Don't Just Be One of the Crowd! Plan a Visit to Martha's Vineyard in the Off-Season ~ Part One

Wait. What? Summer is so far gone that warm temperatures are nothing but a very distant memory, we’re in the middle of yet another interminable winter and you’re thinking that as much as you’d like to make an island escape to somewhere - anywhere - that heading to one like Martha’s Vineyard during winter just isn't an option as there’s simply nothing to do there off-season? Stop thinking like that! Who says that New England islands are only warm weather retreats?  Why wait to go until the next summer season rolls around again when prices are higher and the crowds have returned? Better yet - plan a visit now and experience the Vineyard from a way less-expensive, way less-crowded point of view. As someone who wandered out to the island in the rather bleak month of February last winter (along with my distracted sidekick aka Cousin Amy) and had an absolutely wonderful time, I highly recommend a winter visit as there's still a lot to see and do during the “off season.” Plus, on a very positive note, you won't have to rub elbows with 100,000+ other folks who make Martha's Vineyard their summer playground! Forget the rich, the famous, and the First Family and meet some of the +/- 17,000 hardy souls who make the island their home year-round instead!

Postcard "Map" of Martha's Vineyard
Before I tell you about the wonders of wandering around Martha’s Vineyard during the off-season though, I feel I would be totally remiss and out of character if I didn't give you at least a little bit of history to start things off! I promise I will do my best to keep it brief but as regular readers of this blog know, I do so love my history!
The Landing of Bartholomew Gosnold at Woods Hole, 1602
Part of the Commonwealth of Massachusetts and divided into six towns – Tisbury, Edgartown, Oak Bluffs, West Tisbury, Chilmark, and Aquinnah – Martha’s Vineyard was originally inhabited by the Wampanoag Tribe who called it Noepe meaning “In the Midst of the Sea” or “Land Amid the Streams” depending on which research source you’re looking at. Legend has it that the first Europeans to visit the island were the Vikings in the year 1000 who named it Vinland however there’s never been any graffiti carved into a rock that says “Leif Eriksson was here” so that’s really just speculation that can neither be proved or disproved. When Giovanni da Verrazano, an Italian explorer who has a pretty awesome bridge named for him in New York, saw the island after his ship the Delfina got pushed out of the Bay of New York by a storm in the spring of 1524, he named it Claudia in honor of the mother of Francis II of France. So why then – you may ask - isn’t the place named Claudia’s Vineland? Well, when English explorer Bartholomew Gosnold got blown off course on his way to Virginia in 1602 and inadvertently ended up finding a more direct route from England to the northeastern seaboard of America, he started naming the places he came across himself regardless of whether someone else may have beaten him to the punch.

Captain Bartholomew Gosnold from
First he landed on a cape which he christened Cape Cod due its abundance of codfish and then sailing south from that cape, he landed on a small island that he dubbed Martha’s Vineyard after his daughter Martha who had died in infancy. Continuing his exploration of the area, Gosnold then landed on a larger island - about six miles northwest of the smaller one that he had just named for his daughter - which he named Martin’s Vineyard in honor of the captain of the ship that he was sailing on. After checking it out and finding an abundance of grape vines, beautiful lakes, springs of fresh water, and determining that overall it was a much nicer island, it’s been said that Gosnold changed his mind and transferred the name he had already given to the smaller island to the bigger island while re-dubbing the smaller one as No-Man’s-Land – ouch! I’m not too sure how Martin the Captain felt about that or whether in fact that’s exactly what happened but it’s the best I can piece together from numerous sources as to how the eighth-oldest surviving English place-name in the United States came about!

But wait – there’s more! In 1891 the island underwent another name change when the apostrophe was dropped and the name officially changed to Marthas Vineyard by the United States Board on Geographic Names, a federal body within the U.S. Geological Survey which was set up by President Benjamin Harrison in 1890. Apparently it was the Board’s mission to wipe out apostrophes across the map but perhaps realizing in doing so they made the name of the island seem as if it was named for a multitude of Marthas rather than just one - which was grammatically incorrect - or simply wishing to appear magnanimous following almost four decades of extensive local protest by enraged islanders, in 1933 the Board reversed its decision and replaced the apostrophe it had previously taken away. Permanently and forever now known as Martha’s Vineyard the island can lay claim to one of only five place-names in the United States containing a possessive apostrophe in the 114 years since the Domestic Names Committee of the U.S. Board on Geographic Names was formed. Should you be curious as to the names of the other four, they are Ike’s Point, New Jersey; John E’s Pond, Rhode Island; Carlos Elmer’s Joshua View, Arizona; and Clark’s Mountain, Oregon.

