Aquinnah lighthouse in the distance beyond tall grass

What To Know/Do/See If You Are Cycling Martha’s Vineyard As A Whole (Including with Teens!)

If you’re up for the challenge, you can cycle around the entire island of Martha’s Vineyard. At over 60-miles long, this bike trip is not for the faint of heart, although it’s a great way to see a lot of what Martha’s Vineyard has to offer. This cycle ride is also appropriate for a family cycle ride if you have teenagers who are good cyclists. 

Cycling Martha’s Vineyard

Cycling the whole way around the Vineyard is a fun way to see some of the sights on the island as well as get a nice workout during the process.



Which Way Should You Go?

There’s obviously two ways to circumnavigate the island of Martha’s Vineyard – clockwise and anticlockwise.

Although neither way is particularly easy, it’s advisable to cycle the down Island towns first because it is flatter at the start. We had a friend’s daughter go up island first and by Chilmark, she was exhausted because it is all uphill.

The way from Vineyard Haven to Menemsha is also uphill but a lower gradient. If you go down island first and then return via Chilmark and Aquinnah, you will be going downhill by the end of the ride when you are more tired. 

Aquinnah lighthouse in the distance beyond tall grass
you will pass by Aquinnah Lighthouse on your cycle ride around the island.

We start around 7 AM to beat any crowds and also because it gets hotter during the rest of the day. It can take a decent adult cyclist about 4 hours to do this trip.

cycle on the road alongside the beach
The views can be spectacular as you cycle Martha’s Vineyard

Trail Tips For Cycling Martha’s Vineyard

My husband and his friends have cycled around this island several times. Here are their tips for this ride:

  • Instead of going straight from Oak Bluffs to Vineyard Haven, cycle around East Chop (which only adds about a mile to the journey) but it is a very pretty cycle ride. 
  • If you go via Menemsha you can take the bicycle ferry across to Lobsterville Beach and save yourself a few miles of cycling around the Menemsha harbor. Moreover, this part through Lobsterville is one of the prettiest parts of the whole ride.

Remember! Take money for the bicycle ferry from Menemsha and for refreshments on the way 
      • Around Chilmark and Aquinnah is the on-road section but it’s not particularly busy but it is curvy. You do need to be proficient at cycling with traffic. 
      • On the descend after Aquinnah, make sure to take Moshup trail for prettier views instead of State Road.
A map of a bike trip around Martha’s Vineyard
Either Strava or Garmin can map your bike trip around Martha’s Vineyard.



Tips For Cycling With Children 

Our children have done most of this whole island tour since the age of 13. I  have arranged to meet my kids and their friends at Chilmark General Store after they did about 3/4 of the island.

kids in cycle gear
Our kids have done about 2/3 of the Round-the-Vineyard cycle trip.

If you are cycling this route with children, here are some things you should know:

      • From Edgartown to Oak Bluffs is all cycle lane but there are times when you will need to ride in traffic.
      • It’s all better to start early in the morning because the cycle lane from Edgartown to Oak Bluffs gets busy later in the day. The traffic will also be lighter for the on-road parts.  
      • With children, you will need to spread out the trip. For example, you can have breakfast in Oak Bluffs and an early lunch in Menemsha. When I picked up the kids at Chilmark General Store around two in the afternoon, they were all ravenous and ready for pizza.
N.B. If you have a child in the BSA, to get the bicycle merit badge they need to do a 50 mile cycle ride. This round the island trip is perfect fo this purpose. 

Things To Do/See on This Cycle Ride

Although it’s a long journey, there are several points along the trail where you can stop to admire the striking scenery. For example, you can take a dip at State Beach, get ice cream at either Oak Bluffs or Vineyard Haven, get a lobster roll in Menemsha, visit the Aquinnah Lighthouse or chill on the porch of the Chilmark General Store. 

Morning sun on a bike on Martha’s Vineyard
See Martha’s Vineyard in the morning when you cycle the island everyone else is eating breakfast.


cycle in the morning sun in Martha’s Vineyard with the text: Tips For Cycling The Entire Island, Marthas Vineyard
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