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Monday, June 17, 2019

A Day Trip to Martha's Vineyard

Edgartown Lighthouse Marthas Vineyard

Towards the end of a cold New England winter, and about the time I met Adam, I started putting together a New England summer bucket list.  You know, a list of all the things and places I wanted to see in the near future.  A fun list of places suggested by a friend or found online that I quickly jotted down in a spreadsheet before it was lost in my brain, drifting somewhere between the never-ending "To Do" list and much-needed Grocery list.  But because this is 2019 and I almost always have a computer in front of me or a phone nearby, this list turned into one longggggg google doc I can add to wherever whenever.   Which I can't help but think, how did we live before google docs?

My list ranges from overnight hikes in the Whites to day trips to northern Connecticut dairy farms.  It covers must eat ice cream joints and must-do hikes all over these six states.  As I scribbled typed out destinations and activities I wanted to cover in a New England summer the list grew quite long and before I knew it, there were over 50 bullets on this list.  I started categorizing them by state, and then by regions of states and I quickly realized it would take a few summers to get through it.   Challenge accepted. 

The "Chappy" Ferry from Edgartown to Chappaquiddick Island
The "Chappy" Ferry from Edgartown to Chappaquiddick Island
Overlook Martha's Vineyard
Posing on the deck by the Chappy Ferry 

As I looked at this list, there were so many things I was so eager to plan.  I couldn't wait to get my backpack on and hike the Green's in Vermont.  I had a few lobster shacks to finish for my lobster roll tour.  But of all these bullets, there were two that were jumping off the page at me.  Two quintessential Yankee islands that in all my years as a devoted New Englander, I had never been to.  


I, Katie Wanders, have never been to Martha's Vineyard or Nantucket.



Martha's Vineyard Sunset (Vineyard Haven) Block Dog
A Martha's Vineyard Sunset (Vineyard Haven)
So why did I wait so long to get to the Vineyard?  I guess a few things had stopped me.  First off, Block Island was my go-to island adventure. An easy ferry from New London, Connecticut or Port Judith, Rhode Island and (free) dog-friendly lodging in an iconic house on the island is hard to say no to.  Second, these islands always seemed like these expensive and elusive places. Third, I didn't have any close friends who had been anytime recently and it just wasn't a trip being planned in my friend group or family. 

But the beauty of making a bucket list and having some gumption to tackle it is Martha's Vineyard was there on the list, a big ole' bullet point staring back at me in a bold font and one I wanted to tackle in June.  To make this trip happen, I needed to get a date on the calendar and try to work on the "affordable" angle.   I called up my sister and asked if she and her husband maybe wanted to split a house on the island to help with the costs and put a date on the google calendar.  I was going to the Vineyard. 


Picnic Lunch by the Edgartown Lighthouse
Picnic Lunch by the Edgartown Lighthouse 


A funny thing happened somewhere along the line of that first google search and that final booking.  Turns out, the more I looked into this trip, the more I realized that Martha's Vineyard isn't some far away elusive over the top expensive destination for the rich and famous and trust fund laden.  In fact, we could do this in a way that was actually affordable.  

First, I looked at booking.com and even checked out the campground on the island.  Mediocre lodging on the island was going to run you about $300 a night and the campground was still $200 for two nights (and then there was lugging everything we needed on the ferry and convincing my sister we should camp). 

Shortly after "Let's Camp" Ashley suggested staying in Falmouth or Woods Hole where we pick up the ferry.  Ashley and her husband had spent a weekend in Falmouth for their anniversary and quickly commented on the adorable downtown and seeing signs for the Martha's Vineyard ferry.  The wheels were turning and after a quick look on Groupon, we found a hotel room for $150 a night right by the ferry in Woods Hole, Massachusetts at the top of the cape.  Ashley and Jon stayed here two nights but to make this even MORE affordable, I decided to skip Friday night and get up super early on Saturday to make the early ferry out.  

What started as a full expensive weekend on the vineyard turned into an entire day on the Vineyard, a night in Woods Hole and a day in Falmouth.  A 2.5 hour drive from Guilford and a 45-minute ferry ride later, I had found an affordable way to get to Martha's Vineyard for the first time. 

