- I took a three-day trip to Martha’s Vineyard in October, well after the summer crowds had cleared.
- Visiting in the fall had its benefits, like access to private beaches and shorter lines.
- I even fit in a swim, though 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 small Massachusetts island during the popular summer season.
There were plenty of upsides to living on Martha’s Vineyard, but being there in the summer — when the 17,000-person year-round population can swell up to 200,000 — brought challenges like long lines, large crowds, and a scarcity of reasonably priced rentals.
For these reasons, many full-time residents and frequent visitors prefer to come in the shoulder season, which is April and September.
With this in mind, I decided to come back for an off-season trip of my own in October and brought my partner, a first-time visitor, along for the three-day ride.
The first step was getting to the island, which required a drive and a ferry ride
Martha’s Vineyard is an island, so the only way to get there is by ferry or plane.
We opted to drive and bring my car onto the ferry. Purchasing a ferry ticket that included my car was much more expensive than just walking on. 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 reserved 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 one might expect, with six unique towns and long winding roads leading to hidden beaches.
Walking, biking, or relying on the bus wouldn’t allow you to take advantage of everything the island has to offer in a short amount of time.
Airbnb rentals appeared to be significantly less expensive in October
We were lucky enough to stay with my friend on this trip but a quick perusal of Airbnbs showed a wide array of options to choose from, with fall prices slashed by as much as $150 per night from their summertime rates.
Some hotels were still open in October, but I recommend booking a place with a kitchen if possible, as many restaurants were closed in the off-season. Luckily, Martha’s Vineyard had wonderful farms open year-round where we could purchase meat and produce.
A lot of the shops were still open, and many were running sales
The weather on our first morning was a bit gray, so we took a trip to the Dumptique, a shop run on donations and volunteers. Anyone could walk in, pick something off the racks, and take it home free of charge. It was amazing.
From there, we drove to Main Street in Vineyard Haven to grab lunch. The street was lined with pretty much everything you might look for on vacation: beach gear, clothes, books, coffee, ice cream, and more. We stopped at a few more places to hit the off-season sales.
Do your research and check restaurants’ and shops’ schedules before showing up at their doors. We found that some had amended hours during the off-season.
We split a mouthwatering lunch at Waterside Market
Our stomachs were growling, so we made our way 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 enormous, so be prepared to split it with a friend or bring it to the beach for sustenance when you get hungry again hours later.
Visiting in the off-season gave us access to some beaches that were closed off to the public during the summer
During the summer months, some beaches were only accessible to residents or visitors in certain towns who had purchased a beach pass. But during the off-season, many of these beaches were open for public use.
We took advantage of the access during a trip to Lambert’s Cove, a beach in West Tisbury.
We went on a short walk through the trees to a broad beach nestled into the cove off of the Vineyard Sound.
The clouds cleared, so we decided to lay in the sand underneath the full sun and blue sky, joined only by one other couple and the occasional dog and owner who scampered by us.
The sky was clear enough to watch the sun go down at Aquinnah
When we started to get chilly, we drove up the island to see the sunset in a town called Aquinnah.
We stopped at a few farm stands on the way, grabbing lassis, a yogurt-based drink that originated in India, from Mermaid Farm and fresh produce for dinner from Beetlebung.
The lookout point in Aquinnah was majestic, with striking cliffs and sweeping views of the sun setting over the Atlantic Ocean. It was the perfect way to end our first day.
My partner and I had no problem finding Wi-Fi at a local café
Both my partner and I had to work, so we drove to a café in Edgartown and indulged in fall-spice lattes and a lemon loaf as we shot off emails.
The café closed at 2 p.m., so we called it a day then. If you need to work later when you’re on the island, the West Tisbury Public Library also had free internet and plenty of open tables.
A hike through Menemsha Hills allowed us to admire the fall foliage
With our work done, we met up with my friend for a hike in Menemsha Hills.
If you’re looking for scenic fall foliage, Martha’s Vineyard has it in droves. October was the perfect time to experience the changing leaves in all of their glory.
Menemsha Hills had a few different hiking loops. None of them were particularly challenging, but I still recommend wearing boots or sneakers and packing water.
Once the sun went down, the temperature dropped quickly. Bring layers.
No trip to Martha’s Vineyard is complete without some seafood, and we didn’t have to wait in line for it in October
In my opinion, you can’t come to Martha’s Vineyard without a trip to Larsen’s Fish Market. So for dinner, we drove there for lobster rolls, clam chowder, and oysters.
During the summer months, I’ve seen the line for Larsen’s stretch out the door. In October, we were the first and only people waiting. We got to enjoy our food just as the sun was setting.
We started our last day with delicious pastries from Grey Barn
My friend works at a farm and bakery called The Grey Barn, so I began my morning by visiting her there and grabbing some pastries and bread from the farm stand.
The magnolia trees 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 magnolia trees in bloom, but the arboretum was still a beautiful place to stroll through. What’s more, we had the entire place practically to ourselves. We only saw one other duo the whole time were were there.
The ocean water was cold, but it didn’t stop us from taking a plunge
I promised myself I’d swim at least one time on this trip. So after our arboretum visit, we bundled up and drove to Joseph Sylvia State beach, home to the American Legion Memorial Bridge known as the “Jaws” bridge for its appearance in the 1975 film.
The water was cold but glorious. It glittered in the sun and sent an icy shock through our systems that left us feeling exhilarated. Don’t be afraid of the icy polar plunge — I’ve never regretted a swim on Martha’s Vineyard.
After our final trip to the beach, we went home and cooked a delicious dinner with locally caught scallops. Dessert was a homemade crisp using apples that my friend had picked down the road.
Martha’s Vineyard was quieter and more peaceful in the fall, and I recommend it to those in need of a getaway
As we waited to get on the ferry the next morning, I asked my partner how she would describe our trip. She said, “peaceful.”
You may not get a suntan or the chance to rub elbows with a vacationing celebrity, 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 genuinely relaxed and rejuvenated.