The Perfect Weekend Getaway: Martha’s Vineyard From Boston or New York City

Our new series on weekend road trips aims to inspire you for what's to come as we slowly return to travel.

Covid-19 Disclaimer: Make sure to check the status of the states, regions, and establishments in which you’re planning to visit prior to travel. Many regions continue to see high infection rates and deaths, while many states and counties remain under varying stay-at-home orders. Those traveling from areas with high rates of Covid-19 should consider avoiding travel for now in order to reduce spread.

Located just seven miles south of Cape Cod in Massachusetts, this triangular island is home to pristine beaches and pastoral farm fields, candy-colored gingerbread Victorians and Whaling Captains’ houses, scenic bike rides, and the iconic Jaws Bridge (and if your dreams involve lobster: lobster brunches, lobster rolls, lobster bakes, and lobster ice cream, too).

While it has a reputation as the summer retreat of Hollywood stars and presidential families (Jackie O., Oprah, and the Obamas, just to name a few “O’s”), “the Vineyard” is not at all scene-y. The vibe (and dress code) is “relaxed New England”—casual, laidback, and a lot less popped-collar than its sister island, Nantucket. The island has six towns: the rural and wild Chilmark, West Tisbury, and Aquinnah are referred to as Up-Island, while the more densely-populated and lively towns of Oak Bluffs, Edgartown, and Vineyard Haven are known as Down-Island. The only other directions you need involve getting from Off-Island to On-Island, which includes advance ferry reservations and a salty sea breeze.

Ferries to Martha’s Vineyard leave from several locations along Cape Cod as well as from New Bedford, Massachusetts, and Kingston, Rhode Island; by taking the ferry from Rhode Island, you can avoid the Cape Cod traffic on a busy weekend. The ride only takes about 35 minutes. In addition, there is a SeaStreak ferry from New York City that takes five hours. Flights to Martha’s Vineyard depart from big-city hubs as far south as Washington, D.C.

Allow sufficient time for traffic in summer months from Boston or New York, especially on Route 24 or Route 3 (south from Boston) and near the Bourne or Sagamore Bridges crossing the Cape Cod Canal. Driving time from Boston to Woods Hole is usually about 90 minutes, but can double during the summer. Driving time from New York to Woods Hole is generally around four hours, though in the summer, 5-7 hours is possible.

Fresh off the ferry (before noon if you hit the road early) and clean out of snacks thanks to the seagulls, you’ll want to refuel and gear up for the weekend with a stop at the harborfront Black Dog Tavern. It’s a bit of a tourist-trap but also a local institution (in business since 1971), so line up for lobster eggs Benedict or chowder, and smile your best smile when asking for a seat on the patio. Afterward, walk two minutes to the Black Dog General Store to gear up with t-shirts, sweatshirts, caps, water bottles, and coffee mugs emblazoned with the silhouette of a black Labrador. The Black Dog logo is a signal to everyone On-Island that you are a visitor and to everyone Off-Island that you’ve got great taste in weekend destinations.

Shake off the early-morning-car-ride-cobwebs by swapping four wheels for two for the afternoon. Most bike rental companies on the island offer free island-wide drop-off and pick-up bikes, so arrange to have yours waiting for you at your hotel. The island is home to 44 miles of bike trails but a one-hour ride along the coastline from Oak Bluffs to remote Chappaquiddick Island—aka “Chappy” or “the site of that Ted Kennedy car accident”—provides a great Day 1 intro to the island’s appeal. Stop at the Jaws Bridge (between Oak Bluffs and Edgartown along Beach Road) for the obligatory photo of you jumping into waters that once hosted a movie shark attack.

On Chappy, bike to the island’s most remote lighthouse, relax on windswept beaches, bird-watch in Cape Poge Wildlife Refuge, and visit Mytoi’s Japanese-inspired gardens before heading back to town. The total ride is about 18 miles (nine miles each way), with a two-minute ferry to cross the water.

Keep up your Vineyard-Classics roll by heading to Nancy’s for a classic lobster roll and an iconic Dirty Banana cocktail. In fact, have two, as you’re letting someone else take the wheel for the evening.

Sail into the sunset with Farm Field Sea on a two-hour, BYOB sunset sail to a working oyster farm, complete with shucking demos, tastings, and stunning views of the Vineyard Sound. Back on dry land, head to the Lookout Tavern for brews with killer views. If all that salty air is still keeping you buoyant, hit Offshore Ale Co. for a nightcap.

Kick start your first full day with the best breakfast spot on the island, Art Cliff Diner. This beloved diner has been around since 1943, and you cannot go wrong with its time-tested breakfast menu, especially if you include a side of buttery biscuits.

Today, you should head Up-Island (which now that you’re practically a salty local, you know means head west) to experience the breathtaking natural beauty of Martha’s Vineyard with its storybook fishing villages, dense woods, and abundance of fisheries and farms. Stock up on cheeses, salads, fruits, juices, bread, and—you deserve this—pie(s) at Morning Glory Farm en route, a family-run farm in business since 1975. These pies and other supplies will fuel your morning exploring Long Point Wildlife Refuge, a spectacular 600-acre reservation with woodland hiking trails, salt- and freshwater ponds, windswept dunes, and beautiful beaches. You can rent kayaks and Standup Paddleboards at Long Cove Pond in summer and bird-watch in the off-season here.

