Edgartown: 3 places to know

Out of the five main hamlets on MV, Edgartown is surely the most refined, most WASP-y of them all. The neighborhoods are filled with white clapboard houses topped with widow's walks that date back to the late 1600s. Aside from Florbelle, Portobello Road is a must-stop for me simply because its offerings, while certainly vintage-tinged, are sophisticated and bring a little bit of "city" back into my life when the daily routine in Chilmark gets too, well, routine.

A little peek at what I find there: John Derian decoupage plates and trays
Loads of art and architecture books
A smattering of greeting cards
Lovely children's books
Silly and unusual things like this Jane Austen puzzle, below, in the upper corner
Of course, there's also The Black Dog which originated here. Not sold anywhere else so when people wear Black Dog togs you know that they've either been to MV - not the easiest place to get to - or they hang with someone who makes the trek here.
We always pick up a shirt for someone. It's important to buy a shirt with the year emblazoned on the back. The older your shirt - say 1974 - the more dedicated Islander you're considered. When I was pregnant with my kids - once in 2004, once in 2007 - I made sure to buy adult shirts for them with the year of their births on them. Instead cred when they come back up here as teens.
Espresso Love is the place I love to come for a latte. It used to be a restaurant called Savior Faire and a decade ago my husband and I had the best meal of our lives there and the most unbelievable salad called "Salad That The Chefs Eat" a kitchen sink concoction of greens, tomatoes, and chinese noodles topped with mashed potatoes. Sounds disgusting, but I swear it was delicious.
Like most of the places here, college kids run Espresso Love. When I leave a tip in the plastic tip jar - tip jars are at nearly every little place on the island - I like to read the names of the colleges they're attending which always include Colgate, Boston U, Amherst, Smith, Bennington. I'm still searching for the tip jar with Texas Tech, A&M, or UT scrawled on it.