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8 Great Things To Do Off-Season on Martha’s Vineyard

Sigh… I just returned from a blissful week away with my husband. Alone. Without kids. For the first time in over two years. We celebrated our tenth year of marriage, and we did it the way we hoped we would a decade ago: by staying in the same cottage where we honeymooned.

As a Texan (me) and a Pacific Northwesterner (him), we didn’t know much about New England when we were engaged, but we did know one thing: it’s supposedly beautiful in the fall. So when booked the date for our fall wedding, we thought it fitting to celebrate our marriage in the quintessential destination for colored leaves and maple candy.

Martha’s Vineyard is like no other island. Resting south of the Cape Cod mainland and west of Nantucket, it’s a popular summer destination for much of Massachusetts and Rhode Island. Founded in the early 1600s, it’s one of the earliest settlements in the entire country, and many of the buildings still hail from the 18th and 19th centuries.

There are no stoplights on the Vineyard, and the fastest speed limit is 40 miles per hour. There are no neon or backlit signs on any stores or restaurants: it’s all classic painted signs with a simple spotlight shining in the evening.

Our cottage was in Edgartown, the oldest of the six towns on the island and home to some of the best examples of restored Greek Revival architecture in the U.S. Downtown, you’ll find cozy-quaint streets lined with houses clad with white horizontal siding and black shutters. A few blocks out, and most houses don shakes grayed naturally by the weather. We easily walked from our cottage to the main town.

We spent our days walking, talking, reading out loud, sleeping in, and eating more than we should have. A near-perfect vacation, in other words. Oh, and we completed sentences without interruption. I know every parent reading this appreciates our enthusiasm for this oft-missed activity.

With our car, we explored slow country roads, pulled over for impromptu walks in the field, ate lunch on the beach, and perused old general stores that haven’t changed much in a hundred years.

And in the evening, we’d return back to our tiny little cottage, with room just enough for two, and we’d fall asleep near open windows, listening to the thunderstorm.

Ever thought about taking a trip to Martha’s Vineyard during the fall? Well, I’m no expert, but I’ve been twice now, so I have an idea or three about what’s worth the time. If you haven’t gathered, the most popular activity on the Vineyard is RESTING. Spending quality time with the ones you love and just… being.

And as you’re doing that, here are some of my favorite must-dos on the island.


  • 1. The Black Dog Tavern 1 of 8
    1. The Black Dog Tavern

    You can't go a mile on Martha's Vineyard without seeing the ubiquitous Black Dog logo—it's everywhere. One of the few year-round restaurants, the Black Dog Tavern in Vineyard Haven (right by the ferryboat dock) is a must-go. In the fall, try the Shipyard Pumpkin ale with the cinnamon, sugar, and maple syrup rim. Heaven in a glass. They've also got a bakery and several stores around the island.

  • 2. Sunset on the west side 2 of 8
    2. Sunset on the west side
    The Vineyard is gorgeous on all four sides, but the sparsely-peopled west side is perfect for treating yourself to a sunset. Head to the Gay Head cliffs in Aquinnah and be amazed.
  • 3. Mad Martha’s Ice Cream 3 of 8
    3. Mad Martha's Ice Cream

    It's not cheap at five bucks a scoop, but one bite and you'll know why—Mad Martha's is some of the richest, flavor-packed ice cream I've ever had. Try butter crunch if you'd like your knees to melt.

  • 4. Drive country roads 4 of 8
    4. Drive country roads

    You can drive the 100-square mile in an afternoon, but with a top speed limit of 40, you'll want to spend the day leisurely cruising the back roads. State Road, down the middle of the island, is one of our favorites. Stop by the Granary Gallery not too far off the road for gorgeous art in an unexpected barn. Included are famous photographs from renowned islander Alfred Eisenstaedt.

  • 5. Walk around Edgartown 5 of 8
    5. Walk around Edgartown

    Edgartown is small enough to walk around in an afternoon, but large enough to be wowed on every street. Head to classic stores like Portobello and Edgartown Books, wander the Martha's Vineyard Museum, then enjoy a sandwich and latte at Espresso Love.

  • 6. Buy souvenirs at Alley’s General Store 6 of 8
    6. Buy souvenirs at Alley's General Store

    Open since 1858, Alley's General Store is the oldest store on the Vineyard. Stocking everything from cheese and canned tomatoes to Slinkys and glow-in-the-dark Queen Elizabeth IIs, it has everything you need in a shabby-chic wood clad house. Head behind the store for lovely soups and sandwiches at 7a Foods.

  • 7. Stroll by the gingerbread cottages at the Tabernacle 7 of 8
    7. Stroll by the gingerbread cottages at the Tabernacle

    Oak Bluffs, the original tourist town on the Vineyard, was home to a Methodist revival during the 19th century, and the open-air meeting house tabernacle still stands as the center of the village. Spoked around it are kitschy gingerbread-style Victorian cottages in every color imaginable. Stroll through the narrow streets and imagine the history.

  • 8. Eat chowder on the beach 8 of 8
    8. Eat chowder on the beach

    You can't visit New England and not sample some classic clam chowder (or "chowder"). Martha's Vineyard Chowder Company has boasted titles such as "Best chowder in Cape Cod" for quite a few years running, and our taste buds agreed. Grab some to go and savor it on a nearby beach such as South Beach, where Jaws was filmed.

There are plenty of summer-only activities as well, such as riding the oldest carousel in the country, hiring a day sail, and spending all day swimming in the warm Atlantic. We haven’t done these yet, since we’re fall visitors—but we look forward to heading back during the summer months soon, this time with our kids.

I also found useful the free Martha’s Vineyard app for the iPhone. You’ll want to call ahead at most of these places if you’re on the island any time outside of summer, since many places have different operating hours off-season.

Martha’s Vineyard is truly a magical place, and you don’t realize how tranquil it is until you drive off the ferryboat to head back to the airport and into the real world. Only a 45-minute boat ride from the mainland, but it feels like a place where time stands still.

Have you ever spent time on Martha’s Vineyard? What would you recommend doing?

Read more from Tsh at Simple Mom, or follow her on Twitter, Facebook, or Pinterest.

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(top photo credit)

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