We went to the Vineyard when I was a kid for a week here and there and I spent a summer there between high school and college. I have been back a few times since. Biggest change? Yoga studios everywhere.
  1. Best lobster roll (Grace Church Parish House)
    This church in Vineyard Haven sells excellent lobster rolls on Fridays. Who would have thought? 36 Woodlawn Ave, Vineyard Haven
  2. Best "secret" beach (Chilmark)
    Well, not secret anymore because I am telling you about it. It is actually a private beach so be discreet. This is how you get there - head on State Road to Abel's Cemetery (that is where John Belushi is/was buried). Directly across the street from the cemetery, you will see the sign from the picture.
  3. Best "secret" beach, Part II
    Walk down the hill towards the water for about 5 minutes. You will come to this gate which you can walk around on the left. If the tide is in, the water will be too high to cross to the beach. If it is low tide, you may be able to walk on sand or the water will be about up to your ankles. On the other side of that hill is the lovely, serene beach!
  4. Chilmark Chocolates (Chilmark)
    Stop here after your trip to the secret beach. Awesome chocolatier that employs several handicapped people. It took me all of two hours to eat the half pound I bought and was planning to share. 18 State Road, Chilmark
  5. Aquinnah
    After going to Chilmark Chocolates, keep driving "up island" (meaning away from Oak Bluffs and Vineyard Haven). A bit touristy up at the view of the cliffs and the Gay Head lighthouse, but it is gorgeous.
  6. Gay Head Lighthouse (Aquinnah)
    See above. Also read this recent article from the NY Times on the process of moving the lighthouse:
  7. Beautiful clay cliffs and nude (!) beach (Aquinnah)
    Once you can't take the tourists anymore, turn around and walk down to the beach. There are beautiful cliffs of all different shades due to the clay in them. There is also a nude part of the beach in one section. If this is your kind of thing, beware of a few pervs.
  8. Homeport & Menemsha Harbor
    Get some take out from this seafood restaurant from the back door and sit by the water in this fishing village or at the beach. (As a side note, this is also where I had my first job almost 20 years ago.) 512 North Road, Chilmark
  9. Lambert's Cove (West Tisbury)
    Beautiful public beach. Parking in the lot is only for people from West Tisbury and it gets crowded on the street around the entrance. I recommend riding your bike there instead. The water is gorgeous and there are cool tide pools for exploring too.
  10. Morning Glory Farm (Edgartown)
    Charming, but somewhat expensive farm, bakery, and market. 120 Meshacket Road, Edgartown