The Insider's Guide to Martha's Vineyard, The Off-Season Edition

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Martha’s Vineyard is synonymous with summer, backyard barbecues, beach days and for most, crowds of first timers flocking to the beach. Many people would be surprised by all that Martha’s Vineyard has to offer during off-season, when the summer sun fades away and a crisp air blows through the island. Growing up on an island defined by its seasonal summer activities oftentimes deters  guests from visiting in the off-peak months, when many local residents find that to be the most beautiful time of year.  If you are looking to make a great escape this holiday season, we are here to give you the ultimate one day itinerary around Martha's Vineyard from a man who calls this place home year round. 

Gear: The Pocket Tee, White/Camo | The Hunter's Shirt, Blue | The Roger Tee, White | The Field Hat, Tan | The Field Pant | The 6 Point Denim, Selvage 

9AM: Vineyard Haven

To begin your excursion, you'll arrive to the island to the only remaining open port of entry during the off-season, Vineyard Haven. The boat yards line the shore on the left and a quintessential New England sailboat harbor is nestled in next to where the ferry docks.

Many restaurants and stores close during the winter months but a few local favorites remain open throughout the year and have become staples for those who call the island home. Black Dog Tavern is a must for breakfast and is a stones throw from where you disembark the ferry. Be sure to order the Bob Barker Meat Market – no longer available on the menu but known by all that work there.  Start your day with a heavy breakfast omelette with side of hollandaise sauce, homemade sourdough bread, or a stack of pancakes topped with blueberries and pecans. Enjoy your meal at a cozy tavern table out by the waters edge.

11AM: Oak Bluffs

From Vineyard Haven, take sharp left through Five Corners through Beach Road. Once you pass the draw bridge take another sharp left onto E. Chop Rd. lined with exposed houses located directly on the beach shore. Head to Telegraph Hill winding your way down into Oak Bluffs. Take the opportunity to park bike and check out the Gingerbread Houses. Insiders Note - you aren’t allowed to drive your motorcycles so only do this by car.

If you didn't grab breakfast in Vineyard Haven, make breakfast stop at Off Shore Ale for wings and pizza - a local island brewery and be sure to get the a Hop Goddess, a local islander favorite.This can be a quick pit stop and then it’s time to hit the road again.

12PM: Edgartown

Continue heading down the island with the ocean on your left (Beach Rd). Head into Edgartown and take left on West Main Street and take the opportunity to view Historic Edgartown, including the Captain’s Houses and the Edgartown Harbor Light. This is also a great time to swing by Behind the Bookstore, an incredible coffee shop and eatery located behind the Edgartown Bookstore. Be warned, this closes for the season November 27th.

2PM: West Tisbury

Loop your way back around Edgartown and head towards Katama. Take the left fork to South Beach Martha’s Vineyard. If you are lucky enough to be on a lightweight bike its possible to drive out to Norton Point where only sand vehicles are granted access and cruise the coastline. This is only recommended for those who are comfortable riding on loose sand.

If you are on a bike, here are a few insider tips to navigate this part of the island through quiet dirt roads, away from the main streets. Head down South Beach strip, Katama Airpark will be on right, follow Meeting House Way (dirt road) until it Edgartown Road. Take a right on Fire Road 11 and take second left on Fire Road 58, cross Barnes Road all the way and come out on Old County Road down to South Road. This is a part of the island most islanders themselves never experience - long and winding dirt roads lined by scrub oaks that were coined "Fire Roads" due to emergency vehicles using these lanes to cross the island quickly but during the fall for the name also plays into the burning colors created by fall foliage. 


One stop that can’t be missed is Back Alley’s for food and snacks, conveniently located behind Alleys General Store where you can stock upon any supplies needed for your road trip. Take this opportunity to fill upwith gas at the lowest priced gas station just down the road from Back Alley’s –continue down South Road to keep exploring the island. 

4PM: Aquinnah

Take a left off South Road to explore Lucy Vincent beach with its majestic weather carved rocks. Ride past Squibnocket Road on the way to Aquinnah to see the year-round local surfers enjoying the crisp waters.  Continue down Mashup Trail to Aquinnah Shop restaurant for food and grab a bottle of wine. This is the perfect place to relax and have dinner outside as it offers one of the most beautiful sunsets on the island.

7PM: Menemsha

After enjoying the beaches or even hopping off the bike for a quick dip, take State Road back to Menemsha Road into Menemsha, another quintessential fishing town. It is highly recommended to save some space in your stomach for a pit stop at Larsen’s Fish Market - grab a dozen oysters or have them steam you a lobster. Insider tip: be sure to order the clam bake, it comes with steamed lobster and little neck clams.  It's impossible to go wrong with that combination and a bottle of wine.  If you’re lucky, you’ll still be able to see the final touches of the sun setting over the horizon. 

9PM: Vineyard Haven

Then take North Road (a local favorite if you happen to be on a motorcycle) back to Vineyard Haven and the ferry. The last ferry leaves at 9:30 so be sure not to be late.

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  • What months are considered off season for Martha’s Vineyard

    Cathy Singleton on

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