Martha’s Vineyard, Massachusetts


Serendipidous Discoveries and Dockside Lodgings

By Max Hartshorne
GoNOMAD Editor

Farm Pond Preserve, a hidden nature reserve right off the bike path in Oak Bluffs.

Farm Pond Preserve, a hidden nature reserve right off the bike path in Oak Bluffs.

The island of Martha’s Vineyard and the town of Edgartown, Massachusetts resonates with me deeply. I spent 45 years visiting my grandmother’s house atop a hill in this historic former whaling village.

So when I was asked to come back to the island in 2012, it made me wistful. I quickly gained enthusiasm, knowing we’d be staying in a newly renovated hotel right on the Oak Bluffs harbor, but sad thinking about my granny’s house now demolished to make way for a Edgartown mega-mansion.

We were there to see what was new on this island paradise, this retreat for the rich and famous and for the thousands of tourists who take day trips out and back on the seven ferries that offer service to the island. Our weekend would include kayaking, hiking and biking…and lots of fresh seafood.

Today there is even a ferry that will take you from Manhattan on a summer Friday night and return Sunday afternoon! Other mainland departure ports include New Bedford, MA, Quonset RI, Falmouth and the biggest, out of Woods Hole MA.We departed on a sunny Saturday June morning for the Martha’s Vineyard & Woods Hole Steamship Authority, parking seven miles up the peninsula in Falmouth and joining a legion of pre-season visitors for the ferry terminus in Woods Hole.

The Dockside Inn, newly renovated and right on the Oak Bluffs Harbor, easy walk from the ferry.

The Dockside Inn, newly renovated and right on the Oak Bluffs Harbor, easy walk from the ferry.

People are always friendly on these buses, and we chatted with a couple who were going to the same hotel as we were–for their seventh wedding anniversary.

A Car-less Vacation

One of the things that drew my grandmother Esther to the island back during World War II was that you could exist there without having a car.

Gas was being rationed, and it made a lot of sense to go some place where you could take a train out of Manhattan, board a ferry, and get along without your own wheels.

In 2012, this is even truer. The island is a perfect place to try and live without that American habit of having to drive everywhere. No where in New England are there more bike paths and more transit options than on MV and its neighbor, Nantucket.

After the ferry arrived in Oak Bluffs, we walked the short distance to our hotel, the newly renovated Dockside Inn, right beside the lovely yacht-filled harbor.

Bike paths connect most of the major towns on the island, except for Chilmark and Aquinnah.

Bike paths connect most of the major towns on the island, except for Chilmark and Aquinnah.

The property is one of several small inns in Oak Bluffs owned by Caleb Caldwell and his wife. The Dockside is now owned by the Caldwells and a partner, John Tierney.

I asked Caleb about how the business has fared over these last several years of the national recession. He said the bad years are behind them, the worse being 2008, but today’s visitor is still looking for discounts and bargains–always deals, he said.

One of the factors that has helped Martha’s Vineyard weather the economic storm have been the abundance of ways people can now get to the island. There is seasonal daily air service offered by Jet Blue, Cape Air and USAir, as well as six different ferry services.

You can take your car, but it will cost you just under $200 and getting a reservation takes serious advance planning. If you can be flexible, try going over without your vehicle.

There is also the network of public transportation—busses that can take you just about anywhere on the island and a well laid out grid of bike trails. The only thing lacking in the bike trails is an easy way to navigate to beautiful Chilmark and the town on the tip, Aquinnah. Land is too expensive there to carve out a roadside bike trail, so for this one must rely on the MV Transit buses that can transport up to three bicycles at a time.

Jumping off the bridge at State Beach, Oak Bluffs.

Jumping off the bridge at State Beach, Oak Bluffs.

The “New” Dockside

The Dockside has been a hotel for many decades, but this year’s new ownership team has spruced things up and made it more customer friendly. One of the things we first learned about was an innovation, something I’ve never heard of before–Loomis.

Loomis is the text message concierge. Guest are encouraged to send text messages to Loomis and ask any questions they have about where to eat, what to see, and how to find clean towels.

We tried Loomis out when around dinner time we were contemplating which of Oak Bluff’s two new Thai restaurants to try out. Loomis raved about the food at both, but gave the one on upper Circuit Avenue a nod for atmosphere. We were pleasantly surprised at how inexpensive Sai Mai Thai restaurant turned out to be.

The funny thing to me about Sai Mai was that it’s located inside the famous dive bar known as the Ritz, in a room that once held the pool table. So now you can enjoy delicious and healthy Thai while across the half wall, the patrons of the Ritz enjoy swilling beers and carrying on as they’ve done for decades.

Our comfortable room at the newly renovated Dockside Inn, Oak Bluffs, MA.

Our comfortable room at the newly renovated Dockside Inn, Oak Bluffs, MA.

Nice Touches

There are little touches at the Dockside Inn that really make the guest experience nice. A Keureg coffee machine dispenses fresh brewed coffee at any time of the day or night, free bottled waters, fruit and granola bars are laid out, and there are even some little pastries next to the coffee machines.

They have a shed full of beach towels and beach chairs and right next door is a bike rental outfit that we’d definitely recommend. Martha’s Bike Rentals has many outlets around the island and they provide new bikes and are very helpful.

We had some adventures planned for our weekend, and we jumped on our rental bikes to pedal the bike path over to Edgartown. The highlight of any visit to this old New England whaling village is a trip to the top of the town dock. You pedal all the way until Main Street ends, and then you’re right in the thick of docks, yachts and a big town wharf with a top deck and a glorious view of the Edgartown lighthouse and the ferry that traverses the narrow straight over to Chappaquiddick Island.

