Cape Cod, Martha's Vineyard & Nantucket
September 13-20, $945

What's Included

  • Seven nights motel and inn lodging.
  • Hearty breakfasts and five wonderful dinners - including lobster!
  • 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 & items of interest.

Overview

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.

Itinerary

Day One: Hyannis- Check-in and Welcome

Our bicycle trip begins on Saturday in Hyannis - the Cape's busiest town. You'll check-in throughout the day at the hospitable Hyannis Heritage Hotel - our anchor for the trip, located on Main St. and just a few blocks from the harbor.

If you arrive early, you can walk the harbor area or venture 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 Welcome Dinner in the Heritage House dining room.

 
Cycling alongside the Cape Cod Canal
Cycling alongside the Cape Cod Canal.

Days Two & Three: Martha's Vineyard(44 miles)

Sunday morning, we enjoy a hearty breakfast and embark on a 44 mile pedal to the Cape Cod Canal and along the Shore Road to Woods Hole. There we'll catch the ferry to Martha's Vineyard and begin our weekend on that beautiful island.

Even though we offer group rides, cycling this beautiful island is best done "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 in Oak Bluffs.

 

Day Four:(43 miles or Direct Ferry)

On Day Four, Tuesday, cyclists will be given an option to ride along the Nantucket Sound back to Hyannis or enjoy some more sightseeing on The Vineyard and ferry back to the mainland late in the afternoon. That evening we'll enjoy a Lobster Dinner at the Heritage House Hotel.

 
Our cycling party in front of the Judah Baker windmill in Harwichport
Outside the Judah Baker windmill in Harwichport.

Day Five: Day on Nantucket- Night in Orleans

Wednesday, we eat a sunrise breakfast and scurry 11 miles to catch a high-speed ferry for a day-trip on Nantucket Island. We'll enjoy this small but history rich island at our leisure, walking or bicycling. Our ferry sails back to the Cape mainland by late afternoon and we bicycle a quick 13 mile leg into charming Orleans via the Cape Cod Rail Trail.

 

Day Six: Provincetown(32 short miles- to have the rest of the day for sightseeing!)

Thursday, we'll rejoin the Cape Cod Rail Trail and head to the tip of the National Seashore and one of the Cape's favorite destinations - Provincetown. On our way, we'll visit Wellfleet, - where artists gaining inspiration from the shore landscapes, call home.

Looking down to the Provincetown pier
Looking down to the Provincetown pier.

We'll also travel through Truro - known as the last vestige of "Old Cape Cod". Here we pass lots of restored lighthouses and cycle along expanses of pristine beach and dunes in the wildlife management areas.

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 Seven: Dennisport(43 or 57 miles)

Friday after breakfast we head towards the "elbow" of the Cape and the lovely town of Chatham. Once a prosperous fishing and shipbuilding village, Chatham is now famous for its beautiful isolated beaches and seaside charm. We'll leave town following the Stage Harbor and Chatham Lighthouse, then passing the historic homes and beautiful sandy beaches of the Harwiches we finish our day just a block from the beach in Dennisport.
The 43 mile-shorter/flat route follows the Cape Cod Rail Trail directly to Dennisport.

We'll celebrate a tasty farewell dinner at our waterfront restaurant- The Sailing Cow!!.

 

Day Eight: Back to Hyannis(15 Miles)

A favorite end to our trip, we'll enjoy breakfast at the popular Breakfast Room on Saturday 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!

Trip Difficulty

The terrain in Cape Cod is gently rolling with a hill or two 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 to 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.

Additional Information

Please visit our Trip Information page for more trip and registration information. Upon registration we will send you a Welcome Letter containing lots 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.
We are always happy to receive your e-mails or calls if you have any questions!