There’s always a lot of talk around the end of August about the summer being over. It’s hogwash. Any islander worth his or her salt will tell you that the best time of year is September on Martha’s Vineyard. All of the photos included in this post were taken in September to prove it. June is beautiful, but the water is pretty cold—too cold for most people to swim. July is gorgeous, but the water is just getting there and so are the crowds. August water is gorgeous, but the crowds are in full force. Almost everyone leaves Labour Day Weekend, the line-ups at the restaurants are gone, and even though the water is at its warmest, the beaches are empty. It’s still T-shirt weather. Yes, September on Martha’s Vineyard is where it’s at.
Catching the sunrise—my favourite part of the day—is a little easier in September. I don’t like to miss the moment when the sun breaks over the horizon. It is a time of hope, new beginnings, and wondrous beauty. In June, sunrise is around 5:08am. That means that I have to be up and out the door by around 4:00am. Don’t get me wrong, I do it, and it’s always worth it to me; however, in September, if I want to see the sunrise, it’s at approximately 6:26am. Getting up at 5:30am is a lot easier. I make my way out to Edgartown Lighthouse or Ocean Park in Oak Bluffs, and pull out my camera. A sunrise in September on Martha’s Vineyard never disappoints. The beaches are empty allowing for beautiful landscape shots, although to be fair, they’re usually pretty empty at dawn. That’s one of the reasons I like sunrises so much.
Like everything else in September on Martha’s Vineyard, the crowds are gone! Even The Black dog Tavern, arguably the most popular breakfast spot on-island, will always have room. It will be more crowded on the weekends. There are still day-trippers who know that the island is at its peak in the September season, but that window seat you have been dreaming about all year, the one where you can drink your coffee and watch the ferries go in and out of Vineyard Haven Harbor will be waiting for you. Having said that, I encourage you to try a breakfast spot that you haven’t tried yet. Always try at least one thing new on each and every trip. Get to know your island. I have tried a lot of the breakfast spots on Martha’s Vineyard—I still have plenty to try—and none of them have ever disappointed.
Now, I know that I said that the water is at its warmest, and that’s true—it is! I’m more of an afternoon at the beach kinda guy though. I like to spend the morning heating up and then after lunch, I’ll head to the beach. So, we’ve eaten breakfast. Now, what do we do? Well, as I said the shops are relatively empty and a September stroll on Circuit Avenue is a great way to spend the morning. Start at the northern end—the end by Giordano’s Restaurant—and work your way down.
All of the shops are open in September, so you don’t need to worry about missing out on anything. In fact, you will probably be able to take advantage of a few end of season sales! Tivoli Day hits Oak Bluffs in September too; that’s always a great time. It’s a street festival with street vendors, live music, and food! There is also a parade of sorts in the evening. It’s a live band that marches through town and collects people as it goes. This year, Tivoli Day is on September 14th. I really recommend making a point of checking it out.
I also strongly encourage taking full advantage of the hiking trails on the island. Martha’s Vineyard has many well maintained hiking trails. Some are completely flat and some are quite hilly. Some will take you to the peak of the island’s elevation, some will take you to the beach, and some will take you to both! There is a great app for iPhone called ‘TrailsMV’. Download it and find the trails that suit you best. The September weather is perfect for hiking—not too hot and not too cool.
Lunch in September is great, like it always is, but depending on what part of the month you go, you could be met with some restrictions. A lot of the larger restaurants are trying to empty their freezers and refrigerators, so menu items start to disappear. In fact, some of the larger restaurants, like Giordano’s and Nancy’s, will close before the end of the month. Being the size that they are, it is very expensive for them to stay open. They are always the first to go. If you go to the island in the beginning of the month, you’ll be fine. Even if you do go at the end of the month, there will still be a huge selection, no matter what you desire. I have been to Martha’s Vineyard in eight of the twelve months and I have loved every single trip.
September on Martha’s Vineyard is designed for a lot of things, but one of my favourites has to be beach time. I love lying on the beach and reading a book. Then, when I am nice and hot, I love swimming in the ocean. In fact, swimming in the ocean on the beaches of Martha’s Vineyard has pretty much ruined the beach and/or swimming experience for me anywhere else! Let’s face it, Martha’s Vineyard has beaches that are world class, and when the waters of those beaches have been doing nothing but heating up all summer long, afternoons on the beach are the only way to go.
There are beaches to suit every need—surfing, body-surfing, paddle boarding, pleasure swimming, and beaches to just let your toddlers splash around. There is a cleansing that happens when you walk down the gangplank and step onto Martha’s Vineyard, and the final rinse takes place on its beaches. The salt water comfortably carrying you along under the September sun that gently bakes your skin to a golden brown.
As I mentioned earlier, the time of the month that you are on-island could affect your dining choices. If you are there in the first couple of weeks of September, than I strongly encourage you to make sure that you have at least one evening meal at Nancy’s Restaurant. The great thing about September is that the sun sets early—right around suppertime. The views of the sunset cannot be beat at any other restaurant on-island, in my opinion. Also, if Giordano’s is open try to make sure you go in for a sit down pizza with your friends and family. It’s my favourite pizza on island. Everyone has there favourites, and there are a lot from which to choose, but this one does it for me.
If you’re there later in the month, The Seafood Shanty is open and there is certainly nothing wrong with its views of Edgartown Harbor. Their deck is one of my favourite places to have a meal. I love watching the goings on of the harbour.
Also, one of my favourite places to eat on-island is SeaSmokeMV! It just reopened and the food is delicious! It’s a little off the beaten track in Oak bluffs, right across from Tony’s Market. I love that it’s a little bit out of the way and the traditional southern barbecue is totally worth it. Brisket, ribs, potato salad, macaroni salad, collared greens, peach cobbler—you go to SeaSmokeMV, and tell me that summer’s over. I dare you! Go ahead…I’ll wait.
Some of you know and some of you might not, but the first time I ever went out sailing with Catboat Charters was in September of 2016. I don’t know what makes the September skies so vibrant, but they are. They also incorporate just enough cloud cover to make the sunset spectacular. It was my friend Captain Kurt who pointed that out to me. I had never really thought about it. we were sailing along once, and Kurt said, “It’s the clouds that make or break a sunset.” He’s absolutely right.
I have been fortunate enough to sail with Catboat Charters in June, July, August, and September and the September sails have always been my favourites. They have all been breathtaking, even one surrounded by fog had an ethereal magic, but the September sails are forever embedded in my heart. So, there you have it—after supper, go for a sunset sail with Catboat Charters. You won’t be sorry.
I don’t have enough room to go on and on about things to do in September on Martha’s Vineyard. I haven’t even touched on Mytoi Gardens or Polly Hill Arboretum. The list is endless, so I won’t even try, but I will ask you this: If you are complaining about summer coming to an end, why let it?