Governor Thomas Mayhew, Sr. - image credit to
As to the other island history - in October of 1641 with the permission of the Crown, Thomas Mayhew the Elder, an English merchant, purchased the Elizabeth Islands, Nantucket, and Martha’s Vineyard from William Alexander, the 2nd Earl of Sterling, for 40 pounds and two beaver skin hats, along co-buyer Sir Ferdinando Gorges who expended an undisclosed sum. Establishing himself as governor of Martha’s Vineyard, in 1642 Mayhew sent his son, Thomas the Younger, over to the island along with 40 English families where they landed at a place they called Great Harbor (now Edgartown) along with their domestic animals, tools, and whatever else they needed to start a new colony.

When the English settlers arrived they found that they had built-in neighbors - approximately 3,000 Wampanoag natives living in permanent villages led by four sachems. As Thomas the Younger was a minister and believed in the equality of all men, he was respectful of the native islanders and careful to honor their land rights decreeing that no land was to be taken without their consent or fair payment. Due to the settlers friendly relations with the tribe, when King Philip’s War broke out in 1675 and many tribes attacked and killed hundreds of English settlers in New England, the Wampanoag never rose up against the English on their island even though they outnumbered them by 20 to 1.

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Old Whaling Church, Edgartown
In the 19th century, both Martha’s Vineyard and the nearby island of Nantucket rose to prominence and riches when the whaling industry reached its heyday. Nantucket supplied the ships while Martha’s Vineyard supplied the experienced captains and crews who hunted the whales who would – unwillingly - supply oil and blubber for lighting needs. In the early 1820s, in between rolling in their riches, many of the mariners who traveled the world in search of whales built beautiful homes in Edgartown along with an enormous church that they erected in 1843 that is considered to be one of the finest examples of Greek Revival architecture still standing in New England today. When petroleum was found in Pennsylvania in 1859 the need for whale oil plummeted and the whaling business staggered until it suffered a fatal blow during the Civil War when whaling ships were either captured by the Confederate navy or bottled up in the harbors. By 1870 the industry collapsed completely and though the ship owners were sent into financial ruin, that didn't signal a collapse for Martha’s Vineyard as the island had already started to become a bit of a tourist destination when - glory hallelujah! - Americans started to hear the call to repent.

From 1790 to 1850, the United States experienced what became known as the Second Great Awakening as religious fervor spread through the country resulting in massive conversions and the formation of new congregations. During this time when people were finding religious renewal in groves, in 1835 a small group of Edgartown Methodists held a week-long summer retreat in a grove – an oak grove to be precise -high on the bluffs at the northern end of town. Originally comprised of a group of improvised tents with a speaker’s platform made of driftwood, the area would eventually become known as Wesleyan Grove, a 34-acre summer campground where open-air Christian revivals were held each summer. Every year the Methodists would return in increasing numbers and for longer periods to revel in the word of the Lord and the land’s beauty as they lived in large tents that were maintained by the congregation of whatever church on the mainland from which they had come, all of which were arranged in a circle around a central church tabernacle. As the tents were often cramped and uncomfortable, families soon began to bring their own tents with them – a latter day KOA of sorts if you will.

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Martha's Vineyard Camp Meeting Association cottage during illumination;
photo of photo taken on-board a Massachusetts Steamship Authority ferry
Realizing that they were going to be coming back year-after-year and that the event was definitely growing in popularity, families who attended the yearly revivals decided that it might be easier to have a permanent summer residence rather than just a tent that they brought over with them each year. In the 1860s-1870s the family tents were replaced with permanent wooden cottages built in the “Gingerbread” or “Carpenter Style.” Colorful and ornate, it wasn't long before there were over 500 small camp cottages that families and their friends would flock to every summer. From there things took off as word was passed around New England and other parts of the world how beautiful and charming the Vineyard was and before long, the simple farming community grew into an internationally-known seaside resort.

