It’s no secret – we treasure the island of Martha’s Vineyard. People often ask us to describe what it is that makes the island so special. Is it the natural beauty, the culture, the unique, local businesses? The answer is yes, all of this and more.
While each season is lovely, summer is an especially magical time on the island. With warm weather on the horizon, we want to give you an inside look at the places we recommend our friends and clients explore when they first come to the Vineyard. These are some of our favorite spots to eat, learn, unwind, and soak in all that makes the island unique and endearing.
We provided links for more information and a map listing all of the locations at the end of the post.
After arriving by airplane or ferry, the first stop is Edgartown – a village steeped in history and classic architecture. There are many stellar lodging options and we especially like the Hob Knob Hotel, the newly redesigned Harbor View Hotel and The Sydney, a boutique inn we recently finished. If guests prefer renting a house, a great real estate resource is Point B Realty on Winter Street in Edgartown.
If yours is an early arrival, we suggest stopping at Rosewater Market for a cup of coffee and pastry. From there, walk to The Carnegie, a restored Vineyard Trust property which we recently just helped transform into a visitor’s center with a Living Legends exhibit showcasing The Trust’s 20 working island properties. Next, head to Edgartown Lighthouse, a magnificent and historic working lighthouse that marks the entrance to Edgartown Harbor. If you’re an art lover, walk to the nearby Eisenhauer Gallery and North Water Gallery to see some fabulous local and contemporary artwork.
By now it’s time for lunch. If you prefer to eat on the go, the Quarterdeck on Dock Street is a great option. Or, for something more leisurely, try the Atlantic Fish & Chophouse, which offers terrific food and harbor views. After an energizing lunch, we recommend a walking tour through Edgartown’s historic district, which dates back to 1641. Be sure to check out the Old Whaling Church, one of the “finest examples of Greek Revival architecture in New England.” More walking may call for an ice-cream break – in which case we recommend stopping at Mad Martha’s.
After unwinding back at the hotel, a favorite choice for dinner is Alchemy where the food is delicious and the environment is high-energy fun. Alchemy is a great spot to end your first day in Edgartown, and it’s also walking distance – always a bonus.
There is much to do and see outside of Edgartown, so we highly recommend exploring the unique beauty offered throughout the island. Heading up-island is a must. The term up-island dates back to the Vineyard’s whaling days and refers to the western parts of the island including West Tisbury, Chilmark, Menemsha, and Aquinnah. When you go, be sure to stop at the island’s oldest retail business, Alley’s General Store, the “purveyors in almost everything.” Then make your way up to Aquinnah for breathtaking views of the clay cliffs and historic Gay Head Lighthouse. If you’re a beach-goer, visit Lobsterville Beach while you’re there. (Side note: there are many stunning beaches up-island, but most require a town sticker, so plan accordingly.)
Next, head to Menemsha harbor for a fabulous sunset. If you like seafood, pick up lobster and steamers at Larsen’s for a beach picnic you’ll never forget.
Oak Bluffs is another great area of the island to explore. We love showing people the colorful nineteenth-century gingerbread cottages on the Martha’s Vineyard Campground. With whimsically painted filigree trim, they’ve been called an “immaculate dollhouse village conjured from a childhood fantasy.” If you’re visiting the island on August 14th, head to the annual Illumination Night to see the cottages beautifully lit with Chinese lanterns. Across the way is the beloved Flying Horses Carousel, the country’s oldest working carousel, and always a favorite stop for both young and old.
Boating is also a big part of summer life on the Vineyard, so we highly recommend getting out on the water. You can stay local and explore the inner and outer harbors or Edgartown with Catboat Charters, or choose a more adventurous day trip over to Nantucket on the Inter-Island Ferry from Oaks Bluffs to Nantucket. Being on the water is always a good choice. After all…
“It’s only an island if you look at it from the water.”
Chief Martin Brody, Jaws
Martha’s Vineyard offers endless culture and beauty – and thankfully remains unspoiled in many important ways. There are no chain stores, traffic lights or parking meters. There are miles of walking trails and pristine beaches. We could, of course, go on with other favorite views and haunts, but we will save those for another time. For now, this is a great insider’s start to exploring the culture, beauty, and diversity of Martha’s Vineyard. We hope you find it as endearing as we do.