I want to tell you a secret. Something known only to some very intrepid souls and the locals. Want to know the best time to visit Martha’s Vineyard? No, not during the summer, though that is an ideal time. No, the best time to visit The Vineyard is now. In the winter. Trust me.
My wife and I first spent a few days there following a New Year’s Eve wedding in 1998. A weekend away for just the two of us was certainly intriguing (and welcome after the holidays), but admittedly, I was a bit skeptical of her choice for a long-weekend getaway destination. The Vineyard in January doesn’t bring to mind sitting poolside while cabana boys bring fruity drinks with tiny umbrellas (um…I mean lots of beers) nor does it conjure up sitting fireside after several hours of packed powder. To my less knowledgeable self, the Vineyard in January is biting winds and subzero wind chill; it’s empty storefronts and shuttered restaurants. It’s a ghost town. Well, it is and it isn’t.
Most people know about The Vineyard as a summer playground for the rich and famous. US Weekly and People have no shortage of stars to photograph in Edgartown or Oak Bluffs from June to September. They might even find some stragglers in October. But come winter, they are off to warmer climes leaving the island to the locals and those with a fondness for quiet. During our first visit, we stayed at Martha’s Place, a B&B in Vineyard Haven, a quaint place on Main Street and only steps from downtown. Most of the shops were still open and are exclusive to The Vineyard – Riley’s Reads, Menemsha Blues, CB Stark, among others – and the owners are always willing to engage in some small talk (or full-blown conversations) while you browse. Need a bite to eat or a good cup of coffee? MV Bagel Authority is the island’s premiere bagel shop with locations in Vineyard Haven, Oak Bluffs and Edgartown. For something a little more substantial, hit the world-famous The Black Dog Tavern down by the harbor. If you decide to check out more of island – up-Island if you will (and you will want to) – there is The Black Dog Cafe outside of Vineyard Haven on the way to Chillmark or Aquinnah. You should know, however, that if you want alcoholic beverages with any of your meals, you will probably have to bring your own as Vineyard Haven is a dry town.
To the east, and about a 10-minute drive along Beach Road from Vineyard Haven lies historical Oak Bluffs. During the summer months, Oak Bluffs is a bustling and thriving oceanfront resort. It is also home to many historical and nationally recognized landmarks: the Flying Horses Carousel , the oldest operating platform carousel in America; The Campground, once home to the Methodist summer camp famous for its open-air revivals, now renowned for the Gingerbread-style cottages surrounding the Tabernacle and the yearly Grand Illumination in August. But like any summer resort, the winter months see marked decline in visitors – the perfect chance to get a feel for what’s around and decide if you want to brave the summer throngs. There’s no shortage of places to stay in Oak Bluffs – it is a resort town after all – the trick is finding those that are open year-round if you want to set up camp in town. Dining is less of a challenge. Want a good, diner-style breakfast? Linda Jean’s on Circuit Avenue is just the ticket – even in the winter months nearly every seat is taken. For something a little lighter, across the street you’ll find Mocha Mott’s for a great cup of coffee and some pastries. If you’re interested in pub grub, Seasons is a decent bet, just expect a slower pace than usual. If you’re like me, you enjoy a good craft beer and will not be disappointed by the offerings at Offshore Ale Company on Kennbec Avenue, open seven days a week year-round. The IPA is a great choice. For nightlife, check out The Lampost and Rare Duck or go a little more low-key at one of the island’s movie theaters.
Our favorite town, and the one that caused me to fall in love with The Vineyard, is Edgartown. This tony
harbor town was once one of the primary ports of the whaling industry and where the captains of those vessels built the grand mansions that line Water Street on both sides. Again, there are plenty of places to stay in Edgartown – from the historic Harbor View Hotel to the modest conveniences of the Clarion Carriage House Inn – and many of them are open year-round and offer some great (read: affordable), off-season rates. As in Oak Bluffs and Vineyard Haven, many shops are still open, but may be on winter hours, typically several hours on the weekends. For your dining pleasure, Edgartown is loaded with gret places to eat. David Ryan’s and News from America Pub are two great choices and you won’t be disappointed. But the one that captured our hearts is The Wharf Pub on Main Street. During our first trip, we popped in for lunch and ended up staying for several hours, striking up conversations with the bartenders (locals) and other patrons like us enjoying the Island’s solitude in January. Since this initial visit, our trips to the Vineyard aren’t complete without a significant stay in this great pub.
To get to The Vineyard, take the ferry operated by the Steamship Authority in Wood’s Hole. If you plan on taking your car over (I recommend that during the winter months), you should plan on making reservations in advance as standby travel is not guaranteed. Enjoy yourself. Oh, and dress warmly. Trust me.