Edgartown Lighthouse
Edgartown Lighthouse 

With the logistics out of the way, it was time to focus on the planning. I am often guilty of trying to fit as much as possible into one trip and I knew this wasn't the way to go here. A trip that started off as my sister, her husband, Adam and I quickly grew to the four of us plus my parents, plus my aunt and uncle. We were happy to have them "on board" and they were the perfect excuse to slow the trip down a bit. To try to enjoy the day, not see the whole island.

You really won't be able to experience the island in one day (which I had originally hoped to). Turns out, the island is much bigger than I imagined.  Not only had I never been but I was embarrassed to see how little I know about the island. The fact that it was an island and home to The Black Dog clothing brand and tavern and some scenes from Jaws was filmed here - now that was the extent of my knowledge.  So before we get into the itinerary, some fast Vineyard facts are needed.


Island Map by Town

  • Martha's Vineyard is an island seven miles off the Southern coast of Cape Cod, Massachusetts.
  • Cape Cod was named after the fish by British explorer Bartholomew Gosnold who crossed the Atlantic in 1602.  He named the nearby island Martha's Vineyard after his daughter.
  • During the 19th century, the island was home to a large whaling industry.
  • Martha's Vineyard encompasses Six Towns that are separated into "Down Island" and "Up Island". 
    • Down Island towns include Vineyard Haven/Tisbury (Main Street Shopping district), Oaks Bluffs- ("old school" part, Gingerbread houses, open-air tabernacle, beaches) and Edgartown (largest, old whaling, est 1642, trendier, has Chappaquiddick Island). These are the more popular towns. During this day trip, we covered all of the Down-Island towns. 
    • Up Island Towns include Chilmark (Menemsha - fishing, rolling hills, ocean views, Aquinnah (Gay Head Cliffs, Gay Head Lighthouse) and West Tisbury (rural town). 
  • The island has Five Lighthouses:  the West Chop Lighthouse, the East Chop Lighthouse, the Gay Head Lighthouse, the Cape Poge Lighthouse, and the Edgartown Lighthouse
  • The island is roughly triangular-shaped.   It is 9 miles (12.8k) wide and 26 miles (40k) long at its furthest points; the total land area is approximately 96 square miles.
  • The longest drive would be from Oaks Bluff to Aquinnah which is 19 miles and would take approximately 40 minutes.
  • The island of Chappaquiddick is the famous site where in 1969, Ted Kennedy drove off a bridge, resulting in the death of Mary Jo Kopechne.
  • There is a public bus that will get you around the island for pretty cheap.  
  • In 2007, the cost of living on Martha's Vineyard was about 60 percent above the national average; housing costs were 96 percent above the national average.


Biking Route on martha's vineyard
Biking Route on the Island 

ferry martha's vineyard
Incoming Ferry

ferry martha's vineyard
On the ferry from Woods Hole 

You have several options when it comes to getting to Martha's Vineyard via ferry.  If you are on a budget, you want to be sure you chose the Woods Hole or Falmouth option for the best price. 

Closest/ Top of the Cape, from Woods Hole or Falmouth: 
  • Our Choice: The Steamship Authority 45 minutes (service from Woods Hole* to Oaks Bluff and Vineyard Haven) Tickets (First weekend in June, $8 per person, 4$ per bike one way). We ended up ferrying into Oaks Bluff and out of Vineyard Haven due to the ferry times. Vineyard Haven has a lot more options for early and late times, but we wanted to check out Oaks Bluff as well.
  • Pied Piper one hour (service from Falmouth to Edgartown)
  • Island Queen 35 minutes (service from Falmouth to Oaks Bluff)

**It is important to note that there is no parking at the Woods Hole ferry dock.  You have to park elsewhere and take a shuttle in from one of the several off-site lots in Falmouth. You are encouraged to arrive an hour before your departure time so you have the time you need to park your car and ride the free shuttle service to the terminal. For your convenience, all shuttle buses have bike racks, capable of accommodating two bikes during daylight hours. A bike shuttle bus is available every day throughout the summer season.  

