Visit the beach and get a glass of wine and a mean/ snacks at the Outermost in (make sure to sit outside to get the breathtaking views.) truth be told, there is barely any town. Zach’s Cliffs is a beautiful beach to hike on
Beautiful off season. While during the summer the beach is only open to residents of Chilmark, off season it is open to everyone. Check out gorgeous views of the surf, awesome cliffs and rock structures.
Rent bikes for the day or weekend. The entire island has bike paths along it, so can pretty much bike anywhere. Located next to the Bike Ferry if you feel like taking your bike over to Chappy to explore
Definitely the town with the best shopping on island from clothing to candy stores - personal favorites are Slate, Vineyard Vines, The Great Put on, Mad Martha's Ice Cream
Take the bike ferry across and enjoy a gorgeous ride along the water
Take the ferry across from the port in Edgartown to chappy - walk on or bring your bike, and explore the many secluded beaches, nature conservatory and light houses