, days off feature in Martha's Vineyard and Nantucket, as well as the opportunity to take advantage of the Cape's excellent transportation system.

We advocate social touring and a "smell the roses" philosophy to bike travel.

Getting There

Cape Cod is easily accessible by car and plane-landing in Boston's Logan Airport with a direct bus shuttle with a stop across the street from our hotel in Hyannis.

We offer free parking at our host hotel for those driving to Cape Cod. We are glad to receive your bikes if you ship them to the ride start and will store boxes until the end of the trip. We also offer cross road rental bikes upon request for $125 weekly rate.

Additional Information

Please contact us for general trip information and registration information.

Upon registration we will send you a Welcome Letter full of pre-trip details including how to get you and bike to the trip start, bike rentals, suggestions on packing, trip area and contact information, cycling and travel websites to enhance your trip experience, etc.

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