A Tiny Island "Hike"

July 15, 2013

Cuttyhunk Island, Massachusetts  

down the road.jpg

Unique, quaint, and unlike anywhere I have ever been, Cuttyhunk is a tiny little island on the very tip of Massachusetts.  Like the Vineyard, it has been a vacation spot of ours for many years, but it took me a bit longer (ok WAY longer) to appreciate it as much.  The beaches are beautiful and we usually go waterskiing, swimming, and kayaking, but aside from that, the main attraction of this island has got to be its solitude, which as a kid, I kind of hated.   I have, however, become wise in my old age, learning quickly that a quiet getaway place should not only be appreciated but worshiped, really.

Admittedly, it is much more enjoyable when the weather is nice, and on this trip, it was rainy and cloudy most of the time (so much for the “tropical" weather I boasted about on the Vineyard).  However, we were still able to have a great time and even go on a hike of the entire island one day!  Now when I say, “hike”- I am referring to an “LA Hike”.  For those of you who are not familiar with what I’m talking about: There are several canyons in Los Angeles that are more or less walking paths with great views of the city.  Excellent for people watching, ogling designer puppies, and running into famous people, they’re not exactly challenging (unless you’re one of those people who run the whole way or strap weights to yourself – ha! NOT ME!)

 Oh wow I am loosing track here.  Ok but anyways, we “hiked” the island… the lengthy mile and a half that it was, in just under two hours.  Not too shabby! Now just give me some weights to strap to my ankles and I’ll be a HIKING PROFESSIONAL!

tall shack.jpg
hydranga house shot.jpg

Some of the things that make Cuttyhunk adorable:

-  Because of its size (1.5miles long and ¾ mile wide) most people get around by walking on foot or driving a golf cart!

- Only 1 dinner restaurant (an amazing pizza place where I had “The Don”).  It is outside someone’s house and open 6-8PM.

- Only 1 breakfast place open 8-11AM.

- Only 1 shop and 1 tiny market but they do have an ice cream place on the dock right next to the marina. It serves 5 flavors a night and the flavors change daily (depending on what has been shipped).

- Only about 30-40 year long residents which swells to about 350 during the summertime.

- Local fishermen bring fresh lobster and seafood, ready to eat, right to your boat- YUM!


Island Market.jpg
flowers fence.jpg

Cuttyhunk truly embodies all the beauty that is a New England summer.  It has breathtaking landscapes, plentiful wildlife (we saw deer, bunnies, fish, and crabs while visiting), and incredible seafood.  For me, it has become an indispensable retreat away from the hustle and bustle of my everyday life back in Los Angeles.


The best part about vacationing on the island is that anything goes! In fact, it’s the perfect place to kickback, forget about makeup, and tie your hair up in braids for the day.  My look here is not particularly fashionable but it is fitting for a casual day of “hiking”, or a rainy summer day wherever you might be.


lookat feet.jpg

Pants & Earrings: H&M (Similar) 

Shirt: Backwater (Edgartown, MA) 

Shoes: TOMS

Check out Cuttyhunk! 

closeup cutty.jpg