Fall in LOVE with Martha’s Vineyard

If you’ve never been to Martha’s Vineyard, do yourself a favor and add this to your bucket list. I’m embarrassed to say I’m a New England girl, that had never been to this island until I was well into my 40’s. Now it’s become one of my favorite places on Earth and if I had my choice to live anywhere I want, it would be in one of their many “gingerbread houses”. This historic and quaint neighborhood is like no other, and the photo ops are endless. But, let’s not get a head of ourselves because the island has much more to offer than these unique houses.

Getting There

There are several ways to get to Martha’s Vineyard.

1. By Ferry:

Vineyard Haven is located on the island of Martha’s Vineyard, and the only way to get there is by ferry. The Steamship Authority operates ferries from Woods Hole, MA to Vineyard Haven throughout the year.

2. By Air:

The closest airport to Vineyard Haven is Martha’s Vineyard Airport. It is located in West Tisbury, about 6 miles from Vineyard Haven. Airlines like Cape Air and JetBlue operate flights to Martha’s Vineyard Airport from Boston, New York, and other cities.

3. By Car:

If you are driving from Boston, take Route 3 south to the Bourne Bridge. Cross the bridge and follow Route 28 to Falmouth. From there, take the ferry to Vineyard Haven.

4. By Public Transportation:

There are buses that operate from Boston to Woods Hole, where you can take the ferry to Vineyard Haven. The bus journey takes about 2.5 hours, and the ferry journey takes about 45 minutes.

Ticket Office conveniently located in parking lot.

We took the ferry from Woods Hole to Martha’s Vineyard. We were able to leave our car in Woods Hole, Massachusetts, and purchase ferry tickets right there onsite. Once we got on the island we would rent bikes to get around. We only visited one day but if we were there longer we probably would have brought our car onto the ferry.

For up-to-date-pricing click here to be redirected to the ticketing website.

History of Vineyard Haven

Vineyard Haven, also known as Tisbury, is a historic town located on the island of Martha’s Vineyard in Massachusetts. The town has a rich history, dating back to the early 17th century when the Wampanoag Native Americans inhabited the area. In the 1600s, English settlers arrived on the island and established farms and homesteads. Many of the houses in Vineyard Haven were built during this time, using local materials such as cedar and oak. In the 1800s, the town became a popular vacation destination, attracting wealthy families from Boston and New York. These families built large summer homes and cottages, which still stand today and are a significant part of Vineyard Haven’s architectural heritage. One notable example is the Captain William Tilton House, which was built in 1845 and is one of the oldest and most well-preserved Greek Revival-style houses in the town. Another example is the Union Chapel, a historic church built in 1870 that is known for its beautiful stained glass windows and traditional New England architecture. During the 20th century, Vineyard Haven continued to grow and develop, with new houses and commercial buildings being constructed. Many of these buildings reflect the popular architectural styles of the time, including Cape Cod-style houses and mid-century modern buildings. Today, Vineyard Haven is a thriving community with a mix of historic and modern houses, reflecting the town’s rich history and ongoing evolution. The town’s historic houses are an important part of its cultural heritage, and efforts are made to preserve and maintain them for future generations to enjoy.

Top 10 things to do when you get off the ferry:

1. Visit the Martha’s Vineyard Museum:

This museum is located in the heart of Vineyard Haven and offers a fascinating look at the island’s history and culture.

2. Explore the Vineyard Haven Harbor:

Take a stroll along the harbor and admire the boats and stunning views.

3. Go shopping:

Vineyard Haven has many charming shops and boutiques, selling everything from clothing to antiques to handmade crafts.

4. Take a hike:

There are several scenic hiking trails in the area, including the West Chop Trail and the Vineyard Haven Trail.

5. Visit the Island Alpaca Company:

This farm is home to a herd of adorable alpacas and offers tours and educational programs.

6. Attend a movie at the Capawock Theatre:

This historic theater in the heart of Vineyard Haven shows a variety of movies, including indie films and classics.

7. Enjoy a meal at one of the many restaurants:

Vineyard Haven has a great selection of restaurants, offering everything from fresh seafood to traditional New England cuisine.

8. Take a bike ride:

Rent a bike and explore the island on two wheels.

9. Relax on the beach:

Vineyard Haven has several beautiful beaches, including Owen Park Beach and Tisbury Town Beach.

10. Attend a festival or event:

Throughout the year, Vineyard Haven hosts a variety of festivals and events, including the Martha’s Vineyard Film Festival and the Tisbury Street Fair.

We opted to rent bikes and ride on over to the next town to try a restaurant my son recommended called “Sharky’s” and get some exercise. We were pleasantly surprised when we realized our path would cross with the famous bridge from the movie “JAWS”. In the summers, hundreds of people come to this bridge to jump off and be a part of “JAWS” history, amid all the warning sign that say “NO JUMPING”. We did not jump due to it being too cold. (Oh, and yeah, I’m DEATHLY afraid of sharks)

The famous bridge from the movie “JAWS”.

We enjoyed Sharkaritas and amazing tacos before heading back to Oak Bluffs to explore Gingerbread Village. This would be my favorite part of our visit and one day I hope to be able to go back and rent one of these houses for a few days. It was fairytale, magical, and I will never forget exploring this charming area.

I could go on and on posting photos of these house because they were so unique, there was so many of them, and I took hundreds of photos. But I think it’s best to leave something to the imagination and just tell you to go visit them for yourselves. Don’t be surprised too, if you feel as if you are in a “Candyland” Board game or a “Hansel and Gretel” fairytale. It’s MAGICAL to its core!