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"Gingerbread Cottage" at the MVCMA in February
Now even though you could you follow in the footsteps of those first tourists and stay in one of those cute little campground cottages located in the Martha’s Vineyard Camp Meeting Association during the summer months should you have the financial wherewithal to rent one (which I'll talk about more in Part Two of this series) instead, how about visiting Martha’s Vineyard during the off-season which is a really great way to find the true spirit (and charm) of the third largest island on the East Coast. Should you decide that sounds like a good idea, the first thing you’re going to need to do is plan how you’re going to get there as unfortunately you can’t just hop in your car and drive over. Coming in behind Long Island, New York (a whopping 1,401 square miles) and Mount Desert Island, Maine (108 square miles), at 91 square miles Martha's Vineyard may not be the biggest in size but it is the largest island on this side of the country that‘s not accessible by either a bridge or tunnel which means getting there requires some pre-planning on your part. If you have your own boat or plane getting there is probably not a problem but then again, if you had those you probably would also have the time and money to get to the island during the "high" season so let's assume that you don't and that you'll need to find a way over. Not a problem!

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What? No one wanted to sit outside during the crossing? 
Photo & Video Sharing by SmugMugThe most popular way for tourists to get to the island for years and years has been by boat and today that's no exception however, in spite of the company’s name, travel is no longer via steamship but on board more modern vessels. Offering the lowest fares and most daily departures, The Massachusetts Steamship Authority provides year-round ferry service of both passengers and vehicles - either personal or commercial - to Martha's Vineyard. Created in 1960 by the Massachusetts Legislature to provide “adequate transportation of persons and necessaries of life for the Islands of Nantucket and Martha's Vineyard" the Steamship Authority currently operates nine vessels carrying passengers, automobiles and freight trucks from ferry terminals in Woods Hole and Hyannis on Cape Cod on the mainland which arrive at terminals in Vineyard Haven and Oak Bluffs on the island.

During the off-season, all ferries to the Vineyard depart from Woods Hole and arrive at Vineyard Haven with rates that are quite reasonable even if you wish to take your car over - which you might want to do if you plan to do as much exploring as you can and don't want to rent a vehicle while you're on the Vineyard or rely on bus service. You can get all the information you need to book your trip including schedules, rates (with or without your car), reservations, availability, etc. on the Steamship Authority website. A word of advice: if you're going to take your car over be sure to make your reservations as far in advance as possible as the ferries have strict weight limits that they must adhere to.

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West Chop Light as seen from the ferry approaching Vineyard Haven
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Massachusetts Steamship Authority ferry crossing Vineyard Sound 
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Vineyard Haven Landing Area 
Provided you've opted to take the ferry over and not fly into the Martha's Vineyard Airport which offers more options in-season than off, the trip from Woods Hole to Vineyard Haven is only about 45 minutes. While on-board you can enjoy free Wi-Fi service which is available on all ships, visit the on-board snack bar available on most ships which offer beer, wine and mixed drinks along with a variety of hot and cold menu items, or simply sit back and enjoy the view as you make your way across the scant four miles of Vineyard Sound.

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VTA bus passing through West Tisbury
Arriving in Vineyard Haven, the main village/town center of Tisbury which was named for the hometown of Governor Mayhew - Tisbury, Wiltshire, England - if you didn’t bring your own car with you and you aren’t staying in this part of the island, you can jump on one of the Martha’s Vineyard Regional Transit Authority (VTA) buses at the nearby terminal to head to other parts of the island, rent a vehicle to strike out on your own, or call a taxi to take you where you need to go. The VTA is the only year-round island-wide public transportation system and though it doesn't run as frequently in the off-season, it can still get you to where you want to go as it provides service to all six of the island’s towns and travels down all of the major roads. The VTA offers convenient 1, 3, 7, and even 31-day passes as well as single-ride fares. For more information be sure to check out their website to decide if public transportation is going to work for you of if you’re going to want to make other arrangements to get around during your visit.

If you've decided that you’re going to spend your island adventure in the area of Vineyard Haven you’ll be happy to know that you’re staying in one of the three main population centers on Martha’s Vineyard. During the off-season the population is less than 4,000 people but you’ll still find lodging, dining, and shopping opportunities all within walking distance. Yes, there are going to be some establishments that are closed but some of the best ones are still open and ready for business so you certainly won’t be without something to do!