Off-site Lots are :
PALMER AVENUE LOT - 286 Palmer Avenue, Falmouth, MA 02540
THOMAS B. LANDERS LOT - 22 Technology Park Dr, E Falmouth, MA 02536
CATAUMET LOT - 1251 Route 28A, Cataumet, MA 02534

Other Options include:  SeaStreak  service to New Bedford, New York, New Jersey 

ferry martha's vineyard
Walking down the Ferry Dock - first sigjht of the Vineyard Coastline 


So I finally knew how the island got its name and that it wouldn't cost my firstborn to get there.  The final plan was to take the ferry over from Woods Hole to Oaks Bluff, bike down to Edgartown, and bike back up to Vineyard Haven, allowing us to see three of the six towns in one day, covering all of the "down island" destinations. 
  • Ferry Ride: Woods Hole to Oaks Bluff 
  • Walk around Oaks Bluff
  • Oaks Bluff to Edgartown (Bike Path - 6 miles)
  • Walk around Edgartown
  • Lunch (to-go) Among The Flowers Cafe and Wine (to-go) Wharf Wine and Spirits across the street
  • Edgartown Lighthouse and Fuller Street Beach Picnic
  • Lighthouse through Edgartown back up to Vineyard Haven (Vineyard Haven Bike Path - 7 miles)

Breakfast bagels from the Big Dipper Cafe in Oaks Bluff
Breakfast bagels from the Big Dipper Cafe in Oaks Bluff


A big way I experience the culture of a new town or new part of the world is through the food.  As Amanda once told me, I spent a lot of money on my stomach.   She isn't wrong.  I wanted to know where to eat on the vineyard and how to make it a little more affordable while avoiding lines and crowds while still allowing us to be outside.  The weather gods were good to us and it was a perfect 75-degree day. We ended up doing a quick easy on the go breakfast, a picnic lunch on the beach that allowed us to buy a bottle of wine from the liquor store and grab some restaurant food to go, and splurge for dinner at one of the island's quintessential restaurants. 
  • Big Dipper Icecream: Great spot right off the ferry for a quick breakfast before walking around town and biking down to Edgartown. I had an everything bagel with cream cheese. Rest of the group had some tasty looking breakfast sandwiches.
  • Among the Flowers Cafe - A spot for a sit-down lunch or lunch to go. Sandwiches, salads and more. A little pricey (you are on an island..). We got two salads, a Peach Salad with Grilled Chicken and Cobb Salad with Chicken to the tune of $40. It was good but not sure a salad can be $20 good.
  • Wharf Wine and Spirits - Bottle of Rosé to go. Lots of options including chilled and canned wine.
  • Black Dog Tavern- Well known and great atmosphere, outdoor space, and awesome food. I had the Crusted Cod, Quahog Chowder, and Brussel Sprout app and everything was awesome (especially the chowder).


Biking from Oaks Bluff to Edgartown - start of the bike path
Biking from Oaks Bluff to Edgartown - start of the bike path 


The island is much bigger than I imagined and you will not get very far on foot.  Biking is one of the best ways to get around the vineyard and importantly, one of the most affordable.  Bringing your car allows you to see more of the island on a shorter time scale, but it also comes at a high cost and with limited parking options in some spots. Remember from the ferry category above, $25 RT per person with a bike vs. $82.50 RT with a car if you have four people.  Big difference.  

On top of that, biking allowed us to see the island on a slower pace, be out in the sunshine, and get some exercise to offset some of the wine-ing and dining we would be doing.  Bike path's on the island also make biking safe and easy, an added bonus when traveling with kids or groups or unsteady bikers (sorry, mom).  

Oaks Bluff to Edgartown:  Bike Path C took us from Oaks Bluff to Edgartown on a beautiful flat scenic 6-mile ride.  You basically get off the ferry and take a left onto Shore Road and follow this all the way into Edgartown.  It was incredibly scenic as you follow Shore Road along the water.  It is also flat which makes the 6-mile ride easy. 

Edgartown to Vineyard Haven:  Bike Path D took us from Edgartown and back up to Vineyard Haven where we would grab a later ferry off the island.  This was a much less scenic route through the middle of the island and was hilly, making this 7-mile ride a little tougher for some people in our group.  In hindsight, I would have taken the Edgartown path back (avoiding this hilly not-so-scenic path) and just added some extra mileage at the end to get to Vineyard Haven.  This is the most direct route but not the scenic or flat option in the bunch. 

Whichever way you chose, the bike paths are a perfect chance to safely bike the island, away from traffic in your own lane and most of the time, a protected lane.  

