Martha's Vineyard & CCRT
Bicyling Getaway!
June 9 - 11, 2026
Let's SEE. EXPLORE. EXPERIENCE. the "vineyard!" That's Martha's Vineyard and the Cape Cod Rail Trail! Join your co-hosts Kathy Ryan ( 978 270 9302) and Richard Fishel for a bicycle adventure from Falmouth via Oak Bluffs to Edgartown and return. With "MYOR¨" aka make your own reservations for a 2-night stay in Falmouth. Subj. to availability. Carpooling recommended.
RSVP: $5.00
As a "good faith" measure, a $5.00 nonrefundable contribution is collected at time of rsvp. All monies will be used toward the purchase of snack, ice cream treat, or appetizers. Participants are responsible for purchasing their own Steamship Authority ferry tickets and motel reservations.
Please call for reservations 508-548-1331 directly to the Mariner Motel in Falmouth(Approx. $295.00 for 2 nights/up to 2 persons per night inc. tax).
For Steamship Authority fare information, click here.
Day 1 - June 9: Arrive Marina Motel any time after 4 p.m. We will meet at 6 p.m. and head to a TBD location for dinner/apps/beverages and get a jump start on celebrating the start (almost!) summer!
Day 2 - June 10: Wednesday morning--rise and shine! Let's get an early start by enjoying breakfast at "Pie in the Sky" near the Steamship Authority Terminal in Woods Hole. (Across the street and up the hill.) We will plan on the 9:30 ferry to Oak Bluffs enjoying a 45-minute Steamship Authority ferry ride and full day of scenic bicycling, ice cream cone, and apps or dinner before returning to Falmouth. The pre-peak season Steamship Authority ferry schedule has a 6:15 pm ferry which will allow us to maximize our time on the island. Arrival back to Woods Hole is 7:00 pm and our bike ride back to the Mariner. Anyone renting a bicycle on the island, you may want to park at Woods Hole--Sea to Shining Sea lot by the Peter Pan Bus intermodel.
Tonight we may choose to relax by or in the pool with snacks/apps and our beverages of choice. NO glass containers, please.
Day 3 - June 11: Local or grab & go breakfast and checkout followed by scenic bicycle ride along the Cape Cod Rail Trail. Lodging checkout by 11 a.m. See CCRT ride details at the end of the description. Enjoy the ride and have a safe drive back home. Optional early dinner before heading home. Possibly a great way to miss any commute traffic!
Martha´s Vineyard
We will plan to meet and ride or drive to arrive at the Sea to Shining Sea parking lot on Depot Ave lot (across from the Peter Pan Bus/Bonanza Bus Terminal) between 7:30 and 7:45 am. We will roll out and head to Woods Hole via the Sea to Shining Sea Rail Trail. If you miss "roll out," follow the trail to the Steamship Authority Terminal if you need to purchase your ticket or come directly to the Pie in the Sky.
We will ride our bikes to Woods Hole and arrive in enough time to pick up a coffee and/snack at Pie in the Sky. Roundtrip adult & bike tickets are $33.50 and may be purchased online or at the Woods Hole Ticket Office. Ferry departs at 9:30 a.m. and we can plan on the 6:15 p.m. return. Bike rentals available--e-bikes, too, near the ferry terminal.
Martha’s Vineyard has everything you’ll need to hit the road and explore the Island via bicycle. Even the public buses have bike racks!
Bike riding on Martha’s Vineyard is simply spectacular! What a way to welcome in summer just a few days away!
Arrival Details: We are a small group and should be able to stay together as we disembark. Anyone not accounted for upon arrival in Oak Bluffs, we will meet you in front of the the Oak Bluffs Steamship Authority Ticket Office.
Ready. Set. Go! We will ride along the waterfront and through the Oak Bluffs neighborhoods, including the famous Gingerbread Meeting Campground before heading out on Beach Road to Edgartown. This will be a fun and bike-rider friendly event. Our Beach Road will take us along the stunning six-mile, paved trail travels along the Nantucket Sound on one side and the 7-acre Sengekontacket Pond on the other and is entirely flat. It’s definitely one of the most popular trails on the Island because of its stunning views.
