Day 1: Lexington, MA
Miles: 0
We’ll gather as a group after we check in before 4PM at the start point in historic Lexington, MA where the start of the Revolutionary War began. We’ll greet each other at our orientation meeting at the hotel then stroll to a local restaurant for dinner. We will make sure bikes are fitted, and we are ready to roll in the AM.
Day 2: Lexington to Provincetown
Miles: 29 mi +735 ft / -844 ft Elevation Gain/Loss
Transfer: 1.5 hours on the ferry to Provincetown
Terrain: Rail Trails
We’ll begin our adventure with an early start and ride along The Minuteman Bikeway. It passes through the historic area where the American Revolution began in April 1775. The is one of the most popular and successful rail-trails in the United States. The bike path will lead us to Boston making our way to the ferry that will take us to Provincetown. Once we disembark, we will pedal along the shoreline heading out to the Race Point Ranger Station to tour the Race Point Lighthouse along with viewing the Old Harbor Life-Station museum. We head back into town where you can visit the Pilgrim Monument, relax at a local establishment or stroll through the town.
Day 3: Provincetown to Eastham
Miles: 35 mi +1079 ft / -1036 ft Elevation Gain/Loss
Terrain: Gently rolling hills on quiet back roads & bike paths
We’ll head in the south direction out of Provincetown toward the historic shore road where the views of the bay are breathtaking. We’ll ride rural Truro country roads as we make our way toward the Cape Cod’s Truro Vineyards, there we will sample some of the Cape Cod’s finest local Wines. As we cycle through the small towns heading towards Marconi Wireless Station where we will learn of the first transatlantic wireless communication between the US and Europe. We’ll lunch there with the smell of ocean air will be calling you through sandy beaches, salt marshes, ponds, and uplands. We will then cycle along beach roads to the Cape Cod National Seashore Visitors Center and our hotel for the evening.
Day 4: Eastham to Hyannis
Miles: 41 mi +1015 ft / -1039 ft Elevation Gain/Loss
Terrain: Bike paths
After breakfast, we will ride to the trailhead for the Cape Cod Rail Trail where we will ride most of the morning enjoying the views along the trail and then take the bicycle rotary to get on the Old Colony Rail Trail heading towards the seaside town of Chatham, MA. Chatham is located at the southeast tip of Cape Cod and has historically been a fishing community. While in Chatham you will visit the Chatham Lighthouse and have lunch. We hit the rail trail again and head towards the picturesque village of Hyannis were our hotel awaits us after a long day in the saddle. You may encounter local harvesting of cranberries, but undoubtedly many cranberry bogs ripe with fruit.
Day 5: Hyannis to Martha’s Vineyard
Miles: 30 mi +777 ft / -742 ft Elevation Gain/Loss
Transfer: 50 minutes on a ferry to Vineyard Haven
Terrain: Predominantly bike trails
We’ll head directly to the ferry in Hyannis to board for Martha’s Vineyard. The ferry ride will heighten your senses of the sea salt breeze blowing against your face leaving you feeling like you are in the tropics. Once we disembark, we will pedal along the Seaview avenue with the seagulls chirping to the locals fishing off the piers. We will make our way to Katama Beach Road to cycle along the west side of the island a briefly view the beaches before we head back to the center of the island to a local farm stand and restaurant where we will partake in local pastries and fresh fruit from the island. Once we depart, we set our sites on our local cheese sampling on a farm. We hop on the Vineyard’s State Forest Bike Path on our way back to where we will end our day in Oaks Bluff.
Day 6: Martha’s Vineyard Layover Day
Miles: (OPTIONAL)
Terrain: Predominantly bike trails
On our layover day, you have options to explore Martha's Vineyard Island by bike or use the local transportation around the island on your own. Browse the handicrafts of Vineyard Haven’s beautiful artisan's shops or head over to Edgartown to ride the two car ferry over to Chappiquick Island. Board the “Chappy” ferry for a three-minute sail across the 300-yard-wide strait that separates Martha’s Vineyard from Chappaquiddick Island. Having short trips and no timetable, the Chappaquiddick Ferry is always on time. The island’s main attractions are, of course, the infamous Dike Bridge, along with the Mytoi Japanese Garden. Or you can take a ferry over to Nantucket Island for the day and explore the island by bike. Later return to the inn where there are many options to enjoy one of Oak Bluffs celebrated restaurants. Your trip leaders will have suggestions for you.
Day 7: Martha’s Vineyard to Sandwich
Miles: 30 mi +777 ft / -742 ft Elevation Gain/Loss
Terrain: Bike paths and rail trails
Transfer: 1 hour on Ferry to Woods Hole
We’ll begin with an early morning ride down to Vineyard Haven to catch the ferry over to mainland arriving in the Woods Hole ferry port. Woods Hole is a seaside village on Cape Cod sparkling with surprises. Home to the world-renowned science research facility, the Woods Hole Oceanographic Institution, and several deep-water harbors, numerous beaches, museums, and a working drawbridge. We will continue riding along the Shining Sea Bikeway which avoids much of Falmouth’s notorious summer traffic by winding along the coastline and crisscrossing the Salt Pond Bird Sanctuary and quaint coastal communities of the Cape which will eventually merge onto the Cape Cod Canal Bikeway leading us into our lodging for the night at the Sandwich Inn.
Day 8: Sandwich to Plymouth
Miles: 35 mi +1200 ft / -1183 ft Elevation Gain/Loss
Terrain: Rail Trail and rolling rural countryside
We will begin with an early breakfast and shortly head out to the Cape Cod Canal Bikeway towards The historic Victorian waterfront community of Onset, MA. Onset was developed in the 1880s as a summer camp meeting for Spiritualists. We will cycle over to a local cranberry grower in a cooperative, based in Wareham, it’s the world's largest cranberry grower and learns about the harvesting of cranberries. Then head to the town of Plymouth riding through the Myles Standish State Forest with the beautiful tall pine trees We head toward the water again, Massachusetts Bay, in downtown Plymouth where you will view Plymouth Rock where the history of the Pilgrims began. We will end our day, and our tour, at a historic hotel in Plymouth where we will celebrate our time together and share our stories over a celebration dinner. We will bid each other farewell as we depart for home or rides unknown the next morning.
