Martha’s Vineyard – Old American Charm

Culture Experiential Travel Martha's Vineyard New England Old American Charm

Nestled off the coast of Massachusetts, Martha's Vineyard is a picturesque island that captures the hearts of travelers with its timeless beauty, enchanting charm, and vibrant culture. Renowned for its pristine beaches, rolling hills, and historic architecture, this island oasis also offers an array of delectable dining options and luxurious boutique hotels that elevate any visit to a truly unforgettable experience. Join us on a journey through the charms, great restaurants, and luxury hideaways of Martha's Vineyard.

The Allure of Martha's Vineyard

Martha's Vineyard boasts a captivating allure that beckons visitors from all over the world. From the moment you step foot on the island, you are greeted by its idyllic charm and captivating beauty. With its picturesque lighthouses, quaint harbors, and pristine beaches, the island offers an abundance of opportunities for relaxation and exploration.

Most recognize Martha's Vineyard as being the summertime haunt to presidents and celebrities alike, including the Obamas, who currently own a gorgeous property on the island. Its residents and seasonal visitors are likely its best asset. With a welcoming atmosphere, there is most definitely a vibe that, while intangible, speaks volumes to its reputation as being “the friend you want to spend time with” of New England destinations. 

Due to convenient ferry service from the Cape, most visitors are familiar with Vineyard Haven and Oak Bluffs. Both are walkable areas with loads of shops and restaurants. Inkwell Beach in Oak Bluffs is a great spot (public), and if you’re lucky, you’ll catch a masterful yogi, Christopher, with a large group of locals and visitors at 8:00AM for an hour of peace and serenity.

We loved every minute spent in the Vineyard, and met some amazing people. Edgartown really stole our hearts. Small as it is, it’s loaded with charm. One classic white colonial with black shutters after another. The boutiques and restaurants are fantastic, most of them being locally run and operated. Combine this with some of the most kind, warm, and welcoming folks, the entire island feels like home.

Culinary Delights

For food enthusiasts, Martha's Vineyard is a great place to pay homage to locally owned restaurants – many of whom support their local farms by using island-grown produce. For its size, the island showcases an impressive culinary scene, with a diverse range of restaurants offering both local and international cuisines. Whether you're craving seafood, farm-to-table delights, or gourmet international fare, Martha's Vineyard has it all.

For a great indoor/outdoor atmosphere with a creative, yet classic menu, 19 Raw Oyster Bar (with sister restaurant, 19 Prime) is a total winner. Situated in the center of Edgartown, 19 Raw is an absolute MUST. From fresh Honeysuckle oysters to fantastic ceviche, and a boatload (no pun intended) of creative menu options, this place is hands-down our favorite spot on the island.

The flavor profiles are powerful. You won’t be disappointed. It helps that John Clift, certified sommelier and owner of Vintage MV Wines & Spirits, has his hand in both restaurants’ wine, beer and spirits offering. There is definitely a tasteful intention across the board!

Indulge in a memorable dining experience at the State Road Restaurant, where the artistic menu features a selection of meat and seafood, mixed with fresh produce, and served with best-in-class service. Tucked away in West Tisbury, this spot is beautiful inside and out, surrounded by tall pines and a curated garden.

If available on the menu, the Carrot Crab Bisque is exceptional, and a must-try!

For something casual and fun with a water view and FANTASTIC lobster rolls, stop in at the Lookout Tavern in Oak Bluffs overlooking the marina. These lobster rolls are no joke. The lobster bisque is so tasty and fresh. They’re also known for having a commendable sushi and craft beer selection.

If you want for an elevated, intimate setting, we’d highly recommend Détente. Another Edgartown establishment, this small but mighty restaurant is bursting with powerful flavor profiles, and a stellar wine menu. During our experience, they were featuring the 2021 Austin Hope Paso Robles Cabernet, which is an absolute stunner if you enjoy big red wines. They also have a delectable take on a revitalized Bolognese, incorporating a goat cheese emulsion that places it in another class. Masterful.

Luxury Boutique Hotels

You won’t find any of the big hotel chains here, true to form. Martha's Vineyard is known for luxurious boutique hotels, and they book up fast with such a short season, so plan in advance! These hidden gems combine exquisite design, personalized service, and unmatched comfort. There are also plentiful Airbnb-type properties - some off the beaten path and into the lush green forests the island boasts.

Our favorites are luxury boutique properties. The Charlotte Inn is a great choice if you're looking to be right in town and feel like you've just been transported back in time. It’s reminiscent of a bygone era with its elegant décor and luxurious amenities. Classically elegant, the Charlotte Inn is quiet and pretty. Offering individually designed rooms, The Terrace restaurant for fine dining, and impeccable service, this boutique hotel promises an unforgettable stay.

an aerial view of the hotel with the ocean and buildings

Image source:

For a beachfront retreat, The Harbor View Hotel in Edgartown is a true gem. A historic landmark in Edgartown with over 130 years of service, this property underwent thoughtful renovations in 2020. With its stunning waterfront location and beautifully appointed rooms, it offers a serene escape with breathtaking views of the harbor and Chappaquiddick Island. Pamper yourself with a rejuvenating spa treatment or indulge in a gourmet meal at the hotel's award-winning restaurant. 

Exploring the Island

To really enjoy the island, a rental car is required. Beyond its culinary excellence, boutique shopping and charm, Martha's Vineyard offers a plethora of activities and attractions. Explore the island's charming towns, each with its unique character and historical significance, and also make time to wander off course a bit.

If you you’re drawn to nature, you’ll love getting lost driving through the wooded twists and turns. Surfers can find their own haven at Squibnocket Beach on the southwest end of the island, while the best sunsets can be enjoyed on the shores in Menemsha. Just grab some local food to go, and find a spot on the beach.

It’s a beautiful island. Outdoor enthusiasts enjoy activities like sailing, swimming, kayaking, or cycling along the island's scenic trails. Martha's Vineyard is also home to several beautiful golf courses and nature preserves, providing ample opportunities to connect with nature and enjoy the island's tranquility.

Martha's Vineyard is a destination that seamlessly combines nature, history, culture, and food. Every aspect of a visit to Martha's Vineyard promises to be a relaxed, unforgettable experience. Like anywhere we travel to, there’s always the intangible factor: the people. This is what truly sets the Vineyard apart. It feels like home – even to a newcomer. Martha’s Vineyard has left its mark.

A warm thank you to those I had the pleasure of meeting: John, Suzanna, Misha, Z, Christopher, Erin (and the rest of the staff at State Road), and a number of those whose name I didn't catch, but whose conversation I thoroughly enjoyed!  

Older Post Newer Post