Keep in Mind Laws Applicable to Cyclists
We will stop for scenic views and water breaks before enjoying lunch in Edgartown. You are welcome to pack a lunch, stop at Stop & Shop to pick up snack or lunch (or even a restroom break), or take advantage of the take-out restaurants and concessions in Edgartown. Our plan is to enjoy our lunch at the picnic tables by the Chappaquiddick Ferry launch area. With group consensus we may opt to enjoy lunch at a local restaurant. Anyone interested in heading to the beach? Head out to South Beach and meet us back at the Lookout Tavern - 8 Seaview Ave later in the afternoon. Don't forget your sunscreen. Please let one of the hosts know you are heading to the beach--preferably with a "buddy."
There will be plenty of time in Edgartown for shopping, browsing, photo ops, ice cream, or iced cold refreshments.
Remember to bring a bike lock (offers great peace of mind!), water, and sunscreen (bathing suit for optional jump from the Shark Bridge!)
From Edgartown we will return to Oak Bluffs via the "Jaws" bridge to watch, cheer, or participate (at your own risk) as some more adventurous folks jump off the movie-made-famous bridge. We will remount our bicycles and continue on our way to the center of Oak Bluffs to browse or shop before catching up with your fellow riders at the Lookout Tavern/
We will plan to meet at 4:30 p.m. at the Lookout Tavern - 8 Seaview Avenue near the Oak Bluffs ferry terminal for our apres-bike ride appetizers/dinner and pay-as-you-go refreshments.
Total ride: Falmouth to Woods Hole, local Oak Bluffs, to Edgartown and return to Falmouth is approximately 24 miles.
Overnight Stay in Falmouth
Tonight we will overnight in Falmouth and enjoy an evening by the pool or head out to dinner.
Thursday morning we will head out to the Cape Cod Rail Trail and enjoy the southwestern section of the trail by Peter Homer Memorial Park. We will be passing kettle ponds, a general store, picnic areas, and cranberry bogs and more. We may even choose to take a detour onto the Old Colony Rail Trail.
BIKE RENTALS
If you're planning on renting a bike. Please make arrangements ahead of time with one of the vendors in Oak Bluffs. Before you get off the boat please let your hosts know who you are and we will go with you--as it is right on our route. (It's right off the ferry)
From Edgartown we will return to Oak Bluffs via the "Jaws" bridge to watch, cheer, or participate (at your own risk) as some more adventurous folks jump of the movie-made-famous bridge. We will remount our bicycles and continue on our way to the Lookout Tavern across from the water and the ferry terminal.
Lucky for all of us. The vineyard public buses all have bike racks attached just in case of bike or the rider breaks down. There are also a few bike shops for rentals and even repairs on the road.
CAPE COD RAIL TRAIL
After breakfast and checkout, we will head out to the Cape Cod Rail Trail entrance at Stations Avenue in South Yarmouth and headout to Brewster for water break and snack returning back to the starting point. Optional: Dinner at the Skipper Chowder House.
IMPORTANT: THIS ISN'T A RACE BUT IT CERTAINLY IS NOT FOR THE NOVICE RIDER.
Please don't let this be your first ride of the year.!!!
Get your bike tuned up, pack a tire tube, and have a few rides before you join us.
HELMETS ARE REQUIRED!
We will travel on bike paths for as much as we can. (about 3/4 the day) but some of our trip will be on or crossing regular roads.
WHAT TO BRING
- water - sunscreen - bathing suit - snacks - MORE WATER - a good hat - MORE SUNSCREEN - Camera
S.E.E. you in Falmouth!
AS A CONDITION OF PARTICIPATING IN THIS EVENT, YOU AGREE TO: Hold harmless, and indemnify the organizers and their relations and heirs, and all members and participants of the S.E.E. Mates Ski & Travel group from any and all claims for injury, illness, death, and/or property damage including those caused by negligence, ignorance, inexperience and other reasons. You also agree to assume all mental, physical, financial, and/or other risk associated with this meetup. Bicycling can pose pose inherent risks and dangers. Participation in our event is voluntary and dependent upon your own personal judgment. As organizers, we make no claims regarding any expertise for this outing. This is not a guided tour.
S.E.E. Mates Ski & Travel Club 106 Water Street Newburyport, MA 01950
info@myseemates.com978-270-9302
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