Your Travel Guide to Martha’s Vineyard | Captain Freeman Inn

Byron at Edgartown Light

Byron is the birthday boy this month and his present was a surprise two night getaway to Martha’s Vineyard. Since we now have our trusted new innkeeper Espi- we thought it a perfect time to get away before our season at the Captain Freeman Inn kicks in full force. We had glorious weather for our stay and combined some relaxation time with exploring the island.

Guests frequently ask us about doing day trips to the islands. If you are looking for an unhurried day adventure- we like to recommend the Freedom Ferry to Nantucket where you can visit the whaling museum and explore the downtown area. Because Nantucket is much smaller and the ferry lets you off at the village, it’s a relaxed day of exploring a quaint New England island. For those that want to experience Martha’s Vineyard, we recommend getting an early ferry from Woods Hole- since Martha’s Vineyard is larger, it’s important to plan out your transportation for getting around the island and what you want to see and do. In this blog we are sharing our experiences on this glorious island and what we feel are the most important things to see and do during your trip to Martha’s Vineyard.

Edgartown Harbor


Getting to and around the island

Our ferry ride into Oak Bluffs

We decided to splurge this trip and pay for our car to be ferried over from Woods Hole to Oak Bluffs. ( $170 round trip cost for our car and two passengers) Advance reservations are essential as the summer auto spots get booked up early. We like the Steamship Authority as they are easy to make reservations with and operate year round- except during inclement weather conditions. From the inn, you need to allow two hours to park your car and ride the free commuter bus to the docks. You can also reserve a spot for your bike, if you want to cycle your way around the island. (bike racks are on the pubic transportation buses as well) The Hy-Line Cruises also offers ferries to Oak Bluffs from Hyannis. The fare costs more then from Woods Hole but the car ride to Hyannis is only 30 minutes and the ferry ride about an hour. Either way- its a comfortable ride over. Once on the island you can choose to either get around by your own car, by bike, by public transportation, Uber or sign up for an island tour. We liked Island Excursions which picked us up at our hotel and included a 3 hour excursion around the island with two great stops, the Clay Cliffs of Aquinnah, and Menemsha, a working fishing village. We saw lighthouses, some of the back streets of Edgartown with historic whaling captain homes from the 1800’s, the Oak Bluffs victorian style summer resort built around the historic Methodist campground and the famous Jaw’s bridge. Our tour guide was filled with wonderful information about the island, including historical facts and local tips.

Edgartown homes

History of the Island

I am always interested in the history of places we visit, and it was interesting to learn about Martha’s Vineyard as it coincided with much of the history we have learned about Brewster and Captain William Freeman.

Bartholomew Gosnold was the first European to visit the island in 1602. Gosnold named the island for it’s bounty of wild grapes and Martha may have been his daughter. The island was formally colonized in 1640 when a shipload of English settlers were headed for Virginia and ran out of supplies. They docked in Edgartown and found the resident Wampanoag tribe to be friendly and decided to stay and make the island their home. The settlers learned much from the tribe – including how to whale, farm and fish the area.

During the American Revolution, islanders suffered mightily from the plunder of British soldiers that looted their homes and ships, taking over 10,000 heads of sheep and cattle from island farms. The island didn’t fully recover until the 1820’s when the whaling industry took off.

Historic district in Edgartown

Edgartown was the island’s center for whaling activities. Between 1835 and 1845 alone, 110 whaling captains built homes and lived in Edgartown. Other maritime-related industries, including fishing, salt manufacturing and candle making also strengthened the local economy during this period. We learned that the whaling ships loaded up with wood when they left the shore to burn the whale blubber. Hard to imagine a ship burning wood out in the middle of the sea- dangerous times to earn a wage. It was the whaling captains that took their enormous profits from whale oil to build beautiful Greek Revival and Federalist homes in Edgartown. Many still remain with many haven been reproduced and rebuilt over the years- you can always tell an original home by looking at the basement construction.

During the Civil War many of the whaling vessels were drafted by the Union government and soon the whaling industry as a whole declined.  By 1878 the Methodist Campground of Oak Bluff became popular as a summer resort and so tourism began on Martha’s Vineyard.

What to see on Martha’s Vineyard

Highlight below are the major attractions to see in each town:

Vineyard Haven

West Chop Lighthouse- every town  should have a lighthouse:)


Oak Bluffs

Many describe Oak Bluffs as honkey- tonk. We loved driving around the old Ginger Bread and hearing about it’s history.

East Chop Lighthouse

Flying Horse Carousel – a wonderful way to feel young again

Trinity Park Tabernacle

Norton family home in Oaks Bluff

Ginger Bread Houses- Just loved seeing these houses- complete with bright paint, cupolas, domes, spires & turrets. Our favorite was the home of Peter Norton (Norton Anti-Virus guru) The campgrounds includes over 35 acres with 217 homes. Look for a future blog that will describe the history of these unique homes.