Kayaking at Sengekontacket pond in Oak Bluffs.

Kayaking at Sengekontacket pond in Oak Bluffs.

The Senator’s Story

At this point you might have to spend some time explaining that famous story about the Massachusetts senator who drove off the road in 1969, but after this it’s time to just admire the view and watch the passing parade of large yachts, sport fishing boats and Boston whalers coming and going.

There are bathrooms for the public located up on Church Street at the top of Main Street where the bus stop for all of the various routes is located.

We biked the trail from Oak Bluffs to meet Island Spirit Kayak, at the “little bridge” near the Edgartown Oak Bluffs line. Owner and island native Chick Stapleton maintains a fleet of 50 kayaks, doubles and singles, as well as paddleboards that she can rent or you can join one of her experienced paddling guides for a guided tour.

Seafood doesn't get any fresher than when you buy it at Larsens and take a seat by the Menemsha dock!

Seafood doesn’t get any fresher than when you buy it at Larsens and take a seat by the Menemsha dock!

We joined a young guide named Tex who took us over through Sengekontacket pond on single kayaks where we visited with a group of oystercatcher birds whose unique orange beaks make perfect tools for extracting the meat from their favorite bivalves. The nesting pairs on the island in the cove were used to gawking kayakers and didn’t seem to mind us watching them.

Then we decided to do a little ocean paddling, so we headed for the narrow channel and shot out into the surf. It was a calm day, a perfect day to be in a kayak with seagulls flying over head, and we headed a ways up the shoreline and into another narrow cove. Here a nesting osprey has had a nest atop a telephone pole for many years, we could see the little chicks reaching up to mama osprey for a bite of food.

The Edgartown town dock is a great place to view the harbor and the island of Chapaquiddick.

The Edgartown town dock is a great place to view the harbor and the island of Chapaquiddick.

Al Fresco Dinner on the Menemsha Dock

One treat that no visit to the island should leave out is the trek to Menemsha to Larsen’s fish market. This family-run fish store not only has the freshest island-caught swordfish, tuna and black bass, they also offer a rustic dining treat.

We ordered steamers, clam chowder and freshly shucked oysters and ate them outside on crude wooden boxes right next to the water. With the sun setting and sipping on wine we brought for the occasion, nothing could have tasted better.

When we were full of seafood, it was time to depart, and we checked for the last bus to take us back to Oak Bluffs via West Tisbury.

The aforementioned MV transit buses that we rode for the 25-mile journey to the fishing village can accommodate only three bikes. As we waited we saw that another couple with bikes were already at the stop. OH NO! We were forced to leave one of our rental bikes locked to a pole in Menemsha. Later on the nice people at Martha’s were sympathetic to our plight, but next time I think we should have called them for help rather than leave the thing locked over night there.

Fishing boats at Menemsha's Dutcher's Dock. photo by Mary Gilman.

Fishing boats at Menemsha’s Dutcher’s Dock. photo by Mary Gilman.

Land Bank Discoveries

There are so many little natural discoveries on the island, one of which are the many plots of land owned by the Martha’s Vineyard Land Bank.

Thousands of acres of the island are pockets of preserved land, and most are ones you just stumble upon. The organization’s director, Jim Lengyel, said it’s deliberate. “We want people to slowly come to understand the availability of these properties, the thrill of stumbling across something, that you’re welcomed.”

As we pedaled past an unmarked small road off the bike trail heading back to Oak Bluffs, we found Farm Pond Preserve, with wooden walkways through a swamp and a pretty path through a field. An impromptu hike and as Lengyel said, finding it serendipitously made it all the more of a treat. That’s part of what makes this island so special to so many people!

Find a map of Martha’s Vineyard’s Land Bank properties for hiking and biking.

The Dockside Inn
9 Circuit Ave Ext
Oak Bluffs, MA 02557
Two nights with tax $399

Shucking oysters at Larsen's Fish, Menemsha.

Shucking oysters at Larsen’s Fish, Menemsha.

Larsen’s Fish Market
(508) 645-2680
Open seven days a week
9:00 am to 7:00 pm
On the Menemsha dock
56 Basin Rd
Chilmark, MA 02535

Martha’s Bike Rentals
Oak Bluffs, Vineyard Haven
Pick up and delivery all over the island, hybrids
Kids bikes and trail-a-bikes.

Skinny’s Fat Sandwiches
12 Circuit Ave.
Oak Bluffs, MA 508-693-5281
7 No. Water St.
Edgartown 508-627-6990
Huge and affordable sandwiches for
Breakfast and lunch

Oak Bluffs Cottages, in the Camp Meeting Association.

Oak Bluffs Cottages, in the Camp Meeting Association.

A good website to find out all about Martha’s Vineyard vacations is The Chamber can be reached at 508-693-0085.Oak Bluffs Cottages, in the Camp Meeting Association.
Max Hartshorne.Max Hartshorne is the editor of GoNOMAD and a prolific blogger, who shares his travel and other observations at Readuponit.Read more articles about Martha’s Vineyard on GoNOMAD.

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Max Hartshorne
Max Hartshorne has been the editor and publisher of GoNOMAD Travel in South Deerfield Mass since 2002. He worked for newspapers and other sales positions for 23 years until he finally got what he wanted, and became the editor at GoNOMAD. He travels regularly, enjoys publishing new writers, and watching his grandchildren grow up.