• Skip to main content
  • Skip to header left navigation
  • Skip to header right navigation
  • Skip to after header navigation
  • Skip to site footer
  • Facebook
  • Instagram
  • YouTube
  • Home
  • Blog
Life In Pleasantville

Life In Pleasantville

Food, Travel, Life

  • Work With Me
  • LinkTree
  • Travel
  • Food & Drink
  • Living

Island Hopping In Massachusetts

by Candace Sampson

You’ve no doubt heard of Martha’s Vineyard, Cape Cod and Nantucket. These islands are synonymous with Massachusetts and known the world over for their beauty and authentic charm. They are however, not the only islands to see in Massachusetts. Here are three you may not have heard of, but should definitely seek out when visiting Massachusetts!

Island Hopping in Massachusetts – Three Islands You May Not Have Heard Of

Misery Islands

Well, how’s that for chipper? Misery Island received it’s name after a shipbuilder was stranded there during a winter storm for “three miserable days”. Don’t worry though, misery is the last thing you’ll find on these two islands — Great Misery and Little Misery. Saved from development by The Trustees of Reservations, Misery Islands are actually quite a joy to visit. It’s the perfect place to commune with nature.

island hopping massachusetts

Cuttyhunk Island

Cuttyhunk is actually way easier to announce than it’s original name of Poocuohhunkkunnah. Would I kid you? Home to about 50 residents now, Cuttyhunk Island is the outermost of the Elizabeth Islands in Massachusetts. If you’re seeking tranquility this is probably the island for you. Check out the The Avalon Inn (founded in 1909) for a real taste of Americana. Be sure to pack your sunscreen and beach towels too. Cuttyhunk also has several stunning beaches to enjoy.

island hopping massachusetts

Plum Island

Well this would be a plum location to visit wouldn’t it? Sorry, I get my cheesy humour from my father, it’s unavoidable. I digress. Plum Island is so aptly named because of the wild plums that grow on it’s dunes. Dunes you say? Why yes, big sand dunes! If you haven’t rolled down a sand dune as a child then you’re not living. Also, because the island is unsheltered from the Atlantic, the waves can be quite large here. Likely ideal for windsurfing. You’ll also find the Parker River Wildlife Refuge here where migratory birds come for resting and nesting. Finally, from Newburyport, catch a boat for whalewatching daily from mid-june to Labour day.

island hopping massachusetts
Mass logo_NEW
Category: Massachusetts, TravelTag: Islands, Martha's Vineyard, Massachusetts

About Candace Sampson

Candace Sampson is the founder of Life in Pleasantville and has been writing about Canadian travel for over a decade. She only shares destinations she has personally visited and genuinely loved. Candace is also the creator of Girl Trips, a women-focused travel and retreat brand, and the host of What She Said, Canada’s longest-running women’s talk show turned podcast.

Previous Post:clevelands houseClevelands House – I Had The Time of My Life
Next Post:Relax in Massachusettsrelax in massachusetts

Sidebar

Instagram

Girl Trips Batter Up Babes

Girl Trips Batter Up Babes
Spots are limited — click to learn more →

Acanthus Florist shopfront in Almonte, Ontario

Explore Small Towns in Ontario

Discover charming main streets, waterfalls, antiques, and festivals across Ontario’s most beautiful small towns.

Start Exploring

Categories

Here’s where else you can find me:

Girl Trips Logo What She Said Logo

What’s New

Gen X woman smiling in a Pro Roe t-shirt, done being angry and choosing joy instead

Fuck It. I’m Done.

a feature image for an article about extinction of experience where a woman is experiencing pure joy in a hot air balloon

Extinction of Experience, The Slow Erosion of Real Life!

Girls Gone Mild group wearing matching navy hoodies on snowy Crystal Beach Ontario in winter

We Don’t Hibernate: Girls Gone Mild at Crystal Beach

Enjoying your time in Pleasantville?

From travel tips to personal stories, Life in Pleasantville is powered by caffeine and curiosity. If this post hit home, made you laugh, or helped plan your next trip, please consider buying me a coffee to keep it going.

Buy Me a Coffee

Connect With Me Online

  • Facebook
  • Instagram
  • Threads
  • TikTok

Inspiration

“Every day is another chance to get stronger, to eat better, to live healthier, and to be the best version of you.”

Recent Posts

Gen X woman smiling in a Pro Roe t-shirt, done being angry and choosing joy instead
a feature image for an article about extinction of experience where a woman is experiencing pure joy in a hot air balloon
Girls Gone Mild group wearing matching navy hoodies on snowy Crystal Beach Ontario in winter
Spy Rock overlooking Westport

Copyright © 2026 · Life In Pleasantville · All Rights Reserved