Bike Paths on Martha's vineyard
Bike Paths on the Island 


Spending the day on three different parts of the island gave us three very different "vibes" on Martha's Vineyard if you will.  They all sort of had their own identity.  

Oaks Bluff had the old island feel. The shops and restaurants looked older, and it just had that classic island port feel. Nothing too pretentious, just the right amount of island charm and age. We started the day with breakfast at the Big Dipper Cafe before popping into a few stores in the area. Adam bought me a cute new dress and romper at one of the stores, and we spent a little bit of time regrouping here in Oaks Bluff before biking down to Edgartown. 

If you are traveling with kids, The Flying Horse Carousel right in Oak Bluffs by the ferry dock is the longest continuously running platform carousel.  It is a US national landmark that was moved to Oak Bluffs from Coney Island, New York in 1884. Oaks Bluff is also known for its variety of “Gingerbread houses” in town. Some of the houses look like colorful gingerbread houses and can easily be spotted as you make your way on the bike path from Oaks Bluff to Edgartown.  You will also pass some picture-perfect beaches and Sengekontacket Pond as you make your way down Shore Road.  We spent about an hour in Oaks Bluff having breakfast and wandering the quaint little town before heading on to our next stop, Edgartown. 

The Flying Horse Carousel
The Flying Horse Carousel 

Big Dipper Cafe in Oaks Bluff
Bikes outside Big Dipper Cafe in Oaks Bluff 

Big Dipper Cafe in Oaks Bluff
Adam post breakfast 

beaches along the bike path Martha's Vineyard
One of the beaches along the bike path


As you leave Oaks Bluff and enter Edgartown, you will probably catch kids jumping off the bridge which was made famous on Jaws. Edgartown is that classic preppy New England Island Town you envisioned Martha's Vineyard to be. It is certainly newer, trendier, and a more expensive town on the island. Here you can find all the expensive stores lining an immaculate Main Street that ends at a yacht club on the harbor. You can also catch a 2-minute ferry ride from Edgartown over to Chappaquiddick Island if you fancy a little more solitude on the vineyard.

Edgartown Bridge
Edgartown Bridge 

Bike Rack Downtown Edgartown
Bike Rack Downtown Edgartown 

Walking to the Edgartown Lighthouse
Walking to the Lighthouse 

Set up for a beach picnic 

"Summer Water" at a nearby liquor store
"Summer Water" at a nearby liquor store 

Posing by Edgartown Lighthouse 


The Famous Black Dog on Martha's Vineyard (Vineyard Haven)
The Famous Black Dog on Martha's Vineyard (Vineyard Haven)


After leaving busy Edgartown and biking back to the northern portion of the island, I was shocked to see just how small and quiet Vineyard Haven was.  It wasn't a big harbor town, just shops and restaurants scattered around the ferry docks, quiet communities and empty streets as we made our way into town.  We did a quick lap around the sleepy town before sitting down to dinner to end the day.  Looking at the restaurant list, we saw the famous Black Dog Tavern on the list and put our name in for a table outside.  In the meantime, we walked through the shops, purchasing our Black Dog gear and playing cornhole on the lawn before sitting down for dinner. 

We were all happy with our food and devoured different varieties of seafood while the sun set and the island air cooled off.  Before we knew it, we were paying the check and heading to the ferry dock to catch one of the last boats off the island and back to Woods Hole. 

The Famous Black Dog on Martha's Vineyard (Vineyard Haven)
The Black Dog General Store 

The Famous Black Dog on Martha's Vineyard (Vineyard Haven)
The Black Dog General Store 

No Caption Needed

The Famous Black Dog on Martha's Vineyard (Vineyard Haven)
Black Dog Yacht Club by the Black Dog Tavern 

On the ferry ride back, we reflected on just how amazing our day on the island was, how lucky we got with the weather, and how much fun we had together. Turns out, there are affordable ways to make it to Martha's Vineyard and if you get lucky with the weather, you can spend the day biking, picnicking, and eating your way around the island. You better believe the wheels are already turning with a trip back to see some of the other highlights including Chappaquiddick island, Gay Head Cliffs, lounge at the beaches, and eat seafood while watching the sunset in the small fishing village of Menemsha.

It only takes a sunny 75-degree day on a seafood and sailboat filled island to fall a little more in love with a handsome man and the beauty and charm of New England. 

Martha's Vineyard, 2019 


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