Martha’s Vineyard


Length of stay: 2 days
Visited: October 2018

Martha’s Vineyard is an island located just south of Cape Cod. It is well-known for being a (not so secret) hideaway for the rich and famous and for the filming of Jaws. So you know this island means business: in terms of money and great white sharks. There is always a tradeoff between visiting a popular destination in peak season versus shoulder (or off-season). On one hand, the only way to enjoy the fabulous beaches in the Vineyard is during the summer months. But you’ll be sharing with swarms of other people. And if you visit during the shoulder season, temperatures are too cool to enjoy the water, but the roads, restaurants, and trails are noticeably quieter. We went with the quieter option and visited in October.

Day 1: Around the Island in a Day

We visited Martha’s Vineyard in October, which was a bit of a gamble in terms of the weather. Initially we planned to rent bikes, but the temperature a week out of our trip was forecasted to be in the low teens. And there was also the possibility of rain on both Saturday and Sunday. Instead we forked over the extra money and paid to take our car across the ferry. Best decision ever.

We took the ferry out of Wood’s Hole at 9:30a.m and docked in (a very windy) Oak Bluffs 45 minutes later. We started our trip counter-clockwise around the island. The first item up on our itinerary: Great Rock Bight Preserve. There’s a sandy trail that weaves through an oak forest down to the bight (a word we’ve never heard of before, but according to Wikipedia, refers to a bend or curve in a shoreline that forms an open bay). There’s a large rock located in the bight, hence the name of the area. We walked along the entire stretch of the bight, or at least until we reached a marker to indicate that remainder of the shoreline was private property.


Located nearby are the Menemsha Hills. We hiked the 3 mile loop and passed a number of scenic points and overlooks along the way: including Prospect Hill (the second highest point on the island, panoramic views overlooking Great Sand Bank on top of the cliffs, and some wetlands.


We continued driving south to Aquinnah. We first pulled over at the Gay Head Light, located on the westernmost point of the island. Due to erosion, the lighthouse was moved back 75 feet from the edge of the cliff in the mid 1800s. Remnants of the foundation from the original lighthouse are still visible.

From here it’s a short walk to the Aquinnah Cliffs. Composed of clay, these cliffs were carved out by glaciers millions of years ago.


Afterwards we headed west to the opposite side of the island. We stopped at Edgartown and leisurely strolled around the city centre. Many of the shops and inns were closed for the season and the area felt a bit like a ghost town. This worked well for us because parking wasn’t an issue.

Located close by the downtown core is the Edgartown Harbor Light, marking the entrance to Edgartown Harbor and Katama Bay. There’s a nice flat trail that winds around a marshy area to the shore of the beach where the lighthouse is located.



Afterwards we headed over to our Airbnb in Oak Bluffs to check in. We then headed into town for dinner at the Offshore Ale Co. We walked around the downtown core of Oak Bluffs before retiring for the rest of the evening.

Day 2: Wind Warning

We woke up to another cold and blustery day outside. Combined with rain. Fun. We headed over to the Black Dog Tavern for breakfast, which should not be confused for the Black Dog Cafe (we should know because we made that mistake and headed over there first). We tried to wait out the rain. But it was not letting up.


From there we headed around the corner to East Chop Lighthouse that overlooks Vineyard Haven Harbor and Vineyard Sound. We dashed out in the windy rain, snapped a couple of pictures, and then booked it back to the car.


We then drove along the north coast along Beach Road that passes through Joseph Sylvia State Beach. Fun fact: the “Jaws Bridge” is located along this stretch that separates Edgartown and Oak Bluffs. This bridge, along with many other locations on the island, was used in the filming of the 1975 movie Jaws. You know, that movie about the great white shark that wreaks havoc among swimmers in Cape Cod that inevitably lead to a shark hunting frenzy.

We continued driving clockwise around the island and headed down south to, in our opinion, the nicest beaches on the island. We first pulled over at the sandy beach at Norton Point. This 2.5 mile long strip of sand used to connect Martha’s Vineyard to the small island of Chappaquiddick (better known as “Chappy”). That was until 2007 when a major storm caused a breach in the link. There is a ferry to move between the two islands though.


We hopped back in the car for a short while and turned off at South Beach, which, as its name suggests, runs the entire length of the southern part of Martha’s Vineyard


We continued driving south around the island. Since the clouds were starting to clear, we pulled over at the Long Point Wildlife Refuge Beach to stretch our legs and go for a hike. There are 2.1 miles of trails that weave through oak forests and sand dunes.



Afterwards we headed to Lucy Vincent Beach. During the summer season, this secluded beach is only open to Chilmark residents. There are walk-in passes that can be purchased. But, during the off-season, this pristine sandy beach with colourful sand dunes and interesting rock formations is open to the public. Free of charge. This was hands down our favourite beach on the island.




After strolling along the beach at Lucy Vincent we headed back over to Aquinnah and walked along the beach adjacent to Moshup Trail.


We still had a couple of hours before we had to catch the ferry back to the mainland. So we headed back north and went for a stroll at Felix Neck Wildlife Sanctuary. There are four miles of trails that wind through protected habitats of woodlands, meadows, ponds, and salt marshes.


We grabbed a couple of drinks back at the Offshore Ale Co to warm up after our hike. We then headed towards the ferry at Vineyard Haven. This time the ferry we caught was much smaller and we ended up staying in our car for the duration of the return trip back to Wood’s Hole.

Even though the weather wasn’t ideal (so windy!) and many of the shops and stores were closed for the season, we had the pleasure of exploring many of the trails and beaches in solitude. There’s always a tradeoff between visiting in peak-season and off-season. Either way, we still had a lovely visit.

L & K

4 thoughts on “Martha’s Vineyard

  1. Ab says:

    This looks absolutely beautiful! We had planned a roadtrip in 2016 with friends that included Martha’s Vineyard and then had to cancel it cuz we found out with no notice that we were matched with a child for adoption, our little T, so plans were cancelled. Lol. Will definitely have to do this one summer when things get back to normal!!!

    • WanderingCanadians says:

      That’s too bad that you had to cancel your plans, but that must have been such super exciting news to receive!! New England is one of my favourite areas. It’s especially lovely this time of year with the fall colours. I have such fond memories of visiting Cape Cod, including Martha’s Vineyard. I wanted to also visit Nantucket, but it seems like there’s never enough time to do everything. Hopefully you’ll be able to embark on this road trip one day when life resumes to normal.

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