July 8, 2023

Cape & Islands

Upper Cape, Martha's Vineyard, & Nantucket

Youtube Link

Ride With GPS Link

This was a long awaited trip - in the nearly five years of living in Boston, I had never been to the islands. The first island I went to was Cuttyhunk in May 2022! Even though I’ve ridden my bike on the Cape multiple times, I have always had a very bad experience riding in the Upper and Mid Cape. This is definitely anecdotal, but the most hostility I’ve faced in Massachusetts (and the only hostility that really affected me) was on the Cape. The Outer Cape is fine though, and I’ve only had friendly experiences.

We started our journey by taking an early morning P&B Bus from Boston South Station to the Sagamore Park & Ride. From here, we rode down to Wood’s Hole to catch our ferry to Martha’s Vineyard. This ride was relatively uneventful - this part of the Cape is not unlike the suburban areas of Boston. Until we hit the Shining Seas bike path in Falmouth, it was mostly narrow, but heavily trafficked roads. The weather was very high humidity, so we were drenched by the time we got to the Wood’s Hole Ferry Terminal.

Upper Cape

Shining Seas bike path was nice, if crowded. It went right by the coast - and would have felt brilliant if it was sunny and cool. However, the cloudy and slightly foggy weather had its charm too.

Shining Seas Bike Path, Falmouth MA Shining Seas Bike Path, Falmouth MA

Wood’s Hole to Martha’s Vineyard Ferry, at the terminal, on the deck, and below where our bikes were

Wood’s Hole to Martha’s Vineyard Ferry, at the terminal, on the deck, and below where our bikes were

Martha’s Vineyard

First impressions of Vineyard Haven were, not the best. Along with the Cape, I feel it is suffering from over-tourism. A remnant of the 1960s era of tourism. Its narrow roads with a lack of decent active or public transportation options makes getting around without a car, not ideal.

However, after a less-than-awesome bike ride, we made our way to the fishing village of Meneshma. Meneshma was really nice. We got chatting with an old man who grew up in Meneshma, and after living elsewhere, has moved back. We also got a nice fish sandwich. I 100% recommend visiting Meneshma. To go from Meneshma to Aquinnah, there is a bike ferry in the summer. It is operated by a local guy, and costs justs $5 to cross.

Meneshma fishing village lagoon Meneshma fishing village lagoon

Meneshma bike ferry connecting to Aquinnah Meneshma bike ferry connecting to Aquinnah

After crossing over from Meneshma, the route was much nicer. Actually, it had already become much nicer after turning off the main road towards Meneshma. We made our way towards the Aquinnah Cliffs Overlook. This is a very important cultural site for the Wampanoag people, and there is a very good informative exhibit at this point. The views of the cliffs are also very impressive. We were lucky to see some dense fog roll in. The effect of the fog and the sun together was awesome.

Aquinnah Cliffs Aquinnah Cliffs

After the Aquinnah Cliffs overlook, we were very tired. That night, we were staying at the Hostelling International Hostel in West Tisbury. It is the only affordable accommodation least expensive accommodation on the island. Yes. Martha’s Vineyard is expensive to stay - even at a hostel. We found a grocery store near the hostel, and got a few ingredients to make dinner in the hostel’s communal kitchen. It had been a hot, humid, and tiring day, and we were ready to sleep.

The next day, we had a somewhat leisurely start to a relatively busy and long day. We were taking the noon ferry from Oak Bluffs to Nantucket, spending a few hours on Nantucket, and then take the Nantucket-Hyannis ferry in time to catch the CapeFlyer train back to Boston. After a hostel-provided breakfast of blueberry pancakes and coffee, we set off, along the bike path to Oak Bluffs, via a short detour in Edgartown. We also went via the location where the movie ‘Jaws’ was shot.

Oak Bluffs was a nice town, and had a nice vibe to it. Definitely very tourism focused economy, it was also one of the only places where Black Americans were welcomed and not face apartheid and exclusion on Martha’s Vineyard. As a result, it has a thriving Black community. Trinity Park in Oak Bluffs has a large collection of ‘gingerbread’ houses. These houses developed over time, starting from simple camp structures to these elaborate houses. We spent 15-20 minutes walking around, before heading to the ferry for Nantucket.

Oak Bluffs ‘Campground’ Gingerbread houses Oak Bluffs ‘Campground’ Gingerbread houses

We took an inter-island ferry from Oak Bluffs to Nantucket. While it was expensive, it would have been more expensive to make another trip to Nantucket. This ferry runs only in the peak summer months, thrice a day, so it might not be a feasible option for everyone.

Inter-island ferry between Oak Bluffs and Nantucket Inter-island ferry between Oak Bluffs and Nantucket


Nantucket. Sigh. Is it a cute town? Yes. Are the vibes off? Also yes. I won’t go into a lot of detail, but if you combine the Seaport and South Boston, and plonk it on an island, yeah? That’s the vibe. It was not great. That’s all I’m going to say.

We decided to treat ourselves to a beer at Cisco - again, we really wanted to get out after a beer and a scallop role. I didn’t even see a single picture in my camera roll, so unfortunately (or fortunately?) no pictures to share here. We couldn’t wait to get back to Hyannis.

After a long slow ferry ride (the fast ferry was sold out) we made it to Hyannis, had a nice walk along the main street and harbor, and had another beer at an arcade! We took the CapeFlyer back to Boston, and finally got home after nine o’clock.

Entire Strava Route - also includes ferry rides Entire Strava Route - also includes ferry rides

Overall, I covered 10 new towns - Aquinnah, Nantucket, West Tisbury, Sandwich, Edgartown, Oak Bluffs, Tisbury, Falmouth, Mashpee, and Chilmark - bringing the total to 312/351 - 88.9%!

Cape & Islands