Quiet Luxury and Zero Crowds: What a Long Weekend on Martha’s Vineyard Feels Like After Labor Day
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- After Labor Day, Martha’s Vineyard trades peak-season crowds for quiet streets, shorter lines and end-of-season sales, though some restaurants and shops cut hours or close until spring.
- A long weekend can unfold by free bus or bike through Tisbury, Oak Bluffs and Edgartown, with stops for historic cottages, Black history, beaches and harbor views.
- The island’s quieter pace is the real luxury: leave room for spontaneous discoveries, and consider a longer trip to Aquinnah’s Wampanoag homeland and dramatic clay cliffs.
Martha’s Vineyard is an American icon when it comes to coastal leisure and luxury. It’s a taste of the Caribbean without the tropics; a taste of Europe without a passport; and a taste of well-aged wine without a single vineyard (the last part I only learned upon my arrival, much to my surprise).
Though I expected things to be quieter on a recent trip to the island after Labor Day, I was not prepared for just how completely Martha’s Vineyard emptied out in the New England fall season. Restaurants reduced their hours, while most shops finalized their end-of-season sales or closed outright until next March. Thankfully, the towns still stayed open, and the lack of heavy tourism gave latecomers ample room to enjoy them. Here’s what a long weekend after the holiday actually looks like on Martha’s Vineyard.
Day One: Arrival in Tisbury
Flying into Martha’s Vineyard Airport is the most convenient option, but keep in mind the terminal is in the middle of a roughly $50 million renovation that won’t be finished until 2028. As a result, the baggage claim is under a tent near the outdoor arrival area, with a short walk out to catch a rideshare. The drive into Tisbury takes about 10 to 15 minutes, and it’s a fairly scenic one, with trees all around, quaint cabins and homes and fresh air brisk enough to give you goosebumps. A light sweater or crewneck may come in handy.
Tisbury, not West Tisbury, is the more composed side of the island: more relaxed, with most places closing by 10 p.m. The town was dry for 175 years. Restaurants got permission to pour beer and wine with food in 2009, with full liquor following in 2017. There’s still no liquor store in town, but you can order a cocktail or a glass of wine at most restaurants.
The best way to explore Tisbury and most parts of the island is by electric bike or the free public bus. This is the type of island you want to explore slowly, especially once the heavier tourist season has died down. The streets have fewer cars, less noise and fewer lines, which allows you to hold short conversations with shop owners who will enthusiastically share more about their lovely town.
Every shop you walk by or into is worth a stop, and that is not an exaggeration. You will find lovely sales during this time of year, with fewer people frequenting the stores and an urgent need to offload what’s left of the season. If you’re a seasonal shopper, now is the best time to pick up unique items and handmade designs you may never see anywhere else. The beaches here are mostly connected to private property and homes, so your best views of the water and sailboats will likely be from a distance.
After a walk past the beautiful homes and around the shops of downtown Tisbury, finding a spot for dinner and drinks naturally comes next. Book a table at 9 Craft Kitchen and Bar in advance and order the chicken tagine. Add the lobster risotto and the oysters if you enjoy seafood, and pair it all with an energizing espresso martini or a fun mango margarita. The sun sets between about 6:30 and 7:30 p.m. this time of year, depending on the week, so if your dinner is later in the evening, plan on a ride back because streetlights are sparse to nonexistent. Hailing a taxi might be best at this time of day, since rideshare apps are less responsive in the evening.
Day Two: Oak Bluffs, Without the Crowd
This is the real Oak Bluffs, without the July crowd or the African American Film Festival crowd. Take the free bus to see the Gingerbread Cottages centered around the Martha’s Vineyard Camp Meeting Association (MVCMA) campground. You can’t miss them lining the streets in the same pastel colors you may have seen online, as they have for more than a century. For history lovers, Oak Bluffs is full of African American history.
The best part of exploring Oak Bluffs wasn’t a tour I had booked in advance, but a random conversation on the street with a man I had never met who has lived here for 40 years.
You can start your walking tour at Shearer Cottage, in the Highlands neighborhood of East Chop in Oak Bluffs, which became the island’s first Black-owned inn.
End the tour at Inkwell Beach, where you can spend the rest of your afternoon. The sand is a little softer closer to the water, but at this time of year the air and water are much cooler, so bring a sweater, or a change of clothes and a towel if you plan to cold plunge or swim. You may not see other people swimming, but you will see beachgoers lounging on the shore.
Head to Circuit Avenue by evening and grab food at any open restaurant nearby, or follow the shortest dessert line, usually at one of the doughnut or ice cream shops within a block of each other. Take the free bus back to your home base before visibility diminishes after sundown, which in my case meant back to Tisbury.
Day Three: Edgartown on Two Wheels
Edgartown is where you can plan a real beach day if you don’t mind the cool water. You can rent an electric or manual bike in Oak Bluffs or Edgartown, but you will have to return it to the location where you rented it. Ride slowly. The sidewalks are narrow and the roads bumpy, but the bigger reason is that the ride matters more than the destination.
The views along the way will shape how you remember this side of the island, so be prepared to stop and admire every small shop, house and boat you see. Stop whenever you want, and park and lock your bike at any bike rack to explore on foot.
The atmosphere here is not only picturesque but also welcoming and relaxing. Almost every home, business and restaurant looks like it was built with photographers in mind. It takes very little effort to capture beautiful landscapes, images and videos. Some of my favorite shots were on the beach, on quiet streets, at sunset over the water and at the lighthouses.
Consider trying a local ritual while you’re there: pick up a fresh lobster roll and eat it on the beach instead of at a restaurant table, with the salt air for company. Walk over to the Edgartown Lighthouse for an amazing view of Edgartown Harbor and Chappaquiddick and, on clear days, toward Cape Cod. The lighthouse usually closes for the season in early to mid-October. Martha’s Vineyard Museum members enter free, adults pay $5 and children 12 and under enter free.
If there’s time left in the day, or you can spare a fourth day, visit Aquinnah on the island’s western tip. It is worth the trip out to the other end, and its history is much older and rooted in the island’s Native people. This is Wampanoag land, and it is still home to the tribe today, a federally recognized Tribal Nation on the western end of Martha’s Vineyard. It’s just under an hour by bus each way, so plan accordingly.
The cliffs and views by the lighthouse are worth the trip alone. It is like nothing I have ever seen: from above, the bands of colored clay on the cliff face, surrounded by greenery, fade into the beach and lead into the ocean in a colorful feast for the eyes. You can walk down to Moshup Beach below, but climbing the cliffs or taking clay from them is prohibited. Taking it all in slowly from the overlook is more than enough for this visit.
The Actual Luxury
This Martha’s Vineyard weekend doesn’t need too many reservations or a structured itinerary during this time of the year. That’s the point about slow traveling as the shoulder season begins.
The real luxury on Martha’s Vineyard after Labor Day isn’t a five-star meal, exclusive parties, or private transportation around town. It’s being somewhere that has slowed down enough for you to appreciate your surroundings. So if you’re visiting this time of year, leave room for spontaneity in the day, avoid a packed schedule, and let the pace of the island set the plan, not the other way around.
