Martha’s Vineyard in September: The Off-Season Sweet Spot
If you’re considering a trip to Martha’s Vineyard, especially as a first-timer, let me introduce you to this destination in a way that feels accessible and manageable. September in Martha’s Vineyard means seeing all the beauty and charm of the island after all of the chaos has left.
Why September is a Great Time to Visit
First off, the August summer rush has slowed, but the island hasn’t completely shut down yet. Here are a few of my observations:
The crowds were noticeably thinner, so I was able to walk right into restaurants without a reservation and there was actually room to walk on Circuit Ave.
The weather was in the high 70s, low 80s during my stay, which was warm enough for the beach, especially with the sun out, and it was cool enough to walk around without getting too sweaty or hot.
There were still families but not so many large groups. I saw mostly couples, friend pairs, and solo travelers around the island.
Staying Central
One of the biggest wins of my trip was where I stayed. I chose the Morgan Hotel, and I paid $1,700 for five nights. This hotel self check-in during the off season, it’s within walking distance to the beach and one street over from Circuit Avenue, the heart of Oak Bluffs. In peak summer, that same location would definitely cost $300-500 more if it was even available to reserve at all.
The Island Is Still Open for Business
A common thing about beach town destinations is that many businesses will be open fewer hours or shut down completely. The first week of September in Martha’s Vineyard, restaurants, shops, and cafés were still very much open but without the large crowds. The Sweet Life Café is my favorite restaurant recommendation; read my review here.
A Black Woman’s Experience on the Vineyard
Martha’s Vineyard has a long, real history with Black travelers, especially in places like Oak Bluffs, but many millennials were not aware of this until recently, including me. This destination is not exclusive to rich people or white people. In fact, it’s somewhere that Black travelers historically visited annually, and there are many Black families that still maintain this tradition.
September is an especially nice time for you to visit if:
it’s your first time and you want to get acquainted with the island in a calmer, less crowded atmosphere.
you appreciate exploration and low-energy activities like sightseeing and lazy beach days
you want a trip that is either family-friendly for large groups or romantic for couples that like intimate vibes reflective trip
You can rest and be curious in Martha’s Vineyard, because it’s a destination that doesn’t require early mornings or fully built out itineraries.
What to Pack
The weather was beautiful on my visit, but here are a few things that were necessary for me:
Sweaters, sweatshirts or light jackets for the evenings and time in the shade
Comfortable walking shoes
Plenty of beachwear because you’ll still be able to use it
Nice outfit for dinner
The Bottom Line
You can still experience the true essence of Martha’s Vineyard in September, just without the huge crowds, which is a win in my humble opinion. You still get beautiful weather, walkable towns, great food, beach access, and a nice end-of-summer vibe. If you’ve ever wanted to visit but hesitated because of cost or crowds, early September may be your time.
