Travel Diary: A Guide to the Down-Island Towns of Martha's Vineyard
Welcome to part two of a three-post series on visiting Martha’s Vineyard, MA.
Today’s post dives into the Down-Island towns of Vineyard Haven, Edgartown and Oak Bluffs with tips on the best beaches, restaurants and places to stay.
Let’s dive in!
Edgartown
WET TOWN: Wine and spirits sold in restaurants and also from liquor stores.
Dress code: Shorts with anchors or lobsters embroidered on them, Nantucket reds, Sail to Sable dresses, pastel polo shirts, cashmere over the shoulders, flip flops. Diamonds, darling. A yacht captain’s hat, worn un-ironically.
This is fancy-town (in Gerard Butler/Leonidas voice.)
If you stay in Edgartown you can expect perfectly preserved Cape Cod architectural and landscaping splendor, with a budget to match. Of course, I love it. Edgartown offers fine dining, Relais & Châteaux-level hospitality, and some of the most jaw-dropping views and sunsets I have ever experienced. Stay in a rental home, or in one of the town’s many inns and hotels. The Charlotte Inn is glorious, if a touch stuffy, and boasts gardens, patios, a horse-drawn sleigh and a magnificent restaurant. For more relaxed luxury, consider the newly renovated Harborview Hotel, which offers guests fun local activities such as a three-hour Jaws tour in the summertime (the film was shot on the Vineyard, renamed “Amity” for the movie, in 1975), or an evening with Daniel Boulud during the Martha's Vineyard Food and Wine Festival in October. You will find the very best shopping on the island in Edgartown - distressed denim and crisp cotton shirts at the local outpost of UK retailer Jack Wills, an amazingly curated selection of cocktail dresses and cashmere at Nell, and fancy-pants designer labels at The Great Put-On, to name just a few of my favorites.
Edgartown is where you will find the ferry to Chappaquiddick Island, home to some of Edgartown’s best beaches, as well as one end of kid-friendly, convenient Joseph Sylvia State Beach. You can also visit the beach at Katama, known as South Beach, where the waves are bigger and a bit rough, so it might not be the best if you have small kiddos. Katama, like State Beach, has free parking on the road to the beach and public bathrooms.
In Edgartown you will find the Island’s best variety of dining spots, ranging from local seafood to sushi, Italian, New American and more. There are so many dining choices in Edgartown that you will never run out of new places to try, although your credit card may spontaneously ignite, as it’s one of the Island’s most expensive towns. Popular choices include Atlantic, Atria, Cesca’s, The Newes From America, The Wharf, The Sea Shanty and Behind the Bookstore, as well as the town’s location of the Mad Martha’s ice cream mini-chain of stores. Not only is their ice cream delicious, made with fresh local flavors, but you can take your cup or cone for a walk and enjoy the amazing views of the harbor and Chappy.
The action on Edgartown is on Main Street or just off it on one of the cross-streets parallel to the harbor, which makes it easily the most walk-able of the towns, but parking here is a serious challenge, and Main Street is one-lane and one-way, so plan accordingly!
Perfect day: Drive to to the Chappy Ferry line early with beach chairs, umbrellas, water, fruit and snacks packed away. Make a stop to poke around at Mytoi Gardens (has bathrooms!), then spend the morning on the beach at Wasque. Take the ferry back around 1:30 pm and eat a lobster roll and fries at the Shanty or The Wharf, followed by a Mad Martha’s ice cream-walk.
Perfect night: Arrive in town around 6 pm, park your car someplace remote, walk over to Main Street, stroll down to the waterfront, have a drink at one of the harbor-side bars, eat dinner at Atlantic around 7:30 pm while watching the sunset, and then work it out on the dance floor to their live band, which plays boisterous, happy rock classics a la Summer of ‘69 and Uptown Girl.
Tisbury/West Tisbury and Vineyard Haven
Mostly dry: Alcohol sold only in restaurants.
Dress code: LL Bean, bathing suits, plastic sandals, swimsuit cover-ups, an Alley’s General Store baseball cap.
These three villages are all parts of the same town. As I’ve already mentioned, Vineyard Haven feels fairly suburban and is relatively limited in terms of entertainment options. It is however walk-able from the ferry and boasts a small movie theater, some nice shopping, in particular Murdick’s Fudge (try the cashew brittle!), the wonderful Bunch of Grapes Bookstore, a supermarket, and a terrific fish market, The Net Result. We’ve enjoyed some nice meals in town at The Copper Wok, The Black Dog Tavern, and my own personal favorite, Beach Road, home of the best chowdah on the island (which comes with piping hot hush puppies omg), roasted oysters, amazingly juicy pork chops, and house-made pasta, all with truly remarkable views of Lagoon Pond.
With a more relaxed, horse-farmy/forest-y/beachy vibe, Tisbury/West Tisbury is a great place to rent a house, although there are a handful of nice inns and B&Bs as well. We visited The Lambert’s Cove Inn for dinner a few years back, and I can report that it’s lovely, if a bit stodgier and more formal than we generally prefer. Horses for courses! If you can rent a house with deeded private beach access, that’s the best of both worlds because it also means you’re close to the ocean and its fresh breezes/away from the mosquitoes.
