Arriving by ferry always made the island feel like a true getaway.

Massachusetts Island Adventures

Martha’s Vineyard

Ferry rides, bicycles, hostels, campgrounds, beaches, salt marshes, kayaking, photography, and the pleasure of exploring an island slowly.

Martha’s Vineyard became one of those places I returned to many times while I was living in Massachusetts. During the summer, I went almost every year without fail. I could enjoy the mountains in every season—I loved snow, winter hiking, and fall just as much as summer—but Cape Cod and the islands were mostly summertime places for me.

Most of the time, I traveled very simply. I would bring only my bicycle, walk it onto the ferry, and stay at the youth hostel. The hostel sits right beside the bike trail and almost feels like a biking hostel. At any given time there might be twenty-five, fifty, or even more bicycles lined up outside, with travelers arriving from all over.

The entire island is reachable by bicycle. The terrain is mostly gently rolling rather than brutally steep, and every three or four miles there seems to be another small town or village where you can stop for pastries, ice cream, seafood, coffee, or a beer. That made it ideal for relaxed weekend trips: ride for a while, stop somewhere interesting, talk with people, and continue when you felt like it.

I was never interested in visiting the island as a luxury destination. What attracted me was the chance to stay at the hostel or campground, spend most of the day outdoors, meet interesting people, and explore the beaches, towns, salt marshes, back roads, music spots, and coastal landscapes at a slower pace.

Martha’s Vineyard also always felt unusually tolerant and inclusive. Like much of New England, it was a place where many different kinds of people could relax, be themselves, and feel welcome. That openness was one more reason it became one of my favorite places to spend time.

The Ferry Was Part of the Adventure

Easy passage with a bicycle and no need to hurry

The ferries could be extremely crowded during summer weekends, especially with cars, but traveling as a passenger with only a bicycle made everything much easier. I usually did not need to reserve anything. I could simply show up, roll my bicycle aboard, and take the next available boat.

There were several different kinds of vessels. Sometimes I would ride one of the large ferries with room for cars, trucks, and crowds of passengers. Other times it might be one of the smaller boats. There was also a high-speed ferry for anyone who needed to save time.

I rarely felt any urgency. The crossing was short, and the ferry ride itself was part of leaving ordinary life behind. Whether the boat was large, small, fast, or slow, the moment it pulled away from the mainland the weekend had begun.

A ferry carrying passengers and bicycles to Martha's Vineyard.
Traveling as a walk-on passenger with a bicycle made the ferry simple, flexible, and part of the fun.

Arriving in Oak Bluffs

Color, shoreline, and island energy

Oak Bluffs was often one of the first places that made Martha’s Vineyard feel distinctive. The colorful cottages, busy harbor, shoreline parks, older architecture, and mixture of visitors and year-round residents created an atmosphere unlike anywhere on the mainland.

The famous gingerbread cottages were fascinating, but I also enjoyed simply wandering beyond the busiest streets. A bicycle made it easy to move between neighborhoods, beaches, overlooks, and quieter roads without feeling sealed off inside a car.

Photography was naturally part of every trip. The colors, porches, boats, reflections, old signs, clouds, and changing coastal light provided endless subjects.

Oak Bluffs also had good places to hear live music and meet people. Over the years, I met many interesting travelers at the hostel, on the ferries, in town, and at music spots. Some visits lasted only a weekend, but they still produced plenty of stories, conversations, and spontaneous adventures.

Colorful cottages and coastal scenery in Oak Bluffs on Martha's Vineyard.
Oak Bluffs offered colorful architecture, shoreline walks, and an easy place to begin exploring the island.
The ferry separated the island from everyday life just enough. Once I arrived with a bicycle and simple camping gear, the whole island became something I could explore at my own pace.

Edgartown and the Eastern Shore

Harbors, older homes, beaches, and long walks

Edgartown had a different feeling from Oak Bluffs. Its harbor, older homes, narrow streets, and maritime history gave it a quieter and more polished character. Even when the center was busy, it was easy to move outward toward the beaches, ponds, and less crowded roads.

I enjoyed the contrast between town and open coast. Within a short distance, I could go from historic buildings and boats to wind, sand, water, and long views across the island’s eastern side.

Trips like these were never about checking off attractions. I preferred to spend enough time walking, cycling, stopping for photographs, and following whatever looked interesting rather than rushing from one famous place to another.

Harbor and historic streets in Edgartown on Martha's Vineyard.
Edgartown combined maritime history, harbor views, older homes, and easy access to the island’s eastern shoreline.

Aquinnah and the Western End

Cliffs, open ocean, and a wilder landscape

Aquinnah felt much more open and dramatic. The cliffs, broad views, changing colors, and exposure to the ocean made the western end of the island feel farther removed from the villages and ferry landings.

This was the kind of place where weather and light mattered. Clouds moving across the water, late-day sun striking the cliffs, or a full moon rising over the island could completely change the experience.

I have always paid attention to those natural conditions when planning outdoor trips. Tides, moonrise, weather, wind, and the direction of the light often determined where I wanted to be and when I wanted to arrive.

The beach below the Gay Head—now Aquinnah—Cliffs was also known for its long-standing clothing-optional culture. That openness fit the island’s generally tolerant character. The dramatic cliffs, broad beach, and sense of freedom made it one of the most unusual coastal places in New England. As with any beach, local access rules and protected areas always needed to be respected.

