I went to an island in New England in the fall – what was it like

  • I took a three day trip to Martha’s Vineyard in October, well after the summer crowds had died down.
  • Visiting in the fall had its perks, like access to private beaches and shorter lines.
  • I even managed to swim, although travelers should be warned that the water was very cold.

For many years, my knowledge of Martha’s Vineyard was limited to hazy childhood memories of a family trip there and headlines about celebrities flocking to its shores.

But through a series of pandemic-related twists and turns, I found myself living and working on the tiny Massachusetts island during the popular summer season.

There were plenty of advantages to living on Martha’s Vineyard, but being there in the summer – when the year-round population of 17,000 can reach 200,000 – brought challenges such as long lines, large crowds and a scarcity of reasonably priced rentals.

For these reasons, many full-time residents and frequent visitors prefer to come during the shoulder season of April and September.

With that in mind, I decided to return for an off-season trip in October and brought my partner, a first-time visitor, with me for the three-day ride.

The first step was to get to the island, which required a car and ferry ride

Depart the ferry and onto the vineyard at sunset.

Depart the ferry and onto Martha’s Vineyard at sunset.

Grace Kennedy

Martha’s Vineyard is an island, so the only way to get there is by ferry or plane.

We chose to drive and bring my car on the ferry. Buying a ferry ticket that included my car was way more expensive than just walking. A standard adult ticket was $9.50 and could be purchased on the same day, but a ticket with a car was $100 and had to be booked in advance.

But in my opinion, having my car on the island was worth the extra planning and expense.

If you stay in a central location you can walk or take the bus to many places. However, Martha’s Vineyard is bigger than expected, with six unique towns and long winding roads leading to hidden beaches.

Walking, cycling or relying on the bus would not allow you to enjoy all that the island has to offer in a short time.

Airbnb rentals seemed significantly cheaper in October

We were lucky enough to stay with my friend on this trip, but a quick peruse of Airbnbs showed a wide range of options to choose from, with fall prices down to $150 per night compared at their summer rates.

Some hotels were still open in October, but I recommend booking a place with a kitchen if possible, as many restaurants were closed out of season. Luckily Martha’s Vineyard had wonderful year-round farms where we could buy meat and produce.

Many stores were still open and many were on sale

The weather on our first morning was a little gray, so we went to the Dumptique, a shop that operates thanks to donations and volunteers. Anyone could walk in, grab something off the shelves and take it home for free. It was amazing.

From there we drove to Main Street in Vineyard Haven for lunch. The street was lined with just about anything you might want on vacation: beach gear, clothes, books, coffee, ice cream, etc. We stopped at a few more places to take advantage of the off season sales.

Do your research and check restaurant and store hours before showing up at their doors. We found that some had changed their off-season hours.

We shared an appetizing lunch at the Waterside Market

Our stomachs were rumbling, so we headed to Waterside Market.

You might recognize Waterside from celebrity chef Guy Fieri’s “Diners, Drive-Ins and Dives.” In my opinion it has the best BLT on the island.

The sandwich is huge, so be prepared to share it with a friend or take it to the beach to feed yourself when you’re hungry again a few hours later.

The off-season visit gave us access to some beaches that were closed to the public during the summer

A sunny fall beach day at Lamberts Cove.

A sunny fall day at Lambert’s Cove.

Grace Kennedy

During the summer months, some beaches were only accessible to residents or visitors of certain towns who purchased a beach pass. But during the off-season, many of these beaches were open to the public.

We took advantage of the access on a trip to Lambert’s Cove, a beach in West Tisbury.

We took a short walk through the trees to a wide beach nestled in the cove off Vineyard Sound.

The clouds parted, so we decided to lay down on the sand in the bright sunshine and blue skies, joined only by another couple and the occasional dog and owner who rushed beside us.

The sky was clear enough to watch the sun go down in Aquinnah

sunset at Aquinnah Lookout, the western end of the island.

We caught the sunset at Aquinnah Lookout, which is on the western end of the island.

Grace Kennedy

When we started to get cold, we went up the island to see the sunset at a town called Aquinnah.

We stopped at a few farm stalls on the way, grabbing lassis, a yoghurt drink originally from India, from Mermaid Farm and fresh produce for dinner from Beetlebung.

The Aquinnah lookout was majestic, with striking cliffs and stunning views of the sunset over the Atlantic Ocean. It was the perfect way to end our first day.

My partner and I had no problem finding WiFi at a local cafe

My partner and I had to work, so we went to a cafe in Edgartown and feasted on fall spice lattes and a lemon bun while emailing.

The cafe closed at 2pm so we called it a day then. If you need to work later while on the island, the West Tisbury Public Library also has free internet and plenty of open tables.

A hike through Menemsha Hills allowed us to admire the fall foliage

Enjoy fresh seafood at Menemsha in front of another beautiful sunset.

Enjoy fresh seafood at Menemsha in front of another beautiful sunset.

Grace Kennedy

After our work was done, we met my friend for a hike in the Menemsha hills.

If you’re looking for scenic fall foliage, Martha’s Vineyard has it in abundance. October was the perfect time to experience the changing leaves in all their glory.

Menemsha Hills had a few different hiking loops. None of them were particularly difficult, but I still recommend wearing boots or sneakers and bringing water.

Once the sun went down, the temperature dropped rapidly. Bring layers.

No trip to Martha’s Vineyard is complete without some seafood, and we didn’t have to wait in line in October

In my opinion, you can’t come to Martha’s Vineyard without stopping by the Larsen Fish Market. So for dinner we went for lobster rolls, clam chowder and oysters.

During the summer months, I’ve seen Larsen’s queue stretch out the door. In October, we were the first and only people waiting. We were able to enjoy our food as the sun went down.

We started our last day with delicious pastries from Gray Barn

Devouring Gray Barn pastries on my friend's patio.

Devouring Gray Barn pastries on my friend’s patio.

Grace Kennedy

My friend works at a farm and bakery called The Gray Barn, so I started my morning by visiting her there and picking up some pastries and bread from the farm stand.

The magnolias weren’t in bloom in October, but we still enjoyed our visit to the Polly Hill Arboretum

After stuffing ourselves with sugar, my partner and I went to Polly Hill Arboretum, a 70-acre public garden filled with rare trees and shrubs.

It was too late in the season to see the magnificent magnolias in bloom, but the arboretum was still a lovely place to walk. Plus, we had pretty much the whole place to ourselves. We only saw one other duo the whole time we were there.

The sea water was cold, but that didn’t stop us from diving

I promised myself to swim at least once during this trip. So after our visit to the arboretum, we bundled up and headed to Joseph Sylvia State Beach, home to the American Legion Memorial Bridge known as the “Jaws” Bridge for its appearance in the movie. from 1975.

The water was cold but glorious. It shimmered in the sun and sent an icy shock through our systems that made us elated. Don’t be afraid of the icy polar dive – I’ve never regretted a swim at Martha’s Vineyard.

After our last trip to the beach, we came home and cooked a delicious dinner with locally caught scallops. Dessert was a homemade crisp with apples my friend picked on the road.

Martha’s Vineyard was quieter and more peaceful in the fall, and I recommend it for anyone in need of a getaway

As we waited to board the ferry the next morning, I asked my partner how she would describe our trip. She said “quiet”.

You might not get a tan or the chance to rub shoulders with a celebrity on vacation, but the experience you get in return is just as valuable.

Our October trip to Martha’s Vineyard became one of my favorite memories on the island to date, and I returned home feeling truly relaxed and rejuvenated.


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