There are many other places to go on the Island, but we never got a chance to explore more. Here are a few fun things to do in each town. Hope you find this informative:

Edgartown

1. Visit the Edgartown Lighthouse

This historic lighthouse is located on North Water Street and offers stunning views of the harbor and surrounding areas.

2. Explore the Edgartown Village Center

This charming shopping district features unique boutiques, art galleries, and restaurants.

3. Go on a bike tour

Rent a bike and explore the scenic roads and bike paths that wind through Edgartown.

4. Visit the Felix Neck Wildlife Sanctuary

This conservation area offers hiking trails, birdwatching, and educational programs.

5. Take a sunset sail

Enjoy a beautiful sunset over the ocean while sailing on a classic schooner or catamaran.

6. Tour the Martha’s Vineyard Museum

Learn about the island’s rich history and culture at this fascinating museum.

7. Relax on the beach

Spend a day relaxing on one of Edgartown’s beautiful beaches, such as South Beach or Lighthouse Beach.

8. Take a fishing charter

Go on a deep sea fishing adventure and try to catch striped bass, bluefish, or tuna.

9. Visit the Old Whaling Church

This historic church, built in 1843, is a beautiful example of Greek Revival architecture.

10. Attend the Martha’s Vineyard Film Festival

This annual film festival showcases independent films from around the world and attracts filmmakers and movie buffs from all over.

Aquinnah

1. Visit the Aquinnah Cliffs

The colorful clay cliffs of Aquinnah are a must-see attraction. You can take a guided tour or explore on your own.

2. Relax on the beach

Aquinnah has several beautiful beaches, including Moshup Beach and Lobsterville Beach. Spend a day lounging on the sand and soaking up the sun.

3. Hike through the Aquinnah Loop Trail

This 6-mile trail takes you through the beautiful natural landscapes of Aquinnah, including forests and wetlands.

4. Visit the Martha’s Vineyard Museum

Learn about the history of Martha’s Vineyard at this museum, which features exhibits on local industries, culture, and art.

5. Take a tour of Gay Head Lighthouse

This historic lighthouse was built in 1856 and offers stunning views of the Atlantic Ocean.

6. Explore the Aquinnah Cultural Center

This museum celebrates the history and culture of the Wampanoag tribe, who have lived in the area for thousands of years.

7. Check out the Aquinnah Farmers Market

Held on Wednesdays in the summer, this market features fresh produce, local crafts, and live music.

8. Go fishing or whale watching

Several local companies offer fishing and whale watching tours, giving you the opportunity to see some of the area’s incredible marine life up close.

Chilmark

1. Visit the Chilmark Flea Market

This popular outdoor market is held every Wednesday and Saturday in the summer, and features a variety of vendors selling a range of items from antiques to crafts to fresh produce.

2. Explore Menemsha Beach

This scenic beach offers stunning views of the harbor and the surrounding cliffs. It’s a great spot for swimming, sunbathing, and picnicking.

3. Take a hike in Menemsha Hills Reservation

This 211-acre nature reserve features several hiking trails that lead to scenic overlooks and offer stunning views of the surrounding landscape.

4. Explore the Chilmark Public Library

This small library offers a great selection of books, movies, and magazines, as well as a variety of events and activities for all ages.

5. Visit the Chilmark Community Center

This community center hosts a variety of events and activities throughout the year, including concerts, art exhibitions, and workshops.

6. Enjoy a meal at Chilmark Tavern

This popular restaurant serves up delicious farm-to-table cuisine made with locally sourced ingredients.

7. Go fishing in Menemsha Harbor

The harbor is a great spot for fishing, with a variety of fish species, including striped bass, bluefish, and flounder, commonly caught here.

8. Explore the Chilmark Art and Crafts Festival

Held annually in mid-August, this festival features a variety of local artisans showcasing their work, as well as live music and other entertainment.

9. Visit the Martha’s Vineyard Museum

Located in nearby Edgartown, this museum features exhibits on the island’s history, culture, and natural environment.

10. Attend a movie night at the Chilmark Community Church

The church hosts weekly movie nights during the summer, showing a variety of family-friendly films.

Oak Bluffs

1. Explore the Gingerbread Cottages

Take a walk around the colorful and unique Gingerbread Cottages, a collection of over 300 Victorian-style homes with ornate trim and vibrant colors.

2. Visit the Flying Horses Carousel

Take a ride on the oldest operating carousel in the United States, the Flying Horses Carousel. It dates back to 1876 and is a National Historic Landmark.

3. Go to the Beach

Oak Bluffs has many beautiful beaches to choose from, including Inkwell Beach, Jetty Beach, and East Chop Beach.

4. Visit the Martha’s Vineyard Camp Meeting Association

This historic religious community features many of the Gingerbread Cottages and has a rich history dating back to the 1800s.

5. Explore the Oak Bluffs Harbor

Take a stroll around the harbor and enjoy the scenery, or rent a boat, kayak, or paddleboard to explore the water.

6. Shop and Dine in Circuit Ave

Circuit Ave is the main shopping and dining area in Oak Bluffs, with plenty of options for food, drinks, souvenirs, and more.

7. Attend the Oak Bluffs Harbor Festival

This annual festival in August features food, live entertainment, arts and crafts, and a boat parade.

8. Tour the Island on a Bike

Rent a bike and explore the island’s many scenic bike paths, including the Martha’s Vineyard Bike Path that runs through Oak Bluffs.