My wife (a psychologist) has a continuing education seminar in Cape Cod (Eastham) this summer. We’ve been every other year over the past six years. We’ve developed a pretty good idea of what’s good and what’s not so good.
We’re staying for the second time in the guest rooms over Chillingsworth in Brewster. Obviously, we’ll eat there a couple of times. We’ve discovered the Yardarm in Orleans (my favorite) where we always try to eat at the bar for some local color. We’ve had really good meals at Abba (also in Orleans), the Brewster Fish House, and the Wequasset Club.
So what are we missing?
Also - golf - where to play. My local club pro usually sets me up for a round at Eastward Ho! in Chatham. I’ve tried Ocean’s Edge (meh) and The Captain’s Course in Brewster (double meh!).
The Red Pheasant Inn also has an awesome wine list with very reasonable prices. I drank a 1990 La Chapelle a couple years ago for $225, and they also had a lot of Burgundy gems. That said, that food was a bit tired and not that interesting.
Along with the places already mentioned, I really like the Impudent Oyster in Chatham.
Sandwich is an hour from Eastham (or more dependent on traffic) FYI. In Wellfleet (next town north of Eastham) Moby Dick’s on Rte 6 is legal BYO (no alcohol permit) and is your basic lobster, fish and Wellfleet oysters place. Mac’s Seafood on Wellfleet Harbor (not to be confused with Mac’s Shack in town) is BYO with picnic tables on the harbor beach and is more or less a glorified takeaway but right next to the fishing fleet. Land Ho! in Orleans is good for casual and has the games on (full bar, drink beer not wine).
Also, a wine store next to the Cumberland Farms on Rte 6 in Wellfleet right before th lights to turn into town has 1994 DRC RSV I think that last summer the owner couldn’t sell. The list was like $500, I couldn’t get him below $250 last year but 1994 is a fading year so you might do better if he still has it around. The place seemed AC’ed really well.