Spend the afternoon enjoying the charms of Up-Island’s quaint fishing villages. Wander the picturesque 18th-century town of West Tisbury, where you will find Alleys General Store (“dealing in almost everything” since 1858) and the West Tisbury Congregational Church (dealing in all the rest since 1865). The Field Gallery & Sculpture Garden showcases a whimsical collection of sculptures and local art. Stop at Larsen’s Fish Market in Menemsha fishing village to pick up stuffed scallops and fresh catch to enjoy on the village’s tranquil beach. Wander around the shops here and then head to neighboring Chilmark, known for its rolling hills and meadows and its not-so-secret gem, Chilmark General Store. Then head to the remote town of Aquinnah in the westernmost tip of Martha’s Vineyard, to take in its striking clay cliffs, natural dunes, the historic and active Gay Head Lighthouse (in operation since 1799), and Wampanoag Indian history and art. Follow a scenic trail to Moshup Beach for a quick sunset skinny dip if the mood so takes you. If you’re not ready to retire yet, head to the Great Rock Bight Preserve for even more scenic hiking, views, beaches, and stunning scenery.

Cap off a nature-filled day with a special meal at West Tisbury’s State Road Restaurant (reservations are essential). You’ll find a creative menu filled with local organic produce and served in a rustic-chic dining room with rough-hewn high beamed ceiling, a beautiful stone fireplace, and a shingle-sided porch. If you’re here during the summer, mingle with the island’s artists, writers, poets, and musicians at the Martha’s Vineyard Summer Concert Series at the Old Whaling Church in Edgartown. Depending on your mood, cap the night with a drink at the island’s legendary watering hole/dive bar and rock club, the Ritz Café, or at the more quirky cocktail lounge at the Cardboard Box.

You may have noticed that there are no chain stores or restaurants on the island, which means that every mealtime, coffee, and snack hankering is an opportunity—nay, an excuse—to support a local purveyor and experience local deliciousness. Acknowledge Sunday morning on Martha’s Vineyard in all its glory with sugar-and-cinnamon dusted, fresh-from-the-oven donuts and fritters from Back Door Donuts. Pick up a gourmet coffee to go at Mocha Motts and take a morning stroll in the most charming neighborhood in all of New England. The 34 acres of dollhouse-like Gingerbread Cottages at Oak Bluffs Campground are a wonder to wander. The more than 300 candy-colored Carpenter Gothic Victorian cottages with wedding trim were built in the 1860s and ’70s to replace tents on the site used to accommodate the groups of New England Methodists who gathered for retreats here. In summer, you can take guided tours and enjoy art shows, sing-alongs, and other performances. Be sure to visit the Cottage Museum to learn more about this National Historic Landmark.

If you are renting a property for the weekend, make your last day here special with a lunch delivery of a full clambake from The Kitchen Porch. If not, The Net Result fish market offers individual clambakes, steamed lobsters, and fried oyster plates that you can take to the beach for lunch; be sure to pick up some cold Bad Martha local brews to seal the experience. If the weather isn’t cooperating, stop at Raw 19 Oyster Bar for their “shucking amazing” oysters along with other New England classics like clam chowder, smoked bluefish, and lobster.

After lunch, wander in and out of the cute shops in Edgartown’s historic downtown area. Then, keep the history-appreciation going with a little background in the island’s maritime past at the excellent Martha’s Vineyard Museum. Hop on a bike for one last taste of island life and bike to Edgartown Lighthouse (about 40 minutes) and Lighthouse Beach. Martha’s Vineyard has its share of lighthouses, but this one merits a visit for its stunning views and surroundings. Swing by Mad Martha’s ice cream for an ice cream sandwich made with homemade cookies or a Snickers ice cream before you make your way back to pack up your bags.

There are no chain hotels on Martha’s Vineyard, so all lodging options offer an authentic island experience. There are also plentiful rental opportunities and cute cottages to rent, although it can be hard to rent for a weekend in summer when most rentals are snapped up for extended stays. Stay Down-Island if you want to be close to nightlife and restaurants, and Up-Island if you want the opposite. The charming and luxurious Hob Knob boutique hotel and spa in Edgartown is close to the summer scene but far enough away to be peaceful. The hotel provides guests with beach cruiser bikes, gourmet picnic lunches, beach chairs, and umbrellas. The elegant Harbor View Hotel has one of the most iconic views on the Vineyard (enjoy Edgartown Lighthouse views from the expansive wraparound porch) and is just a 10-minute walk from Edgartown’s historic mansions. The Beach Plum Inn in rural Chilmark is located on seven acres of land overlooking Menemsha Harbor.

Peak season begins on Memorial Day weekend and ends on Labor Day weekend. There is a reason the island is so busy in summer: the weather is perfect (warm but rarely uncomfortably hot); the water is less frigid (but rarely comfortably warm), and the weather is ideal for hiking, biking, beaching, and sailing. If you’re planning to stay overnight on a summer weekend, be sure to make reservations well in advance; spring (as in, last spring) is not too early. Avoid July Fourth and Labor Day weekends as they are the busiest and most expensive weekends on the island. Things stay busy for September and October weekends, a favorite time for weddings, but begin to slow down soon thereafter. Inns and hotels offer discounted rates in the spring, fall, and winter months, and many island restaurants, shops, and bars are open year-round.