Martha’s Vineyard in October

During our Cape Cod staycation this past summer of 2020 we have visited the island of Martha’s Vineyard several times (and told you about it in our blog story).  On each of these trips, we have enjoyed our favorite places on the island (the Aquinnah Cliffs) but have been also adding our new favorites (Chappy Ferry).   After 3 trips in 5 weeks we were still NOT done with the day trips to our beloved island!  October weather has been mild in Massachusetts so we came back last weekend for one more trip to Martha’s Vineyard – in the fall.

Something New

Being true to the tradition of varying our day trip itineraries on the island, on this October trip to Martha’s Vineyard we have added some new places to our day.  In fact, this trip included several such new places and activities, including admiring the fully blooming fall colors!

Martha's Vineyard in October
We rode our bikes from the center of Oak Bluffs all the way to Mytoi Gardens and East Beach (via Chappy Ferry) on the Island of Chappaquiddick.

Let me tell the full story of our day:


Martha's Vineyard in October
Map of Our Day

Two Boats, One Car and 5 Bicycles

I already told you about the options to get to the island from Cape Cod (yes, they mostly involve boats) but this time we took our car AND our bikes with us on the Steamship Authority 9:30 am ferry from Falmouth.  On top of this three forms of transport, we took a little “Chappy” Ferry across the little channel from Edgartown Harbor and onto the island of Chappaquiddick.  Steamship ferry passenger roundtrip tickets (45-min ride each way) are very reasonably priced at $17 ($9 for kids) but taking a car with you is not the cheapest although the most convenient option (around $180 round trip on top of the passenger tickets).   (alternatively, check the MV public transit schedule here; there are also taxis and uber on the island).

One of the adults in our little group drove the car to Edgartown while the others biked from the ferry landing in Oak Bluffs to Edgartown Harbor.  It is a 20-minute ride on the bike path that runs along the road and along several beautiful beaches, including Joseph Sylvia State Beach. You also pass the Jaws Bridge at the edge of this beach, although I doubt you will be tempted to jump into the water in October (a different story altogether in August).

Edgartown Harbor.  Ferry to Chappaquiddick.

It was easy to find a street parking along North Water Street in Edgartown (again, it’s a different story in August) and this is where we based our car while we spent time in Edgartown and Chappaquiddick.

On our trips to Martha’s Vineyard this summer we rediscovered Edgartown and its beautiful 19th century architecture – we even joined an architecture tour on a recent trip.  (We also love the refreshing energy of the Edgartown Harbor and the shops on Maine street.)

Daniel Fisher House (1840) is one of the historical properties in the care of Vineyard Trust

This time we rode our bikes along North Water Street (another favorite of ours) to Among the Flowers café where we got our “second cups” of coffee and our picnic supplies.   We then rode our bikes straight onto the nearby  Chappy Ferry.  This old fashioned 3-car ferry takes 3 minutes to cross 527-foot channel but adds a whole other layer to our day trip island adventure.  After all, it’s an island off the island island (ok, the latter- quite possibly -a peninsula).

Day trip to Martha's Vineyard
Chappy Ferry

So you don’t think our day was only full of roses, I have to admit that the bike ride on Chappy was not very enjoyable.  There is no dedicated bike path and although there were barely any cars on this October day- you have to ride on the road (that is also pretty uneven in places giving more than a good exercise to my knees).  The ride to the Mytoi Gardens is about 20 minutes and another several minutes to East Beach.  At some point after the Dyke Bridge you need to park your bike and continue through the sand dunes to the ocean.  At that point it felt like we have reached the end of the world (but in a very good way)!

On our way to East Beach, Chappaquiddick

We had a refreshing picnic on the beach; with the ocean winds blowing hard that day we did not stay long.  East Beach is a gorgeous stretch of beach but being spoiled this summer with the abundance of gorgeous beaches all over the coast of Cape Cod we found the East Beach beautiful but not an unusual sight for us.

East Beach, Chappaquiddick

The nearby  Mytoi Gardens surrounding the small pond was a serene and unusual sight; blooming with fall colors, the native and exotic greenery had an eye pleasing and soul calming effect (both the East Beach and the Gardens are in the care of the Massachusetts Trustees).

Plan to spend at least 30-60 minutes here in a quiet serenity and choose the fall foliage time for your first visit here if you can.  We will be back- but most probably with our car, not the bikes.

Mytoi Gardens

Fish Markets of Menemsha.

Japanese aesthetic was good for our eyes and spirits.  We continued on to the village of Menemsha (by car).  (There was also a plan to harbor watch at Seafood Shanty over the Edgartown Harbor but it just closed for the season).

Menemsha Harbor

Menemsha is a busy but picturesque fishing village with a beautiful beach of its own.  We walked the beach, climbed the beach stones and briefly considered staying on for sunset (Menemsha is a famous sunset destination).   We decided to continue to our final destination of the day- Aquinnah Cliffs.  Before we left town, we explored a couple of fish markets – those where fish gets unloaded off the docks right at the back of the store.  We got our second picnic supplies at the store called the Fish Market (think lobster bisque and lobster rolls).  We already plan to return for fresh seafood to take home with us next summer.

Minemsha Beach

Aquinnah Cliffs in the Autumn Glow.

From Menemsha it was only a 15-minute drive (and no beach parking queue)  to get to Aquinnah – the western-most village on the island.  The Moshup Beach by the Aquinnah Cliffs is part of the Wampanoag Reservation land and is a National Historic Landmark. It is our favorite place on the island and quite possibly in the entire New England.

Martha's Vineyard in October
Acquinnah Cliffs. Photo: Sveta Burea
Sunset over Aquinnah Beach

Once the sun was set it got colder so we headed back to Edgartown for drinks and small plates.  There are several places still open on Main street.

Our 8 45pm ferry brought us back to Woods Hole at 9:30 pm.

Tips on Visiting Martha’s Vineyard in October.

The great features of October visit to the island (in no particular order) were the absence of crowds on beaches and Main streets, gorgeous fall colors, easy street parking, and- if you are staying overnight – it is much easier to find an affordable hotels on the Island. Some of the disadvantages worth mentioning are the many restaurants that already closed for the season and (my personal pet peeve) – there are quite a few dogs running on the beach (if you are timid around running dogs like myself, it might be something to consider; if you are a dog lover- this would obviously be an advantage).

Here are some tips on visiting Martha’s Vineyard in October:

  1. Dress in (many) layers. It will certainly be windy on the ferry boat but it may get almost hot during the day. Be prepared to take those layers out again in the afternoon once the sun is set for the day.
  2. Many restaurants do close for the season, so plan ahead (and maybe even bring snacks).
  3. Pay attention to your dates of travel when planning your ferry trips as the schedule changes seasonally.
  4. Parking is easier to find but do read the signs.

Have you been to Martha’s Vineyard in the Fall? What are some of your favorite activities there?

Check out our Day Trip to Martha’s Vineyard video:


Martha's Vineyard in the fall


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