For lodging choices, one of the nicest places to stay in Vineyard Haven is the Mansion House which was established in 1791 and last rebuilt in 2003. Just a short walk away from the ferry, the Mansion House is an inn, health club, and spa all-in-one and offers a variety of guest rooms and suites along with eight pet-friendly rooms. All guest rooms feature the amenities that discerning travelers have come to expect like flat-screen TVs and comfy linens while many offer spectacular views with some rooms even having their own balcony overlooking Vineyard Sound. For an extra-special stay, the inn’s deluxe rooms and suites offer extra-special amenities like a soaking tub or fireplace and all rooms feature island-inspired décor. If by chance your room doesn't have one of the more spectacular views, you can still head up to the cupola and take in the beautiful views of the harbor from there.

Mansion House Pool; photo credit
Guests have free access to the inn’s Vineyard Health Club which is also open to the public from 6 am to 9 pm, 7 days a week and boasts the island’s only indoor pool along with state-of-the-art exercise equipment, tanning, and over 20 classes including Kripalu Yoga, Pilates, Zumba and more. If working out isn't your thing and you’d prefer something a lot more relaxing, the Spa at Mansion House offers facials, massages, and body wraps to help relax and rejuvenate. For a real treat, try one of the Mansion’s Moshup Mud Wrap body treatments– with or without honey. Named for the legendary father of the Wampanoag Tribe of Gay Head, the first inhabitants of the island, the special clay is known for its therapeutic properties and is legally harvested by Wampanoag tribal members for exclusive use at the spa.

During the summer season rooms at the Mansion House start at over $300 but if you take an off-season trip to the Vineyard rates start below $180 in the spring/fall and less than $100 in the winter. Check their website for last-minute Internet specials that can save you a good chunk of change that you can then spend elsewhere on good food or something to take home to remember your trip by!

If a Bed & Breakfast is more to your liking, the Thorncroft Inn offers year-round comfort in a classic craftsman-style bungalow on the former estate that was built between 1908-1918 for Chicago grain merchant John Herbert Ware I. During its years serving as the guest house for Ware’s estate which he named Thorncroft, the 6,000-square foot “Little House” provided comfortable accommodations for friends, relatives, and dignitaries visiting Martha’s Vineyard. In later years the “Little House” became a rest home until it was converted to a lodging establishment in 1971.

One of the dining rooms at the Thorncroft Inn
When the Haven Guest House – as it was known then – was sold to its current owners Lynn and Karl Buder, they turned it into a romantic, 14 room, couples-oriented country inn. Located on 2-1/2 acres of landscaped grounds just one block from the Atlantic Ocean, the Thorncroft Inn has received a Four Diamond Award from the American Automobile Association every year since 1990 and is a distinguished member of Select Registry which assures you that you are staying in one of the best of the best properties in North America with high standards of hospitality.

Cottage Room at the Thorncroft Inn
The Thorncroft Inn features romantic rooms that are all unique in their appearance and amenities. One has a private hot tub, another a two-person whirlpool, and five feature working fireplaces with real wood that is provided at no charge; should you not be experienced in fire-making, assistance is happily provided! The inn offers a smoke-free environment along with complimentary high-speed internet and luxurious bath amenities along with deluxe, custom-made bathrobes in all rooms. Included in the room rate is a homemade full country breakfast served in the inn’s two dining rooms or a substantial continental breakfast delivered to your room should you choose to have breakfast in bed. Off-season rates vary from $195.00 a night to $425.00 depending upon the room you select; you can check availability and reserve a room online or text 508-335-7873.

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West Chop Light overlooking Vineyard Sound
Located a mere 1.2 miles away from the Thorncroft Inn overlooking the Vineyard Sound you’ll find West Chop Light, a 45-foot tall conical tower that was built in 1891 and which still uses its original fourth-order Fresnel lens even though the light was automated in 1976 (the last of the Vineyard’s five lighthouses to become so.) The lighthouse was added to the National Park Service’s National List of Historic Places in 1987 and the former lightkeeper’s house now serves as living quarters for the Officer in Charge of Menemsha Coast Guard Station. The grounds are closed to the public but you can still get a great view from the road!

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Lantern Room of West Chop Light with its original Fourth-Order Fresnel Lens
Back down in town, if you’re a shopper you’ll love Main Street in Vineyard Haven with its independent stores and boutiques that offer a wide variety of unique gifts and goods; yes, there are a lot that are closed for the season but there are also a lot that are open for your shopping enjoyment. As there are virtually no chain stores or malls on Martha’s Vineyard, you’re sure to find something distinctive and different for either yourself or as a gift that you might not find anywhere else.

