Even if you don't feel like getting sand in your shoes, Water Street is still the ideal spot for a casual stroll. Part of the Edgartown Village Historic District, the lane boasts gorgeous mansions built by wealthy whaling captains as well as other restored 19th-century structures, such as civic buildings and churches.
Peaceful Chappaquiddick Island can be reached via a short trip aboard the Chappy Ferry at 53 Dock St. (the vehicle waiting line forms on Daggett Street); phone (508) 627-9427. The small, isolated community gained notoriety in 1969, when the car of Massachusetts Senator Edward M. “Ted” Kennedy plunged off Dike Bridge and into the channel, killing the politician's sole passenger, Mary Jo Kopechne.
Visitor Centers
Edgartown Visitor Center 29 Church St. Edgartown, MA 02539. Phone:(508)627-6100
Shopping
Seeking a lazy day of window-shopping on the Vineyard? Edgartown is your best bet. The town's compact commercial district (centered on and around Main Street near the harbor) includes art galleries, high-end boutiques and casual clothing depots.Founded by two brothers who had tired of the corporate world, Vineyard Vines (27 N. Water St.) originated on the island in the late 1990s but has since grown into a national chain. The pair started off by hawking neckties out of their boat and Jeep. The successful enterprise now deals in of all kinds of preppy attire for men, women and children. To find the Edgartown location, just look for the company's mood-lifting mascot: a cheery pink whale.
For the perfect summer read, stop at Edgartown Books (44 Main St.), a two-level indie bookstore boasting a cute front porch (with comfy rocking chairs), a courtyard garden and a backyard coffee shop (the appropriately named Behind The Bookstore). Another showroom where you could easily lose track of time is Portobello Road (4 Dock St.), which draws in passersby with a quirky selection of glossy coffee table books and vintage and reproduction odds and ends—everything from tin signs to paper weights.
Need to satisfy your sweet tooth? You can't go wrong at Murdick's Fudge and Mad Martha's Ice Cream, both on Water Street. Another good option is Black Sheep (18 N. Summer St.), a stylish European-style market hawking gourmet pastries and chocolates as well as picnic-ready artisanal cheese and charcuterie platters.