Aquinnah cliffs and ocean scenery on Martha's Vineyard.
Aquinnah offered some of the island’s most dramatic scenery, especially when the cliffs, ocean, clouds, and late-day light came together.
Coastal landscape and broad ocean view on Martha's Vineyard.
Much of the pleasure of Martha’s Vineyard came from simply stopping somewhere beautiful and giving the landscape enough time to reveal itself.

Menemsha and the Working Waterfront

Fishing boats, simple food, and evening light

Menemsha had the feeling of a working harbor rather than a polished resort. Fishing boats, docks, small businesses, weathered buildings, and people actually making a living from the water gave the village a character I appreciated.

It was also a natural place to slow down near the end of the day. The western light, boats in the harbor, changing sky, and people gathering near the water made it especially good for photography.

I have always preferred places where the scenery and local life are still connected. Menemsha felt like that—a beautiful place, but also a place with a real purpose beyond tourism.

Fishing harbor and evening light in Menemsha on Martha's Vineyard.
Menemsha’s fishing harbor, boats, working waterfront, and evening light made it one of the island’s most memorable places.

Campground Trips With Friends and Family

Different decades, different companions, the same island

Marty and I camped on Martha’s Vineyard many decades ago, back when getting a campsite and bringing a car over seemed much easier than it later became. Those early trips were part of my introduction to the island long before the bicycle-and-hostel routine became my usual way of visiting.

Another memorable trip was with Bernie and his sons Noel and Sean. That time we brought the car, stayed at the campground, and rode bicycles all over the island. It was a perfect family-style adventure: enough transportation to carry the camping gear, but bicycles for actually experiencing the island.

Those trips reminded me that there was no single correct way to visit. I enjoyed going alone with a bicycle, traveling with Marty, camping with Bernie and the boys, meeting strangers at the hostel, or joining friends for only a weekend. Each version created a different Martha’s Vineyard story.

Camping and bicycle travel with friends or family on Martha's Vineyard.
Campground trips with Marty, and later with Bernie, Noel, and Sean, added another chapter to the island memories.

Exploring Beyond the Villages

Cycling, hiking, kayaking, marshes, beaches, and tides

The villages were only part of what brought me back. I enjoyed linking them together by bicycle, walking quieter trails, exploring beaches, and looking for opportunities to get onto the water by kayak.

The coastal environment itself was always fascinating. Salt marshes, tidal creeks, ponds, sandbars, tidepools, dunes, and changing shorelines made the island a natural laboratory. I often planned around the tides because an extreme low tide could open areas that were completely inaccessible a few hours later.

On some coastal trips, I carried gear such as mudshoes so I could explore soft tidal areas more safely. That kind of preparation let me move beyond ordinary sightseeing and experience the island more directly.

For me, the best days combined several activities: bicycle somewhere interesting, walk a beach or trail, spend time photographing the landscape, paddle if conditions were right, and then return to a simple campsite or hostel at the end of the day.

Bicycle, beach, salt marsh, or kayaking exploration on Martha's Vineyard.
The island was best explored slowly—by bicycle, on foot, and by kayak whenever the tides, wind, and weather allowed.
I did not need luxury accommodations to enjoy Martha’s Vineyard. A ferry ticket, a bicycle, a simple place to sleep, good weather, and a full day outdoors were more than enough.

Photography and Natural Light

Clouds, moonrise, reflections, and coastal weather

Martha’s Vineyard was naturally suited to photography. The island offered colorful buildings, old harbors, beaches, marshes, boats, lighthouses, cliffs, wildlife, and constantly changing light.

I have always been especially interested in clouds and weather, so I never needed a perfectly clear day. A cloudy sky often made the colors richer, softened the light, and created more interesting photographs than bright midday sun.

I also liked planning around moonrise and sunset. Being in the right place when the moon rose over the water, or when the last light reached the boats and cliffs, could turn an ordinary day into the memory that stayed with me longest.

Sunset, moonrise, or changing coastal light on Martha's Vineyard.
Photography encouraged me to pay attention to weather, tides, clouds, moonrise, reflections, and the changing direction of island light.

Combining Martha’s Vineyard and Nantucket

A full week divided between two islands

When I had an entire week available, I sometimes turned one island trip into two. I would spend about three days on Martha’s Vineyard, take another ferry over to Nantucket, stay there for roughly three days, and then return.

That made the journey feel much larger without requiring a long drive. Each island had its own personality, and traveling between them by boat kept the whole trip connected to the water.

Because these were summer trips, the days were long and ideal for bicycling, beaches, hostels, music, photography, and exploring until evening. It became one of the traditions I looked forward to almost every year.

Island ferry route connecting Martha's Vineyard and Nantucket.
With a full week, I could divide the time between Martha’s Vineyard and Nantucket and make the ferries part of the journey.

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Martha’s Vineyard was never only one town, one beach, or one scenic overlook. It was the combination of ferry travel, bicycles, hostels, campgrounds, harbors, music, cliffs, salt marshes, tides, photography, good food, and the freedom to explore without a rigid schedule.

The bicycle made the island feel human in scale. A few rolling miles led to another village, another bakery, another beach, another seafood stop, another beer, or another conversation with someone I had just met. Even a two- or three-day weekend could feel like a complete adventure.

I remain grateful that I had so many opportunities to visit while living in Massachusetts—alone, with Marty, with Bernie and the boys, and alongside the many interesting people I met at the hostel and around the island. Martha’s Vineyard offered a kind of travel I have always valued: simple, active, inclusive, curious, close to nature, and open to whatever the day happened to reveal.

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