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One of those stores is Midnight Farm, an indie-chic boutique located in a nondescript former hardware store on Main Street co-owned by Tamara Weiss and Carly Simon - yes, Carly Simon of “You’re So Vain” fame. Its eclectic inventory includes a wide variety of textural, organic, reclaimed, handmade and unique products including home goods, bedding, toys, furniture, jewelry, clothing, and local foods. One of the items that the store stocks and which is a favorite with customers – locals and tourists alike - is a mango-lime salsa made especially for the store. Just because celebrities like Steven Tyler, Meg Ryan, Spike Lee and others like to shop at Midnight Farm where “unique” is definitely the watch-word, doesn't mean that you can’t also!

Bunch of Grapes Bookstore in Vineyard Haven
If you like independent bookstores then you are really going to love Bunch of Grapes Bookstore which has been operating for over 40 years and is everything an independent bookstore should be and more. In addition to a terrific inventory of sidelines, they offer a great selection of books from not just well-known national and international authors but they also have a large variety of books written by local authors and books about the local area. The bookstore hosts author events year-round and are more than happy to give back to their local community as they help support education and the arts.

Vineyard Books at Bunch of Grapes Bookstore 
If you've worked up an appetite it’s no problem getting something good to eat year-round in Vineyard Haven! A very easy stroll from the ferry terminal you’ll find The Black Dog Tavern as well as The Black Dog Bakery where you can find good eats regardless of the season. The tavern has been a fixture at the head of Vineyard Haven harbor ever since Captain Robert S. Douglas – a former jet fighter pilot for the U.S. Air Force from 1956 to 1958 who used to spend his summers as a boy on the island - decided that the Vineyard needed a year-round restaurant. His paper napkin sketch came to life on New Years’ Day 1971 and The Black Dog Bakery followed in 1973 opening up in the former Vineyard Haven Firehouse when the need arose for a bigger place to bake the breads and desserts that were being served in the tavern.

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A mug of chowder at the Black Dog Taven
It was at the bakery where the very first Black Dog t-shirts were sold and though there’s a retail store there keeping that tradition alive, it’s no longer the place where the baking is done though you can certainly buy all sorts of freshly baked goods along with assorted sandwiches and soups including The Black Dog’s famous clam chowder along with a t-shirt should you choose. When the baking needs outgrew the space available at the building, the baking operations moved to The Black Dog Bakery Café on State Road which is open daily from 7:00 am to 6:00 pm and offers daily lunch specials along with their artisan breads, fresh baked pies and pastries, delicious sandwiches, salads, and more.

Also located on State Road, Little House Cafe serves up breakfast, lunch, and dinner with the motto “Always Fresh, Always Delicious!” Many of the café's original recipes were created by owners Merrick Carriero and Jenik Munafo who opened their restaurant in July of 2010 and have received rave reviews ever since including the accolade for “Best Lunch” on the Vineyard in the Martha’s Vineyard Magazine Best of the Vineyard 2014 poll.

Two miles away from the Vineyard Haven ferry landing you’ll find an antique post-and-beam barn that once stood in the town of Export, Pennsylvania which is now the home of the Island Alpaca Company of Martha’s Vineyard. Starting out with eight alpacas in 2004 the herd now totals 69 Huacaya alpaca – and one llama who is definitely a bit of a ham!

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The gang poses for a photo at Island Alpaca
With a gift shop that carries a wide variety of goods that include gifts for baby, mittens, gloves, & glittens, sweaters, yarn, and lots of stuff in between, Island Alpaca is a terrific place to find something great to take home for yourself or a loved one. They also offer workshops & events, Alpaca Sponsorship, or simply the chance to come by and visit with the herd daily from 10 am to 4 pm during the winter, spring, summer, and fall. From May 20 to October 29 there’s a $5 per person charge but if you go off-season they simply suggest a $5 donation if you’d like to make one.

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When visiting the alpacas, there are few simple things you can do to make the visit more enjoyable for both of you.

In Part Two of this series, I'll explore the other towns of Martha's Vineyard and some of the things there that make an off-season jaunt across Vineyard Sound more than worth it including the fabulous grand dame of Martha's Vineyard - the Harbor View Hotel in Edgartown - and some of the most spectacular sunsets on the East Coast in Oak Bluffs.  Just to make sure you come back, here's a bit of a tease!

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February Sunset over Oak Bluffs, Martha's Vineyard


  1. We visited Martha's Vineyard during our honeymoon. 30 years ago. Thanks for the trip down memory lane.


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