The main public beach in Tisbury is Lambert’s Cove, on the road of the same name, set about 1/4 mile from the parking lot through the woods. You can get a beach pass for parking or walk-ons with your rental agreement or other proof of residence. It is a lovely beach with a creek for kids to explore, as well as clear waters with a sandy bottom and great town services, including support for the mobility-impaired. This beach is really nice for walking, and if your legs will carry you, you can stroll down to the Split Rock at Makonikey Head. I was pleased to learn recently that Makonikey is a corruption of a Wampanoag word for “ancient place.” The split in the rock is positioned such that it allows the sunset to shine through it, if you find the right angle at the right moment. There’s also swimming until 9 pm on summer evenings at Seth’s Pond, which is a good deal closer to the road than the beach, but with a lot less space to sit. When you’re done, check out the ‘pacas at Island Alpaca (Clicking on this, I learned that alpaca boarding is a thing that exists. Otherwise, theirs is an amusingly terrible website so, good luck… Check with Google Maps for directions) You could also stop in at Morning Glory Farm to buy fresh berry pies, gourmet prepared foods like meatloaf and farmer’s market gazpacho, and bunches of flowers to spruce up your room.
For dinner, I recommend you hit up Cronig’s Market on State Road for produce and staples, and stop in for a couple of pounds of the catch of the day at The Net Result. Then return home and cook it all up in your rental’s kitchen/backyard BBQ, while drinking some nice cold wine you lugged from home, or wisely purchased earlier at one of the Vineyard’s very, very few package stores (aka “the Packie”, which is what they call liquor stores in New England, because liquor is sold inside of packages. Yep.) of which there are none here.
Forget a pit-stop in the dry towns at your own risk, is what I’m saying. Pro tips!
If you aren’t handy around the kitchen and don’t want to go into Vineyard Haven, head over to State Road for a magnificent feast of someone else’s making.
Oak Bluffs
Dress code: Khaki shorts, athletic sandals, tie-dye or macrame, an Inkwell Beach sweatshirt, a bright blue polo shirt with the Nancy’s logo (because you are working there for the summer until you go back to college), toe rings, New England Patriots baseball caps.
Wet town! Get down!
Oak Bluffs is the most casual and accessible of all the towns, and the most diverse, thanks to its affluent African American, West Indian and Latin American summer residents. You can walk off the ferries from various mainland ports and straight into the middle of downtown, which has a family-friendly classic mid-Atlantic beach resort vibe, with a lot of souvenir shops and candy stores, and hippie shops with Nag Champa incense, crystal pendants and Indian scarves. It is the only town on the island which was designed with tourism in mind, unlike the other towns on the island, whose origins lie in the fishing and whaling trades, and is home to a host of picturesque Victorian cottages with multicolored gingerbread-y trims and whimsical names, as well as the stunning Ocean Park, with its ocean views, perfectly cropped emerald grass, pond and fountains. Oak Bluffs is family summer vacation heaven. Children love the historic carousel, with a real brass ring you can grab for, and families roam the area with kids darting around everywhere, and teenagers lurking. This is a fine spot to go to get a memorable summer job, if you are a lucky teenager or college student*! After dark, there’s a fun, lively night-time scene down Lake Avenue and around through Circuit Avenue and environs where live music can be heard and people line up in the supermarket parking lot for a hit of cinnamon sugar from Back Door Donuts.
I highly recommend a visit to Nancy’s Restaurant, where you can devour tasty burgers, grilled fish, sushi, lobster rolls, and shrimp cocktail, while ordering drinks from the hopping bar and checking out the boats and tenders as they come and go in the harbor. At night, the marina is lit up from all the crafts’ lights and is transformed into a kaleidoscope of aquamarine, glimmering with tiny silver fish. Our family loves Nancy’s. *Hey, If it’s good enough for the Obamas, it is 100% good enough for us! Martha’s Vineyard Chowder Company (very good chowdah!), The Red Cat, The Oyster Bar and Giordano’s are among the best of the plentiful dining options you will find lining Circuit Ave and nearby side streets.
Oak Bluffs is lined by two fine beaches on the stretch of the Oak Bluffs-Edgartown Road. There’s the historically significant Town Beach, known as the Inkwell, and the swimming-pool calm waters and white sand of Joseph Sylvia State Beach. State Beach is the site of some key scenes in Jaws (along with the marina in Menemsha), in particular the bridge from a tense scene in the film. Today, young people can seen leaping from it’s wooden railing and into the crystalline waters just below fairly frequently, despite prohibitive signage. One of these days I may try it myself!
Both beaches are free, although parking requires planning, luck or a bit of patience. If you don’t have a car, you can walk to either from accommodations in town, of which there are loads, most notably Summercamp on the marina, and a number of very pretty B&Bs dotted throughout the immediate environs. There is also a lovely salt pond for kayaking, in our case with guidance from the nice folks at Island Spirit Kayaks located conveniently on the Oak Bluffs-Edgartown Road near the aforementioned bridge.
If you’ve never been to the Vineyard, I hope this guide will be a great start for your exploration of the island. If you’re a Vineyard lifer, please post away in the comments and let me know about your favorite spots, so I can try them when we return in 2021!
TIPS
For more recommendations by town, please check out our post on the Up-Island Towns of Martha’s Vineyard.
If you’re a Martha’s Vineyard rookie, please make sure to visit our Newbie’s Guide for tips to make your first visit the start of a memorable vacation tradition.
For deep discounts on beach access and parking, become a member of the Trustees of the Reservation and enjoy the righteous pride of supporting amazing places all over Massachusetts.
It’s not to early to start planning a trip to the Vineyard for next summer. If you’re planning a trip, here are some of my very best packing tips.
If you like my travel diaries for Martha’s Vineyard please pop over and have a look at the one for Dublin, Ireland!