We stayed in Edgartown and loved everything- from the quaint seaside streets, to the wonderful dining and shopping.

The Edgartown Harbor Light was the first lighthouse constructed at the Edgartown Harbor entrance. The first light was built in 1828 when Congress appropriated $5,500 so the federal government could purchase a plot of land from Seth Vincent for $80, and build a light at the entrance of Edgartown Harbor. The necessity for a lighthouse at this location was precipitated by the large number of vessels frequenting the harbor during the whaling boom of the late 1700s and early 1800s

Dr. Daniel Fisher House- The island’s best example of Greek Revival architecture,  built in 1840 with an enclosed cupola. Dr. Fisher was quite the man. He was a local doctor, a whaling magnate, a banker- he founded the local bank, a merchant and a miller. Tours of his home are offered in combination with the Old Whaling Church.

Whaling Church

Old Whaling Church- built in 1843, this original church now serves as a performing arts center.

North Water Street- we loved walking down this street to see all of the Colonial, Greek Revival and Federal styles homes- complete with the most magnificent rose gardens. I was in heaven-

I also loved the charming features throughout the area including this driveway-

Jaw Bridge – it tickled us to no end to stop at the bridge where part of the Jaws movie was filmed. There is a very large sign that says “NO JUMPING OR DIVING” Clearly the rules were not being followed.

The Jaws Bridge


We loved this stop and went back again for sunset. This cliff use to be called Gay Head – it was renamed Aquinnah in 1997- “Land under the Hill”  The Wampanoag own the brilliantly colored bluffs and Clay Cliffs. Many celebrities live in this area as it is very secluded and plush with green vegetation.

Clay Cliffs of Aquinnah

Abel’s Hill Cemetary- John Belushi.  John Belushi had a summer home on the island and he always said he got the best night’s sleep here, and so it seems fitting that he would have his final resting home here as well.


A small, picturesque working harbor with several charter fishing vessels along with some Coastguard Station. This harbor was used to film the movie Jaws. I had a bowl of the most delicious clam chowder in a clam shack in this lovely little fishing town.

Oxen on Brooks Side Farm

West Tisbury

Is often called the Athens of the Vineyard because of the grand New England Congregation Church, Town Hall, Music Sreet- where the wealthy sea captains built grand homes and purchased pianos to show off their wealth. We stopped and got a picture of Zeus and Apollo- oxen from the Brooks Side Farm


Here you will find peaceful rolling hills with original stone fences. This area is still farmed by some of the original European settlers.

Landing at Chappaquiddick


Only accessible by the “Chappy Ferry” – this area of the island has beautiful beaches, a wildlife preserve and wonderful bike paths. A new bridge is in the works to connect this area to the rest of the island.

We were especially impressed with the wide open land on Martha’s Vineyard. We later learned that the island has a Land Preservation program that puts aside a 2% sales tax on all homes sold to purchase land that will not be developed. At present the society has accumulated over 40% of the land on the island- quite a feat and includes 22 miles of bike paths and a state forest.

Where to dine

While only there for 2 days we ate our way across Edgartown and loved every minute of it!

Offshore Ale Company, Oak Bluffs: If you like trying local brews, you’ll enjoy this pub. The beer selection is all brewed in house and the atmosphere woodsy.

Among the Flowers in Edgartown: We had breakfast at this adorable little cafe with indoor/outdoor seating.

Menemsha Fish Market. Located in Menemsha,  the island’s fishing village, you can get a delicious cup of clam or lobster chowder and the most amazing warm lobster roll you’ve ever had! Since it’s basically a fish market there is not great seating.

Port hunter Raw Bar

Port Hunter– We had an amazing meal here complete with fish tacos, oyster steam buns and hanger steak. The atmosphere is lively in a  brick-accented restaurant offering live music on a seasonal basis

Atlantic Fish and Chop House in Edgartown: Delicious steak and scallops- right on the water!

Toccopuro Coffee Shop – We had the best cup of coffee at this coffee house which also specializes in tea.

What we loved most about the island

We loved the views form our hotel room

We loved walking the street in Edgartown and enjoying coffee, art galleries and incredible restaurants.

We loved seeing the beautiful homes in Edgartown and were amazed at how expensive they were- fast approaching Manhattan prices. It’s definitely an area that only billionaires can afford and our tour driver told us that many of the homes are only occupied for 1-2 weeks each summer:(

And lastly we loved sitting on our hotel’s front porch while reading a book and relaxing. It also made us aware of how special our front porch is at the Captain Freeman:)

Let us help you plan a getaway to Cape Cod and the Captain Freeman Inn where we can help you plan your day trip to Martha’s Vineyard.


Select Registry, Cape Cod Chamber, AIHP
PackagesOur quiet season is a perfect time to enjoy our romantic Dinner Package

Join our Newsletter

Do NOT follow this link or you will be banned from the site!